In Depth
In Depth is a podcast from The First Round Review that surfaces tactical advice for founders and startup leaders. Hosted by Brett Berson, a partner at First Round, it covers topics such as hiring executives, becoming a better manager, and the importance of storytelling inside an organization. Each interview aims to reach the level of tactical depth where the best advice is found.
Episodes
The fastest way to learn is to run two competing bets | Jay Parikh (EVP CoreAI, Microsoft)
In the latest episode of Executive Function, Brett sits down with Jay Parikh, Executive Vice President of CoreAI at Microsoft. Before joining Microsoft, Jay spent over a decade as Facebook's global head of engineering, scaling the company from a few hundred engineers to billions of users, then ran the cybersecurity company Lacework as CEO through its acquisition by Fortinet. In this conversation,
What startups get wrong about enterprise | Lindsey Scrase (COO, Checkr)
In the latest episode of Executive Function, Brett sits down with Lindsey Scrase, COO of Checkr. Before joining Checkr as CRO and later stepping into the COO seat, Lindsey spent nearly a decade at Google Cloud as global managing director for SMB, mid-market, and startups. In this conversation, she breaks down why moving upmarket into enterprise trips up so many startups looking to scale, how Check
How Gamma pulled off their AI pivot | Jon Noronha (Co-founder and CPO of Gamma)
In this episode of In Depth, Brett sits down with Jon Noronha, co-founder and CPO of Gamma, the AI-native presentation platform used by more than 100 million people. In this conversation, he walks through Gamma’s distinct eras of product-market fit: from a pre-AI struggle with a year of runway left, to an overnight AI-fueled explosion, to today’s unplanned scramble into enterprise sales. Jon also
Why Plaid’s COO cold-calls new hires | Eric Sager (COO of Plaid)
In the latest episode of Executive Function, Brett sits down with Eric Sager, COO of Plaid, following stints as CRO of Bluevine and Head of Sales at Square. During his seven-year tenure at Plaid, Eric has helped lead the business through a pandemic, Visa's collapsed acquisition, a fintech downturn, and the AI boom. In today’s conversation, he unpacks how he kept teams focused during turbulent time
How Supabase became the essential infrastructure for the AI era | Paul Copplestone (Co-founder, CEO)
In this episode of In Depth, Brett sits down with Paul Copplestone, co-founder and CEO of Supabase, the open-source Postgres platform now serving more than seven million developers. Before Supabase, Paul launched a Thumbtack-style marketplace in Southeast Asia and co-founded an office-management startup called Nimbus, experiences that taught him to separate fundraising from building and to find pr
How to build a beloved tech brand | Sheila Joglekar Vashee (CMO, Figma)
In today's conversation, Brett sits down with CMO of Figma, Sheila Joglekar Vashee. Previously the second marketing hire at Dropbox, where she helped scale the company past $1 billion in revenue, she now leads marketing at Figma fresh off its IPO. In an industry that has spent a decade trying to turn marketing into something closer to hedge fund trading, Sheila argues the art was always the point
Why old-school sales work still wins in the AI era | Graham Moreno (Head of GTM, Parallel)
In the latest episode of Executive Function, Brett sits down with Graham Moreno, Head of GTM at Parallel Web Systems. Before Parallel, Graham scaled Windsurf's GTM organization from three sellers to seventy-five in under a year, served as President through the Cognition acquisition, and earlier built and led enterprise sales teams at Grafana Labs and MongoDB. In this conversation, he unpacks why t
Why founders should bet on first-time executives | Praveer Melwani (CFO, Figma)
In this latest episode of Executive Function, Brett sits down with Praveer Melwani, CFO at Figma. Praveer joined Figma in 2017 as the company's first business operations and finance hire—when the team was around 30 people and not yet charging for the product—and stepped into the CFO seat in 2022, helping to lead the company’s IPO in 2025. In today’s conversation, Praveer breaks down the step funct
Why great product leaders should stop obsessing over the roadmap | Diya Jolly (CPO & CTO of Xero)
