In Depth

Dennis Pilarinos is the founder and CEO at Unblocked, a developer tool that lets you talk to your codebase. In 2018, Dennis’ first company, Buddybuild, was acquired by Apple, and he was subsequently appointed Director of Development Technologies. Before that, Dennis was a Senior Director at AWS and a Director at Microsoft.

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In today’s episode, we discuss:

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Referenced:

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Where to find Dennis Pilarinos:

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Where to find Brett Berson:

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Where to find First Round Capital:

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Timestamps:

(00:00) Introduction

(02:18) Why building for developers is different

(07:28) Buddybuild’s origin story

(10:40) Early signs of product market fit

(12:22) Managing mental health as a second-time founder

(21:09) Building and scaling Unblocked

(29:52) Dennis’ cautious take on AI

(34:20) Being customer-obsessed

(35:25) Unblocked’s decision-making process

(38:31) Don’t over-index on competency when hiring

(43:36) Why great product is everything

(45:41) Monetizing product market fit

(48:21) The power of positioning

(51:48) Why Dennis doesn’t do demos

(54:45) How to deal with customer feedback

(57:29) Stewart Butterfield’s impact on Dennis

May Habib is the co-founder and CEO of Writer, a full-stack generative AI platform built for enterprises. The model is trained on a customer’s own data to create content that is consistent with their brand style and voice. Writer recently raised $100M at a valuation of around $500M. Prior to Writer, May co-founded Qordoba, an AI writing assistant.

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In today’s episode, we discuss:

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Referenced:

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Where to find May Habib:

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Where to find Todd Jackson:

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Where to find First Round Capital:

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Timestamps:

(00:00) Introduction

(02:34) Writer’s origin story

(06:30) Building a full-stack generative AI platform for enterprise

(11:56) The #1 challenge building Writer

(15:41) Writer’s approach to finding champion customers

(20:29) How Writer is winning the enterprise space

(27:11) Signs Writer found product-market-fit

(29:26) Scaling LLMs for specific use cases

(31:53) Writer’s goals for 2024

(33:57) Advice for 0 to 1 founders

(35:53) Creating a culture of “connect, challenge, and own”

Amjad Masad is the co-founder and CEO of Replit, an online platform designed for collaborative coding in multiple programming languages. Replit boasts over 30m users, has secured $200M in venture funding, and was recently valued at $1.2B. Before Replit, Amjad was a Software Engineer at Facebook, and a Founding Engineer at Codecademy.

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In today’s episode, we discuss:

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Referenced:

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Where to find Amjad Masad:

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Where to find Todd Jackson:

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Where to find First Round Capital:

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Timestamps:

(00:00) Introduction

(02:31) Replit’s origin story

(08:24) Starting Facebook’s JavaScript infrastructure team

(10:36) Amjad’s unique path to entrepreneurship

(16:04) How Replit got its early users

(17:00) Replit’s fundraising difficulties

(17:54) Why YC almost rejected Replit four times

(20:23) Building Replit’s distribution engine

(22:08) Drivers of Replit’s growth

(27:41) What Silicon Valley gets wrong

(30:09) Replit’s monetization strategy

(32:29) Integrating AI into the platform

(36:18) The impact of AI on software engineering

(39:40) Defining the new “software creator” role

(41:43) How to keep up with developments in AI

(46:24) Replit’s goals for 2024

(48:11) Advice for founders: defy conventional wisdom

(51:12) Amjad’s 4 favorite books

Michael Cieri is the Chief Product Officer at Gusto, an HR and payroll platform used by more than 300,000 businesses. With a decade of experience, he has led successful SMB product development and scaled high-performing orgs. Before Gusto, Michael was also the Head of Product at Square, where he led a team of 15+ PMs responsible for $600m in annual revenue. Michael was also the VP of Product Management at Opendoor.

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In today’s episode, we discuss:

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Referenced:

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Where to find Michael Cieri:

• LinkedIn: https://www.linkedin.com/in/michaelcieri/

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Where to find Brett Berson:

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Where to find First Round Capital:

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Timestamps:

(00:00) Introduction

(02:41) Why SMBs require unique software solutions

(05:58) The level of specificity required when building for SMBs

(08:47) Finding Square’s form-fitting solution

(11:48) Building vertical versus horizontal SaaS

(14:34) Inside Square and Gusto’s decision making framework

(16:15) How to build horizontally from a wedge product

(23:00) Using the Three Horizons Model

(25:29) How to craft a compelling vision for products

(28:51) How to assess Horizon 3 bets

(32:08) How to give employees the freedom to try things

(34:24) Creating a risk-taking culture

(37:27) Essential advice for new PMs

(40:27) Common thread with bad product pitches

(42:29) Applying the Horizon framework at Gusto

(44:46) Developing good product sense

(47:43) 5 signs of great product sense

(49:03) Why product sense is like athletic ability

(51:43) How to ship faster without increasing headcount

(56:10) People who had an outsized impact on Michael

Stephanie Berner is a Customer Success Executive at LinkedIn. Since 2018, Stephanie has spearheaded all post-sales functions at LinkedIn Sales Solutions through its period of rapid growth. With a background in building and scaling customer success teams at Box, Medallia, and Opower, Stephanie has extensive experience in delivering exceptional customer experiences across various company stages.

