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Newsletter Archive
How to make your AI brand stand out (when everything else feels the same)
A playbook from First Round’s Head of Brand & Product Marketing
From the inside: What it's like to work at Clay
A personal essay from the company’s tenth employee.
You don't know Lenny Rachitsky
Read our in-depth profile
What really motivates Lenny Rachitsky?
Read our in-depth profile
How fixing 401(k) the hard way led Guideline's founder to a major exit
Inside Guideline's path to PMF
Listen: Why crazy deadlines produce better products than strategy docs
Vanta CPO Jeremy Epling is on Executive Function
Stop asking “What’s your biggest pain point?” in customer discovery
The discovery question that uncovered a billion-dollar startup idea
Listen: Snowflake’s former CRO on scaling from $0 to $3.5B (and surviving 4 CEOs)
Chris Degnan joins Executive Function.
Do you really need a forward deployed engineer?
A founder’s guide to building an FDE team
Listen: Most CROs are salespeople. Vanta’s CRO says that's changing
Stevie Case joins Executive Function
Listen: Why Rippling’s VP of Design thinks speed improves quality
Ryan Lucas joins Executive Function
A new podcast from First Round: How the top 0.001% of scaleup execs operate
Listen to the first episode with Vercel’s COO
Mastering the skill of company-building, from Applied Intuition’s founder
The $15B vehicle intelligence company’s origin story
What cold-calling from a closet taught Gusto’s founder about PMF
A laser focus on what customers really want paid off.
The unconventional growth levers that made Canva a $42B company
Early evangelists and an ambitious SEO strategy
The best company building advice we heard in 2025
The 13th edition of our annual roundup is here
The most honest lessons about the path to product-market fit
Featuring founders from Gusto, Mercury, Meter and more
Notion put an engineer in sales to build better AI tools
This week on Applied Intelligence, we learn how an AI engineer at Notion joined the sales team for a month to understand their challenges and build better tools to solve their problems. Context Before Code: How Notion Put an AI Engineer on the Sales Floor to Discover What Actually Needed
The merger playbook: A founder’s firsthand story of the deal that beat the odds
And how it changed the trajectory of both companies
Listen: How this two-time billion-dollar founder wins in the enterprise
GTM lessons from Jyoti Bansal
The process I've used to name dozens of companies
A note from the essay's author
The other PMF: how personality-message fit helps founders communicate better
The 30-second prep habit, learning to read a room, and more
How a high school dropout built one of the world’s most-used developer tools
From bootstrapping to a $3B company
When founders should quit as head of product — and hire the first PM
4 heuristics for deciding when it’s time
The trap of weak product-market fit — lessons from Mercury’s founder
Inside the fintech unicorn’s path to product-market fit
The compensation rules to follow (and break), according to experts
Compensation leaders from Clay, Google and Instacart share the rules early-stage founders can break — and the few they should actually follow.
How to avoid a co-founder breakup before Series B
Rituals to strengthen the most important relationship in your startup
Inside Warp’s coding by prompt mandate (and how the CEO follows it too)
Every coding task starts with a prompt — even the CEO’s
Founders, you’re missing this key step on the path to product-market fit
A research toolkit for the discovery phase
How Brex is building an AI-first operations org
Changing roles, workflows and skills around AI
Why Sierra built a design partnership program on “hard mode”
Sierra’s first GTM hire, breaks down every step of their playbook.
Idea validation tactics they won’t teach you in business school
How founders from Linear, Mercury and other startups found conviction before the build
What your startup does (and doesn’t) need to come out of stealth
A launch plan from Figma’s first marketer
Scale smarter, not bigger: Inside Linktree’s internal AI adoption playbook
How Linktree kept headcount steady at 190 while boosting shipping velocity and AI adoption
How to use your industry outsider status to your advantage
Product-building lessons from a Twitter PM turned healthcare founder
Don’t ship your pitch deck to your website
How to translate investor talking points into a marketing story
Inside Owner’s zigzag path to a billion-dollar business
Dropping out of high school. A six-figure Minecraft server. A failing dog grooming business. A pandemic pivot.
Why Linear puts craft above all metrics
Inside the company’s slow and deliberate path to product-market fit
How Carta saves 3,500+ hours per month using AI agents
An 11-min task completed in seconds
A new publication from First Round: Applied Intelligence
Learn how companies are actually using AI, and the results they’re experiencing
Stop playing customer success hero. Here’s how to build your first team.
From hiring to metrics to first systems to set up
How to go from random wins to repeatable revenue
A formula for sales repeatability
Can you be a good micromanager?
How to toggle between details and delegation
Rent-an-exec: Should you hire a fractional leader?
