A few people have asked what I'm swinging for now that I’ve left the fast-paced VC CRO track fueled by gasoline and anxiety. Honestly, I’m not entirely sure, but it probably involves starting my own venture. Whether that’s a business, consulting practice, or something else.

Since quitting my job four weeks ago, I’ve explored several product ideas (here and here) and spent a lot of time researching how to leverage my experience building sales teams to start my own consulting or fractional business.

The latter are often called expert-led businesses. Identify your unique skills and find a niche where you can make a greater impact than others. Begin sharing your expertise tailored to that specific audience. Grow your own email list to maintain direct contact, regardless of platform changes. Engage your audience by asking about their main pain points or bottlenecks. Use their feedback to develop relevant content and future products. Etc. Etc.

This is a cool tool to help you figure out your “expertise” and niche. And this is a good post about growing an audience on LinkedIn. Both were helpful tools, but neither ultimately helped me figure out what to do and when to take certain actions that could actually translate into income.

In addition, I have conducted outbound outreach to understand what resonates with my future customers (experts and CEOs). See two examples below.

Fractional VP Outbound

Hey [Name ] — As VP of Sales at Flock, I built the mid-market business from the ground up, scaling it from $0 to $45M in ARR in under eight quarters (>100% attainment for eight consecutive quarters).

Then I took the playbook to Edia (Series A Felicis backed), hired 7 reps, 2 managers, and ramped up one into the VP role while growing revenue from $xm to $ym in 2 quarters and driving operational rigor that created predictability for the CEO

Do you have 15 minutes tomorrow or Wednesday to see what a 90-day engagement could look like?

Best,

Ben

benjaminjfoley.com

Product Validation Outbound

To date, using the outbound approach, I’ve had 10+ product validation calls on my product ideas and landed a few consulting gigs. However, I’ve been distracted by interviewing for several jobs simultaneously. I plan to be fully focused on building my own income to support my family.

The clearest, shortest path is through fractional/consulting work, so that is where I am initially focused. This is the first time I’ve done this, so I am going to share all the lessons, pitfalls, and wins with you so that you can do the same.

Ultimately, I only have three requirements for what I do next:

1/ I need to build

2/ I need to be creative

3/ It must be local

Outside of that, I am pursuing any “green light” that comes my way, as Matthew McConaughey would say, hoping to find a path to sustaining my life without needing a full-time job.

PS: If you're also considering doing your “own thing,” what is the biggest obstacle keeping you from trying?

-Ben

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Team - it’s been a few weeks since my last post.

Since I started writing again, I’ve changed this blog’s name three times and reconsidered what I should write about more than a dozen times.

to be frank. i was terrified to share the journey. i was worried i’d lose out on opportunities. i was afraid to let go truly. I had no idea what decision to make or what direction to choose.

i still don’t.

But for the first time in my professional life, two things are true: 1/ I’m unemployed, and 2/ I'm not in any interview processes.

The anxiety spikes just writing that.

what will they think? will they think i lost my mind? lost my edge? worse?

I’ve worked at 9 companies and had 14 different roles in 11 years since graduating. I’ve received well over 30 job offers. Getting jobs was my way of propping myself up and lowering my anxiety because if I had something on deck, I could fail/leave/screw up and have a backup plan.

For the first time, I have no backup plan. And in reality, I don’t even have a primary plan. And if you know me, you know what that is likely doing to me (cough, cough).

When I left my job as SVP of Sales at a high-growth startup based in the Bay Area on April 28th, I was already in 5 interview cycles. I ended up getting 4 of the jobs. I turned them all down.

None felt right, and for the first time, I listened to myself.

But it was so freaking hard. Still is.

My anxiety is higher than it has been in a long time. My brain is searching for an answer, and most moments I try to find one, but I’m getting slightly better at not doing that.

I feel like a significant part of me is dying and is desperately screaming for help.

Since leaving my job, I have had 83 meetings with execs and founders in Indianapolis and on the coasts. My goal was 30. To say I’m compulsive would be an understatement.

I thought that by having a ton of conversations, I’d learn what my passion was, but that hasn’t been the case.

Don’t get me wrong, I’ve learned a lot and a lot of really interesting pathways have appeared, but I kept running back to the status of a job to soothe my anxiety about truly, once and for all, swinging for the f**king fences.

My whole life, I’ve been bunting. Little hits here and there to get on base. It’s kept the game alive, but deep down, I’ve always known I’d never feel authentic without stepping up to the plate and ripping it.

While I have had to pull myself, feet dragging, to the base. I’m here.

Will I swing the bat? I’m not sure, but I plan to document the journey.

1 post a day. Raw. Unfiltered musings on going from a high-status VP of Sales role at one of the top companies in the world to a 34 (soon to be 35) year old, fumbling my way to a more authentic way of living.

If that’s not for you, I get it. Feel free to unsubscribe. No hard feelings at all.

But if you are someone who may also feel that there is something deeper inside you that you’re not sure how to access, I’d love for you to join me.

Share

Not at the end, when I brag about getting through, but from the beginning.

And if you think anyone else might be curious about the journey from high status to something more authentic, please share this with them below.

As I always used to tell my sales teams, you build something great brick by brick.

I’ve never had to lay the first brick. Here goes nothing.

with gratitude,

foley

Wars are not won by evacuations.” — George Marshall, 1940

Exclaimed General George Marshall to Winston Churchill at the lowest moment of the Allied war effort, just after Dunkirk had happened.

330,000 British troops were pulled off the beaches of France, and they were celebrated at home as a miracle, but Marshall saw it for what it meant strategically, a retreat dressed up as a victory.

Marshall understood something Churchill kept resisting: you do not win wars by surviving them. You win wars by concentrating overwhelming force on the one front that ends them.

He would spend the next four years fighting for that principle in every Allied strategy session, and the argument he won is the reason you’re reading this in English.

Who was George Marshall?

If the name doesn’t stop you the way Eisenhower or Patton does, that’s by design.

George Catlett Marshall was the U.S. Army Chief of Staff from 1939 to 1945. He was the architect of the largest military force ever assembled. He built it from 189,000 soldiers to over eight million. He selected the generals who led it, designed the strategy that guided it, and held the Allied coalition together when it threatened to fracture.

Winston Churchill called him “the greatest man he had ever met.”

After the war, Marshall served as Secretary of State and designed the Marshall Plan. He is the only professional soldier in history to receive the Nobel Peace Prize.

He is not a household name to many. He spent his entire career making sure the credit went to someone else.That, too, was part of the principle.

In his essential biography George Marshall: Defender of the Republic, David Roll traces the through-line of Marshall’s life and leadership. He is a man whose defining conviction was that the greatest danger to any fighting force isn’t the enemy in front of you. It’s the dispersion of your own energy across too many fronts.

The greatest danger to any fighting force isn’t the enemy in front of you. It’s the dispersion of your own energy across too many fronts.

The argument he kept losing

From 1941 through 1944, Marshall fought the same strategic battle on repeat, to no avail. Churchill wanted flexibility.

North Africa. Italy. The Aegean. Anywhere the Allies could probe and pressure without committing fully.

Churchill’s instinct was to keep forces moving, maintain flexibility, and avoid the danger of a single decisive battle that could lose the war. However, the issue with this approach, whether in war or business, is that without strategic focus and commitment, you might not lose, but you're unlikely to win.

For Marshall, the objective was to win the war, not to extend the struggle.

“Marshall and most military strategists at the time regarded as an essential condition of success in war — concentration of effort on the decisive front.”

He lost the argument more than once. North Africa happened. Italy happened. Each time, the decisive front got delayed. And each time it got delayed, the war lasted longer.

When the Allies fully and decisively committed to Operation Overlord in June 1944, the European war concluded within a year. Although the principle was eventually secured, it took three years of Marshall's persistent refusal to abandon it before it was achieved.

What he learned from Pershing

The conviction didn’t come from nowhere.

Marshall had served under General Pershing in WWI and absorbed a lesson that shaped everything that followed. Pershing had fought the same political battle against allied commanders who wanted American troops parceled out across French and British units rather than concentrated as an independent force.

Pershing resisted. Marshall watched. And what Marshall took from it wasn’t just tactical, it was philosophical.

“From Pershing, Marshall also learned that in an allied coalition one should strive to minimize the dispersion of forces to other fronts and instead concentrate overwhelming power against the enemy.”

Minimize dispersion. Concentrate overwhelming power.

He carried that sentence into every room he entered for the rest of his career.

The cost of being right

The hardest part of Marshall’s story isn’t that he fought for concentration. It’s what it cost him personally.

He had advocated for the Normandy invasion for nearly two years. He believed in it completely. Pershing had recommended him for a star after WWI. He had spent thirty-seven years preparing for exactly this kind of command.

And when Roosevelt asked him whether he wanted to lead Operation Overlord — the invasion he had designed, argued for, and refused to abandon — Marshall declined to express a preference.

He told the president to make whatever decision was best for the country, and not to consider his feelings.

The command went to Eisenhower.

“It required extraordinary moral discipline — strength of character — for Marshall to refrain from asking FDR for the command when he knew it would be granted.”

He never complained. Never made his feelings known. The principle mattered more than the recognition.

That, too, is part of what concentration requires. You don’t get to fight on every front.

How does this essay relate to growing durable businesses?

I’ve spent the better part of ten years inside GTM orgs at every stage of growth.

The recurring issue I observe isn’t related to poor reps, weak pipelines, or incorrect CRM choices. Instead, it's dispersion: pursuing three ICPs simultaneously, juggling five incomplete initiatives, and distributing energy across numerous urgent opportunities. This scatter prevents any one effort from gaining the momentum necessary to close successfully.

Marshall would recognize it immediately.

The founders and CEOs I collaborate with aren’t failing due to a lack of effort. Their setbacks stem from not choosing the right front to focus on.

That’s what this newsletter is for.

Join 2,100 founders and operators who read the Decisive Front every Saturday. One short essay on concentrating overwhelming force on the one front that can drive durable growth, in business and life.

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This is The Decisive Front.

Welcome.

— Ben

Roy Williams was struck afterward by how little it took. One conversation with Jordan, and no one would ever outwork him again.