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In this episode, we discuss:

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Referenced:

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Where to find Stephanie Berner:

• LinkedIn: https://www.linkedin.com/in/stephanieberner/

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Where to find Brett Berson:

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Where to find First Round Capital:

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Timestamps:

(00:00) Introduction

(02:21) Formalizing customer success at a startup

(05:01) Hiring ICs before CSMs

(06:22) Tactics for hiring standout talent

(11:39) 3 questions to ask candidates

(15:38) Fail-case patterns among customer success hires

(17:49) Considering candidates with non-traditional backgrounds

(21:21) Indexing toward a bias for action

(24:17) What v1 of customer success looks like

(26:03) Key early-stage customer success metrics

(28:21) Whether customer success or sales should own renewals

(30:40) Where customer success fits into the org

(32:14) Why customer success doesn’t report to an executive

(33:48) Distinguishing a product problem from a customer success one

(35:18) Simple way to deal with customer churn

(39:21) Tactics to get customers to give honest feedback

(40:58) What happens when customer success and product teams collaborate

(44:14) Rituals for zero-to-one customer success

(48:23) How to structure an early customer success team

(52:01) Structuring compensation packages

(54:35) Aligning customer success with the business model

(60:14) The role of customer success in B2B software

(62:17) Common customer success mistakes

(67:44) People who had an outsized impact on Stephanie

Michael Lopp is an experienced engineering leader known for building products at iconic companies like Apple, Borland, Netscape, Palantir, and Slack. Since 2002, Lopp — as he’s more commonly known — has written about engineering, management, and leadership on his popular blog ‘Rands in Repose’. He is also the renowned author of three books: Being Geek, Managing Humans, and The Art of Leadership.

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In today’s episode, we discuss:

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Referenced:

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Where to find Michael Lopp:

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Where to find Brett Berson:

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Where to find First Round Capital:

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Timestamps:

(00:00) Introduction

(02:20) Beginning career at Borland

(05:41) The difficulty with shipping software at scale

(07:52) Why it’s harder to ship today than ever before

(09:42) What makes a startup operationally sound

(11:23) Why engineers should have concrete time to invent

(19:42) How PMs can improve engineering culture

(21:35) An engineer’s perspective on good product management

(23:36) The role of product compared to design and engineering

(26:38) How micromanagement kills creativity

(29:35) Fostering a debate culture in an org

(31:26) Declarative versus prescriptive leadership

(36:09) 3 ideas on leadership from Lopp’s upcoming book

(38:29) Understanding employee motivation

(42:28) Advice on discovering what motivates people

(46:06) Why teams should reorg every 6 months

(48:32) One thing all successful leaders do

(52:22) Why sound judgment is crucial for decision-making

(53:45) Crystallized lessons from working at software giants

(56:19) Why Lopp is afraid of becoming irrelevant

(57:58) The number one leadership lesson from Lopp’s career

(59:32) What Lopp has changed his mind on over time

(61:12) People who had an outsized impact on Lopp

Kareem Amin is the co-founder of Clay, a lead-generation software that uses AI to scrape 50+ databases and help companies scale their outbound campaigns. Before Clay, Kareem was the VP of Product at The Wall Street Journal. Kareem also co-founded Frame (useframe.com) which was acquired by Sailthru in 2012.

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In today’s episode, we discuss:

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Referenced:

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Where to find Kareem Amin:

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Where to find Todd Jackson:

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Where to find First Round Capital:

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Timestamps:

(00:00) Introduction

(02:36) Clay’s origin story

(05:54) Building for a specific customer

(10:42) Knowing when to build for a broader customer-base

(12:46) The life spiral framework

(15:52) How founders can make better decisions

(18:57) Kareem’s principles for product-market-fit

(25:36) Clay’s customer journey

(30:04) Interesting tactic to find power users

(34:00) How to know you have product-market-fit

(37:11) The impact of founder psychology on the business

(39:41) Mastering commitment to sprints

(40:47) How Kareem’s own personality affected his company

(43:31) Actionable advice to understand founder psychology

(46:25) Why focus is misunderstood

(47:09) The mindset shift from a first to second-time founder

(50:28) What’s next for Clay

(52:14) The best piece of advice Kareem has actioned

Kyle Parrish, Figma’s first sales hire, built the company’s zero-to-one sales engine from scratch. Figma now has more than 3 million monthly users. Prior to Figma, Kyle spent 5 years at Dropbox in various sales roles. At Dropbox, Kyle successfully launched and scaled the Austin office to 100+ people, and then led the enterprise sales function in San Francisco and New York.