A fractional COO explains
Inside Figma's human-centered approach to building AI
From determining success metrics to structuring qualitative feedback
How to hang on to conviction in an emerging market: Braze's long game to PMF
The origin story of the now publicly traded company
How to spot the wrong customer before they burn your roadmap
How Vanta, Clay, Retool & more startups found their ICP
Thinking about becoming a founder? Here’s how to emotionally prepare
A psychologist’s advice on preparing to take the founder leap
How to make craft your moat
How Stripe, Linear, Square & more top companies operationalize taste
How to build and grow the human side of your engineering org
Lessons from Apple, Palantir and Slack
From weekend project to Fortune 10 adoption
How this founder closed millions in ARR with no sales hires
Inside Superhuman’s onboarding strategy: from human-led to self-serve
An extremely detailed look at building and scaling onboarding
From two-person consultancy to $4.2B software business — dbt Labs’ Path to PMF
Co-founder Tristan Handy shares the startup’s unconventional backstory
A playbook for running “founder-led” growth
You're not ready for a Head of Growth — yet.
Square’s former CEO on the two crucial components of org design
Building a structure to enable scale.
A playbook for building deep tech startups
When traditional startup advice falls short
17,784 hours: Exactly how one startup founder spent 5 years building
Sam Corcos, co-founder & CEO of Levels, on tracking every 15-minute block
How Plaid, Clay, Lattice & other startups pivoted to find PMF
Why & when these founders knew it was time to switch
A complete guide to your startup’s first sales hire
Expert advice from first hires at Dropbox, Figma, Stripe & more
How Figma chooses, builds & launches new products
From spotting user hacks to the “screenshot test”
The rotation program that keeps this startup’s engineers learning (and not leaving)
How Checkr’s VP of Eng squashes attrition
EvolutionIQ’s path to product-market fit — and a $730M acquisition
Lessons from a vertical AI success story
An engineering leader’s advice for pivoting from manager to IC
A 90-day plan to land the jump
10x, 10x, 6x — The exact GTM moves behind Clay’s explosive revenue growth
Lessons from a newly minted unicorn
The inside story of the idea & launch of Figma Slides
How PM Mihika Kapoor built momentum for her product idea
The 30 best pieces of advice we heard in 2024
The 12th edition of our annual roundup is here
Fight off organizational entropy with this guide from Rippling’s COO
Matt MacInnis on becoming a more impatient (and effective) exec
25 tough questions for founder self-reflection
Questions to size up your decision making, team, product & more
How Figma taps into product taste, simplicity and storytelling
An interview with Chief Product Officer Yuhki Yamashita
What this founder learned from losing product-market fit
Lessons in intellectual honesty from a 3X founder
A growth expert’s guide to building billion-dollar marketplaces
Your annual plan is already obsolete: here's how to fix it
How Replit went from side project to a $1B business
A step-by-step guide to starting a B2B marketing engine from scratch
Non-obvious signs of early traction — and how to spot them
Why startup marketers should be diagnosticians
How Gong used design partners to prove a bet on AI in 2015
Here’s what you can really expect from a VC partner meeting
Why founders should be suspicious of symmetry in their org chart
How to launch your second (or third, or fifth) product
Tips for scaling analytics at startups
A seven-year “overnight success” story — Clay’s Path to PMF
Three unexpected anti-patterns for engineering leaders
Three unexpected anti-patterns for engineering leaders
Will Larson, CTO at Carta, shares unconventional leadership strategies he’s learned from scaling teams at Stripe, Uber and Calm.
20 lessons from 20 different paths to PMF
20 lessons from 20 different paths to PMF
Our favorite lessons from founders who tackled the winding journey to product-market fit
Asana’s Head of People opens up her company culture playbook
Seasoned founders share their best advice for first-timers
A founder-friendly playbook for early customer discovery
This week, we’re sharing a step-by-step playbook for how to approach early customer discovery and user research the right way.
After a decade of entrepreneurial pursuits, a $4B unicorn emerges
This week, we’re back with the latest installment in our Paths to Product-Market Fit series.
Why you shouldn’t focus on building the best product — and what to do instead
This week, we're diving into the how, what, when, and why of going from single product focus to multi-product strategy, a common stumbling block for startups.
Dig deeper in reference calls with these 25 questions
Happy Valentine's Day! This week, we’ve pulled together a mega-guide for falling back in love with reference calls.
Why the key to extreme product-market fit is simplicity & velocity
This week, a step-by-step guide on how to turn your startup into a learning machine.
How to make your AI brand stand out (when everything else feels the same)
A playbook from First Round’s Head of Brand & Product Marketing
From the inside: What it's like to work at Clay
A personal essay from the company’s tenth employee.
You don't know Lenny Rachitsky
Read our in-depth profile
What really motivates Lenny Rachitsky?
Read our in-depth profile
How fixing 401(k) the hard way led Guideline's founder to a major exit
Inside Guideline's path to PMF
Listen: Why crazy deadlines produce better products than strategy docs
Vanta CPO Jeremy Epling is on Executive Function
Stop asking “What’s your biggest pain point?” in customer discovery
The discovery question that uncovered a billion-dollar startup idea
Listen: Snowflake’s former CRO on scaling from $0 to $3.5B (and surviving 4 CEOs)
Chris Degnan joins Executive Function.
Do you really need a forward deployed engineer?
