Founder @MSP Consulting | Enterprise Sales for Startups | $2M => $10M ARR

Most founders aren't bad at sales. They're just alternating between winging it and following playbooks that were built for companies 10x their size. I never planned on a career in sales (I studied International Relations). But when I ended up in sales I realized it was the same skill...understand a situation deeply, then tell a persuasive story around it. The further I got in my career the more I kept seeing the same thing. Companies hit the same walls at the same stages and made the same (avoidable) mistakes. And most of the advice for founders was either way too complicated or built for someone else's business. I didn't want to manage bigger teams at bigger companies. I wanted to help founders solve sales problems before they burned 12-18 months figuring it out the hard way. I work with B2B SaaS founders between $1-$10M in revenue who are building enterprise and mid-market sales orgs. I help them cut through the noise, find the highest-leverage fix, and build something repeatable (without overcomplicating it).  No generic advice or playbooks borrowed from $500M companies. Just proven frameworks built for your stage. If you're a founder building enterprise sales or leading a team that needs to get unstuck, I can help. I'm also open to podcasts, speaking, and brand partnerships. I work with brands whose products I use and love and that aligne with my values. Book a strategy session below. You'll leave with clarity on the biggest thing slowing you down right now, and how to fix it. 

Monica Stewart

Building things with soul. ex-McKinsey, Harvard Business School, and B2B founder ($0-$4M ARR in 2 years).

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I help founders navigate the early, messy, founder-led sales stage, 0->$1M ARR. Follow my newsletter for thinking on product-market fit you won't find elsewhere: howtogrow.substack.com

When you're ready, join my PMF Camp, where I'll personally review your sales calls, decks, outreach, and give you a ton of examples and templates. Learn more at robsnyder.org

Rob Snyder

Fun news - I'm joining Grix VC as an Operating Partner! 

Grix is a rare kind of fund. They are intentionally small. Just two people -  Randall Lloyd and Haoran J.. They stay small so they can make just a few early-stage investments per year, then get extremely involved helping the founders find product-market fit and scale. I love this. It is a craft business, and they are great people.

I am plugging in to help Grix's startups find product-market fit. Everything from fixing their sales calls and demos to helping them make the tough decisions on beachhead markets, product direction, etc.

(If you want my help with your sales calls, demos, and overall product-market fit, but you are not in Grix's portfolio, never fear - I can still help, just have a little less bandwidth!)

And no, I am not investing, but if you are raising a pre-seed or seed, feel free to reach out, I can forward your info along.

Founder + Advisor | Fellow @ Harvard Innovation Labs | Founder @ Restack | Operating Partner @ Grix VC | HBS, ex-McK

Now that AI is making it easier to build software, can we admit that the hard part of startups was always finding demand and figuring out distribution?

And I think AI makes the hard parts of startups even harder in two specific ways.

1. It's easier than ever to avoid selling / working with customers because it *feels* like you're making way more progress for every minute spent building.

2. It's easy to offload the difficult and painful thinking about PMF to AI. I have tried in about 58,000 different ways; AI doesn't know how PMF works because *we humans don't really understand it very well*. (Worse, it gives you the illusion of knowledge and progress... which makes it easier to think you're further along than you are)

Startups always required founders to be super disciplined and focused on demand, distribution, and product-market fit. This wasn't easy a decade ago, jeez is it not getting any easier.

Fellow @ Harvard Innovation Labs | Founder @ Reframe + Restack | Harvard Business School, ex-McKinsey

This might sound exaggerated, but I can assure you that it is not: In the average sales call recording I watch, the VAST majority of sentences the founder says about their product are *counterproductive.*

Counterproductive = they *dissuade* the customer from buying.

The four most common patterns I see:

1. The "totally irrelevant info" bucket: Things like "why we built this" or "our perspective on how X should work" - their eyes glaze over. 