In the latest episode of Executive Function, Brett is joined by Diya Jolly, Chief Product and Technology Officer at Xero. Before Xero, Diya was CPT at Okta and led YouTube's advertising monetization products at Google. In this conversation, she unpacks her three-bucket framework for delegating decisions, why the most important part of a CPO’s role is to drive team-wide ambition, and why the best e
Inside Artemis' "AI vs AI" war | Shachar Hirshberg & Dan Shiebler (Co-founders, Artemis)
In this episode of In Depth, First Round Partner Josh Kopelman sits down with Shachar Hirshberg and Dan Shiebler, co-founders of Artemis, the AI-native security platform that just emerged from stealth with $70M in combined seed and Series A funding. Shachar and Dan unpack how they built a 30-person team in seven months, why AI-native companies are outperforming their AI-enabled counterparts, and w
Scaling DoorDash to market dominance | Christopher Payne (Former COO, DoorDash)
In this latest episode of Executive Function, Brett sits down with Christopher Payne, who spent a decade as President and COO at DoorDash, helping scale the company from roughly 70 employees to the dominant food delivery platform in the US. Before DoorDash, Christopher held senior operating roles at Amazon and eBay, where he led a sweeping overhaul of marketplace search. In this conversation, he u
The most politically dangerous role in the C-suite | Katie Burke (COO, Harvey)
In the latest episode of Executive Function, Brett sits down with Katie Burke, who recently became COO of Harvey after joining as Chief People Officer. Before Harvey, Katie spent 11 years in HR leadership at HubSpot, where she built one of tech's most distinctive cultures. In this conversation, she unpacks her marketing-minded approach to HR, why she hired deliberately from hospitality rather than
What nobody tells engineers about becoming a CEO | Jay Kreps (Co-founder and CEO, Confluent)
Jay Kreps is the co-founder and CEO of Confluent, the company built around Apache Kafka — the open-source data streaming platform he originally built while at LinkedIn. In this conversation, Jay shares his full journey: how Confluent grew from a scrappy group of engineers with no go-to-market experience into a publicly traded enterprise software company. He makes the case that the difference betwe
The product wisdom every CPO should ignore | Jeremy Epling (CPO, Vanta)
In the latest episode of Executive Function, Brett is joined by Jeremy Epling, CPO of security and compliance platform Vanta. Jeremy details his career journey, unpacking what it took to make the jump from tenured Microsoft executive to startup CPO. He also shares hard-won insights: how to maintain shipping velocity as headcount explodes, how to manage performance without the safety net of big-com
Building Zipline: From launch disaster to drone-delivery giant | Keller Cliffton (Co-founder, CEO)
Keller Cliffton is the co-founder and CEO of Zipline, the world's largest commercial autonomous delivery system, which today serves 5,000 hospitals across multiple countries and saves an estimated 17,000 lives per year. In this episode, Keller breaks down his extreme hiring philosophy that has powered Zipline for over a decade. He also walks through Zipline’s full origin story: from a near-dead ho
Snowflake’s first sales hire on scaling from $0 to $3.5B | Chris Degnan (Former CRO, Snowflake)
Chris Degnan was the first sales hire at Snowflake and spent 11 years scaling the company from zero to $3.5 billion in revenue as its CRO, working alongside four different CEOs and learning from each one. In this episode, Chris breaks down what it actually takes to scale an enterprise sales organization, why MEDDIC is the methodology every founder should know, and what working under Frank Slootman
Why 90% of CROs will fall behind in the next 2 years | Stevie Case (CRO, Vanta)
Stevie Case is the CRO of Vanta, the trust management platform serving everyone from founders to Fortune 100 CISOs. A former pro-video gamer who stumbled into sales through a mentor's bet, Stevie has built one of the most unconventional paths to the C-suite in tech. In this episode, she unpacks why early revenue hires fail, what separates a true CRO from a VP of Sales, and why she believes fewer t