A founder’s guide to building an FDE team
Listen: Most CROs are salespeople. Vanta’s CRO says that's changing
Stevie Case joins Executive Function
Listen: Why Rippling’s VP of Design thinks speed improves quality
Ryan Lucas joins Executive Function
A new podcast from First Round: How the top 0.001% of scaleup execs operate
Listen to the first episode with Vercel’s COO
Mastering the skill of company-building, from Applied Intuition’s founder
The $15B vehicle intelligence company’s origin story
What cold-calling from a closet taught Gusto’s founder about PMF
A laser focus on what customers really want paid off.
The unconventional growth levers that made Canva a $42B company
Early evangelists and an ambitious SEO strategy
The best company building advice we heard in 2025
The 13th edition of our annual roundup is here
The most honest lessons about the path to product-market fit
Featuring founders from Gusto, Mercury, Meter and more
Notion put an engineer in sales to build better AI tools
This week on Applied Intelligence, we learn how an AI engineer at Notion joined the sales team for a month to understand their challenges and build better tools to solve their problems. Context Before Code: How Notion Put an AI Engineer on the Sales Floor to Discover What Actually Needed
The merger playbook: A founder’s firsthand story of the deal that beat the odds
And how it changed the trajectory of both companies
Listen: How this two-time billion-dollar founder wins in the enterprise
GTM lessons from Jyoti Bansal
The process I've used to name dozens of companies
A note from the essay's author
The other PMF: how personality-message fit helps founders communicate better
The 30-second prep habit, learning to read a room, and more
How a high school dropout built one of the world’s most-used developer tools
From bootstrapping to a $3B company
When founders should quit as head of product — and hire the first PM
4 heuristics for deciding when it’s time
The trap of weak product-market fit — lessons from Mercury’s founder
Inside the fintech unicorn’s path to product-market fit
The compensation rules to follow (and break), according to experts
Compensation leaders from Clay, Google and Instacart share the rules early-stage founders can break — and the few they should actually follow.
How to avoid a co-founder breakup before Series B
Rituals to strengthen the most important relationship in your startup
Inside Warp’s coding by prompt mandate (and how the CEO follows it too)
Every coding task starts with a prompt — even the CEO’s
Founders, you’re missing this key step on the path to product-market fit
A research toolkit for the discovery phase
How Brex is building an AI-first operations org
Changing roles, workflows and skills around AI
Why Sierra built a design partnership program on “hard mode”
Sierra’s first GTM hire, breaks down every step of their playbook.
Idea validation tactics they won’t teach you in business school
How founders from Linear, Mercury and other startups found conviction before the build
What your startup does (and doesn’t) need to come out of stealth
A launch plan from Figma’s first marketer
Scale smarter, not bigger: Inside Linktree’s internal AI adoption playbook
How Linktree kept headcount steady at 190 while boosting shipping velocity and AI adoption
How to use your industry outsider status to your advantage
Product-building lessons from a Twitter PM turned healthcare founder
Don’t ship your pitch deck to your website
How to translate investor talking points into a marketing story
Inside Owner’s zigzag path to a billion-dollar business
Dropping out of high school. A six-figure Minecraft server. A failing dog grooming business. A pandemic pivot.
Why Linear puts craft above all metrics
Inside the company’s slow and deliberate path to product-market fit
How Carta saves 3,500+ hours per month using AI agents
An 11-min task completed in seconds
A new publication from First Round: Applied Intelligence
Learn how companies are actually using AI, and the results they’re experiencing
Stop playing customer success hero. Here’s how to build your first team.
From hiring to metrics to first systems to set up
How to go from random wins to repeatable revenue
A formula for sales repeatability
Can you be a good micromanager?
How to toggle between details and delegation
Rent-an-exec: Should you hire a fractional leader?
A fractional COO explains
Inside Figma's human-centered approach to building AI
From determining success metrics to structuring qualitative feedback
How to hang on to conviction in an emerging market: Braze's long game to PMF
The origin story of the now publicly traded company
How to spot the wrong customer before they burn your roadmap
How Vanta, Clay, Retool & more startups found their ICP
Thinking about becoming a founder? Here’s how to emotionally prepare
A psychologist’s advice on preparing to take the founder leap
How to make craft your moat
How Stripe, Linear, Square & more top companies operationalize taste
How to build and grow the human side of your engineering org
Lessons from Apple, Palantir and Slack
From weekend project to Fortune 10 adoption
How this founder closed millions in ARR with no sales hires
Inside Superhuman’s onboarding strategy: from human-led to self-serve
An extremely detailed look at building and scaling onboarding
From two-person consultancy to $4.2B software business — dbt Labs’ Path to PMF
Co-founder Tristan Handy shares the startup’s unconventional backstory
A playbook for running “founder-led” growth
You're not ready for a Head of Growth — yet.
Square’s former CEO on the two crucial components of org design
Building a structure to enable scale.