Early in his career at UNC, Jordan was seen as too casual and abrasive. His effort didn’t match his goals. He wanted to be the best, but his actions showed his immaturity.

Williams, then the assistant coach, challenged him on it. Jordan said he was trying as hard as everyone else. Williams told him that if he wanted to accomplish great things, trying as hard as everyone else wasn’t enough. He had to work that much harder than everyone else.

It’s advice we’ve all heard. What’s rare is what Jordan did with it.

Reflecting on it later, Jordan said: “My greatest skill was being teachable… I was like a sponge… even if I thought my coaches were wrong, I tried to listen.”

Most people believe Jordan’s drive was innate; something he was simply born with. The reality is that without a great coach in Williams, and without Jordan’s willingness to listen and adapt, he might have been successful, but nothing close to what he became.

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Recently, I came back to Roland Lazenby’s Michael Jordan: The Life. This book is arguably one of the best written about MJ, thanks to its personal insights into his upbringing. It shows how his father's fear imposed on the family fueled his relentless ambition and drive. Notably, one sentence stood out more than others, resonating so deeply that it has been identified as the core influence behind the famously competitive athlete.

From Lazenby:

The same teachability that made Jordan great is also what made the anger permanent. He was a sponge, but a sponge soaks up whatever it’s sitting in. He absorbed the coaching and the resentment, and he never wrung either one out.

I’ve been thinking about this a lot in my own life. Not only am I trying to be much more cautious with the words I use with my boys, but also working to uncover the beliefs or resentments that may be unconsciously driving my life.

What we absorb, absorbs us.

Jordan’s story ended with him as the greatest of all time; someone people around the world look to as an inspiration of dedication, perseverance, and craft. But what most people don’t see is isolation, the anger, and the negativity that still drive him today.

If you don’t believe me, watch his Hall of Fame speech and tell me that’s a happy man. I don’t know him. But to me, he looks like someone still trying to prove the world wrong, decades after he won.

So I have to ask myself the same question about my own ambition.

I have driven myself so hard to succeed in my professional life, but I have never stopped long enough to ask myself why I want to succeed in the first place.

When you look in the mirror, do you see someone with a genuine passion for your craft? Or do you see someone eager to show other people that you matter, that you are important, that you are worth their time?

For me, the answers are hard to face, but I am working on facing them, writing them down, exposing the flaws in my pyche that have been unconsciously ruling my mind for far too long.

I don’t want to wake up at 50 as a successful, angry, lonely man. Surrounded by everything I acquired, and none of what I actually wanted.

I won’t pretend I’m not ambitious. I am. I’m building something, and I want it to be excellent. The question isn’t whether to want greatness; it’s whether the work itself can be the reward rather than needing the outcome or approval of others.

I will never reach greatness the way Jordan did. I’ll never be widely known around the world. But my new north star is to be in the “Hall of Fame” in the minds of the people I care about the most. To have them be able to say that I lived my life, authentically, the way only I could.

It’s a high bar, but it’s worth chasing, don’t you think?

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Hey there!

If you’re reading this, you probably have a job you’re not psyched about and an idea rattling around in your head that you don’t know what to do with. I’ve been there.

I’m going to walk you through exactly how I built my own app, Chalk, in two weeks.

What worked, what was a massive waste of time, and the specific tools and templates I used. You can take all of it. This is what I wish someone had handed me before I started.

A little context on who I am and why I built this

I spent years in B2B sales. Eventually helped scale a company from $30M to $450M in ARR. I hired and onboarded 80+ reps. I ran enablement. I sat in on hundreds of calls. And the thing that kept bugging me was simple: sales training is broken.

We’d fly a team to a resort, run a two-day offsite, spend $500K on a methodology firm, get everyone hyped — and then watch reps go right back to doing exactly what they were doing before. Nothing stuck. Not because the content was bad. Because that’s just not how humans learn.

I knew what actually works. Short daily practice. Repetition. Feedback loops. Accountability. That’s it. Duolingo figured it out for language learning. Nobody had done it for sales. So I built Chalk.

Chalk is a gamified B2B sales training platform. Reps do 5-minute daily drills. AI analyzes their gaps and gives each person a personalized path. Managers get a leaderboard and real visibility into who actually knows their stuff.

The mistake I made. Don’t do this!

I had the idea. I thought it was good. I started building. I spent two weeks putting together the actual product — the logic, the UI, the drill flow, all of it. I was proud of it.

Then I showed it to people. Nobody would buy it.

Do not build anything until someone has told you they will pay for it. Not that they like it. Not that it’s a cool idea. That they will actually pay.

This is not a new lesson. Every startup book tells you this. Every founder podcast tells you this. I still did it wrong. You probably will too if you’re not careful. So let me be clear: your first job is not to build. Your first job is to find people who will pay.

Two things I should have done before touching any product tool:

1/ Build an audience of people who might care about the problem I was solving

2/ Talk to them and ask if they’d buy it — before building a single thing

Everything below is the order I wish I’d done it in.

Step 1: Build an audience before you build a product

This is the most boring advice and also the most important. You need to build an audience of people who share the problem you’re trying to solve. Not friends. Not family. Not people who will be nice to you. People who actually live in the problem every day.

For me that meant VPs of Sales, team leads, revenue leaders at Series A through C companies. Those are my people. I needed to find them and start talking before I built anything.

The tool: Substack

Substack is free. It takes 20 minutes to set up. And it is the single best way to start building an audience of people who care about what you’re thinking about. You don’t need to be a writer. You just need to be honest and useful.

Here’s what I’d do if I were starting today:

1. Pick one specific problem your audience deals with. Not “sales is hard.” Something specific — like why reps forget everything from training within 30 days.

2. Write a post about it. 400–600 words. Share what you actually know. Don’t try to sound smart. Just be direct and useful.

3. Post it. Share it in two or three places where your people hang out — LinkedIn, a Slack group, a community forum.

4. Do that every week. Not every day. Every week.

5. After 4–6 posts you will have a list of people who actually care about the problem. Those are your first conversations.

The real goal of the newsletter isn’t to become a content creator. It’s to build a list of warm contacts who already know you understand their problem. When you message them later and ask if they’d pay for a solution, it’s not cold outreach — it’s a conversation with someone who already trusts you a little.

Step 2: Do discovery outreach before you build anything

Once you have even a small list (20 will do), start talking to them. Not pitching. Not selling. Asking. This is called customer discovery, and most people skip it or do it badly.

The goal is not to validate your idea. The goal is to understand the problem deeply enough that your solution actually solves something real.

The outreach template

Adam Robinson from Retention.com talks about this framework in his content and it’s the cleanest outreach approach I’ve found. The structure is simple: be a real person, name the problem, ask for time. No pitch. No deck. No “I’d love to pick your brain.”

Here’s the message:

Hey [First Name],

I’ve been following your work at [Company] — congrats on [specific recent thing: a hire, a post, a funding round, a launch].

I’m working on something in the [sales enablement / sales training] space and I’m trying to talk to as many people as I can who actually run sales teams before I build anything.

Not looking to pitch you. Just trying to understand if the problem I’m seeing is real for teams like yours. Would you be open to a 20-minute call this week?

[Your name]

That’s it. It’s short. It’s honest. It doesn’t pretend. And it works because nobody is asking people to share their real problems — everyone else is pitching immediately.

What to ask on the call

You have 20 minutes. Ask these 5 questions. These come from Adam Robinson’s great YouTube channel on building a SaaS company in 2026.

• Do you understand the problem I am try to solve?

• Do you have the problem I am trying to solve?

• How are you solving this today?

• What else would this solution have to have in order for you to pay for it?

Near the end, ask one more question: “If I built something that solved exactly what you described, would you pay for it?”

This is THE key question. Not if they are interested. Not if they think it is cool. Not even if they want to use it.

No, will they pay you for it TODAY if you could get it to them.

Do this with 15–20 people before you write a single line of code or touch any design tool. The thing I built that nobody wanted? I talked to four people and heard mostly positive reactions. Four people is not a signal. Fifteen honest conversations is a signal.

Step 3: Now you can actually build — here’s how I did it fast

Okay. You’ve talked to enough people. You’ve heard the same pain point in enough different ways. You know what you’re building and you know someone will pay for it. Now you can build.

Here’s the stack I used. All of it is fast, cheap, and doesn’t require you to be a developer.

Polsia — [my referral link here] This is the main tool I used to actually build the product. It handles the app infrastructure, hosting, and the backend without you needing to write code from scratch. Genuinely the thing that made this possible on the timeline I had.

Claude Design — I used this to build all the design elements, generate copy, think through product logic, and move fast on things that would have normally taken me days. Claude design is so killer. It helps you build fonts, brand colors, even full UI wireframes. Try this out.

Substack — already set up in Step 1 It becomes your ongoing distribution channel as you build. Every time you ship something new, your audience is there to see it.

LinkedIn — free, already where your customers are. Post about what you’re building, what you’re learning, and what surprised you. People root for founders who are transparent about the journey.

The one rule I kept for what to build first

I did not try to build everything. I picked the one thing that would prove the concept and built only that.

For Chalk, that was the drill experience. If a rep couldn’t sit down, open the app, do a five-minute drill, and walk away feeling like they actually learned something — nothing else mattered. The gamification, the leaderboards, the manager dashboards — all real, all in the product — but they came after I knew the core experience worked.

Your MVP is working when a stranger can use it without you explaining anything and they come back on their own the next day. Not “it has all the features.” Not “it looks great.” They came back without being asked.

Step 4: What I built and why it’s different

Every VP of Sales I talked to said some version of the same thing: we spend a lot of money on training and we can’t tell if it’s working. No visibility. They didn’t know which reps had actually internalized the methodology and which ones were faking it in pipeline reviews. They knew results — but by the time those numbers show up, it’s too late to fix anything.

Chalk works like this. Every day, a rep opens the app and does a 5-minute drill. It’s tied to the actual stage of the sales process they’re in — pre-call prep, discovery, champion building, demo delivery, post-demo follow through.

The AI analyzes their responses over time and figures out where their actual gaps are. Not where they think their gaps are. Where they actually break down. Then it builds them a personalized path. One rep is doing advanced discovery drills because they’re solid on the basics. Another rep is back to fundamentals because the AI caught that they don’t actually know how to find a real champion.

