This week, we’re looking at how founders can build out the initial version of their customer success orgs, from identifying the right people to hire, to the best early metrics to track.

The Founder’s Guide to Building a V1 of Customer Success

At some point, founders can no longer moonlight as customer success leaders.

The moment you realize it’s time to turn off support notifications can come in different forms — maybe something breaks and you’re drowning in tickets, or maybe too many high-profile customer requests pull focus away from other responsibilities.

Knowing when it’s time to build the CS function is one thing. Knowing how to build it is another.

Stephanie Berner, Atlassian’s SVP of Customer Success, is here to give you a blueprint. Prior to Atlassian, she led customer success for LinkedIn’s Sales Solutions arm, was the Senior Director of Customer Success Management at Box and gained early startup experience at Medallia, all the while learning the ins and outs of delivering strong customer experiences.

“Customer success is all about getting your product into your customer's hands as fast as possible,” she says. “If founders and product builders are spending disproportionate amounts of their time solving customer experience problems instead of driving the mission forward, it’s time to formalize your customer success operations.”

In this exclusive interview, Berner breaks down the crucial components of building an early customer success org, with specific zero-to-one tactics for founders standing up CS from scratch. Here’s what you’ll learn:

• Whether your first hire should be someone technical or an industry specialist
• Interview questions to ask that will evaluate drive, self-awareness and customer empathy (which are the most important traits of first hires)
• Why your CS leader should report to the CEO instead of the CRO or CPO
• Target ratios for the number of CSMs on SMB, mid-market and enterprise accounts
• Why customer health and renewal rate are the most important early metrics to track (and why NPS and CSAT can wait)

This is an invaluable, tactical approach for founders who are just starting to build their customer success functions.

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-How to calibrate your gut for hiring

-How to build a “board of brains” with AI

This week, we’re publishing the fourth installment in our new series on going from 0 to multiple millions in ARR. Today's guide tackles one of the trickiest transitions in startup growth: building sales repeatability.

0-$5M: From Random Wins to Repeatable Revenue

Every founder knows the feeling: You just closed another deal, but if someone asked you to replicate it exactly, step-for-step, you’d be at a loss.

Maybe it started with a random LinkedIn message. Then there was that impromptu coffee meeting. A few calls and product demos later (was it three or four?), some back-and-forth on pricing, a last-minute feature request, and somehow — miraculously — they signed.

Now multiply that chaos by your first 10 or 20 customers. Each deal feels like its own adventure, with different timelines, stakeholders and objections.

As you look to what’s next, what probably comes to mind is the same old go-to-market advice you’ve heard before: hire more reps, close more deals.

But without a proven process, adding headcount usually just accelerates your burn rate, not your growth. And when your first 10 deals all closed differently — through warm intros, random inbounds, pure founder hustle and maybe your sister's college roommate with spare budget — it’s tough to figure out where to even start.

That's exactly what First Round Partner Meka Asonye dug into for this month's installment of his 0-$5M series. As one of Stripe’s first AEs who now spends his days supporting pre-revenue founders as they hunt for PMF, he’s focused on crowdsourcing tactical advice to more thoroughly unpack the nitty-gritty GTM details that often get glossed over.

Today, he dives into how successful startups decoded their early sales chaos to find true repeatability, interviewing a stable of operators who've navigated this transition multiple times before, including:

• Sam Taylor (first enterprise sales rep at Dropbox, also scaled GTM at Quip and Loom)
• Mike Molinet (built Branch to $100M+ ARR, now doing it again at Thena)
• Marta Bralic Kerns (founder/CEO of Pomelo Care, early at Flatiron Health)
• Michael Loiacono (has been in the first 20 employees six times, recently heading sales at Testlio)
• Peter Kazanjy (co-founder of Atrium, who literally wrote the book on founder-led sales)

This group shares candid advice about turning scattered early wins into a repeatable sales playbook, including:

• A clear four-step framework for going from early wins to repeatable revenue.
• Practical guidance on avoiding common traps in headcount and compensation, and getting early sales hires to reverse-engineer that founder-led sales magic.
• Plus, a bonus waterfall forecast template from First Round’s VP of GTM.

