Lenny's Written Position
Traditional B2B growth channels (inbound, outbound, product virality, events, lifecycle emails) are becoming less effective because AI has made it easy for everyone to produce content and flood channels.
Ecosystem -- leveraging partners, creators, communities, and integrations who already have trust with your audience -- is emerging as the most important growth channel for B2B startups.
A well-designed ecosystem strategy makes every other growth channel more effective by serving as both a distribution path and a source of content.
Every ecosystem partnership must be a win-win-win for you, the partner, and the prospect -- never just one or two out of three.
When starting an ecosystem strategy, pick one partner program that fits your product and audience and prove it works before expanding, rather than launching every kind of partnership at once.
Individual people (employees, customers, partners) perform eight times better than brand accounts on LinkedIn for content engagement.
Invented names like Pentium actually take less money to build into brands than existing words because they signal 'new and innovative' and generate more attention due to being unexpected.
Effective naming requires building for trust, communicating an original idea rather than describing what the company does, and making the name accessible and easy to process.
Products click with customers when they make a simple, compelling promise that combines a clear target customer, their problem, a differentiated approach, and why it beats competitors.
Bundling is a powerful distribution strategy but can only get you so far before well-crafted alternatives eat your lunch, as seen with Jira, Microsoft Teams, and Google Slides facing insurgent competitors.
Web conversion flows can boost subscriber LTV by 30% to 50% by avoiding app store fees and reducing involuntary churn from payment failures.
Internal linking is the highest-ROI quick win for SEO, yet more than 90% of websites are not utilizing it effectively.
Editorial SEO with manually written content has become more effective at driving traffic than programmatic SEO and is broadly underappreciated.
AI is useful for content workflow steps like extracting structure, identifying topics, and keyword research, but should not be used for the actual writing because factual accuracy cannot be guaranteed.
A page's proximity to a high-authority crawl point directly influences its share of link equity, so you want the shortest path from a crawl point to every important page.
59% of tech companies bundle AI features into existing packages rather than charging separately, making it the predominant monetization strategy.
If over 70% of users are likely to use an AI feature, it should be bundled into a standard package; below 70%, consider offering it as an add-on.
Per-user monthly fee remains the preferred pricing structure for AI features across nearly all 44 companies reviewed, prioritizing adoption simplicity over usage-based pricing.
Intercom's pay-per-resolution model for its AI bot Fin is one of the only examples of true pricing model innovation among major tech companies monetizing AI.
Branding AI-powered products as 'AI-powered' increases initial engagement and helps users understand feature capabilities, contrary to the conventional wisdom that users don't care how something is built.
Out-of-home billboard campaigns can deliver a 25%+ uplift in branded search traffic during the campaign and sustain a 10-15% uplift after billboards come down.
Effective out-of-home advertising requires either a lot of placements, an extremely resonant message that goes viral, or a mix of both to achieve recall through frequency and resonance.
Billboard campaigns should not exceed 20% of your marketing budget and work best as brand awareness amplifiers rather than direct demand generation.
A Highway 101 billboard in San Francisco costs about $20,000 minimum per month, with high-profile locations running $50K-$80K, delivering 400,000 to 1 million impressions per week.
Only 20-30% of signups actually matter in most products; hyperfocusing on the segment driving revenue rather than growing overall signup volume can drive non-linear business growth.
Startups that do well on Product Hunt invest 50 to 120 hours preparing for launch, and most founders launch too late; launching early and often is recommended to get market signal.
Product Hunt's algorithm favors steady engagement throughout the day rather than a single spike, making time-zone strategy and staggered outreach critical for ranking well.
A valuable long-tail effect of launching on Product Hunt is SEO benefit from a high-authority backlink, which can make a big difference for brand-new startups that have not yet focused on SEO.
Price is perception: changing how a product is described or positioned can change willingness to pay without changing the product itself, as demonstrated by pasta described as 'sauceable' commanding 80% higher prices.
Your initial target audience should be almost comically narrow with at least three narrowing characteristics, because focus enables solving one problem better than anyone, and narrow audiences are easier to reach and convert.
An ICP must describe a single market segment where the value of solving the problem and the way to reach them are roughly the same; allowing your ICP to fray across use cases confuses every downstream decision.