A playbook for building deep tech startups
When traditional startup advice falls short
17,784 hours: Exactly how one startup founder spent 5 years building
Sam Corcos, co-founder & CEO of Levels, on tracking every 15-minute block
How Plaid, Clay, Lattice & other startups pivoted to find PMF
Why & when these founders knew it was time to switch
A complete guide to your startup’s first sales hire
Expert advice from first hires at Dropbox, Figma, Stripe & more
How Figma chooses, builds & launches new products
From spotting user hacks to the “screenshot test”
The rotation program that keeps this startup’s engineers learning (and not leaving)
How Checkr’s VP of Eng squashes attrition
EvolutionIQ’s path to product-market fit — and a $730M acquisition
Lessons from a vertical AI success story
An engineering leader’s advice for pivoting from manager to IC
A 90-day plan to land the jump
10x, 10x, 6x — The exact GTM moves behind Clay’s explosive revenue growth
Lessons from a newly minted unicorn
The inside story of the idea & launch of Figma Slides
How PM Mihika Kapoor built momentum for her product idea
The 30 best pieces of advice we heard in 2024
The 12th edition of our annual roundup is here
Fight off organizational entropy with this guide from Rippling’s COO
Matt MacInnis on becoming a more impatient (and effective) exec
25 tough questions for founder self-reflection
Questions to size up your decision making, team, product & more
How Figma taps into product taste, simplicity and storytelling
An interview with Chief Product Officer Yuhki Yamashita
What this founder learned from losing product-market fit
Lessons in intellectual honesty from a 3X founder
A growth expert’s guide to building billion-dollar marketplaces
Your annual plan is already obsolete: here's how to fix it
How Replit went from side project to a $1B business
A step-by-step guide to starting a B2B marketing engine from scratch
Non-obvious signs of early traction — and how to spot them
Why startup marketers should be diagnosticians
How Gong used design partners to prove a bet on AI in 2015
Here’s what you can really expect from a VC partner meeting
Why founders should be suspicious of symmetry in their org chart
How to launch your second (or third, or fifth) product
Tips for scaling analytics at startups
A seven-year “overnight success” story — Clay’s Path to PMF
Three unexpected anti-patterns for engineering leaders
Three unexpected anti-patterns for engineering leaders
Will Larson, CTO at Carta, shares unconventional leadership strategies he’s learned from scaling teams at Stripe, Uber and Calm.
20 lessons from 20 different paths to PMF
20 lessons from 20 different paths to PMF
Our favorite lessons from founders who tackled the winding journey to product-market fit
Asana’s Head of People opens up her company culture playbook
Seasoned founders share their best advice for first-timers
A founder-friendly playbook for early customer discovery
This week, we’re sharing a step-by-step playbook for how to approach early customer discovery and user research the right way.
After a decade of entrepreneurial pursuits, a $4B unicorn emerges
This week, we’re back with the latest installment in our Paths to Product-Market Fit series.
Why you shouldn’t focus on building the best product — and what to do instead
This week, we're diving into the how, what, when, and why of going from single product focus to multi-product strategy, a common stumbling block for startups.
Dig deeper in reference calls with these 25 questions
Happy Valentine's Day! This week, we’ve pulled together a mega-guide for falling back in love with reference calls.
Why the key to extreme product-market fit is simplicity & velocity
This week, a step-by-step guide on how to turn your startup into a learning machine.
Subject: How to make your AI brand stand out (when everything else feels the same)
In the first couple years after the ChatGPT moment, slapping “AI” on your product was good enough to get buyers to pay attention. It’s not anymore.
“AI powered” worked as a differentiator when it felt new. But that stops being a position when five other credible “AI-powered X” companies are out there. And now there are — because models are shared, infrastructure is abstracted and products that once required months of engineering can launch in days or hours. Worse, all these companies use the same gradients, sterile screenshots and LLM-smoothed copy, making it impossible for customers to tell them apart.
Arielle Jackson has spent over a decade working with First Round founders on positioning, brand identity and launch communications. Her advice has shifted a lot over the last two years. The new problem she sees founders faced with: AI accelerates sameness.
In her new piece on The Review, Jackson lays out what founders need to do instead:
She walks through how Cursor had to reframe its positioning twice in under two years, why Clay’s recent out-of-home campaign is the cleanest expression she’s seen in the category and what Anthropic’s Department of War standoff actually did for Claude’s App Store ranking.
Thanks, as always, for reading and sharing!
-The Review Editors
Subject: From the inside: What it's like to work at Clay
So much writing about great companies comes from founders. But some of the most revealing and thoughtful stories we’ve heard over the years have come from someone else entirely — the early employees who were in the room for everything, but rarely get asked to tell their side.
In our new essay series, “Firsthand,” we partner with early employees to tell these inside stories in their own words.
We’re launching the series with Mishti Sharma, Head of Narratives at Clay.
Sharma joined as employee number ten. The morning she signed her offer letter, it felt like she was admitting defeat. She hoped to pursue journalism and filmmaking, and instead, was joining a B2B data company to write about cold email.
Three years later, she’s still there. Her essay is about why — and what happens when a company finds uniquely talented people and builds roles around their skills, rather than shoving them into job descriptions.
Subject: You don't know Lenny Rachitsky
Many of us feel like we know Lenny Rachitsky because we see him everywhere. He’s on our commutes, in our ears as we do weekend chores, or with us at work as we’re trying to get better at our jobs.