Thanks, as always, for reading and sharing!

-The Review Editors

Meka’s already covered founder-led sales, making your first sales hire and finding your ICP. Got other GTM topics you’d love advice on? Just hit reply or find Meka at @BigMekaStyle.

Recommended resources:

- The prompt to make prompts better

- A crash course on sharing revenue or ARR numbers when fundraising

- An experiment to predict viral Hacker News headlines

This week, we rounded up advice from top founders and startup execs for wielding micromanagement effectively.

Is All Micromanagement Bad? Here's How the Best Startup Leaders Balance Details and Delegation

“I’m not a micromanager, but I’m microinterested.”

This pithy remark from Rippling COO Matt MacInnis reframes the "don't micromanage" advice that has become canon for new and experienced managers alike. It means well. But if you take it too literally and step all the way out of the codebase or sprint plans, you risk losing a grip on important parts of your business.

With so much buzz around the notion of the “hands-on founder,” MacInnis’ take got us thinking about altitude shifting as a founder or exec. The collective wisdom around micromanagement tends to fall into two extremes: never micromanage and delegate everything, or control every single detail and delegate nothing. But we’ve found that advice for the middle ground — how to keep a hawklike eye on the important details without stripping teams of autonomy — is in short supply.

So we dug through our archives to put together a tactical guide on when to wade into the minutia, and how to step back to empower your team. Here’s who you’ll hear from:

• Jack Altman, co-founder and former CEO of Lattice
• Matt MacInnis, COO at Rippling
• Krithika Shankarraman, Stripe’s and OpenAI's first marketing hire
• Mike Brown, early Uber employee and former COO at Newfront Insurance
• Will Larson, CTO at Imprint, formerly Carta, Calm and Stripe
• Jay Desai, founder and former CEO of PatientPing
• Sidharth Kakkar, co-founder and CEO of Subscript
• Hareem Mannan, Head of Product & Design at Squint, formerly Pave and Segment
• Michael Lopp, Senior Director of Engineering at Apple
• Sam Corcos, co-founder and CEO of Levels

Here's a preview of their (sometimes-contradictory) advice for wielding micromanagement effectively — and refraining from the unproductive kind:

• Look for data anomalies as a cue to micromanage. One of Rippling’s leadership principles is “go and see.” MacInnis enacts that by jumping into the field to investigate whenever the dashboard tells a different story from the department heads. “When the anecdotes disagree with the data, you've got a problem,” he says. “You have to go and see for yourself, which means getting straight down to the atomic level of the function you're interested in to gather context.”
• Gather micro-context with ICs. To get up to speed on a new system or culture, whether that’s in a new company or a new function, former Carta CTO Will Larson likes to talk to the people closest to the ground truth: individual contributors. “You can usually get buy-in from other executives pretty easily, but it’s much more difficult to get buy-in from people with the most context around a given problem,” he says. “Their opinion is most valuable because they are the ones who live in the details. You can’t lie to them. They know the truth of how things run.”
• Treat micromanagement like a symptom — and get to the root cause. Former PatientPing founder and CEO Jay Desai brings a diagnostic lens to micromanagement. If he catches himself leaning on it more than usual, he takes it as a sign that he’s losing trust in his report and quickly takes action. “It’s important to intervene early as soon as you recognize you’re starting to lose trust in a report. Micromanagement is a great trigger that this is happening,” says Desai. “That’s when I tell them I'm starting to lose confidence in them."
• Empower team members a few rungs below you to deliver feedback. Hareem Mannan (ex-Pave and Segment) created weekly peer office hours as a feedback mechanism to help ship higher-quality work at scale. “When I felt like the work of a direct report was not of the quality I expected, instead of using my 1:1 time critiquing, I would ask them to go to office hours that week,” says Mannan. “Sometimes I’d chat with the person who was leading the office hours and let them know the challenges I was seeing and where I’d like to see improvement, without dictating exactly how to get to that end result.”

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-A Maven Lightning Lesson on how to delegate with AI

-A 10-minute LinkedIn audience research hack

This week, a fractional COO answers all the FAQs she gets from early-stage founders about working with this type of leader.