True switching costs include politics, emotions, career ambitions, competing priorities, and sheer laziness far beyond the time and money to install a new solution, which means old and clunky products can be much more durable than they appear.
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.
B2B founders should charge sooner and more than they think; founders are biased to undervalue their product, and early revenue provides freedom and discipline.
A practical pricing strategy for early B2B startups is to keep doubling prices until customers push back, then revisit pricing every six to twelve months.
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.
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.
Every successful B2B startup landed on at least three attributes to describe their ICP, and founders should aim to get super-specific and almost comically narrow with their initial ICP definition.
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.
Four signs you are converging on the right ICP are: a significant increase in conversion rate, a significant increase in enthusiasm, a stronger desire from prospects to take action now, and 'the nod' when you describe the pain.
Miro's AMPED structure (Analytics, Marketing, Product, Engineering, Design) brings all required functions into product teams from the start, resulting in more effective product development.
Standout PLG products disproportionately attract users through organic search/SEO (40% of new users) and product virality (16% of new users).
Building free sidecar products specifically designed to attract users through SEO is one of the most effective product-led marketing strategies.
The most durable growth inflections come from doubling down on a company's primary growth engine like SEO or virality rather than from one-off events.
Product-led activation should be product-led, not product-only, using a multi-channel approach including lifecycle marketing, human assistance, documentation, and forums alongside product onboarding.
True virality is mostly a myth; what we call viral growth is almost always driven by one-to-many broadcasts from people with large audiences rather than many-to-many friend-to-friend spread.
To sustain growth, you need both mechanisms of virality (word of mouth, invites, referrals) and a strategy of ongoing one-to-many broadcasts (PR, influencers, TV) to keep reigniting spread.
Building a startup in stealth mode is always a mistake because it inhibits frequent market signal and greatly increases time to product-market fit.
The Racecar Growth Framework identifies five components of startup growth: growth engine, kickstarts, turbo boosts, lubricants, and mid-stage accelerants.
There are only four common growth engines: SEO, paid ads, sales, and virality, and the growth engine is the most important component because it is the only one that can be self-sustaining.
The GACCS framework (Goals, Audience, Creative, Channels, Stakeholders) is a marketing brief that keeps teams from doing busywork and drives cross-team alignment before work begins.
Much marketing work misses the mark because of six common failures: no goal, no prioritization, created for no one, work that does not stand out, no distribution plan, and experts excluded from the process.
Distribution is just as important as, if not more important than, what you are creating in marketing; if no one will see it, all the time spent making it is wasted.
Channel partnerships and geographic expansion are two mid-stage growth accelerants that are rarely useful in early stages but can significantly accelerate growth when used effectively at the right moment.
Channel partnerships are game-changing when they work but normally go nowhere or take far too long to make a dent; founders should treat them like any high-risk/high-reward opportunity.
There are four strategies for crafting a remarkable hook: identify what is unique about your product versus alternatives, listen to how your most obsessed users describe it, determine what job your product does for people, and find what about your product grabs attention.
If your pitch is not resonating, one of three things is happening: your pitch is bad, you are pitching the wrong people, or your product is not something people want.
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.
When deciding who to target early on, the target customer definition must be almost comically narrow, aiming for three very specific characteristics of your ideal early adopter.
Udemy purposely had instructors set prices very high at $199 then discounted to $10 because high prices signal quality and trust to students while the low actual price drives conversion.
Companies should go with a trial instead of freemium only if their product requires significant hand-holding, has complex integration needs, or has a high price point.
There are seven common ways to differentiate a product: be cheapest, highest quality, most convenient, safest, proprietary, feel-good to buy, or focused on a niche underserved market.
A product's first atomic network is probably smaller and more specific than expected, often on the order of hundreds of people at a specific moment in time rather than a city or segment.
A growth model consists of growth levers (acquisition, retention, monetization) and growth motions (product-led, sales-led, marketing-led), and the unique combination creates a defensible growth strategy.
A wedge is a strategy to win a large market by initially capturing a tiny part of a larger market or a large part of a small adjacent market, then expanding from that foothold.
Positioning defines how your product is a leader at delivering something that a well-defined set of customers cares a lot about, and a shift in positioning can mean the difference between success and failure.
