Lenny's Written Position
Founders should not confuse people rooting for them (investors, personal connections, early supporters) with real market signal, because the earliest deals done on personal relationships do not prove the business can run on its own.
The biggest growth channel for top B2B companies is organic inbound (word of mouth), and eventually 100% of B2B businesses build a sales team regardless of their initial growth motion.
Databricks' revenue flatlined when they tried a pure zero-touch PLG motion in 2015, and their CEO now believes PLG without a sales force does not work for enterprise products.
40-60% of B2B purchase processes result in 'no decision' not because the status quo won, but because buyers could not figure out how to confidently make a decision.
A sales pitch should be structured as a setup (market insight, alternative approaches, perfect world) followed by a follow-through (differentiated value), rather than a feature walkthrough.
Your real competition in B2B sales is not other vendors but buyer indecision, because B2B buyers are more worried about messing up than missing out.
Every B2B founder should start with founder-led sales and wait until $300-500K ARR before hiring their first full-time salesperson.
Your first sales hire should be a 'hungry senior AE' who can break new ground rather than someone who excels only at repeatable processes from later-stage companies.
None of the seven strategies for finding your first 10 B2B customers scale, and that is precisely why they work: in B2B it always starts with hand-to-hand combat.
Trust is the secret weapon for winning early B2B customers; start with channels that have the most innate trust (personal network) and work outward to cold outbound.
Cold outbound works for finding early B2B customers if done creatively; Figma's Dylan Field built a custom script to find influential designers on Twitter, and Retool used filtered Crunchbase data to target operationally heavy companies.
Outbound sales signal is the cleanest data for identifying your ICP; leads from investors and friends muddy the signal because people may take meetings out of relationship obligation rather than genuine interest.
Having sales reach out to free accounts is the single biggest driver of increasing free-to-paid conversion; nearly half of free-trial companies have sales contact more than half of sign-ups.
PMs should find, pitch, and close the first 5-10 customers for their products themselves before handing off to sales.
The biggest challenge when layering PLG onto an existing sales-led company is resistance from sales teams worried about quota impact and marketing teams worried about PQLs replacing MQLs.
The primary growth engine for nearly all of today's biggest B2B products is sales, though some have a product-led or self-service element.
DoorDash's Tony Xu spent weeks pitching restaurants on food delivery technology with slow results until he reframed the pitch as 'we are selling revenue' which changed the company's trajectory.
100% of bottom-up B2B companies eventually layer on a sales team, and waiting too long to do so often leads to competitors firewalling you out of enterprise segments.
Podcast Moments
“The go-to-market is going to get turned on its head. People start evaluating products in Gemini or ChatGPT. Your website is a lot less important. Sites will change to have a high quality avatar that knows everything about your products.”
Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot) · Brian Halligan
“However you get those first 10, 15, 20 customers, be honest. If they need a sales type motion and you say 'I don't like sales, so I'm going to do a PLG motion,' you'll fail.”
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr) · Jason M Lemkin
“Almost all founders are A+ middlers. Any founder should be there by day one. And prospects love it — they get to talk to you. It's magical for early adopters.”
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr) · Jason M Lemkin
“Those first couple reps have to be people you would buy your own product from. We're looking for pirates and romantics in the early days.”
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr) · Jason M Lemkin
“You need two sales reps hitting quota before you're ready to hire a manager for them. If you hire a VP of sales before then, it's approaching 100% chance of failure.”
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr) · Jason M Lemkin
“What do you want to do your first 30 days? In B2B, if I don't hear 'I'm going to go meet customers,' I'm out.”
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr) · Jason M Lemkin
“Trust me, hire someone whose last product was harder to sell. If you hire someone from something easier, they will have none of the skills.”
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr) · Jason M Lemkin
“In sales, there's rules of eight. Eight SDRs need one manager, eight AEs need a director above them. You can build your whole org with eights.”
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr) · Jason M Lemkin
“80% of customers buy to avoid pain or reduce risk as opposed to increased upside. For enterprises, you're avoiding the risk of not making your revenue target next quarter.”