Should You “Rent” an Exec for Your Startup? A Fractional COO Weighs In

If LinkedIn chose a word of the year like Merriam-Webster, it might be “fractional.” Suddenly, it seems like every former startup C-suite leader has adopted this new title.

Amanda Schwartz Ramirez is part of this wave of seasoned operators moving into fractional work. After a decade of standing up new business units and corporate functions at PayPal and a stint at a hypergrowth startup, she now works with early-stage founders as a fractional COO. Many folks like her are making the same transition to bring their expertise to early-stage startups without the gamble of betting on a single company.

So what’s the appeal on the hiring side? Bringing on a fractional leader, says Schwartz Ramirez, can be a safer alternative to “building” or “buying” an exec. Instead of promoting an existing teammate or hiring externally, you can “rent” first and tackle immediate needs without the commitment (and cost) of a full-time hire.

“Finding the perfect executive is like trying to throw darts at a moving dartboard and hit a bullseye. A fractional leader can help you understand what you need while you're figuring out what it is you're building,” she says.

In this exclusive interview, Schwartz Ramirez demystifies the role of the fractional exec at an early-stage startup, laying out how “renting” senior leadership can help founders avoid costly detours and multiply their team’s impact. She digs into:

• What a fractional exec really does and how they’re different from a consultant or advisor
• How to weigh your options when your startup needs a new capability: hire someone full-time, promote a star player, “white-knuckle” internally (and tack the scope onto everyone’s role) or go the fractional route
• The type of work and functions fractional execs can help establish and amplify at each level of PMF
• How to find and vet the right fractional exec

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-More of Schwartz Ramirez’ ops wisdom

-Clay is hosting an inaugural conference for go-to-market leaders in San Francisco

-An ultra-detailed survey of how tech workers are feeling right now

This week, we’re detailing Figma’s eval process for its new AI product, Figma Make — one that centered around scaling human judgement.

The Art of Evals: How Figma Put People at the Center of Its AI Product 

Building an AI product requires a fundamentally different process. Unlike traditional software where there’s a clear path to see what’s possible, the capabilities of an AI product exist in a foggy middle ground that’s only validated through actual user testing.

“There’s a different playbook being developed inside every product team right now about how to scale human taste,” says David Kossnick, Figma’s Head of Product, AI. And to create its new prompt-to-functional-app experience, Figma put human craft and creativity at the center — from defining success metrics, to the process for gathering qualitative feedback, to exploring how to assess and structure this data.

In this essay, you can expect to learn more about:

1. Figma’s decision tree for assessing AI product viability — the four paths Kossnick considers before investing further into any AI product, depending on current technology and if you can spend time making adjustments to your product scope or features.
2. Tips for constructing an AI team — AI tools can make product teams smaller and more nimble, which is extremely valuable as prototypes enable faster iteration (just don’t forget to include the target persona on the team).
3. The importance of prototyping — which Kossnick says is the new gold standard as a validation mechanism. He and the team got an “unoptimized prototype” to users as fast as possible to see what they did with the product and if it met their expectations, which shaped its development.
4. How to think about measuring success — especially when there are multiple facets of success and you need to determine which is the right one for your product.
5. The concentric circles of feedback Figma used for evals — starting small and getting broader, but always making sure the product was measured against the expected quality of its outputs.

The ground is constantly shifting under those who are building, testing and validating AI products. As new technologies and standards emerge, thinking at a higher level about how to approach these challenges can give you a way to navigate that ever-present movement.

Thanks, as always, for reading and sharing.

-The Review Editors

This week, we trace Braze’s decade-long journey from an early bet on mobile to IPO.

Braze’s Path to Product-Market Fit — How to Build for a Market That Doesn’t Exist Yet

Page the calendar back to 2011, and the state of mobile looks a lot like AI in 2025. The release of the iPhone brought mobile to the mainstream in 2007 much like ChatGPT did for AI in 2022. Within a few years, the first wave of consumers had caught on — but existing businesses hadn’t yet figured out how (or why) to treat mobile as a growth lever.

That year, a few recent M.I.T. grads and Bridgewater alums had the idea to help mobile devs monetize their apps. They called their new startup Appboy (before later rebranding to Braze).