The five components of positioning must be evaluated in a specific order: competitive alternatives, then differentiated capabilities, then value, then target customers, then market category.
The key to generating buzz at launch is doing something remarkable -- literally worth remarking about -- because no one cares about your new product and everyone's time is already allocated.
Podcast Moments
“Don't delegate the storytelling. The story is not a marketing exercise after you built the product. The story is why you build the product. If you have seven or eight layers between you and the front line, you can't play the telephone game. Always own telling the story yourself.”
Jeetu Patel · Jeetu Patel
“The six things you need to build a great company, in descending order: timing, market, team, product, brand, distribution. You don't have all six, you don't win. A great team in a bad market gets dragged down — the market always wins.”
Jeetu Patel · Jeetu Patel
“Permission to play means asking: is this logical for us? Do we have the route to market for mass scale distribution? If you dissipate your caloric burn across too many areas, nothing gets enough girth to drive all the way through. Be extremely selective where you expend your calories.”
Jeetu Patel · Jeetu Patel
“Starting a company has never been easier. The flip side is the number of companies formed is going to mushroom. There's so much noise and competition, it's just going to be hard to stand out and really accelerate and scale. It's never been easier to start, never been harder to scale.”
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
“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
“The market is immutable. No amount of tweeting, advertising is going to change whether the market wants your product.”
10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · Matt MacInnis
“With AI, it's just intensified because you have 10 players pursuing the same market opportunity and so your ability to actually bring the product to market has become more strategically important.”
What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · Jeanne Grosser
“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
“You're not just responsible for creating the product, but also creating the market. It's almost impossible to create a new idea in someone's head.”
Slack founder: Mental models for building products people love ft. Stewart Butterfield · Stewart Butterfield
“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
“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
“Investors gave really helpful feedback, often in the form of rejection. I would add a new page showing how big the market was.”
The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins · Melanie Perkins
“Answer Engine Optimization is how do I show up in LLMs as an answer? You need to get mentioned as many times as possible.”
The ultimate guide to AEO: How to get ChatGPT to recommend your product | Ethan Smith (Graphite) · Ethan Smith
“LLM leads are significantly more valuable. Webflow saw a 6X conversion rate difference between LLM traffic and Google Search traffic.”
The ultimate guide to AEO: How to get ChatGPT to recommend your product | Ethan Smith (Graphite) · Ethan Smith
“For Google SEO, you need domain authority. For AEO, you can get mentioned by a citation tomorrow. Early-stage companies can win quickly.”
The ultimate guide to AEO: How to get ChatGPT to recommend your product | Ethan Smith (Graphite) · Ethan Smith
“Reddit is hugely cited in LLMs. Find a thread that is part of a citation. Say who you are and give useful information. Even five comments could be great.”
The ultimate guide to AEO: How to get ChatGPT to recommend your product | Ethan Smith (Graphite) · Ethan Smith
“One out of 20 landing pages drive roughly 85% of all your traffic. If you knew the few things that would work, you could push all that money to that one page.”
The ultimate guide to AEO: How to get ChatGPT to recommend your product | Ethan Smith (Graphite) · Ethan Smith
“ChatGPT and Google Search citation overlap was around 35%. Perplexity was around 70%.”
The ultimate guide to AEO: How to get ChatGPT to recommend your product | Ethan Smith (Graphite) · Ethan Smith
“We started to see direct outreach from the Frontier Labs trying to cut out the middleman. Five months later we were working with arguably the number one lab.”
Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO) · Garrett Lord
“90% of customers who claim to have a land and expand strategy are only landing. They're not expanding because they gave their farm away.”
Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam · Madhavan Ramanujam
“Charlie Munger says, 'Fish where the fish are.' Find a small fishing hole with lots of fish and very little competition.”
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · Andrew Wilkinson
“Your brand name, nothing's going to be used more often or for longer than that name. Design will change, messaging will change, products will change, but that name is there.”
Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding) · David Placek
“Just draw a shape of a diamond on a piece of paper. On the top put the word win. How do you define winning? On the next corner, what do you have to win? On the bottom, what do you need to win? And then on the left-hand side, what do you have to say to win?”
Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding) · David Placek
“The .com or URL address has become an area code. And whether you're in 415 or 615, it doesn't really matter to people. And now with AI, SEO is going to be less important. The principle in play is let's get the right name first.”
Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding) · David Placek
“Instead, look yourself in the mirror and embrace who you are and what you could be rather than who others are. We have a super strong developer brand. Can we lean into the fact that builders love using Claude? Those builders aren't all just engineers.”
Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram) · Mike Krieger
“Everyone knew of ChatGPT, but when you clicked one zoom level further, the thing that came up was, 'I don't know what to use it for.' The work of marketing ended up becoming creating this use case epiphany where people could say, 'I had no idea ChatGPT can do that.'”
Growth tactics from OpenAI and Stripe’s first marketer | Krithika Shankarraman · Krithika Shankarraman
“A lot of marketing metrics tend to be vanity metrics about the number of clicks, views, and impressions. I think those are all bullshit numbers. What is that experience that you want your customers to come away with when they interact with your brand?”
Growth tactics from OpenAI and Stripe’s first marketer | Krithika Shankarraman · Krithika Shankarraman
“Capital-M Marketing, the marketing team, is responsible for channels and artifacts driving the funnel. But lowercase-m marketing is what do you stand for as a company? It's a whole company motion where the product team, the sales team, and everyone joins to make that happen.”
Growth tactics from OpenAI and Stripe’s first marketer | Krithika Shankarraman · Krithika Shankarraman
“The conventional wisdom for many CMOs is to be a T-shaped marketer. I think this chameleon CMO concept means modern marketing leaders have to be really good at a bunch of different things. Maybe going from T-shaped to comb-shaped is probably the right approach.”
Growth tactics from OpenAI and Stripe’s first marketer | Krithika Shankarraman · Krithika Shankarraman
“Taste is going to become a distinguishing factor in the age of AI because there's going to be so much drivel that is generated by AI. The companies that are going to distinguish themselves are the ones that show their craft and their true understanding of their product and customer.”
Growth tactics from OpenAI and Stripe’s first marketer | Krithika Shankarraman · Krithika Shankarraman
“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
“Three inflection points for great products: technology shift, consumer behavior shift, and business model shift. At least two out of three should be true for any good product. With AI, the monetization is a whole different story -- we've just barely scratched the surface.”
Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada · Aparna Chennapragada
“We actually announced five different new products simultaneously. People said we're going to confuse our current users. But we managed to transform the company in a very short amount of time. Not taking bold risks is a risk for itself.”
Inside monday.com’s transformation: radical transparency, impact over output, and their path to $1B ARR | Daniel Lereya (Chief Product and Technology Officer) · Daniel Lereya
“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
“At Captions, we're going even one step further. Why shouldn't the PM understand marketing? I actually think PMs should own all the way to marketing. Search marketing is just placing a button to your product in Google. That's almost a product surface.”
How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can't copy | Gaurav Misra (CEO and co-founder of Captions) · Gaurav Misra
“I believe that every product should be positioned around a single primary attribute. In our case, that attribute is speed. Now, lots of products try to be good at everything. That tends to be a mistake, because if you try to stand for everything, you stand for nothing.”
Superhuman's secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO) · Rahul Vohra
“I'm throwing everything against the wall. I'm looking at what's going to stick. I am looking to try to find the winning tactic and turn it into a winning strategy.”
Behind the founder: Marc Benioff · Marc Benioff
“AI very soon is going to stop being a feature the same way electricity is not a feature. What AI companies and all companies need to do is say, what's in this for the user? What promise do I want to make, a difficult promise, a remarkable promise, and then how do I keep it?”
Seth Godin's best tactics for building remarkable products, strategies, brands and more · Seth Godin
“When you choose your smallest viable audience, what language they speak, how much money they have, what problem they're trying to solve, you have chosen everything that's going to go into the product and what your future is going to be like.”
Seth Godin's best tactics for building remarkable products, strategies, brands and more · Seth Godin
“We would have 10 to 15 meetings every day with potential customers. At the time, we didn't really have a solid product yet.”
Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy) · Raaz Herzberg
“Think of SEO as a product. The product managers are the people that should be thinking about this SEO question because it's a product question. This is a user that's doing their own self-discovery journey. If you can't answer the question about what is it that someone's going to do a search on, then don't do SEO.”