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In today’s episode, we discuss:

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Referenced:

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Where to find Kyle Parrish:

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Where to find Brett Berson:

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Where to find First Round Capital:

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Timestamps:

(00:00) Introduction

(02:10) What founders need to figure out before hiring salespeople

(03:48) Who to hire as your first salesperson

(05:34) Transitioning away from founder-led sales

(07:07) Tactics for hiring great salespeople

(12:50) The ideal experience sales candidates should have

(13:49) Common traits of successful salespeople

(18:45) What it was like being Figma’s first sales hire

(19:59) Interesting tactic to integrate the first sales hire

(21:16) How Figma executed its early sales motion

(32:27) Why Figma changed its customer narrative

(34:03) Building outbound sales strategy at Figma

(36:17) Segmented pricing and no discounts

(41:55) Kyle’s transition from Dropbox to Figma

(47:25) Creating a world-class sales culture

(51:46) How Figma does sales differently

(54:02) Building the initial sales team around a passion for the product

(57:12) Figma’s unique hiring process for salespeople

(60:40) Advice for founders hiring their first salesperson

(63:18) The secret to Dylan Field’s success

(64:33) How to scale yourself as an early hire

(66:25) Oliver Jay’s impact on Kyle

Oliver Jay is a sales and expansion specialist. Oliver was Chief Revenue Officer at Asana and led the company’s global expansion. He grew the team from 20 to 450 people and increased international income to 40% of Asana’s total revenue. Prior to this, Oliver built the first business sales team at Dropbox, and led the company’s expansion into the Asia-Pacific region while tripling ARR. Oliver is now an advisor and leadership coach focused on assisting founders and executives in scaling their businesses.

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In today’s episode, we discuss:

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Referenced:

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Where to find Oliver Jay:

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Where to find Brett Berson:

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Where to find First Round Capital:

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Timestamps:

(00:00) Introduction

(02:23) Differences between PLG and enterprise companies

(05:56) Avoiding the “PLG trap”

(07:39) Transitioning to enterprise feels like building two companies

(10:57) Thinking about user value versus company value

(13:58) The relationship between OKRs and executive champions

(14:59) Dropbox had almost no company value

(15:33) The strategy PLG companies should avoid

(18:30) Why Dropbox is worth $10b, not $50b

(19:41) The story of Asana’s expansion

(21:16) Asana’s unique customer success team

(23:27) How product strategy relates to finding champions

(25:03) How Asana structured its GTM org

(27:11) What Oliver would have done differently with Asana’s GTM

(29:45) Getting executive-level buy-in

(31:49) Asana’s concept of “selling clarity”

(33:18) An inside look at Asana’s transition into enterprise

(37:59) The champion tree framework

(40:43) Structuring Asana’s early enterprise sales team

(44:27) The impact of company size on GTM

(47:20) Common sales mistake

(48:29) The seed, land, and expand framework

(51:43) Oliver’s advice to founders

(54:13) Why building horizontally may be a mistake

(55:32) Common challenges faced by PLG companies

(58:30) How PLG companies can break the $10b market cap

(60:17) Why emulating Atlassian’s playbook is difficult

(63:21) People who had an outsized impact on Oliver

Steve Blank, an Adjunct Professor at Stanford University, is widely regarded as the father of modern entrepreneurship. Prior to academia, Steve’s career spanned eight different startups. Credited with launching the Lean Startup movement with his May 2013 Harvard Business Review cover story, Steve has changed how startups are built, and how entrepreneurship is taught. Steve is also the renowned author of The Four Steps to the Epiphany and The Startup Owner’s Manual.

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In today’s episode, we discuss:

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Referenced:

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Where to find Steve:

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Where to find Brett:

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Where to find First Round Capital:

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Timestamps:

(00:00) Introduction

(02:20) Why there aren’t more successful startups

(06:07) Outlier founders have similar childhoods

(10:34) How to be a successful founder CEO

(12:00) Why entrepreneurship should be taught in schools

(16:39) The importance of curiosity

(19:57) The role of instincts in entrepreneurship

(22:31) Having profound beliefs in a vision

(24:17) Building in existing versus new markets

(29:09) What second-time founders can get wrong

(33:49) Why founders need to be irrational

(39:28) Common traits shared by outlier founders

(45:05) Evaluating what makes a startup successful

(49:44) Steve’s assessment of Satya Nadella at Microsoft

(52:26) What it takes to build an incredible company

(60:45) The Four Steps to the Epiphany in 2023

(64:36) The origins of The Four Steps to the Epiphany