There was just one problem: “The market wasn't ready for us to sell to it yet,” says Bill Magnuson, Braze’s co-founder who was originally CTO before becoming CEO in 2016. You could scroll Facebook or play Angry Birds on your phone, but it would be a while before major enterprises like banks and retailers — the types of customers Braze now has an extensive roster of — set up shop in the App Store.

“Our best answer to ‘why now?’ was to get a multi-year head start on something we had strong conviction in. But not everyone agreed with that. In the early days, it was sometimes difficult to maintain that full conviction because of how long it took,” he says.

Today, the customer engagement platform pulls in hundreds of millions in of dollars in Committed Annual Recurring Revenue (CARR) and has a multi-billion dollar market cap and a listing on Nasdaq. But the company’s path to get there was lined with doubts and detours:

• When they first launched a public beta in 2012, most of the 1,000 users that signed up churned because many of those apps went under (their ICP of mobile marketers wouldn’t emerge for another few years)
• Investors told them to build for gaming apps instead of building a horizontal platform, because at the time, that’s where all the money was
• It wasn’t until the Braze team raised a Series D that they received more than one term sheet

It took several years after founding to see the first meaningful sparks of traction — signing and retaining enterprise customers who were early experimenters with mobile marketing.

In the latest installment in our Paths to Product-Market Fit series, Magnuson and Chief Product Officer and early employee Kevin Wang take us through how they built a product for a market that was just starting to coalesce.

“A lot of people fall for the headlines of this or that acquisition happening quickly and in the early years,” says Magnuson. “So when they guess how long it takes on average for a company to IPO, they grossly underestimate it.” In Braze's case, it took a full decade from founding to IPO.

Braze’s story serves as a reminder that no matter how fast today’s buzziest startups zoom to revenue milestones in record timelines, building an enduring company is a long game. Magnuson and Wang share plenty of tactics and reflections for builders eyeing a market that’s still in its infancy.

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-Tips for choosing the right OKRs for early-stage startups

-Inspo for a “how to work with me” guide (and check out this Review article for more pointers on how to write your own)

This week, we’re publishing the third installment in our new series on going from 0 to multiple millions in ARR. Today’s guide is all about how now-massively successful startups found their initial ICP.

0-$5M: How to Identify Your ICP — Lessons from Vanta, Clay, Retool

In the early days of building a startup, there’s a certain dopamine hit that comes from hearing:

"This product is so powerful. We could use this for all kinds of things!"

But that excitement can quickly fade into something more dangerous: Inconsistent usage. Feature creep. A tangled roadmap that tries to be everything for everyone — and ends up serving no one particularly well.

That’s exactly what happened to Clay, for example. Early users were enthusiastic, but their use cases were wildly different — from recruiters to accountants to engineers. And Clay tried to hang onto each and every one of these early customers. In turn, it caused a years-long spiral as the team kept switching who they were building for, chasing the loudest feedback and watching momentum stall again and again.

In the latest installment of our 0-$5M series with First Round Partner Meka Asonye, we dig into how now-massively successful startups finally cracked the code on their ICP. In addition to Kareem Amin, here’s who else you’ll learn from:

• Christina Cacioppo, co-founder and CEO of Vanta
• David Hsu, founder and CEO of Retool
• Waseem Daher, co-founder and CEO of Pilot
• Bryant Chou, co-founder and Chief Architect of Webflow
• Eric Berg, former Chief Product Officer at Okta
• Hubert Palan, founder and CEO of Productboard
• Mike Molinet, founder of Branch and now building Thena

Small spoiler alert here: For most of these startups, their first crack at an ICP was way off the mark. We unpack the pivotal moments that happened behind the scenes to find ICP clarity, like:

• How Vanta’s aha moment came from a single conversation with an engineer at Figma
• How Retool invalidated their initial ICP hypotheses — and found a Fortune 250 customer instead
• How Productboard used green/yellow/red scoring to rein patterns emerge

If you’re in the early stages of building — or trying to rein in a sprawling roadmap — this one’s worth the read. Because the wrong customer doesn’t just waste your time, they shape your product in all the wrong ways.

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-Is your AI idea any good? A 5-question stress test

-The GAINS comp negotiation playbook.