The First Round Review got a rare opportunity to profile Rachitsky, spending hours with him at his home to understand the person behind the screen. What motivates him is far more interesting than what you might think.
Rachitsky was born in Ukraine to Jewish parents who applied to emigrate but were denied exit, being labeled “refuseniks.” Wanting to leave the country was itself an act of treason, and Rachitsky says his parents had a difficult time once their application was denied. He watched his parents navigate a lack of choice — as they figured out how to live in Ukraine and also when they finally did make it to the US, establishing their careers here.
Rachitsky says he always had a chip on his shoulder and wanted to show people what he could do. Starting a company was the ultimate form of autonomy, so that’s what he did (which he eventually sold to Airbnb).
Once Rachitsky became “Lenny,” he was driven by creating value for his audience. He dedicates between 5 - 100 hours to each newsletter, poring over it 50 times before it’s published. And as he adds new things to his network — a conference, other podcasts, his Product Pass — he always views these through the lens of value delivery.
Now that he’s built one of the most influential platforms in tech, what motivates him to keep doing it?
“I’m very afraid of moving into a place of just talking about things that aren’t real and just sound true, but aren’t true at all,” he says. He doesn’t want to pontificate or become a talking head, being so far removed from the day-to-day work of a PM that he loses grounding with what his audience wants.
Subject: What really motivates Lenny Rachitsky?
“I have a rule: no meetings before 3pm,” Lenny Rachitsky says. The retro analog clock on the wall ticks past 9:30am. “This is an exception.”
Our writer spent hours with Rachitsky — the PM turned reluctant influencer — to see what happens when the podcast camera turns off. He learned that after you peel back Rachitsky’s layer of equanimity, what you find is someone who has something to prove.
Rachitsky started Lenny’s Newsletter to live a “chill life.” And on the surface, it seems he’s achieved that: walk into his home and the floors are heated, there are lit candles, steam rises from the mug Rachitsky sips.
But with all his success and how much he works, our writer wonders if that goal of living a chill life is still even possible.
This is the central contradiction of Rachitsky. The chill life made his insanely high quality bar possible. The quality at which he does everything made the chill life sustainable.
Subject: How fixing 401(k) the hard way led Guideline's founder to a major exit
This week, Guideline founder Kevin Busque shares how a contrarian bet to fix 401(k) launched a decade of building — and an eventual acquisition by Gusto.
It’s 2014 and Kevin Busque is too busy to be verifying 401(k) contributions on every pay period. As co-founder and VP of Technology of TaskRabbit, the same-day service platform widely credited with catalyzing the gig economy along with Uber and Airbnb, he is focused on scaling the company rapidly. TaskRabbit recently launched in London, its first international market, and its headcount has grown to 70.
Compared to his days as a scrappy early-stage founder, figuring it out on the fly with a small band of early hires, things now look very different for Busque. He spends a lot of time thinking about leadership. Thinking about hiring. Thinking about HR and employee benefits. It’s the latter in particular that begins to keep him up at night, after he stumbles upon a discovery that makes him do a double take: a mere 36% of TaskRabbit employees are enrolled in the company’s 401(k) plan. It doesn’t make sense.
“I remember the number, because when I found out, I was flabbergasted,” Busque recalls.
He begins trying to understand why so few of his employees are making use of this company benefit, which costs TaskRabbit more than $20,000 annually. As he takes a closer look at their 401(k) providers, he starts to grasp the issues.
Subject: Listen: Why crazy deadlines produce better products than strategy docs
Jeremy Epling joins Executive Function this week for a deep dive on what it takes to become an incredibly effective CPO.
After a 16-year run at Microsoft overseeing just about every major product line, Jeremy Epling joined GitHub as VP of Product. For one of his first projects, then-CEO Nat Friedman assigned him to a mission impossible: Get GitHub Actions to GA in nine months. No budge on the timeline.
It seemed absurd to Epling on paper, but he says Friedman’s confidence and coaching ultimately pushed him to get it done. “I did better work than I thought I could on a faster schedule than I thought I could. It was a career-defining project for me,” he says.
Epling’s now CPO at Vanta, where he’s modeled his own leadership MO after Friedman to help his team do great work faster than they thought possible.
He shares more gems in this episode of Executive Function, which is well worth a listen for executives across the org chart — not just on the product side:
Explore more Executive Function episodes:
Subject: Stop asking “What’s your biggest pain point?” in customer discovery
This week, we’re back with another installment of our Paths to Product-Market Fit series with Serval, an AI startup taking a swing at a hundred-billion dollar ITSM incumbent.
When hunting for startup ideas, Jake Stauch opened with the textbook discovery question: “What’s your biggest pain point?” It got him nowhere.
He’d had dozens of conversations with IT buyers, a persona he’d spent a lot of time with as a product leader at security platform Verkada and wanted to build for at his new startup.
“Nowadays people have mostly solved the problems they're aware of. They've already got some tool in place,” says Stauch. “I did a lot of interviews where I’d ask, ‘What keeps you up at night?’ And I just didn’t hear anything very interesting.”