What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · Jeanne Grosser
“A lot of early stage founders get tripped up taking late stage sales advice. The founder is the product.”
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · Jen Abel
“One of the worst things someone can say is 'we're better than X product.' Better is a dangerous place. You need to be different, not better.”
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · Jen Abel
“Founder led sales is not about revenue on day one. It is about learning as fast as humanly possible.”
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · Jen Abel
“On the first call, the demo is the only card you control. Once they see it, that dreaminess is gone. Leave them wanting more.”
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · Jen Abel
“Everyone says they have a bottom of funnel problem. It's never a bottom of funnel problem. It's always qualification.”
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · Jen Abel
“40 to 50% of B2B SaaS startups have to sell some form of service before they can sell a technology.”
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · Jen Abel
“Trust is the number one currency in sales. Don't try to sell something just to prove to investors you sold something.”
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · Jen Abel
“We launched Stripe Relay back in 2014 for social commerce buy buttons. It launched to a lot of fanfare, but eventually failed. The learning was we hadn't gone deep enough into the market dynamics. We hadn't done enough user research on whether people really wanted this.”
Growth tactics from OpenAI and Stripe’s first marketer | Krithika Shankarraman · Krithika Shankarraman
“We hired our VP of sales over a year ago. The go-to-market team is now over 80 people. Technical founders sometimes think sales is negative. I think enterprise sales is really valuable.”
Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO) · Varun Mohan
“When you're talking to someone and explaining something, there's usually a moment where their eyes light up because they are genuinely interested. Make note of those moments because their face can't lie. Cut out all the parts that make people go dead in the eyes.”
Become a better communicator: Specific frameworks to improve your clarity, influence, and impact | Wes Kao (coach, entrepreneur, advisor) · Wes Kao
“The founders had a principle: always sell to the CISO, never to the security engineer. Because if you sell to the engineer, you get a pilot. If you sell to the CISO, you get a deployment.”
Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy) · Raaz Herzberg
“The PM job can become a little too internal, influencing my stakeholders and getting alignment and all these things. But if you can't sell or support your own product, I don't trust you to build the product.”
Unorthodox PM wisdom: Automating user insights, unselling job candidates, logging every decision, more | Kevin Yien (Stripe, Square, Mutiny) · Kevin Yien
“Most people are missing the most important slide of their presentation is the first slide. This slide is going to be presented for the longest period of time. This is the place that you're going to put your strongest point.”
Lessons from a two-time unicorn builder, 50-time startup advisor, and 20-time company board member | Uri Levine (co-founder of Waze) · Uri Levine
“And that indecision stems from their fear of failure. Dialing up the FOMO backfires 87% of the time. They're not afraid of missing out, they're afraid of messing up.”
The surprising truth about what closes deals: Insights from 2.5m sales conversations | Matt Dixon (author of The Challenger Sale and The JOLT Effect) · Matt Dixon
“JOLT them forward. The first thing is we've got to judge their level of indecision. The second thing is we've got to offer a recommendation. The third thing is we've got to get them to start trusting us and we call it limit the exploration, and the T is we've got to de-risk the deal.”
The surprising truth about what closes deals: Insights from 2.5m sales conversations | Matt Dixon (author of The Challenger Sale and The JOLT Effect) · Matt Dixon
“The Challenger Sale insight is that the best salespeople don't just build relationships. They actually push back on customers. They teach them something new about their business that reframes how they think about the problem.”
The surprising truth about what closes deals: Insights from 2.5m sales conversations | Matt Dixon (author of The Challenger Sale and The JOLT Effect) · Matt Dixon
“The best way to de-risk a deal is to take risk off the table proactively. Don't wait for the customer to ask. Offer a pilot, offer a guarantee, offer an easy way out. That confidence actually makes them more likely to buy.”
The surprising truth about what closes deals: Insights from 2.5m sales conversations | Matt Dixon (author of The Challenger Sale and The JOLT Effect) · Matt Dixon
“When we looked at the highest performing reps, one thing stood out. They were very good at limiting the exploration. Too many choices paralyze people. The best reps would say, 'Based on what you've told me, here's what I'd recommend,' and just give them one option.”