Managers log in and see a leaderboard — not of quota attainment, but of skill development. Who’s practicing. Who’s improving. Where the gaps are — before those gaps show up as lost deals.

The research behind it

There’s a 40-year-old study called Bloom’s 2 Sigma problem. Benjamin Bloom found that students who got one-on-one tutoring performed two standard deviations better than students in a regular classroom. Two standard deviations. The difference between an average student and a top 2% performer — just from the format of the learning, not the quality of the content.

You can’t give every sales rep a personal coach. It doesn’t scale. What you can do is use AI to deliver that kind of individualized, adaptive practice at scale. That’s what Chalk is.

Step 5: How I thought about pricing

I made the free tier permanent on purpose.

The best salespeople are always trying to get better on their own. They don’t wait for their company to buy them training. If I can get a rep using Chalk on their own and they love it, eventually their manager sees the leaderboard and wonders what it is. That’s how the team plan gets sold — not from me cold-calling VPs, but from a rep inside the company becoming a champion for the product.

That’s the flywheel.

Free: 1 drill per day, forever. No credit card. Unlimited drills, full AI gap analysis, personalized path.

What I’d do differently

• Talk to 20 people before building anything. Not 4. Not 8. 20.

• Start the Substack six weeks before I started building so I had a real audience when it launched.

• Nail the outreach message earlier. The template above would have saved me a lot of awkward intros.

• Build even less at first. The first version had too much. I should have launched with just the drill experience and gotten that right.

Okay. Go build something.

You don’t need to be a developer. You don’t need funding. You don’t need permission. You need a real problem, a list of 20 people who have that problem, and the willingness to have honest conversations before you touch any tools.

The tools are easy now. What used to take a team and six months takes one person and six weeks if you use the right stack. The hard part — the part that actually matters — is finding out what’s true before you build.

If you work in sales and want to try what I built, go here. Free. Always will be. No credit card.

[Link to Chalk]

Five minutes a day. Real skill development. Built for people who actually want to get better.

Over the past decade, I’ve received more than 30 job offers. I’m not especially proud of that, because if I’m being honest, some of it probably stems from a deep need for external validation, but I digress...

I’ve never applied through a job board. And until my most recent position, I’d never spoken with a recruiter. Every opportunity followed the same pattern, and I’ve never written it down until now.

Recently, I’ve been talking with many people who are genuinely struggling to find work. That has never been a challenge for me. Luck and privilege are real, and I’m grateful for both.

But I also believe there’s a process that actually works, and if you’re searching right now, I hope this helps increase your odds of finding the next thing.

Step 1: Start with accounts, not job boards

The first thing I do when I’m looking for a job is to build a list of companies I’d actually want to work for. Not a list of open roles. Not a LinkedIn search. A list of companies that fit my criteria for something I’d be excited to do next.

The best jobs are never posted. They get created for people who show up before there’s a job description.

The question isn’t “what’s open?” The question is “who would I want to work for?” Get that list. Then go do outbound.

Find people inside those companies, in the department you’d want to work in, and reach out to them. Not to ask for a job. To learn.

Come curious, with real questions. You’re doing discovery: what do they actually do, what does the company look like from the inside, what do they care about?

Here’s what most people miss about this: it’s not just a tactic to get in the door. Every one of these conversations compounds. That person now knows you. They’ve seen how you think. They can refer you, introduce you, and give you inside intel during the interview process. A decade from now, when you’re both somewhere different, that relationship is still there.

Currently, I’m holding 30 of these meetings while searching for my next opportunity. After just one week, my calendar is already packed with referrals from those initial meetings. Yours can be too, with the right messaging.

After these meetings, you’ll understand the landscape: who’s building, who’s coasting, and what kind of work you actually want to do.

You’ll leave some of those calls with more energy than you walked in with. Others you’ll leave thinking, “absolutely not.” That signal is gold.

Run it like a sales process.

Confirm the meeting the day before. Follow up within 24 hours with what you took away from the conversation.

And before you leave every call, ask: “Who are one or two other people you think I should know?”

Nine times out of ten, they’ll make the intro. Your network multiplies whether you get a job from that person or not.

Step 2: Stand out before the interview starts

Let’s say there’s an open role or a first meeting on the calendar. Your job is to prep like you mean it.

Find two or three people at the company on LinkedIn, not the hiring manager, just people who work there, and message them directly. Tell them you’re interviewing for the role and ask for 10 minutes to hear about their experience there.

Nobody does this.

I’ve been a VP of Sales for 3 years. I can count on one hand the number of candidates who reached out to me directly about an open role on my team. Every single time it happened, I gave them a first interview. Every time.

You can also reach out cold to the person doing the hiring. Keep it sharp and specific. Here are two examples from different career stages.

The first is from a place where the track record speaks for itself:

Hey [Name], at [Company] I built our mid-market business from the ground up, scaling it from $0 to $45M ARR in under eight quarters, hiring 60+ reps, and putting in place the culture and operating rigor that made it repeatable. I’m interested in joining the GTM leadership team at [your company] to help grow another rocket ship. Thanks for considering the outreach. Ben

The second is from earlier in my career, before I had numbers to lead with. Here I leaned on genuine curiosity and a specific reason I cared:

Dan, my name is Benjamin Foley. I came across your profile after doing research on Sigstr. I hope you don’t mind me reaching out cold. I’ve spent the last two years building and selling an e-commerce business I started at IU. Starting my own thing taught me a lot about attracting and retaining customers, but after two years working alone, I had a real desire to build something bigger with a team of talented people. My interest in Sigstr is specific: I’ve seen the value of a great email signature CTA firsthand growing a blog that just passed 7,000 subscribers. I believe Sigstr is poised to execute on a huge opportunity and I’d love to add value to your growth. If you’re willing to connect, I’d love to grab a coffee and learn more about your vision for the company. With gratitude, Benjamin Foley.

Different career stage, same idea. Do the work, be specific, make it about them.

Step 3: Nail the first call

Here’s the thing nobody tells you about first calls: your job is not to talk about yourself.

I know that sounds backward. But when I get on a first call, I have a list of questions I want to ask. I open like this:

“Hey [Name], I’m really excited to learn more. I have a bunch of questions I’d love to ask. I’m sure you have questions too, so we can start wherever you want.”

Nine times out of ten, they say, “What questions do you have?” Now I’m running the meeting.

They talk. They tell me what they actually care about, which is almost never what the job description says. They like me more because people like those who are curious and let them talk about themselves and their company. And I’m learning exactly what I need to know to decide if I want this job and how to get it.

Confirm pain. Build the champion. Close with the next step before you hang up.

One more thing: send an agenda email 24 hours before the call. Here’s an example of what that looks like:

[Name], I’m looking forward to connecting. I’ve spent some time digging into [company’s] mission and customer stories and it’s clear you’re not just solving a compliance problem, you’re redefining how scale and trust coexist in regulated markets. I also really enjoyed your conversation on [podcast] and your piece on [topic].

To make sure we cover what’s most useful to you, here’s a loose outline I can tailor based on your priorities:

• My background: building high-rigor, high-growth sales orgs in complex environments

• Your ideal future state and success metrics at 90, 180, and 365 days

• Enterprise traction, expansion opportunities, and current limiters

• How you think about GTM structure, methodology, and enablement

Looking forward to the conversation. With gratitude, Ben

Nobody does this either. It takes 15 minutes, and it always lands.

Step 4: The 24-hour follow-up

Within 24 hours of every conversation, send a follow-up. Not a transcript. Not “great chatting.” Something that shows you were actually listening and adds something back.

Here’s what that looks like in practice:

[Name], thanks for the time today. I came away more excited about the role. The territory setup, the way you think about running the business, the anchor account focus, the 90-day ramp bar, the pipeline metrics. That’s a structure I understand and know how to operate in. I know the concern around recent IC execution is real, and I don’t want to paper over it. What I’d say is this: I’ve spent the last two years coaching 60+ reps through exactly this motion. I know what good looks like, and I’m motivated to close that gap in the first 90 days. Looking forward to speaking with [next person]. Ben

Do the work

Then go further. Based on what you heard on the call, whether it was a problem they mentioned or a challenge they’re stuck on, build something.

A framework, a short plan, a model. Send it over with a note: “Probably way off base, but based on what I heard, I put together some quick thoughts on how I’d approach this.”

With Claude/ChatGPT and your call notes, this should take you all of 1 hour, but you will move yourself into the top 1% of candidates. Not because you’re the most qualified, but because you showed them what it’s like to work with you before they’ve hired you.

The meta-point

Run this whole thing like a sales process. Research before every meeting. Send the agenda the day before. Follow up within 24 hours. Always close with a next step. Ask for two introductions on every call before you leave. Build champions. Go out, learn, iterate, go out again.

Most people are too lazy to do this. That’s the opportunity.

The best jobs are never posted. They get created for people who show up as if they already work there.

[Last week, I started building a tool called Chalk. An AI Native Sales Enablement platform that helps every rep crush quota in 5 minutes a day. Think Gamma meets Duoling for sales. Check it out. Use the promo code chalkdemo to use it for free. Let me know your thoughts]

I was talking with a mentor of mine this week about the future of the CRO role in an AI-native world.

The tools in sales leaders' hands today are incredibly powerful and have the potential to unlock an enormous amount of latent talent that has been dormant because, in the past, it was either too hard to do or not a priority.

But today everything is different.

If you are a sales leader in a high-growth company, it isn’t optional anymore to get familiar with these tools. But familiarity isn’t enough. You need to learn how to operationalize them to improve outcomes for your organization.

In my opinion, this cannot be a skill set you outsource to RevOps, or else you will be left behind.

In the future, I think the CRO will look a lot more like Varun and a lot less like John McMahon. Part brand/marketing, part GTM Engineering, part sales leadership. Not quite RevOps. Not quite Sales Leadership. Not quite Marketing. A combination of the three that can leverage AI, data, and relationships to accelerate growth.

Undoubtedly, the last two decades of SaaS enterprise sales fundamentals will be important. Still, the leader or founder today needs to be much more AI-native, much more systems, data, and analytics-driven. I’m not sure whether the actual profile in person changes, or whether the RevOps role becomes a C-suite role that sits adjacent to the CRO. I don’t think RevOps is the right name for this either.