So he swapped in a new question: “If you could hire somebody today to sit next to you and do your work for you, what would you have them do?”
“When you frame the question as, ‘Hey, if you had somebody else here to help you, what’s the work that you'd give them?’ That's a nonjudgmental way of asking for pain points because you're saying, ‘What would you push over to this new person?’” says Stauch. “That way, they can be much more free to say, ‘I don't like to do these things or I am doing a lot of this and I think somebody else could do it for me instead.’”
The answers to that question sparked the idea for Serval, an AI platform that automates help desk requests and other IT workflows.
Stauch had these discovery conversations in April 2024, while still at his day job at Verkada. Serval’s now a billion-dollar startup that nabbed a $75M Series B just one month after announcing its Series A, with customers like Notion, Clay and Vercel.
On The Review, Stauch shares his biggest PMF lessons two years into building, before the early decisions blur into a glossy timeline.
Subject: Listen: Snowflake’s former CRO on scaling from $0 to $3.5B (and surviving 4 CEOs)
This week on Executive Function, former Snowflake CRO Chris Degnan shares lessons from a decade scaling a single company to billions in revenue.
“I need to know how to sell the product better than anyone else. Otherwise, how will I be able to judge if we’re hiring the right salespeople? Or what a good sales call looks like? How can I trust the forecast I’m being given?”
Chris Degnan joined Snowflake as employee #13 — the first sales hire. He scaled revenue from $0 to more than $3B ARR, his tenure as CRO spanning 11 years and four CEOs. He now advises startups on building a disciplined go-to-market strategy.
On the latest episode of Executive Function, Degnan sits down with First Round partner Brett Berson to discuss how the CRO role changes from $10M to $1B+, what he learned working under four different CEOs (including Frank Slootman), why he stays hyper-paranoid about competition, and more.
He shares:
Explore more Executive Function episodes:
Subject: Do you really need a forward deployed engineer?
We spoke to founders and operators who’ve hired (and been) FDEs to find out what it takes to build the model at your company.
Once written off as a glorified consultant, the forward deployed engineer is now the hottest gig at AI startups.
The FDE was originally conceived by Palantir to wrangle value out of a non-prescriptive product. The title is descriptive: Palantir FDEs spent most of their time literally deployed with customers, and were still very much engineers, writing and debugging production code for some incredibly niche use cases, from government to supply chain to energy.
Now as AI products collide with the reality of legacy systems and thorny codebases, founders have turned to the forward deployed model to send engineers onsite to help speed the time to value for enterprise customers.
But what’s missing from the FDE hype cycle — no doubt also buoyed by Palantir’s outlier success in recent years — is that the role isn’t one-size-fits-all for every AI startup. It takes a ton of intentional design to actually get a return on investment.
“Forward deployed engineering is being framed as a panacea right now. But it’s a lot more complicated than that,” says James Honsa, who previously built and scaled Ironclad’s equivalent of an FDE team, called “legal engineering.” “There are times in a company's lifecycle where it makes sense, and there are customer segments where it makes sense, but it's a pretty blunt instrument to try to use for your entire business.”
We sat down with founders who’ve hired FDEs and former Palantir FDEs and recruiters to break down what justifies adding forward deployed headcount, and how to find the right folks for the job.
Our panel covers:
Thanks, as always, for reading and sharing!
-The Review Editors
Subject: Listen: Most CROs are salespeople. Vanta’s CRO says that's changing
Vanta CRO Stevie Case is on Executive Function this week to unpack how revenue leadership is evolving in the AI era.
“In 2028, CROs will need to be systems-first instead of human capacity-first. That's not to say we won’t have large go-to-market teams, but we’re going to have to have CROs who know both sides of that equation. And I think less than 10% of current CROs are capable of making that transition.”
Stevie Case is no ordinary revenue exec. A former pro gamer, she found her way into sales when a mentor took a chance on her, climbing her way up as a sales leader at Twilio before joining Vanta as CRO.
She sat down with First Round Partner Brett Berson to dissect how she operates as CRO today, and how she thinks her role is going to change over the next few years.
She shares:
We’ve got a lot more interviews lined up in the coming weeks. Here are some of the incredible execs you’ll be able to learn from:
Subject: Listen: Why Rippling’s VP of Design thinks speed improves quality
On our second episode of Executive Function, Rippling’s VP of Design, Ryan Lucas, discusses how to build a fast, demanding, supportive place for designers to do their best work.
“Figma is not the source of truth. It’s a bunch of rectangles in a vector drawing program,” says Ryan Lucas, VP of Design at Rippling. “The source of truth is the thing that customers experience.”
This exemplifies Lucas’s approach to building products, teams and cultures — utility above all else. In conversation with First Round partner Brett Berson, Lucas explores why you can’t scale taste, how his background as an industrial designer shaped his thinking and how to create a demanding yet supportive environment as a manager.
Here are a few of our favorite moments from the conversation:
We’ve got a lot more interviews lined up in the coming weeks. Here are some of the incredible execs you’ll be able to learn from:
Whether you’re a senior IC who wants to know what it takes to get to the top, or a founder building out your C-suite, we hope you’ll walk away from these conversations with a new model for what executive excellence looks like.