Rethinking SEO in the age of AI | Eli Schwartz (SEO advisor, author) · Eli Schwartz
“Transparently, I thought this was going to be an apocalypse. Up until AI Overviews, whoever won on that long form piece of content would get that first click. But now that doesn't exist anymore.”
Rethinking SEO in the age of AI | Eli Schwartz (SEO advisor, author) · Eli Schwartz
“In their documentation, they say that AI itself is not the problem. It's the helpfulness, the usefulness of the content that would be a problem.”
Rethinking SEO in the age of AI | Eli Schwartz (SEO advisor, author) · Eli Schwartz
“I looked on the App Store and the number one app in the United States was an app called Surah, but the entire app was in Arabic, like the strongest signal that you could ever have that people want something.”
How to consistently go viral: Nikita Bier’s playbook for winning at consumer apps (co-founder of TBH, Gas, advisor, investor) · Nikita Bier
“Hot take, paid is for everyone. If you look at the way each platform is doing, Google, you have to scroll pretty far down to get to an organic listing. Meta, it's almost a pay for play now.”
The ultimate guide to performance marketing | Timothy Davis (Shopify) · Timothy Davis
“Instead of thinking about being on top of the page, and that's like ego marketing, I want to be number one. I want to be there all the time. It's about showing to the right person as often as possible.”
The ultimate guide to performance marketing | Timothy Davis (Shopify) · Timothy Davis
“Way underestimating the power of creative. Do you remember Dollar Shave Club? There you go. You remember it. That was creative.”
The ultimate guide to performance marketing | Timothy Davis (Shopify) · Timothy Davis
“I'm always forward thinking, backwards planning. 'Where do you want to be and ultimately how do you think you're going to get there?' Because say your goal is to be on all platforms... forward think, that's where you want to be. Now let's backwards plan.”
The ultimate guide to performance marketing | Timothy Davis (Shopify) · Timothy Davis
“The value is not about what the product does. The value is about the problem you solve. If you can describe the problem in a way that the person you're talking to says, 'oh my God, I have that problem,' you've won.”
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
“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 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
“Another part that goes unspoken, still critical to this day was the celebrity partnerships was critical, because basically they had this wonderful partnerships team that basically took Instagram and taught celebrities how to use it, how to make it work for them, how to tell their own story.”
Unorthodox frameworks for growing your product, career, and impact | Bangaly Kaba (YouTube, Instagram, Facebook, Instacart) · Bangaly Kaba
“Counter-positioning is when a newcomer adopts a new, superior business model that the incumbent can't adopt because it would damage their existing business. This is what Netflix did to Blockbuster.”
Business strategy with Hamilton Helmer (author of 7 Powers) · Hamilton Helmer
“The best signal that you have nascent product-market fit is when customers start pulling the product from you. You don't have to push it anymore. They're asking you for it. That's a qualitative signal that data won't show you.”
A framework for finding product-market fit | Todd Jackson (First Round Capital) · Todd Jackson
“At the developing stage, the biggest mistake I see is premature scaling. You have a few happy customers and you think you should hire a sales team and start marketing. But you haven't really nailed what makes those customers happy.”
A framework for finding product-market fit | Todd Jackson (First Round Capital) · Todd Jackson
“The tendency when you're in the chasm is, 'I just need more customers. I should take any customer I could find,' because we need revenue. It's like taking a match and running it back and forth under a log. It's not going to light the log.”
Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market · Geoffrey Moore
“So how do you start a fire? Well, you start it by putting a little kindling, little crumpled up paper, and you hold the match in one place until the fire starts.”
Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market · Geoffrey Moore
“The editor, the writer, I'll just say it as plainly as possible. They don't care about you. They don't care about you. They care about their reader or their listener or their viewer. That's who they care about.”
How to get press for your product | Jason Feifer (editor in chief of Entrepreneur magazine) · Jason Feifer
“Sometimes you are not the story, but you can be part of the story. Sometimes that means you could just be a writer. You might try to just pitch authoritative articles by you to different publications.”
How to get press for your product | Jason Feifer (editor in chief of Entrepreneur magazine) · Jason Feifer
“We had Coda. They were our first user, and they were based in Palo Alto. Dylan and I drove down and demoed the product to them, and they were the first ones. Their designer, Jeremy was like, 'Yes, we'll take this on full time.' And I remember we were both like, 'What? Really? You will?'”