2. The "too much tech" bucket: We talk through forty features and modules and the architecture of our product. This doesn't meet them where they are, so they tune out.

3. The "wrong angle" bucket: The buyer is trying to accomplish X, and we focus on Y. Even though our product fits X, they come away thinking it doesn't.

4. The "too big" bucket: We think we need to pitch a big product, because the bigger we pitch, the more valuable it seems. They are still just trying to accomplish X, and just want the best-fit thing that helps them accomplish X.

Interestingly - this is not just for founders, I've even seen this watching sales calls from sales reps.

The game is finding the fewest possible words and concepts that fit what they are looking for, that cause them to "get it".

My framework for this is:

It sounds like you are trying to accomplish X right now because Y, but your existing methods aren't good enough because of Z.

We offer an ABC (product category) that helps you accomplish X without Z.

Does that sound like what you're looking for?

All of 15 seconds. Then you might double click from there - but again, it's another 15-20 seconds.

The more info you give, the more they need to process, and the less likely it is to "fit" what they're trying to accomplish. Each extra word convinces them that this isn't a fit.

"Sales is a lot of rejection" is a common belief that, I think, is wrong.

If you experience the feeling of rejection, you're probably thinking about sales backwards. (And you're likely to avoid sales, because rejection isn't fun!)

How most people think about sales:
-> It is about me selling you my product
-> If you say no, you're saying no to me and/or my product

This sounds right, until you ask yourself: Why do people buy things?

They don't buy things because they like us.
They don't buy things because we convince them to buy things.

They buy things when they are trying to accomplish something, and the current methods/tools available to them are insufficient.

So when you talk to someone who doesn't buy from you, they aren't rejecting you or your product.

They are just telling you something about the state of their priorities, and where they do or don't believe they need outside help.

(And experiencing this as "rejection" is, honestly, quite strange.)

I promise that if you embrace this, you will be much better at sales, you'll avoid sales a lot less, and you'll actually build a better product.

I've seen founders spend days in a funk after a particularly uncomfortable sales call.

"It seemed like they were a perfect fit... then they just said 'no'... why?!" 

"They really hated our product idea..."

"They just totally didn't get it... I feel like I totally messed up."

I've had worse sales calls than you (I promise) and I've felt this too. It's brutal, and calls like this make you question whether (1) you know anything at all, and (2) if you're building anything that actually matters.

You can't stay in a slump, though. Here's what I've found helps:

1 - Treat bad calls as INTERESTING. This is your chance to learn something fascinating about the world, about the market, about your customer. Re-watch the call, as painful as it might be, and play "detective" - what *really* happened?

When you reframe it to be something interesting, it makes you focus less on the gut-wrenchingness of it.

2 - Do more sales calls. You're going to want to pause selling to "figure it out" or "build more" or whatever, so this doesn't happen again. Don't fall into that trap. Keep selling while you improve things. Stay on the horse.

Here's a very simple way to start your sales calls, that I wish someone had taught me years ago:

Step 1: Learn why they're there

"Thanks so much for taking the call today - I'm sure you get a bunch of people reaching out to you, why'd you decide to take this call today? What were you hoping to get out of it?"

(For outbound - inbound is slightly different.)

Step 2: Set agenda

"Awesome - that's exactly what I thought we'd cover today. {X, Y, Z} - does that work for you?"

Step 3: Earn the right to ask discovery questions

"Great - before we get there, mind if I ask you a few questions so I have full context?

Steps 1-3 helps you earn the right to ask discovery questions, so the sales calls does not feel like an interrogation.

Step 4: Ask a few discovery questions

(These evolve based on your situation - I have found that you can sometimes predict a purchase with ~90% accuracy based on responses to a few discovery questions)

Try it, report back

I gave two talks at Harvard this week. The topic: The way we are taught to approach startups *causes* founders to fail.

The typical approach is taught as:
-> Do discovery interviews and customer research
-> Find big problems and pain points
-> Get design partners

All of this sounds totally plausible. And it causes founders to feel productive while spending years building things nobody wants. (I did this!)