There is no one currently sitting in a CRO seat with a decade of experience in this role. At the same time, there is no one sitting in the VP of RevOps or Marketing role who understands how to do enterprise sales.

And to be honest, this is where the massive gap and opportunity sit.

And the market? They are expecting these individuals to be out there already.

I talked with a recruiter a couple of weeks ago who said a founder was looking to exit their CRO after 8 months because he wasn’t “AI native enough.” This guy had an amazing background. Long runs at great companies. Only been in the seat for just over 2 quarters. The company was set to 3x. Yet the CEO was looking to replace them because he lacked this skill set.

I just had to laugh, though. No one has that experience in the market right now. But that is where the opportunity is.

There is a huge opportunity for mid-to-early-stage career professionals to dig in deeply, become highly adept with these new AI tools, and operationalize them across the sales organization. I think you can let people take multiple steps in their career if they possess this.

I could be wrong here, but there is low to zero risk in figuring this out.

I was talking with an early-stage founder recently about landing their first two partner logos.

Not building a sales org. Not hiring SDRs. Not standing up some overbuilt outbound machine. Just the first two real companies willing to take a bet, spend time, give feedback, and help prove the product solves a real problem.

Before you start rewriting emails, buying tools, or convincing yourself the market is broken, you need to diagnose the actual problem.

I always think about sales cycles in three stages:

1. Getting in a deal

2. Winning a deal

3. Closing a deal

Getting in a deal means you can create enough curiosity and urgency to get the first real conversation.

Winning a deal means that first conversation turns into an actual sales cycle with a real problem, real owner, real next step, and real path to value.

Closing a deal means the customer commits. Pilot, paid contract, design partnership, whatever the right motion is for your stage.

Founders blur these together all the time.

They say, “We need more pipeline,” when the real issue is that every first call dies in polite interest.

They say, “Our close rate is low,” when they are not actually in deals yet.

They say, “The market is slow,” when they are chasing giant logos that were never going to move quickly in the first place.

Founder sales is not scaled sales. You are not trying to build a perfect revenue machine on day one. You are trying to find the sharpest path from conversation to conviction to commitment.

That means you need to know where the motion is breaking.

Are you not getting enough first meetings?

Are you getting meetings but not creating a real sales cycle?

Or are you getting real interest but failing to define what yes means?

That diagnosis matters, because the fix is different.

1. Stop Chasing Shiny Logos

In this case, the founder was building in physical AI space. Real problem. Real stakes. This isn't just “workflow efficiency” pain. Real operational pain. Brand risk. Failed tests. Delayed results. Line shutdowns. Recalls. Regulatory pressure. Bad rooms. Bad conversations.

That kind of pain can turn into a company, but only if you aim it at the right customer.

The instinct was to go after the giant household names. The logos that would look incredible on the website. The logos that make investors feel good.

I get it. Every founder wants the logo that makes the company feel real.

But early, shiny logos can be a trap.

Big companies are amazing at taking meetings. They are amazing at saying “this is interesting.” They are amazing at innovation theater. They will pull you into a long process with six stakeholders, unclear ownership, procurement drag, legal review, and a bunch of people who are excited but not actually accountable for solving the problem.

You can spend six months with a giant company and still have nothing.

At the early stage, you do not need the most impressive logo. You need data. Data on what works and what doesn’t. What pitch resonates. Where is your product strongest. What bugs happen when the thing goes GA.

In reality, you need users, testers, and innovators to be willing to test your product because their pain is large enough.

That usually means mid-market companies. Big enough to feel the problem. Small enough to make a decision. Close enough to the pain that the person on the call actually cares.

That is where the first logos usually come from.

2. Build a Sniper List, Not a Database

Do not build a list of 5,000 accounts and pretend that is GTM. You do not need Clay, Outreach, Hubspot, and Gong.

That is not focus. That is avoidance with a spreadsheet.

Build a list of 100 accounts. Hand-picked. Researched. Stack-ranked. Ugly but useful.

For every account, know why they are on the list. Not because they are “in market.” That is lazy. Because there is a real reason to believe the pain might exist there.

Maybe they operate in a category with high contamination risk. Maybe they have multiple plants. Maybe they had a recall or quality issue. Maybe they are a contract manufacturer working across several brands. Maybe they are hiring quality leaders. Maybe they are expanding production. Maybe they are in a product category where delays are expensive.

Your list should answer this:

Account:
Why this account:
Likely pain:
Likely buyer:
Warm path:
Why now:
Next action:

That sounds simple because it is.

The problem is most founders skip the simple stuff because it does not feel sophisticated enough.

But this is the work.

You are not building a database. You are building a target map.

3. Find the Person Who Owns the Mess

Early founders love talking about the economic buyer.

Fine. But before you obsess over who signs the contract, find the person who feels the pain.

In food safety, that might be the VP of Quality and Food Safety, QA lead, plant manager, lab head, or whoever gets the call when something breaks.

That is your starting point.

The person who knows what happens when a test is delayed. The person who knows what it costs to hold product. The person who has lived through the escalation. The person who can tell you if the pain is real or if it just sounds good in your pitch deck.

They may not sign the contract.

But they will tell you where the decision lives.

4. Use the Three Whys

Most founder messaging is too long because the founder is trying to explain everything.

Do not explain everything.

Use the three whys.

Why anything? Why should this company care about the problem at all?

Why you? Why is your approach different from the status quo?

Why now? Why does this need to happen now instead of six months from now?

That is the whole narrative.

If you cannot answer those three questions clearly, you do not have a messaging problem. You have a clarity problem.

For this founder, the message should not be:

“We modernize food safety workflows.”

That is dead.

It should be closer to:

“Most teams are still waiting 24 to 72 hours for results that determine whether product ships, gets held, or gets escalated.”

That is alive.

It creates stakes.

The buyer can feel the gap.

5. Shorten the Dang Emails

The first email has one job.

Earn the conversation.

Not explain the origin story. Not recap the market. Not show how smart you are. Not tell them every feature in the product.

Just earn the conversation.

Use the three whys and make the ask clear.

Subject: faster way to catch contamination risk?

Hey [First Name],

I’m reaching out because [Company] looks like the kind of team where delayed food safety testing can create real operational pain, especially around held product, line delays, and escalation risk.

We’re building [Company] to help quality and food safety teams detect issues faster without relying on the same slow, manual workflows.

We’re looking for 2 to 3 early partners to run a lightweight pilot against a real workflow.

Would you be open to a 30-minute conversation next week? If you’re not the right person, who owns this on your team?

That is enough.

The goal is not to sound impressive. The goal is to sound relevant.

6. Use Warm Paths Like an Operator

At this stage, do not act like you are running a scaled outbound motion.

You are not.

You do not have the brand. You do not have the customer proof. You do not have the category clarity. So use the assets you do have.

Investors. Advisors. Professors. Former coworkers. Friends. Operators. Industry people. Second-degree LinkedIn connections. Anyone who can credibly get you closer to the right person.

And make the ask easy.

Do not say, “Would love any intros you think make sense.”

That puts the work on them.

Send this:

Hey [Name],

I’m working on a company focused on helping [specific customer type] solve [specific problem].

We’re trying to learn from people who own [pain area], especially [titles] at [types of companies].

I noticed you’re connected to [Person] at [Company]. Would you be open to making a quick intro?

You could say: “Wanted to intro you to [Founder]. They’re working on [specific problem] for [market], and I thought it might be worth a quick conversation given your work around [area].”

Appreciate it.

Simple. Specific. Forwardable.

7. Make the Pilot Concrete

A lot of founders get the first meeting and then lose the deal because the ask is mush.

They say they are looking for design partners.

Cool. What does that mean?

If I am the buyer, what am I agreeing to? How long does it take? Who needs to be involved? What do you need from my team? What do I get? What does success look like?

If you cannot make the pilot clear, the deal will drift.

Say this instead:

We’re looking for a few early partners to run a 30 to 45 day pilot. The goal would be to test [Product] against one real workflow, with one primary owner from your team and a few structured feedback sessions. At the end, we would give you a clear readout on whether we improved [speed, visibility, manual work, detection, decision-making], and then decide together whether it makes sense to expand, adjust, or stop.

Now the buyer knows what yes means.

Vague asks create vague deals.

8. Run the First Call With a Backbone

The first call is not there for you to vomit your pitch.

It is there to find the truth.

Is the pain real? Is this the right person? Is there urgency? Is there a path to a pilot? What would need to happen next?

Open with a frame:

Appreciate you making time. My goal is to understand how your team handles [problem] today, share a little about what we’re building, and then figure out if it makes sense to keep talking. If there’s a fit, we can talk through what a lightweight pilot could look like. If not, totally fine.

Then ask real questions.

How do you handle this today? What happens when something goes wrong? Where does the process slow down? What is still manual? How long do results take? What happens while you are waiting? Who gets pulled in when there is an escalation? What would make this a priority now?

Before the call ends, ask for movement.

Based on what we discussed, it sounds like there may be a fit around [specific pain]. Does it make sense to schedule a second conversation with [stakeholder] and talk through what a pilot would look like?

Or:

Is this a real priority right now, or more of an interesting future-state idea?

That question might feel uncomfortable.

Good.

You need truth more than you need a nice call.

9. Kill the Maybe

“This is interesting” is not pipeline.

“Let’s stay close” is not pipeline.

“Send me some info” is not pipeline.

“Circle back in a few months” is usually not pipeline.

The maybe zone is where early deals go to die.

Every call should end with one of these outcomes:

A second meeting is scheduled.
They introduce you to the real owner.
They agree to review a pilot plan.
They send you what you need.
They tell you no.
They tell you now is not the time.

All of those are fine.

The only unacceptable outcome is mush.

10. Build the Three-Slide Deck

You do not need a 20-slide investor deck pretending to be a sales deck.

You need three slides.

Slide one: why this problem matters.
Slide two: what is different about your approach.
Slide three: what the pilot looks like.

That is it.

The point of the deck is not to impress them. The point is to make the idea simple enough that they can repeat it internally after you leave.

Can the buyer explain the pain, the product, and the pilot to someone else?

If not, your message is too complicated.