Subject: A new podcast from First Round: How the top 0.001% of scaleup execs operate
Introducing our new podcast, Executive Function, where we sit down with the best scaleup execs operating today: The ones up-and-coming tech leaders wish they could have as a mentor, and founders wish they could hire.
Our first episode with Vercel COO Jeanne DeWitt Grosser just dropped — and stay tuned for future interviews with execs from Rippling, Harvey, Cognition & more.
There's a lot of knowledge floating around the Valley about what makes a great founder, engineer or PM. Some names and faces, or heuristics and frameworks probably come to mind.
But we’ve found there's remarkably few resources available for folks stepping into the C-suite, specifically at hypergrowth companies — these people are forced to keep pace with a company that changes 5-10x in a year.
Our new podcast, Executive Function, aims to fill this gap. Think of these conversations like office hours with the execs driving the growth of today’s best companies, like Rippling, Harvey and Cognition.
Our first guest, Jeanne DeWitt Grosser, exemplifies operational excellence. She spent nearly a decade at Stripe, leading growth and product before stepping into the role of Chief Business Officer. She’s now the Chief Operating Officer at Vercel.
First Round Partner Brett Berson sat down with Jeanne to unpack why most execs fail, how she interviews exec hires and why context is the biggest rate limiter of impact. Some highlights from their conversation:
We’ve got a lot more interviews lined up in the coming weeks. Here are some of the incredible execs you’ll be able to learn from:
Whether you’re a senior IC who wants to know what it takes to get to the top, or a founder building out your C-suite, we hope you’ll walk away from these conversations with a new model for what executive excellence looks like.
Subject: Mastering the skill of company-building, from Applied Intuition’s founder
This week, Qasar Younis shares all the personal and professional moves he made to found Applied Intuition.
For Qasar Younis, the path to product-market fit dates back to childhood.
He grew up in a Detroit suburb, where the auto industry was the backdrop to his whole life: His father was an auto worker whose job security wavered as production moved to China. Younis studied engineering at the General Motors Institute. He worked part-time on the factory floor.
Younis always knew he wanted to be a founder, inspired by watching his dad reclaim his autonomy. “He started his own small business, which he still runs today. That’s been hugely informative to me. I saw him get his dignity that way. He really became a master of his own destiny,” he says.
So he designed his career to optimize his own founder training: engineering jobs at General Motors and Bosch, business school, a stint at a holding company to “learn finance,” investing at Y Combinator. He tried his hand at starting two companies, the second of which he sold to Google.
At Google he’d meet Peter Ludwig, a PM and fellow Detroit kid who was also interested in starting a company. Their shared experiences, from growing up in Motor City to building sensors for a Google Street View car, materialized in a startup idea that only they could pursue: software for automakers developing self-driving cars, which would become Applied Intuition.
Subject: What cold-calling from a closet taught Gusto’s founder about PMF
This week, Gusto co-founder and CPO Tomer London shares how relentlessly cold-calling potential customers taught him to recognize what PMF really feels like.
It’s 2012 and Tomer London has locked himself in a closet, phone in hand, to dial the numbers of small business owners he finds on Yelp, taking rejection, after rejection, after rejection on the chin. He’s recently dropped out of an electrical engineering PhD program at Stanford to focus on the payroll startup he co-founded with Josh Reeves and Edward Kim that will eventually become Gusto.
“We were hustling, trying to find who would trust the three of us to run their payroll,” London says. “We had a swimming class for kids. We had a flower shop where Eddie was buying flowers, and he asked her, ‘Who do you use for payroll?’ She didn’t have a provider, so we set her up.”
They were concurrently exploring building an API payroll product for enterprise platforms. But all that cold-calling had revealed a surprising truth: Among prospective customers, SMBs were much more enthusiastic than ENTs.
“I remember going to some of these big platforms and we were sure they were going to love it. But the response we mostly got was, ‘This could be cool, but it’s not a priority right now.’”
SMBs, meanwhile, were clamoring for a product to solve their payroll problems …
Subject: The unconventional growth levers that made Canva a $42B company
Cameron Adams barely knew Melanie Perkins and Cliff Obrecht before the three decided to build Canva together. In a recent conversation, Adams shared how he knew it was the right choice, how SEO and localization unlocked massive growth, and more.
In March 2012, Cameron Adams returned to Sydney from San Francisco at an uncertain moment. The Google alum had just come back from a fundraising trip for Fluent, the email startup he’d co-founded, without securing the backing he’d hoped for. He also had a newborn at home.
“We spent two months traipsing up and down Sand Hill Road and all over the Bay Area. We thought we would come back with a novelty-sized check of $2 million. Didn’t pan out that way."
He’d left his role as a user interface designer at Google to give the startup his full attention — a decision that left him taking stock of what came next.
That’s when Lars Rasmussen, the co-founder of Google Maps and Adams’s former boss at Google, came to him with a serendipitous suggestion, encouraging Adams to meet a young entrepreneur he’d recently been introduced to: Melanie Perkins. Perkins, with her partner Cliff Obrecht, had built an online yearbook business called Fusion Books, which was pulling in $2-3 million a year.