🎙️ On the In Depth podcast:

The story of Rick Song and Persona is not the standard founder story. Rick was incredibly reluctant to leave Square and become a startup founder (his mantra at the time was "Life's too short to try new things," he joked). He set out to invalidate the idea early on, convinced that a horizontal approach to identity verification simply wouldn't work.

Rick gets candid about imposter syndrome, the evolution from engineering to commercial thinking and his vision for who we are online in an AI-dominated world.

From reluctant founder to $2B valuation: The story of Persona | Rick Song (Co-founder and CEO)

Rick Song is the co-founder and CEO of Persona, the identity verification platform used by some of the world’s largest companies. Before starting Persona, Rick worked on identity fraud and risk products at Square, which laid the groundwork for what would become Persona’s highly technical, horizontal platform. Since

First Round ReviewFirst Round Staff

This week, we’re tackling the work before the work — how to start building your emotional toolkit for the founder journey ahead.

Thinking About Taking the Founder Leap? Here’s How to Prep for the Emotional Gauntlet

Psychologist Dr. Emily Anhalt was sitting in a coaching session with a founder who just finished a successful Series A raise. It was a major milestone — but instead of feeling triumphant and celebratory, the founder was more anxious than ever. “I thought that once we raised money, the stress would ease,” the founder said. “But now I’m terrified of letting down our investors, my team and our customers.”

In her 15 years of experience as a therapist and executive coach, Dr. Anhalt has sat across from countless founders echoing the same sentiment. They certainly expect that starting a company will bring its fair share of lows where they are forced to just grind it out, against all odds. But what is much less expected is the realization that achieving one goal becomes the starting line for ten new ones.

That’s why she’s adamant that founders who are early in their journey start taking this work seriously now, or even better, before they put “Something New” at the top of your LinkedIn profile.

“Think of it as creating shock absorbers for your emotional vehicle — they don't eliminate the bumps in the road, but they make them more manageable,” says Anhalt.

On the Review, she picks up the pen and sketches the four steps for getting started. Here’s a preview of what’s in store:

Step 1: Identify your fears so you can face them. “When you’re riddled with anxiety about taking the founder leap, start by pinpointing the fear and naming it. Is it financial instability? Judgment from others? Torpedoing a relationship with a friend-turned-co-founder? Not being able to raise funding? Getting specific makes it easier to take tactical steps to address that specific fear.”

Step 2: Figure out your “why to address uncertainty. “Ask yourself: In five years, will I regret not trying more than trying and it not working?”

Step 3: Create systems for longer-term resilience. “Don't wait until you're burning out to create boundaries or for time to open up to take care of yourself. Put structures in place before you need them. The most successful founders I work with aren't the ones who can push through anything — they're the ones who build sustainable practices.”

Step 4: Find circles of trust to manage founder loneliness. “There's a fundamental shift that happens — from fear about uncertainty (’Will this work?’) to pressure about sustainability (’How do I keep this going?’).”

You can also pick up her brand-new book, “Flex Your Feelings: Train Your Brain to Develop the 7 Traits of Emotional Fitness,” on virtual and physical bookshelves today.

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-This conversation between Stripe CEO Patrick Collison and Sir Jony Ive (former Chief Design Officer at Apple).

-Startups rarely die from bad code. They die from false confidence.

This week, we assembled advice from an all-star group of founders, product leaders and first marketing hires for a tactical guide to taste.

The Unsung Ingredient in Stripe, Square and Linear’s Success: Taste

Taste is trending — in Substack newsletters, X replies, and LinkedIn posts, conversations about craft are spilling out from the artistic world and popping up in tech circles more than ever.

There have long been companies (like Apple and Stripe) revered for their taste and quality. So why does it seem like the rest of tech is just starting to catch on now over the past couple of years?

To put it simply (and to borrow from product designer Shane Levine), code is no longer a moat. We are living in the most accessible time in history to build software — and AI’s flood into the mainstream has lifted all boats. It’s faster and cheaper than ever to build, market and sell new products — just executing quickly is not a differentiator anymore. You’re probably not the “first of” anything; or if you are, a competitor is likely not far behind, nipping at your heels.