11. Record the Calls and Tighten the Motion

You are an operator. Act like one.

Record the calls. Listen back. Find where the interest drops off.

If people stop asking questions when you talk about the pilot, your pilot is too complicated.

If they tune out during the intro, your “why anything” is not sharp enough.

If every call ends with “this is interesting,” you are not pushing hard enough for truth.

That is not a sales problem.

That is a reps problem.

And reps can be fixed.

The Whole Game

The first two logos are usually not hiding inside the biggest companies.

They are hiding inside the companies that hurt enough to care and move fast enough to act.

That is the game.

Figure out where your sales cycle is actually breaking. Are you failing to get in deals, win deals, or close deals?

Then fix that specific problem.

Pick the right segment. Build the sniper list. Find the person who owns the mess. Use the three whys. Keep the message short. Make the pilot concrete. Run the first call with a backbone. Kill the maybe. Record the calls. Tighten the motion.

Get the first two logos on the board.

Everything else is noise.

I want to be upfront about something.

I’m not a sales coach. I don’t have a methodology named after me. I came out of real estate investment banking, spent time in custom suits, started two businesses that failed, and somehow talked my way into a sales job at a company selling email signatures in 2019 with zero SDR background and no business getting the role.

The way I learned was embarrassingly simple. I consumed everything Chris Orlob was putting out on Gong. Every John Barrows podcast. Three or four books. Every piece of content I could get my hands on. Then I went to work. Within a year I had closed more revenue than any rep in that company’s history. Not because I was talented. Because I got obsessed with the craft and ran the process.

That led to Sonar. Then Flock, a $30 million company that grew to $450 million over three and a half years, and my teams were responsible for over $50 million of ARR during my tenure.

I’m telling you all of that because what’s in here isn’t regurgitated from a book. This is the process I built by being in it. Every piece of it is earned.

Most deals aren’t lost on the demo

They’re lost in the gaps between meetings.

In the follow-up that never went out. In the demo where a senior exec joined cold because nobody sent them a pre-call agenda. In the deal that quietly died because the rep was single-threaded into one person with zero power to close anything.

Your product is probably fine. Your pitch probably works. What’s killing your win rate is the space between meetings and the rep discipline to treat every single step like it matters on every single deal.

Five stages.

• Stage 01 — Pre-Call: Build value before the meeting

• Stage 02 — Call 1: Nail discovery

• Stage 03 — Between Calls: Build the champion

• Stage 04 — Call 2: Demo to decide

• Stage 05 — Post-Demo: Keep the line open

Stage 01: Before the First Meeting

The best relationship-building I’ve ever seen doesn’t start with a cold sequence. It starts months earlier, at conferences or in communities, with no pitch, no ask, just genuine usefulness. By the time a deal formally kicks off, the best reps have two or three people inside the account who are already selling for them.

You can’t always be in the room. But you can do the equivalent. Send your prospects things that are actually useful and have nothing to do with your product. Research relevant to their business. Articles about their company or peers. Funding news, policy updates, an intro to someone they should know. In long-cycle B2B, your buyers aren’t going anywhere. They remember the rep who taught them something. They forget the one who pitched them.

The miss I see constantly: a rep builds real credibility with someone over months, and then when that person is ready to move, they have to find the demo form themselves. No direct outreach. And then no follow-up when they fill out the form. Inbound is not the finish line. It’s the starting gun.

The pre-call agenda

Send one before every first call. Four minutes to write. It changes how the call opens.

Three things it does: tells them what you’re covering, how long it takes, and who should be in the room. That last part is the one almost every rep ignores completely. Suggest who else should join. By name if you have it, by title if you don’t. You’re giving your champion a reason to loop in stakeholders without them having to manufacture one themselves.

Subject: AGENDA · [COMPANY] <> [YOUR COMPANY] TOMORROW

Hi [Name],

Looking forward to learning more about [Company] and how [Your Company] may be able to help with [problem 1], [problem 2], and [problem 3].

To make the most of our time tomorrow:

Introductions [Company]’s current state around [problem/challenge] Quick [Your Company] overview Alignment on next steps, likely a deeper demo if there’s a fit

Is there anyone else we should include to make the conversation more productive? We typically find that having [persona 1] and [persona 2] involved early helps teams evaluate fit faster and avoids extra back-and-forth later.

[Name]

The three problems you name in line one come from your research. You’ve named their pain before the call starts. That’s not an accident.

Research

I’ve watched too many reps run an AI summary of an account and call it prep. That’s not prep. It shows up on the call when you can’t go two levels deep on anything.

You need two things. Something personal about the contact you can use to build real rapport. And something recent on the account that proves you actually understand what they’re dealing with right now, a board decision, a funding announcement, a strategic shift. The research isn’t to impress them. It’s to ask sharper questions than they expected.

Stage 02: Call 1

Your time is just as valuable as theirs. Stand on that.

Don’t have slides up. Don’t dump. Don’t try to prove you did your homework by reciting it back at them. Your one job on Call 1 is to talk less than 50% of the time and learn exactly where their pain lives.

The opening two minutes

“Did you get my agenda email?” Yes or no. “Anything you want to make sure we cover that wasn’t on there?” If yes, write it down visibly. Tell them you’ll get to it. But don’t let them pull you off track before the call starts. Confirm timing and hard stops. Then move to introductions.

Introductions are discovery. Don’t waste them.

Most reps treat this as a formality. Names, titles, move on. Especially when there are multiple people in the room, this is where you find out what each person actually cares about and what would make this hour worth it for them. Ask that before you say a single thing about your product.

Prompts that actually open things up:

“What does your day-to-day look like in your role?” “What put us on your radar?” “What would make this hour feel worth it for you today?” “How does this fit into what you’re working on this quarter?”

Discovery

First answer is almost always surface. Stay curious. Go two, three levels deeper.

They say: “Rep productivity is a real problem for us right now.” You ask: “How bad is it, and who owns solving it internally?” Then: “What have you tried, and why didn’t it stick?”

That third question is where the real stuff lives. That’s where you find out if there’s actual pain or just a conversation.

Your research gives you a starting point. Your second and third questions turn that starting point into something that moves a deal.

Company overview

Problem, solution, proof. In that order. No founding story, nobody cares.

Use their exact words back at them. Name companies that look like theirs. Use numbers, not adjectives. “8 to 23 points of improvement” beats “meaningful gains” every single time.

If they push for a demo early, deflect it: “I want to make sure I understand your situation well enough to make this worth your time.” That’s not a stall. That’s you respecting the room.

Next steps

Do not leave Call 1 without a calendared next step. This is not the closing move. This is the whole point of the call.

If you have confirmed pain and an active buyer, cut the discovery short and go book the meeting. A confirmed second call is worth more than another fifteen minutes of questions.

If they push back: “Let’s just put a placeholder, we can always move it.” Pull up your calendar live on the call. Suggest who else should join by name or title. Send the invite before you hang up.

Stage 02 (continued): The 24-hour follow-up

Has to go out within 24 hours. No exceptions.

And it cannot be a transcript. I see this constantly. Reps send three pages of meeting notes with no asks, no owners, no dates. Nobody reads that. Definitely not the exec you’re trying to close.

What it needs: a sharp recap using their exact words back at them, clear next steps with named owners and real dates, and any major objection addressed right here, not saved for a future email.

When you quote someone’s exact words back at them in writing, they feel heard and the urgency they expressed is now on the record. That’s not a trick. That’s what it looks like when you actually listened.

Here’s a real example of what a great post-call follow-up looks like. Sent within 24 hours. Specific. Actionable. Uses direct quotes from the call. Addresses the biggest objection by name before it becomes a blocker.

Hi [Name] and [Name],

Great connecting today. Appreciate the context throughout.

Quick recap: [Restate their core problem in their exact words. The urgency they put on it. The specific thing they said that anchored the conversation.]

Where [Your Company] fits: [Map your solution directly to what they said, specifically. Not features. The problems they named.]

For [skeptic’s name] specifically [if there’s a “why not just build this ourselves” or “why not just use X” objection already on the table, address it here by name. Don’t wait.]: [Specific answer to that objection grounded in proof, not pitch.]

Next steps by [specific date]: [Owner]: [Specific action] [Owner]: [Specific action]

If there’s anything [exec joining next call] wants me to address live, pass it along and I’ll prep.

[Name]

Exec-to-exec right after Call 1

Your CEO emails their CEO. Your CRO emails their VP. Right after the call. Two or three sentences. No ask. Just opening the line.

[Their name],

[Your name] here, CEO at [Company]. Our team has had some great conversations with [names], and I wanted to say hello before they connect again [day].

[One line that shows you understand their situation.] We’d love to help you get there.

If I can be a resource, whether that’s questions on the product, how we’ve helped similar teams, or just a sounding board, feel free to reach out.

[Your name]

Two emails. No ask. You’ve just opened two new channels inside the account without burning a single ounce of your champion’s political capital.

Stage 03: Between Call 1 and Call 2

This is where most deals quietly die.

The rep goes dark. The prospect moves on to the twelve other things they’re dealing with. And by the time Call 2 rolls around you’re starting from scratch.

The best reps do the opposite. Short, frequent, high-value touches from multiple directions. Your AE is emailing the champion. Your CRO is emailing their VP. Your CEO is emailing theirs. Three layers of communication in four days, none of them with any ask, all of them adding value.

The emails between calls should not be random. They need to be specific, tied directly to what you heard in discovery, and used to build out what you’re going to show them on Call 2. Every piece of information your champion gives you should show up in the demo. They need to see that what they shared actually mattered.

The pre-demo Loom

Record a five-minute walkthrough of what you’ve built for the demo. Send it to the champion. Ask: “What should I add or subtract?”

This does four things. It de-risks your demo by surfacing problems before they show up as dead air in front of a senior exec. It builds your champion because they now co-own the demo’s success. It’s async so they can watch it whenever it works for them. And if it’s short and tight enough, they’ll share it up the org before the call even happens.

Hi [Name],

I’ve put together a short Loom walking through what I built for [day]’s call. Take a look and let me know what I should add or change before we’re live. Want to make sure this is dialed in for [exec name].