An inside look at Figma’s unique GTM motion | Claire Butler (first GTM hire) · Claire Butler
“Being technical is important. And caring about your tools, that's another one. Designers, specifically, and I think engineers are the same way, have deep passions for their tools. Probably because they're in it eight hours a day. So, it certainly helps if your target audience already cares deeply about what their tools are.”
An inside look at Figma’s unique GTM motion | Claire Butler (first GTM hire) · Claire Butler
“I do think there's actually a general path that most B2B companies take and should take. My view is you start off with founder-led sales, the early team needs to know how to actually sell.”
Lessons from scaling Ramp | Sri Batchu (Ramp, Instacart, Opendoor) · Sri Batchu
“Then you hire your first couple of salespeople, then you start some very low cost targeted marketing efforts. So whether it's content, community, small scale events, and then PR, after all of that is when you start paid and brand effort.”
Lessons from scaling Ramp | Sri Batchu (Ramp, Instacart, Opendoor) · Sri Batchu
“That's how we got our very innovative go-to-market motions because a lot of those people then moved into different functions at the company. They had all this context on who the user was.”
Building high-performing teams | Melissa Tan (Webflow, Dropbox, Canva) · Melissa Tan
“Every movie starts with some kind of shift in the world, and I call this shift the shift from the old game to a new game. The archetypal example of this in the business world is what Benioff did with Salesforce. He comes in and he says, 'Hey, software is over and there's this new world called the cloud.'”
The power of strategic narrative | Andy Raskin · Andy Raskin
“Something that the Substack founders have always done so well is propagate product updates out in concentric circles. There's a general who said if there's a problem I look for it in concentric circles going back to my own desk. If you want to spread something you go out in concentric circles starting from your own desk. Employees, co-founders, executives, investors, power users, and out from there. You can't skip a circle.”
Navigating comms and PR | Lulu Cheng Meservey (Substack, Activision Blizzard) · Lulu Cheng Meservey
“When you're building a category, you need to make sure that there is a category that's validated by analysts and directory sites. But also, you want to have a lot of traction in terms of thought leadership like why is this the category? What are the unique value propositions? When you're generating a new category, you're also needing to educate buyers that there is a category that they can now budget for.”
Category creation and brand building | Barbra Gago (Pando, Miro, Greenhouse, Culture Amp) · Barbra Gago
“All the things that you're making, all the things that are going to add value. An engine is how you get it out to the right people. And all of the tracking of that and sort of the ops work I put under engine, everyone needs an engine.”
How to build a powerful marketing machine | Emily Kramer (Asana, Carta, MKT1) · Emily Kramer
“Positioning is the act of deliberately defining how you are the best in the world at providing something that a well-defined set of customers cares a lot about. If you don't deliberately position your product, customers will position it for you, and they'll almost certainly get it wrong.”
April Dunford on product positioning, segmentation, and optimizing your sales process · April Dunford
Cutting Room Floor
Guest insights on this topic that Lenny hasn't (yet) written about in his newsletters. Potential material for future posts.
“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
“Investors gave really helpful feedback, often in the form of rejection. I would add a new page showing how big the market was.”
The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins · Melanie Perkins
“ChatGPT and Google Search citation overlap was around 35%. Perplexity was around 70%.”
The ultimate guide to AEO: How to get ChatGPT to recommend your product | Ethan Smith (Graphite) · Ethan Smith
“Charlie Munger says, 'Fish where the fish are.' Find a small fishing hole with lots of fish and very little competition.”
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · Andrew Wilkinson
“Just draw a shape of a diamond on a piece of paper. On the top put the word win. How do you define winning? On the next corner, what do you have to win? On the bottom, what do you need to win? And then on the left-hand side, what do you have to say to win?”
Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding) · David Placek
“Instead, look yourself in the mirror and embrace who you are and what you could be rather than who others are. We have a super strong developer brand. Can we lean into the fact that builders love using Claude? Those builders aren't all just engineers.”
Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram) · Mike Krieger
“The conventional wisdom for many CMOs is to be a T-shaped marketer. I think this chameleon CMO concept means modern marketing leaders have to be really good at a bunch of different things. Maybe going from T-shaped to comb-shaped is probably the right approach.”