But they had their eyes on a much bigger prize. If students could easily create and publish their own yearbooks online with zero design skills, it stood to reason that with the right tools, anyone should be able to design anything…
Subject: The best company building advice we heard in 2025
Sharing our favorite snippets of startup advice we published last year.
Happy 2026!
We’re kicking off the new year with a tradition we’ve upheld ever since The Review was born in 2013. Every January, we comb through all the articles we published over the past 12 months to pull out 30 pieces of standout advice.
We spoke with some incredible founders and builders in 2025, filling out an archive that covered topics from launching out of stealth to user onboarding to landing your first design partners.
As we assembled this guide, the snippets that stood out to us were the seemingly small tactics and against-the-grain approaches that led to outsized impact. They came from folks who weren’t afraid to take risks long before their strategies became consensus, or before their companies became household names.
Here’s a taste of the advice that made the list:
We hope you’ll find something in here you can put to use to build an incredible company, whether that’s today or 10 years from now.
Thanks, as always, for reading and sharing!
-The Review Editors
Subject: The most honest lessons about the path to product-market fit
All companies start with a founder who asks some version of the same question: Imagine if this could be different?
What happens next is where the real story lives — when ideas become real. That path is hardly ever a straight line. But what’s shared among those who walk it is an obsession with building something truly great.
This year on our podcast, In Depth, we asked founders to retrace the steps they took to find product-market fit in more detail than they’ve ever shared before.
Owner co-founder and CEO, Adam Guild, takes us through how the idea for the company started after saving his mom’s struggling dog grooming business. Braintrust founder and CEO Ankur Goyal recounts first feeling PMF when he didn’t have to convince anyone to use the product. And Jyoti Bansal, founder and CEO of Harness, shares why the hardest decision he ever made was to break up with Netflix as a customer. You’ll also hear from the founders of Gusto, fal, Meter, Postman, Reducto, Sentry, Serval and Stedi.
Of course, this is only a sliver of the advice shared across dozens of episodes of In Depth this year. Here were some more of our favorites:
Thanks, as always, for watching and sharing!
-The Review Editors
Subject: Notion put an engineer in sales to build better AI tools
This week on Applied Intelligence, we learn how an AI engineer at Notion joined the sales team for a month to understand their challenges and build better tools to solve their problems.
His first day on Notion’s sales team, AI engineer Theo Bleier made 40 cold calls. He didn’t land a single meeting — but he did discover insights that would change how Notion built internal AI sales tools.
Instead of just throwing AI at the sales team and expecting results, Bleier became a card-carrying member of the sales pod for a month. He had named accounts. He learned about objection handling. He (unsuccessfully) cold-called.
Sitting with Notion’s most successful salespeople, Bleier noticed they spent extra time doing account research before any outbound. But he learned the result of that research wasn’t better email messaging — these reps developed a better understanding of when to reach out to these accounts and prioritize them accordingly.
“From the outside, it seems obvious we should make the sales team move faster by doing account research for them. But when Theo came in and did research, where he ended up was actually account prioritization."
- Pravesh Mistry, Notion’s Head of Global Sales.
This led to Bleier’s framework for a successful sales process: “Right messaging to the right person at the right company at the right time — and right time is step zero.”
As a result, Bleier created an internal tool called “Salestino bot” to automate that process. It gives reps specific product signals they use to better prioritize which accounts to reach out to, while also providing them with customized messaging to edit and use in that outreach.
In this exclusive interview, we learn about Bleier’s immersion process to find the right problems and exactly how he built the tools to solve them. If you’re developing internal AI tools, Bleier’s process is a clear example of how to find the real problem before writing a single line of code.
Thanks, as always, for reading and sharing,
-The Review editors
Subject: The merger playbook: A founder’s firsthand story of the deal that beat the odds
This week, Bob Moore, co-founder and CEO of Crossbeam, details every aspect of merging with a fast-growing competitor.
75% of mergers fail. But Bob Moore, co-founder and CEO of ecosystem revenue platform company Crossbeam, knew a deal with fast-growing competitor Reveal could materially change the trajectory of his company.
Leading up to the deal, Crossbeam was approaching $10M ARR and had 800 customers (including Snowflake, Okta and Shopify). But uncover the up-and-to-the-right metrics and you’d see a different story — the company was spending too much cash to generate each incremental dollar of revenue and that revenue was coming too slowly.
“Our journey to $10M ARR had felt like chewing glass, and we still saw a buffet of it ahead of us,” Moore says.
In this essay, Moore goes into extreme, firsthand detail about how he and Reveal’s co-founder and CEO, Simon Bouchez, architected a merger that beat the odds. He takes us through:
Moore’s account of the merger goes beyond the vague headlines and PR talking points you normally get when it comes to M&A. If you’ve never run a real process yourself, you might be surprised at the sheer number of details to make it work. It’s a fascinating look at how two companies actually come together.
Thanks, as always, for reading and sharing!
-The Review Editors