[Loom link]

[Name]

Pre-Call 2 agenda to the full cohort

Same move as before Call 1, but this is where the miss is even more common. Reps send it only to the champion they’ve been emailing. A senior exec joins the demo cold. The first ten minutes are wasted getting them up to speed. Send it to everyone, every time.

Subject: DEMO AGENDA · [COMPANY] <> [YOUR COMPANY], TOMORROW

Hi [Names],

Looking forward to tomorrow with you, [Name], and [Exec].

Based on our first conversation and your follow-up, we’ve built the demo around [priority 1], [priority 2], and [priority 3].

Here’s the plan:

Quick recap of what we heard on the first call Demo walkthrough built around your priorities and real examples How this fits into your current workflow [Exec]’s questions and feedback Next steps if there’s a fit

Anything specific you want us to make sure we hit live, especially for [Exec] since they’re coming in fresh?

[Name]

Stage 04: The Demo

By the end of this call you need to know two things. Can they buy, and when. Everything is built around getting those answers.

Open with confirmation

Pull up a slide with specific phrases, quotes, and numbers from your prior calls. Read them back. Then ask “What would you add?” not “Did I miss anything?” One lets them say no. The other puts the ball in their court.

If a new exec is in the room, do not move off that slide until you’ve heard from them. Whatever they add becomes the center of your demo.

Before you show anything, run the problem

Between Call 1 and Call 2 your prospect had ten other fires. They have not been thinking about you. Sixty seconds. Problem, what you do about it, who you’ve done it for. Remind them why they’re in the room. Then make the demo a conversation. Ask questions constantly. If you’re talking for more than 90 seconds straight, you’ve lost them.

Get the read

With multiple stakeholders in the room, this call gives you the clearest signal you’re going to get before a proposal. Are they willing to buy? Are they able to buy? On what timeline? If you can’t answer those three questions when you hang up, you didn’t close the call right.

And like every other call: do not leave without a calendared next step. One of the best moves you can make is reaching out before Call 2 to pre-book the feedback call. Book it before the demo even happens.

Post-demo follow-up

Same rules. 24 hours. Named asks. Real dates. Address the biggest objection in this email, not the next one.

The most powerful thing you can do in this email is use the decision-maker’s own words as the setup for your answer to their biggest concern. Quote them directly. It anchors the whole conversation in something they already said and believed.

Hi [Names],

Thanks for the time today. [New exec], great to meet you.

What we heard you’re solving for: [Restate their goals in their words. Specific. No fluff.]

Where [Your Company] fits: [Map to what they said. Keep it tight.]

On [biggest objection], [exec name], you said it well on the call: “[their exact quote].” [Two to three sentences of proof that directly answers it. Numbers. Real customers. Not pitch.]

Next steps: [Name]: [Specific action by specific date] [Name]: [Specific action by specific date]

[Name]

Stage 05: Keep the Line Open

If the deal is moving, the exec alignment doesn’t stop.

After every meaningful call, your CEO and CRO send short follow-on emails to their counterparts. Three to five sentences. No ask. Just keeping the line warm.

What this builds over time: multiple layers of champion at levels of the org your rep can’t reach alone. A signal to the buying committee that your whole organization is invested, not just the person who needs the commission. And a way to surface concerns before they become blockers.

The more layers of champion you’ve built before a deal hits procurement or legal, the harder it is for that deal to quietly disappear.

The misses that kill more deals than anything else

After reviewing a lot of tape across a lot of teams, three gates fail more than all the others combined.

No pre-call agenda, or no follow-up to inbound. The prospect fills out a form. You wait. Stop doing that. Treat inbound as the start of outreach. Get the agenda out within four hours of booking.

Pre-Call 2 agenda sent only to the champion. A senior exec joins cold. Full cohort, every time.

Follow-ups that read like transcripts. Dense, no owners, no dates, no asks. Put next steps first. Make it scannable in 30 seconds.

Run this every Monday

Against every live deal. Twenty minutes.

What stage is each deal actually in, not aspirationally, actually? Which gate is the bottleneck right now? What is the one move I’ll make this week to unblock it? Which deal needs an exec-to-exec touch this week?

I spent years consuming other people’s content to figure this out. Now I’m putting out my own. If this was useful, subscribe below. More where this came from.

Everybody says they want to grow as quickly as possible. What they do not talk about enough is how hard it is to make the choices that enable it, mainly hyper focus on a few variables that matter at the expense of everything else.

Because early on, focus feels terrifying.

It feels like you are giving up opportunity. It feels like you are leaving money on the table. It feels like you are shutting down vectors of growth before you have earned the right to. If you go all in on one vertical, one market, one geography, one wedge, and it does not work, then what?

So instead, most companies do the opposite. They spread themselves too thin across too many buyer types, too many personas, too many geographies, too many use cases. They tell themselves they are being ambitious. They tell themselves they are creating optionality. A lot of the time they are just making it harder to learn. Feedback loops slow down. The message gets muddy. The product gets pulled in too many directions. Brand compounds incrementally because nobody really knows what you stand for. It looks like motion, but it usually does not create momentum.

I have been thinking about this a lot over the last couple of weeks because I have now seen the same pattern show up three different ways. I saw it in a conversation with a close friend who runs a really successful consulting shop. I saw it at Flock when we were rolling out a new segment. And I am seeing it now at Edia as we reorganize the business around a smaller set of states.

The lesson in all three cases is the same. Most companies are not losing because they are too focused. They are losing because they are not focused enough.

A close friend of mine runs a really successful consulting shop. They work across Fortune 100 companies, nonprofits, and state and local government. On paper, that sounds great. Broad customer base. Diverse revenue. Lots of ways to grow. But as we started digging into how they actually scale growth, the issue became obvious. They had not really built a repeatable go to market motion outside of the founder selling by word of mouth.

That is not uncommon. A lot of good businesses get built that way at first. But there comes a point where you have to stop confusing founder led selling with an actual GTM engine. And as we got deeper into the business, one thing became clearer and clearer. They had a massive opportunity in one of those verticals. Better fit. Clearer pain. Better proof points. More natural momentum. A real shot to become known for something specific instead of being vaguely relevant to a bunch of different buyers.

That is where the fear kicks in.

It feels scary to go all in on a vertical, especially early. You feel like you are giving up opportunity. You feel like you are giving up vectors of growth. You start asking yourself what happens if you commit and it does not work. But what I have seen time and time again is that being very specific about what you do and who you do it for is, by far, the best way to grow. Not because it sounds good in a deck. Because it is how you actually learn fast enough to build something repeatable.

I saw this at Flock too. When we were rolling out a new segment, we could have told ourselves the aggressive move was to go broad and launch in all 50 states. Instead, we focused on five. We went really deep in places where we already had customers. That gave us the ability to test the motion where we already had some credibility. It gave us a better chance to find repeatability. It gave us customer stories. It gave us a shot to tighten the message and actually understand what was working before trying to force a national motion.

That depth mattered way more than breadth. Going deep in five states taught us more than being loosely active in fifty ever would have. It let us build around real signal instead of fake scale. It let us create proof before trying to create reach. That is the part a lot of teams miss. Winning in one market is not just about the revenue from that market. It is about the learning. It is about the references. It is about understanding why customers buy, what stories resonate, what objections keep coming up, and what actually feels repeatable.

I am seeing the same thing now at Edia. We are underway with reorganizing the business around the top 10 states we are most keenly focused on. That is not because the other states do not matter. It is because especially in SLED and gov tech, one of the best ways to get a customer in a state is by already having a customer in that state.

These markets are more local than a lot of people want to admit. Trust compounds geographically. References matter more. Familiarity matters more. A district or agency does not just want to know that somebody somewhere uses you. They want to know who near them uses you. They want to know who took the risk first. They want proof that feels close enough to matter. In these markets, density matters. Focus is what creates density.

This is why I keep coming back to the same point. Most companies do not struggle because they are too focused. They struggle because they try to do too much before they have earned the right to expand. They want the map of a broad business before they have actually won somewhere specific. They want more markets, more products, more personas, more geographies, when what they really need is more signal. More repetition. More proof. More understanding of where they actually create value.

There are plenty of examples of this outside my own experience too. Veeva is a good one. They did not try to be generic enterprise software for everybody. They went deep in life sciences and stayed there long enough for that focus itself to become part of the advantage. The company still describes itself as the industry cloud for life sciences. That kind of clarity matters. It sharpens the product, the message, the customer base, and ultimately the moat.

That is also why focus feels so uncomfortable. Saying no always feels like loss in the moment. Every opportunity you walk away from feels like revenue left on the table. Every market you do not enter feels like a missed shot. Every persona you ignore feels like a growth vector you are giving up. But the trade is usually worth it.

Focus speeds up learning. It sharpens the message. It improves the product because you stop bending it around edge cases. It helps brand compound faster because the market can finally understand what you are actually for. And once the market understands that, growth gets a lot less random.

The hard truth is that a lot of teams hide inside breadth because breadth gives them cover. If you are chasing everything, you can always tell yourself something is kind of working somewhere. You never have to fully confront whether the pain is real, whether the message lands, whether the product actually solves the problem, or whether the motion is repeatable. Narrowing strips all that away. It forces honesty. That is what makes it hard. It is also what makes it valuable.

So yes, going narrow feels terrifying. It feels like you are betting too much on too small a slice of the market. But over and over, what I have seen is that the teams that get painfully specific are the ones that actually create real momentum. They learn faster. They build conviction faster. They get references faster. They become known faster. They earn the right to expand because they first proved they could win.

Most companies are not losing because they are too focused. They are losing because they are not focused enough.

Go smaller than you want to. Stay there longer than feels comfortable. Get known somewhere specific. Then expand from strength.

The two sales metrics I would watch closest as a VP of Sales, CRO, or early-stage CEO are rep productivity and rep capacity.

First, rep productivity. What percent of your reps are actually hitting quota?

If one rep is carrying the number and everyone else is struggling, that is usually not a sales execution story. That is a GTM story. It usually points to issues in territory, pricing, positioning, enablement, ramp, or management. One great rep can make a bad system look better than it is.

Second, rep capacity. How much quota have you deployed relative to the revenue target?

This one is easier to solve mechanically because you can hire into it. That is exactly why founders often overreact to it too early. They see a gap, hire more reps, and end up scaling a motion that is still broken.

Productivity has to come first.