Growth tactics from OpenAI and Stripe’s first marketer | Krithika Shankarraman · Krithika Shankarraman
“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
“Three inflection points for great products: technology shift, consumer behavior shift, and business model shift. At least two out of three should be true for any good product. With AI, the monetization is a whole different story -- we've just barely scratched the surface.”
Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada · Aparna Chennapragada
“We actually announced five different new products simultaneously. People said we're going to confuse our current users. But we managed to transform the company in a very short amount of time. Not taking bold risks is a risk for itself.”
Inside monday.com’s transformation: radical transparency, impact over output, and their path to $1B ARR | Daniel Lereya (Chief Product and Technology Officer) · Daniel Lereya
“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
“At Captions, we're going even one step further. Why shouldn't the PM understand marketing? I actually think PMs should own all the way to marketing. Search marketing is just placing a button to your product in Google. That's almost a product surface.”
How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can't copy | Gaurav Misra (CEO and co-founder of Captions) · Gaurav Misra
“I'm throwing everything against the wall. I'm looking at what's going to stick. I am looking to try to find the winning tactic and turn it into a winning strategy.”
Behind the founder: Marc Benioff · Marc Benioff
“When you choose your smallest viable audience, what language they speak, how much money they have, what problem they're trying to solve, you have chosen everything that's going to go into the product and what your future is going to be like.”
Seth Godin's best tactics for building remarkable products, strategies, brands and more · Seth Godin
“We would have 10 to 15 meetings every day with potential customers. At the time, we didn't really have a solid product yet.”
Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy) · Raaz Herzberg
“Think of SEO as a product. The product managers are the people that should be thinking about this SEO question because it's a product question. This is a user that's doing their own self-discovery journey. If you can't answer the question about what is it that someone's going to do a search on, then don't do SEO.”
Rethinking SEO in the age of AI | Eli Schwartz (SEO advisor, author) · Eli Schwartz
“Transparently, I thought this was going to be an apocalypse. Up until AI Overviews, whoever won on that long form piece of content would get that first click. But now that doesn't exist anymore.”
Rethinking SEO in the age of AI | Eli Schwartz (SEO advisor, author) · Eli Schwartz
“In their documentation, they say that AI itself is not the problem. It's the helpfulness, the usefulness of the content that would be a problem.”
Rethinking SEO in the age of AI | Eli Schwartz (SEO advisor, author) · Eli Schwartz
“I looked on the App Store and the number one app in the United States was an app called Surah, but the entire app was in Arabic, like the strongest signal that you could ever have that people want something.”
How to consistently go viral: Nikita Bier’s playbook for winning at consumer apps (co-founder of TBH, Gas, advisor, investor) · Nikita Bier
“Hot take, paid is for everyone. If you look at the way each platform is doing, Google, you have to scroll pretty far down to get to an organic listing. Meta, it's almost a pay for play now.”
The ultimate guide to performance marketing | Timothy Davis (Shopify) · Timothy Davis
“Instead of thinking about being on top of the page, and that's like ego marketing, I want to be number one. I want to be there all the time. It's about showing to the right person as often as possible.”
The ultimate guide to performance marketing | Timothy Davis (Shopify) · Timothy Davis
“Way underestimating the power of creative. Do you remember Dollar Shave Club? There you go. You remember it. That was creative.”
The ultimate guide to performance marketing | Timothy Davis (Shopify) · Timothy Davis
“I'm always forward thinking, backwards planning. 'Where do you want to be and ultimately how do you think you're going to get there?' Because say your goal is to be on all platforms... forward think, that's where you want to be. Now let's backwards plan.”
The ultimate guide to performance marketing | Timothy Davis (Shopify) · Timothy Davis
“The value is not about what the product does. The value is about the problem you solve. If you can describe the problem in a way that the person you're talking to says, 'oh my God, I have that problem,' you've won.”
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
“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
“Another part that goes unspoken, still critical to this day was the celebrity partnerships was critical, because basically they had this wonderful partnerships team that basically took Instagram and taught celebrities how to use it, how to make it work for them, how to tell their own story.”