The surprising truth about what closes deals: Insights from 2.5m sales conversations | Matt Dixon (author of The Challenger Sale and The JOLT Effect) · Matt Dixon
Cutting Room Floor
Guest insights on this topic that Lenny hasn't (yet) written about in his newsletters. Potential material for future posts.
“Those first couple reps have to be people you would buy your own product from. We're looking for pirates and romantics in the early days.”
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr) · Jason M Lemkin
“Trust me, hire someone whose last product was harder to sell. If you hire someone from something easier, they will have none of the skills.”
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr) · Jason M Lemkin
“In sales, there's rules of eight. Eight SDRs need one manager, eight AEs need a director above them. You can build your whole org with eights.”
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr) · Jason M Lemkin
“80% of customers buy to avoid pain or reduce risk as opposed to increased upside. For enterprises, you're avoiding the risk of not making your revenue target next quarter.”
What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · Jeanne Grosser
“One of the worst things someone can say is 'we're better than X product.' Better is a dangerous place. You need to be different, not better.”
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · Jen Abel
“Trust is the number one currency in sales. Don't try to sell something just to prove to investors you sold something.”
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · Jen Abel
“We launched Stripe Relay back in 2014 for social commerce buy buttons. It launched to a lot of fanfare, but eventually failed. The learning was we hadn't gone deep enough into the market dynamics. We hadn't done enough user research on whether people really wanted this.”
Growth tactics from OpenAI and Stripe’s first marketer | Krithika Shankarraman · Krithika Shankarraman
“We hired our VP of sales over a year ago. The go-to-market team is now over 80 people. Technical founders sometimes think sales is negative. I think enterprise sales is really valuable.”
Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO) · Varun Mohan
“When you're talking to someone and explaining something, there's usually a moment where their eyes light up because they are genuinely interested. Make note of those moments because their face can't lie. Cut out all the parts that make people go dead in the eyes.”
Become a better communicator: Specific frameworks to improve your clarity, influence, and impact | Wes Kao (coach, entrepreneur, advisor) · Wes Kao
“The founders had a principle: always sell to the CISO, never to the security engineer. Because if you sell to the engineer, you get a pilot. If you sell to the CISO, you get a deployment.”
Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy) · Raaz Herzberg
“Most people are missing the most important slide of their presentation is the first slide. This slide is going to be presented for the longest period of time. This is the place that you're going to put your strongest point.”
Lessons from a two-time unicorn builder, 50-time startup advisor, and 20-time company board member | Uri Levine (co-founder of Waze) · Uri Levine
“And that indecision stems from their fear of failure. Dialing up the FOMO backfires 87% of the time. They're not afraid of missing out, they're afraid of messing up.”
The surprising truth about what closes deals: Insights from 2.5m sales conversations | Matt Dixon (author of The Challenger Sale and The JOLT Effect) · Matt Dixon
“JOLT them forward. The first thing is we've got to judge their level of indecision. The second thing is we've got to offer a recommendation. The third thing is we've got to get them to start trusting us and we call it limit the exploration, and the T is we've got to de-risk the deal.”
The surprising truth about what closes deals: Insights from 2.5m sales conversations | Matt Dixon (author of The Challenger Sale and The JOLT Effect) · Matt Dixon
“The Challenger Sale insight is that the best salespeople don't just build relationships. They actually push back on customers. They teach them something new about their business that reframes how they think about the problem.”
The surprising truth about what closes deals: Insights from 2.5m sales conversations | Matt Dixon (author of The Challenger Sale and The JOLT Effect) · Matt Dixon
“When we looked at the highest performing reps, one thing stood out. They were very good at limiting the exploration. Too many choices paralyze people. The best reps would say, 'Based on what you've told me, here's what I'd recommend,' and just give them one option.”
The surprising truth about what closes deals: Insights from 2.5m sales conversations | Matt Dixon (author of The Challenger Sale and The JOLT Effect) · Matt Dixon