Personally, I want to see at least 50% of AEs hitting quota for two consecutive quarters before I push hard on adding capacity. Once you have repeatability, capacity starts to matter a lot more. That is when missed hiring timelines or unexpected attrition can become the constraint on growth.

A lot of companies get this backward. They add heads before they have a system. Then they wonder why growth stalls.

You need both productivity and capacity to scale. But they do not matter equally at every stage. First, prove the motion works across the team. Then add the capacity to go faster.

I built a rep capacity model for early-stage founders and sales leaders. Share or comment if you want a copy.

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I still remember getting the call in my home office.

“You’re being promoted to Vice President. You’ll make $xxx, xxx a year. We’re so excited for you.”

I should have felt excitement. Or relief. Or something.

But I didn’t.

I felt emptiness.

It was almost an out-of-body experience, like I was hovering above myself, listening to someone else’s life being announced back to him.

And underneath the numbness, there was something even harder to admit:

terror.

I had worked hard to get there. I knew how to do the job. I knew how to perform. I knew how to keep pushing. I knew how to make people believe in me.

But there was also a deeper part of me that did not want this life.

That was hoping someone else would make the decision for me to reclaim my life. Quietly hoping they would close the door so I would not have to be the one to walk away.

But the doors never closed. They kept opening.

The promotions came.
The money went up.
The titles got better.
The reasons to keep going kept stacking up.

And the gap between who I was and who I was becoming kept getting wider.

When I hung up the phone, I lay on my back and stared at the ceiling.

That has become a familiar posture for me over the last few years.

Staring.
Numb.
Too exhausted to keep going, but too scared to stop.

For a long time, I ignored that quiet part of me asking for something different.

I buried it under ambition.
Under optimization.
Under performance.
Under the next plan, the next job, the next title, the next comp package, the next story about why this next move would finally make everything feel right.

I told myself the next opportunity would fix it.
That if I chose better, performed better, optimized harder, I would finally arrive somewhere that felt like peace.

But nothing changed.

The house changed.
The comp changed.
The title changed.

The emptiness remained.

The most confusing part was that nothing was outwardly wrong.

I was succeeding.
People respected me.
More doors were opening, not fewer.

That made it harder to admit that something inside me was dying, but I’m losing the energy to keep lying.

Not because I had some epiphany. That would be too clean.

I’m just too tired to keep doing this the same way.

I think the most painful truth is not that I built a successful career. It’s that I used my career to avoid myself.

I used it to stay distracted.
To stay in motion.
To avoid the harder questions waiting underneath all of it.

Questions like:

What if I’m living someone else’s life?

What if achievement has become my way of hiding from myself?

What if all this striving has been less about desire and more about fear?

On paper, things kept working. In reality, I was losing myself.

It is terrifying to wake up in a life you built with your own hands, only to find it unrecognizable.

And for some reason, I can’t ignore it as easily as I used to.

That may be the hardest part.

When your identity is built on being competent, ambitious, high-performing, and always moving forward, even a small crack can feel like your whole world is collapsing.

I don’t fully know what’s on the other side of this.

I just know that something deep in me is asking me to stop abandoning myself.

To stop using achievement to numb out.
To stop confusing momentum with alignment.
To stop waiting for a closed door to make the decision for me.

For the first time in my life, I am trying to sit with the pain instead of immediately turning it into a plan.

That doesn’t feel brave.
It feels disorienting.
It feels unstable.
It feels like risking the identity that has carried me for a very long time.

But it also feels more honest than anything I’ve done in years.

And for now,
that honesty is enough.

with gratitude,

Ben

PS: thanks to , someone I’ve never met, who gave me the courage to write from a place of truth.

I’ve spent my career inside high-growth GTM orgs. Some were successful (Flock $7.5B), others weren’t. This newsletter is where I write about what I learned, and what it cost me.

Subscribe now to get 5+ templates (Ideal rep profile, TAM analysis, etc) you can use today to build your GTM org.

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I’ve hired over 60 account executives in the last three years.

I’ve failed a lot. Bad hires that cost us quarters. Candidates I let slip because I wasn’t paying attention. Roles I filled with the wrong profile because I hadn’t done the work up front.

I’ve also gotten it right.

At Flock Safety ($7.5B valuation), we built a new segment from 0 to 50 reps in 7 quarters.

At Edia, we hired 7 AEs in 10 weeks at a Series A edtech company (a vertical most AEs are not interested in) by going on offense and treating recruiting the way the best AEs treat pipeline generation.

I’m writing this in response to Jake Cronin’s (CEO of Siro) post about needing to hire 5 AEs in 5 weeks. I’ve structured the specifics around Siro so you can see the framework applied to a real company in real-time. But everything here applies to your org. Adapt freely.

If you’re a founder hiring your first sales team, or a VP trying to scale from 3 AEs to 15, this is for you.

The thing I wish I’d known earlier

When I took my first sales leadership role, I thought the most important thing was helping reps close deals.

I was wrong.

The more experience I gain, and the more AI removes friction from operational work, the more I believe that the single most important activity of a sales leader is recruiting elite talent.

Recruiting is pipeline generation for a sales leader.

That reframe changed how I operate. Our team blocks time for it. We track it weekly. We don’t wait until a seat opens. We’re always building a bench.

The best hire I ever made came from an InMail I sent when I had no open roles. Six months later, I had a seat and they were the first call I made.

Poor recruiting is the most common reason sales leaders fail. I’ve watched it happen. I’ve been the reason it happened.

The uncomfortable part: only the hiring manager can do this well. Not your recruiter. Not HR. Not a third-party search firm. You.

Delegate this and you’re outsourcing the most important piece of building a durable organization.

Align on the plan

Most leaders start recruiting before answering the foundational questions. I’ve made this mistake. You source 50 candidates, get to final rounds, and realize your comp structure is wrong or your quota is too aggressive to attract the person you actually need.

I am not going to go deep on this in this essay, but know this, without a clear 36 month rolling ARR / Revenue target it’s impossible to build a clear hiring roadmap.

(If a full post on capacity planning would be helpful, let me know in the comments below)

Do this work first.

• Align on your 24-month target. What does the number need to be? Work backward from there.

• Align on segmentation. Are you hiring Enterprise, SMB, or both? These are different profiles. Do not conflate them.

• Align on quota and OTE by segment. What’s the quota? What’s the OTE? What’s the bookings-to-OTE ratio? If you can’t answer these clearly, you’re not ready to hire.

• Align on ramp time. Enterprise ramp is typically 6-9 months before full quota. SMB might be 3-4. Model this. It matters for when you hire, not just how many.

• Build the capacity model. Now you know the number, the segment, the comp, and the ramp. Back into how many reps you need and in what sequence. Hiring 5 people at once is usually worse than hiring 2 strong people early. Sequence matters.

For this post, we’ll use the details Siro has shared publicly: 5 Enterprise AEs / $250k OTE ($125k/$125k) / NYC / 5 weeks

Step 1: Identify: Nail the ideal rep profile (IRP)

This is where most leaders fail. Not because they don’t have a profile. They do. It’s just too vague or too aspirational for the stage of company and the reality of the opportunity.

The classic mistake: searching for a unicorn without a unicorn pitch.

“I want a $2M closer who’ll relo, take a pay cut, thrive in ambiguity, and be excited about a market they’ve never sold into.” That person may exist, but they’re not leaving a cushy job with RSUs vesting every month without a really compelling reason.

You have to earn that conversation.

Here’s the IRP I built out for Siro from what I could learn from their site and job postings.

Build your Ideal Rep Profile (IRP)

How to build your list

I copy and paste my IRP components directly into Juicebox (see below) and its AI functionality auto-populates the specific filters, criteria that I want to search for. This saves HOURS of time that I would normally put into building boolean searches in LinkedIn.

Now I have a list of 500+ candidates.

The next step will be to comb through these profiles to find good matches for your outbound.

I spend 1hr a week adding new folks to my Human Capital Pipeline (below). I find doing this Friday afternoons is the best.

Do not do this during your Recruiting Pipe Gen (RPG) times. This is the prep. Prep is key to do BEFORE you start outbounding so when you sit down for your RPG block you are just executing.

Here is a super simple Human Capital Pipeline template to keep you organized if you don’t want to use Juicebox.

Step 2: Attract: Now you need to go on offense

Here’s the thing about recruiting at a Series A that no one wants to hear: The best candidates aren’t applying to your job posting. They’re not even looking.

They’re 110% of quota at a company they know and trust, their manager loves them, and their stock is vesting.

You have to go get them.

And here’s the asymmetry that most leaders don’t use: it is rare for an actual hiring manager to reach out to an AE.

Recruiters reach out all the time. Generic InMails are noise. But when the hiring manager sends a personalized note? Response rates go through the roof.

We hired 6+ AEs cold at Edia in 10 weeks, a Series A edtech company that most AEs had never heard of, by going on offense against our IRP.

I see leaders do this backwards constantly.

They lead with “are you open to new opportunities?” They ask about compensation in the first message. They disqualify before they’ve even created interest. That kills the conversation before it starts.

Subscribe and get 5 GTM templates I actually use —> hiring playbooks, rep profiles, outbound scripts, and more. Sent to your inbox immediately.

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The Hooks

You need to know your story cold before you send a single message. Here are Siro’s hooks that I built based on what I can see on their site. . Use these as a template and then paste them into your AI of choice and ask it to build the same for your company.

Hook 1: The market nobody is looking at

Gong, Chorus, every other conversation intelligence tool was built for inside sales. Zoom calls. Recorded on a laptop. The field sales rep, the one sitting at someone’s kitchen table closing a $15k home improvement deal, has been completely ignored. That’s 12 million field sales reps in the US alone. Siro is the first company to actually solve this. The TAM is massive and the competition is effectively zero in the space that matters.

Hook 2: The company momentum: $75M raised total. $50M Series B just closed in May 2025. Led by SignalFire. Backed by 01 Advisors (Dick Costolo and Adam Bain), Index Ventures, CRV. This is not a bet. This is a funded rocketship with serious institutional conviction behind it.

Hook 3: Our customers are winning: 36% higher close rates. 30% lower rep turnover. 10x faster coaching cycles. These aren’t vanity numbers. These are the metrics that make a CFO sign a PO.