Unorthodox frameworks for growing your product, career, and impact | Bangaly Kaba (YouTube, Instagram, Facebook, Instacart) · Bangaly Kaba
“Counter-positioning is when a newcomer adopts a new, superior business model that the incumbent can't adopt because it would damage their existing business. This is what Netflix did to Blockbuster.”
Business strategy with Hamilton Helmer (author of 7 Powers) · Hamilton Helmer
“The best signal that you have nascent product-market fit is when customers start pulling the product from you. You don't have to push it anymore. They're asking you for it. That's a qualitative signal that data won't show you.”
A framework for finding product-market fit | Todd Jackson (First Round Capital) · Todd Jackson
“The editor, the writer, I'll just say it as plainly as possible. They don't care about you. They don't care about you. They care about their reader or their listener or their viewer. That's who they care about.”
How to get press for your product | Jason Feifer (editor in chief of Entrepreneur magazine) · Jason Feifer
“Sometimes you are not the story, but you can be part of the story. Sometimes that means you could just be a writer. You might try to just pitch authoritative articles by you to different publications.”
How to get press for your product | Jason Feifer (editor in chief of Entrepreneur magazine) · Jason Feifer
“We had Coda. They were our first user, and they were based in Palo Alto. Dylan and I drove down and demoed the product to them, and they were the first ones. Their designer, Jeremy was like, 'Yes, we'll take this on full time.' And I remember we were both like, 'What? Really? You will?'”
An inside look at Figma’s unique GTM motion | Claire Butler (first GTM hire) · Claire Butler
“Being technical is important. And caring about your tools, that's another one. Designers, specifically, and I think engineers are the same way, have deep passions for their tools. Probably because they're in it eight hours a day. So, it certainly helps if your target audience already cares deeply about what their tools are.”
An inside look at Figma’s unique GTM motion | Claire Butler (first GTM hire) · Claire Butler
“I do think there's actually a general path that most B2B companies take and should take. My view is you start off with founder-led sales, the early team needs to know how to actually sell.”
Lessons from scaling Ramp | Sri Batchu (Ramp, Instacart, Opendoor) · Sri Batchu
“Then you hire your first couple of salespeople, then you start some very low cost targeted marketing efforts. So whether it's content, community, small scale events, and then PR, after all of that is when you start paid and brand effort.”
Lessons from scaling Ramp | Sri Batchu (Ramp, Instacart, Opendoor) · Sri Batchu
“That's how we got our very innovative go-to-market motions because a lot of those people then moved into different functions at the company. They had all this context on who the user was.”
Building high-performing teams | Melissa Tan (Webflow, Dropbox, Canva) · Melissa Tan
“Every movie starts with some kind of shift in the world, and I call this shift the shift from the old game to a new game. The archetypal example of this in the business world is what Benioff did with Salesforce. He comes in and he says, 'Hey, software is over and there's this new world called the cloud.'”
The power of strategic narrative | Andy Raskin · Andy Raskin
“Something that the Substack founders have always done so well is propagate product updates out in concentric circles. There's a general who said if there's a problem I look for it in concentric circles going back to my own desk. If you want to spread something you go out in concentric circles starting from your own desk. Employees, co-founders, executives, investors, power users, and out from there. You can't skip a circle.”
Navigating comms and PR | Lulu Cheng Meservey (Substack, Activision Blizzard) · Lulu Cheng Meservey
“When you're building a category, you need to make sure that there is a category that's validated by analysts and directory sites. But also, you want to have a lot of traction in terms of thought leadership like why is this the category? What are the unique value propositions? When you're generating a new category, you're also needing to educate buyers that there is a category that they can now budget for.”
Category creation and brand building | Barbra Gago (Pando, Miro, Greenhouse, Culture Amp) · Barbra Gago
“All the things that you're making, all the things that are going to add value. An engine is how you get it out to the right people. And all of the tracking of that and sort of the ops work I put under engine, everyone needs an engine.”
How to build a powerful marketing machine | Emily Kramer (Asana, Carta, MKT1) · Emily Kramer
“Positioning is the act of deliberately defining how you are the best in the world at providing something that a well-defined set of customers cares a lot about. If you don't deliberately position your product, customers will position it for you, and they'll almost certainly get it wrong.”
April Dunford on product positioning, segmentation, and optimizing your sales process · April Dunford