Why doesn't this stuff work?

Discovery interviews -> A way to not really learn anything, but feel like you learned something. How do you know if what you've 'learned' is true?

Big problems and pain points -> Things that sound like they should lead to purchases, but rarely do. How many pain points do we have in daily life that don't lead to purchases?

Design partners -> We think they're a real customer, they're LARPing as Steve Jobs. 

The result is basically always a logically coherent concept, even a functional product with happy users, that sounds really impressive... *yet would be weird if it actually worked as a business in the real world.*

Nobody wants this to happen, obviously. But it is the default outcome of the current ways of teaching entrepreneurship.

Instead, I believe we need to teach:
-> Sell from day 1
-> If you don't know what to sell, don't do interviews... get firsthand experience
-> Focus on the buyer's priorities, not pain points & problems

Sell from day 1 -> Selling is reality serum. Most methodologies avoid sales or delay it, mistakenly thinking sales is about persuasion. 

Firsthand exposure vs. interviews -> Go do the buyer's job with them to figure out what they need. Or serve them as a consultant / agency. Anything less and it would be weird if you built something they wanted.

Priorities vs. pain points & problems -> If it's their top priority right now and they don't have a good way to get that priority done, they will rip the product out of our hands. If not, it would be weird if they bought it.

These things are simple to say, and very hard to do. Perhaps the complication is a function of us avoiding the simple, difficult things???

The sales call is where every aspect of your startup's product-market fit gets tested. And you get immediate feedback on if it's working or not, and *how well it's working.* Sales calls are a goldmine.

For every single startup I've built/advised - especially the fastest-growing ones - the big unlock came down to understanding what was happening in their sales calls.

Here's what I look for: Is this a product-market fit problem, or a sales problem?

1 - PMF problems are, generally:

DEMAND -> What is this potential customer trying to achieve, if anything?

SUPPLY-FIT -> Does our product actually fit their demand?

These are existential problems, and ones that basically everyone misdiagnoses when they look at their own sales calls.

2 - There are a variety of sales problems. The most common are:

- Did we describe and demo our product in a way that fit what the prospect needed, with the fewest possible extraneous words?

- Did we even ask what the prospect needed?

- Did we misinterpret what the customer said?

- Did we use time wisely?

In any particular sales call, you will see a *lot* of things that are not quite right. The question is - what is the highest-leverage change? 

In my experience, it mostly comes down to the product-market fit pieces. They cover a lot of sales sins. (But you still need to get the sales pieces roughly right.)

The difference is nonlinear. Does a customer rip the product out of your hands, or do you have to push, follow up, etc?

come hang with us next week! I have been building a model of the physics of startups, and am currently hard at work pulling everything I've learned into a new presentation that will help you figure out who *wants* to buy right now, and how to sell to them, etc. this will be the first time I'll be sharing it publicly...

Hey Boston founders and startup operators! I'm hosting Rob Snyder for a workshop on Mar 5 on how to nail early stage sales.

Rob has helped a ton of startups figure out how to use sales to find PMF. Out of all the startup advice out there, I've found his to be the most immediately actionable.

Join us if you're free on Mar 5!

https://luma.com/6mys18li

Open article: Founder-led Sales Workshop with Rob Snyder: How to Find Real Customer Demand · Luma by luma.com

Founder-led Sales Workshop with Rob Snyder: How to Find Real Customer Demand · Luma

There is product-market fit, and then there is Dunkin' Donuts Product-Market Fit.

A Dunkin' franchisee once explained it to me:

"When someone gets your order wrong at any other coffee shop, you grumble about it and never go back."

"When someone gets your order wrong at Dunkin, you tell them they better get it right when you come back tomorrow."

If you want to see Dunkin' Donuts Product-Market Fit in action, just look at your conversation history with ChatGPT/Claude

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