Hook 4: The Servicetitan & Salesforce partnership: Siro has been embedded with the most consequential software provider in the field services industry (ServiceTitan) and just announced a product partnership with Salesforce ahead of Dreamforce. That’s the distribution. That’s credibility. In a world where software is easy to create, distribution is so key

Hook 5: The earnings opportunity: $$250k OTE at a Series B. Uncapped. If you’re a top performer at a mature company making $180k and wondering when you’re going to catch a real wave, this is the conversation worth having.

Block the time to do Recruiting Pipe Gen (RPG)

We run Pipe Gen Tuesdays at Edia. Reps spend the day outbounding on key accounts. Leaders spend at least 2 hours doing outbound on key AE prospects. Non-negotiable. Tracked weekly.

We don’t rely on TA to fill our pipeline just like our AEs don’t rely on BDRs to fill theirs.

The added benefit: your AEs watch their leaders do something hard every single week. That cultural signal is real.

The outbound message

A message from a hiring manager is 5x more likely to get responded to than a message from a recruiter. The truth is PG is hard, whether it’s for a lead or a recruit, but the rewards can be massive. If you put in the work, you will see the results.

The anatomy of a great outbound recruiting message:

1. Personalize. One sentence. Something specific. Their company, a promotion, a mutual connection, something they posted. Signals you’re not blasting a template.

2. The hook. Lead with what’s in it for them. Their career. Their earnings. The opportunity. Not your company overview.

3. The 8 Mile move. Name the objection before they raise it, then flip it. Disarm the skeptic before they dismiss you.

4. Clear CTA. Not “let me know if you’re interested.” Give them something specific. One question. One ask.

Objections & 8-mile response

Knowing your objections cold is as important as knowing your hooks. The rep who pushes back hard on the opportunity is exactly the rep you want on your team. Don’t get defensive. Meet it directly.

Outbound Templates

Two specific templates you can use today, change to fit your org or role type:

Version 1: The category play

Subject: Field sales AI just raised $50M. Nobody has cracked this yet.

[Name],

Saw your run at [Company] — [X] years closing enterprise deals with real field complexity. That background is exactly what I’m looking for.

I’m building the founding Enterprise AE team at Siro. Quick version of the story:

No one thought restaurant POS was enterprise software. Then came Toast ($24B). No one thought HVAC scheduling could scale. Then came ServiceTitan ($10B). No one thought field sales needed AI. That’s where we come in.

Siro is conversation intelligence for in-person sales. The 12 million field reps that Gong was never built for. We record, transcribe, and analyze real-world sales conversations — at the kitchen table, on the job site, in the showroom. Customers are seeing 36% higher close rates and 10x faster coaching cycles.

$50M Series B just closed. Led by SignalFire. Backed by 01 Advisors, Index Ventures, CRV. Salesforce partnership announced at Dreamforce.

I know the instinct: field sales sounds unglamorous. That’s exactly what people said about construction software before Procore. About legal tech before Harvey. The best GTM bets always look a little weird at first.

$250k OTE. NYC. Uncapped. Founding team seat.

Worth 20 minutes? Open Thursday or Friday.

Ben

Version 2

Subject: You’ve been selling into the real world. So has Siro.

[Name],

Your time at [Company] caught my eye — specifically [the tenure / the move from MM to ENT / selling into services companies]. That trajectory is rare and it’s exactly the profile I’m building around.

I’m the [title] at Siro and I’m putting together the founding Enterprise AE team in NYC.

Here’s the pitch:

Gong changed inside sales forever. Every Zoom call, every email, every digital touchpoint — captured, analyzed, coached. But the 12 million field sales reps sitting at kitchen tables closing $15k home improvement deals? They’ve been completely ignored. No conversation intelligence. No coaching at scale. No visibility for managers.

That’s the problem Siro solves. And it’s a massive one.

We just raised $50M in a Series B led by SignalFire. Customers seeing 36% higher close rates, 30% lower rep turnover.

The objection I always hear: “field sales sounds like door-knockers, not enterprise.” Fair. But the buyer isn’t the HVAC technician. It’s the VP of Sales at a company with 500 reps trying to figure out why her team closes at 22% instead of 40%. That’s an enterprise problem. That’s your deal.

$250k OTE. NYC. Uncapped. Early enough to matter.

If the timing is even slightly right — worth a quick conversation. Thursday or Friday work?

Ben

Step 3: Qualify: Nail the interview process

Five stages. Each with a clear purpose.

1. Screen Call with Recruiter/Hiring Manager

2. Topgrading - Tangibles (PG, Champion Building, Qualification ability)

3. Deep Dive: Intangibles (Drive/Grit, Intelligence, Character, Coachability)

4. Executive - 2 Cs - Culture and Commitment

5. Challenge / Presentation

Stage 1: Screen call.

Recruiter or HM. First filter. Basic fit, interest, logistics. Most importantly: keep selling. Don’t flip into full interrogation mode before you’ve established genuine interest.

Stage 2: Topgrading the Tangibles.

Three areas.

1/ Pipeline Generation. Questions to ask:

• Tell me about the composition of your book.

• How much net new versus existing?

• Where do leads come from?

• What percentage is self-sourced?

• How do you plan your week?

• What are your top three target accounts right now, and who specifically are you targeting at each?

• Why that person?

The last question is the tell.

• A vague answer (”whoever is the decision maker”) means they don’t actually run a disciplined outbound motion.

• A specific answer (”I’m targeting the VP of Curriculum because they own the ed tech budget and they just posted about struggling with student proficiency data”) means they know how to hunt.

2/ Champion Building. Questions to ask:

• Who’s the champion you’re most proud of building?

• Walk me through it.

• How did you build them?

• How did you know they were a real champion and not just a friendly coach?

• Why were they the champion?

I’m listening for specificity.

The rep who says “I built a great relationship with the principal” is not telling me the same thing as the rep who says “I knew she was a champion when she sent me the internal slide deck from their budget meeting unprompted.”

3/ Qualification. Questions to ask:

• How do you know if a deal is good or not?

• What criteria matter to you when evaluating whether to push or disqualify?

• What’s the top reason your deals go closed lost?

The best answer to that last question involves self-awareness.

Not “the competition undercut us on price.”

Something like “I waited too long to identify a real champion and ended up with a coach who couldn’t move the deal when the budget got cut.”

Stage 3: Deep Dive on Intangibles.

This is the most important stage. I take my time here.

Drive/Grit. Questions to ask:

• Tell me your story. Don’t accept a resume recitation. Push on the circumstances.

• Why did you leave that job?

• What led you to make that move? This is where motivation lives.

• What’s the hardest thing you’ve ever had to do? Not in sales, in life.

• How’d you get into sales in the first place?

I’m looking for a chip on the shoulder. Some version of needing to prove something. The reps who are running toward something are good. The reps who are running away from something are often better.

Intelligence.

Questions to ask:

• In the story they just told you, could they explain what the companies they worked for actually do, in simple terms? Not jargon. Simple.

• Can they connect facts to conclusions?

• If they did something, do they know why it worked?

• Can they articulate the insight, not just the action?

Character.

Questions to ask:

• Tell me about a deal you lost because of something you did or didn’t do. What did you learn?

• If I asked one of your teammates to describe you in three words, what would they say?

• Then: who are the top three people you work with? Would you mind if I reached out to them?

That last question is a test in itself. The rep who hesitates, that’s data. The rep who immediately gives you names and says “please do, they’ll tell you everything,” that’s also data.

Back-channel when you can, but be careful here. You don’t want to upset your candidates.

Coachability.

Questions to ask:

• What’s the most impactful piece of constructive feedback you’ve received from a manager?

• What’s an area of your sales game you know you need to improve, and what have you done about it?

Red flag: “I can’t think of any real feedback, I’ve always exceeded quota.”

Every rep has something. If they can’t name it, they’re either not self-aware or not being honest. Neither is what you want.

Stage 4: The Challenge.

• 15 minutes: walk me through your territory attack plan for our market.

• 20 minutes: role play. I’ll be the prospect.

• 10 minutes: what feedback do you have for me? What questions do you have about the role, the company, the leadership?

That last piece, the candidate’s questions, is one of my favorite signals. The rep who asks sharp, specific questions about attainment, about what success has looked like for top performers, about where the product roadmap is going, that’s someone who’s evaluating you the way you’re evaluating them. That’s who you want.

Stage 5: Executive (The Two Cs).

Culture and Commitment.

• Culture: will they thrive in high-growth, high-ambiguity? Give me an example of when you had to pivot fast because the business changed underneath you. What happened? What do you do to continuously improve your sales skills?

• Commitment: are they here for the mission or just the paycheck? Why this role, why now, where do you see yourself in three years? I want to hear genuine interest in the problem we’re solving, not just the comp.

At Edia, the mission is changing the life trajectory of every student in America. When a candidate lights up at that, when they have something real to say about education, or about being a first-gen student, or about having a teacher who changed their life, I pay attention.

Always be recruiting.

Celebrate your recruiting wins with your team the same way you celebrate closed deals. Make it a metric.

And remember: the candidate you’re talking to is evaluating you as much as you’re evaluating them.

How you show up in this process, the thoughtfulness of your outreach, the quality of the conversation, how you handle their objections, that’s the first signal they get about what it’s like to work for you.

Make it a good one.

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And if you want the Juicebox setup, the HCP template, or the capacity model — drop a comment or shoot me a note.

Fear kept me away for four years.

If you don’t try, you can’t fail. That’s what my lizard brain told me. So I didn’t try.

But something shifted last month. I can’t quite name it. I just knew it was time to start again.

Banksy once said the world belongs to people who show up. I stopped showing up here. That ends now.

So here we are.

Quick reminder: my name is Ben. We probably met through this newsletter. It’s been ~4 years since my last one. A lot has changed. Not much has changed.

I’m calling this Substack Exit Through the Comp Plan. A play on my love of Banksy, showing up unexpectedly, art as protest, and leaving a mark.

It will be musings at the intersection of high-growth GTM and living a meaningful life. The comp plan. And everything that can't be measured.

Your inbox is sacred. If that’s not your thing anymore, no hard feelings, please unsubscribe.

With gratitude,

Ben