We’d rather not add to the cacophony of voices echoing each other about how taste and craft are important. Instead, what we’ve found underexplored is discussions on operationalizing taste.

So, we mined the Review archives and the In Depth podcast airwaves for the best bits of advice we could find from folks at companies like Stripe, Square, Linear and Slack. As it turns out, at First Round we’ve been asking people about craft long before taste was taking over the zeitgeist. Here’s who we spoke to:

• Krithika Muthukumar, Stripe’s first marketing hire and former VP of Marketing at OpenAI
• Karri Saarinen, founder & CEO of Linear
• Alyssa Henry, former CEO of Square
• Milin Desai, CEO of Sentry
• Julie Supan, YouTube’s first Head of Marketing
• Anthony Casalena, CEO of Squarespace
• Noah Desai Weiss, former CPO of Slack
• Jiaona “JZ” Zhang, CPO of Linktree

And here’s a preview of some of the advice that's in store:

• Implement reviews at the 20% and 80% mark. Do not wait until a project is nearly out the door to review it. “At Stripe, we would do a 20% strategy review to make sure that we were aligned on the goals and intent of any big project. Then we would do an 80% review for the execution and check in on how things were going, like what the collateral looked like,” says Krithika Muthukumar, who was Stripe’s very first marketing hire. “It’s important that you review at the 80% mark, not the 99% mark because you still want the ability to make changes based on what comes up.”
• Test drive taste with a work trial. Probing for something as nuanced as taste can be exceptionally difficult in an interview setting. That’s why, before committing to any full-time hire, Linear has candidates complete a paid 2-5 day work trial, where they work with the team on a real project.
• Codify your product principles. To distill Slack founder Stewart Butterfield’s distinct product intuition throughout the rest of the company, Chief Product Officer Noah Desai Weiss instituted a set of product principles (like “don’t make me think” and “be a great host”). “They are all a bit simple and almost glib when you hear them, but when you unpack them, there’s a whole set of stories and examples around them. They created a shared language within the product org for not just our values, but how we apply those values in instances where it’s more subjective and about taste.”

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-Vercel's CEO Guillermo Rauch on building taste

-How to build your early marketing team (from Notion’s former CMO)

-4 questions for assessing new job fit

Today on The Review, we explore the human side of engineering orgs, with Apple engineering leader and veteran of Palantir and Slack, Michael Lopp.

Mastering the Human Side of Engineering: Lessons from Apple, Palantir and Slack

Even though it’s never been easier to create software, Michael Lopp — engineering leader at Apple and veteran of Palantir and Slack — still believes the center of exceptional engineering orgs are its people and their dynamics.

Good judgement. Incredible operations. Sound decision-making. “When I look at the last three companies I was at, they’re all completely different businesses,” Lopp says. “But they all shared the same ethos that prioritized engineering, rapid growth and smart people.”

In this exclusive interview, Lopp goes beyond the technical aspects of the engineering function, instead turning his attention to its people. He provides founders and managers with tactical advice for structuring their engineering org and how to get the most out of the people who comprise it.

1. Encourage “wolf time” — in Lopp’s ideal world, engineers split their time 71/29. 71% of the time is for doing the things they need to get done. The other 29% of the time is doing whatever is inspiring based on the 71% stuff.
2. Keep debate regular — specifically, debate between product, design and engineering. He believes companies give themselves the best chance at making sound decisions by having a steady stream of cross-org debate.
3. Build operational systems that can scale while maintaining quality — Lopp says having sound judgement and maintaining sound operations leads to creating and scaling good products.
4. How to foster the relationship between product and engineering teams — make sure PMs are telling the story of the “why” behind the product, and engineers understand that, so they can focus on the “how.”

Lopp also shares the traits he’s seen successful leaders possess across his career, from being malleable, to a good storyteller, to understanding individuals’ goals (so leaders can help them grow).

Whether you’re a new engineering manager or are seasoned in leading teams, Lopp’s insights are rooted in the ever-present, yet always-changing thing that powers your org — your people. Knowing what motivates them and how they work together is a vital component to the success of the engineering function and thus, your company.

As always, thanks for reading and sharing.

-The Review Editors