Figma is not the source of truth | Ryan Lucas (VP of Design, Rippling)
In the second Executive Function episode, Brett sits down with Ryan Lucas, VP of Design at Rippling. Before Rippling, Ryan led design at Retool and co-founded multiple startups, bringing a rare founder's perspective to design leadership. A trained industrial designer, Ryan traces the roots of modern software design back 2,000 years to make the case that products must be useful, usable, and desirab
Executive Function: Building systems that can make decisions without you | Jeanne DeWitt Grosser (COO, Vercel)
In the first Executive Function episode, Brett sits down with Jeanne De Witt Grosser, Chief Operating Officer at Vercel. Before Vercel, Jeanne spent nearly a decade at Stripe, where she built and scaled global revenue teams and led product partnerships. In this conversation, she unpacks what separates good executives from extraordinary ones, shares her rigorous executive hiring process, and reveal
Building Meter for decades, not an exit | Anil Varanasi (Co-founder and CEO)
Anil Varanasi is the co-founder and CEO of Meter, which provides full-stack networking infrastructure as a service for businesses. Since founding Meter with his brother Sunil in 2015, Anil has been playing a distinctly long game in one of the most entrenched markets in technology, betting on vertical integration, business model innovation, and a multi-decade time horizon. In this conversation, he
How Harness runs 16 “startups within a startup” at scale | Jyoti Bansal (Co-founder and CEO)
Jyoti Bansal is the co-founder and CEO of Harness, the software delivery platform used by thousands of engineering teams, and previously founded AppDynamics, which he led from inception to a multibillion-dollar acquisition by Cisco. In this episode, Jyoti unpacks what it really takes to move from mid-market to enterprise, why he thinks in terms of “product-market-sales fit,” and how he structures
How to build a company you’ll run forever | Zack Kanter (Founder and CEO of Stedi)
Zack Kanter is the founder and CEO of Stedi, an API-first healthcare clearinghouse. After bootstrapping a wildly profitable auto-parts business, he sold it to tackle "the most complicated problem" he'd ever encountered: business-to-business transaction exchange. He spent years building EDI infrastructure, threw away the entire codebase eight times, and found extraordinary traction in healthcare. S
Go hard early: How lessons from Verkada shaped Serval's AI agents for IT teams | Jake Stauch (Founder and CEO)
Jake is the founder and CEO of Serval, an AI-driven IT automation and service management platform that just raised $47M in Series A funding this week. Before founding Serval, Jake spent over five years at Verkada, where he led multiple products from 0-1 and helped scale the company across hardware and software. His years at Verkada taught him that winning in enterprise means delivering consumer-qu
The pivot that paid off: How fal found explosive growth in generative media | Gorkem Yurtseven (Co-founder and CTO)
Gorkem Yurtseven is the co-founder and CTO of fal, the generative media platform powering the next wave of image, video, and audio applications. In less than two years, fal has scaled from $2M to over $100M in ARR, serving over 2 million developers and more than 300 enterprises, including Adobe, Canva, and Shopify. In this conversation, Gorkem shares the inside story of fal's pivot into explosive
From dorm room to life-saving AI | Prepared’s story | Michael Chime (Co-founder & CEO of Prepared)
Michael is the co-founder and CEO of Prepared, the AI assistant for 911 calls that helps dispatchers capture information faster, translate emergency calls in real time, and deliver lifesaving context to first responders. Founded out of Yale in 2019, Prepared grew from a school safety app into a critical platform for emergency communications, disrupting a notoriously tough market. This mission-driv
Saying yes to everything: How customer obsession built Samsara | Kiren Sekar (CPO)
Kiren Sekar is the CPO of Samsara, a company that brings real-time visibility, analytics, and AI to physical operations. Before Samsara, Kiren was an early leader at Meraki, which was acquired by Cisco for $1.2B.
In this episode, he walks us through Samsara’s origin story: from hardware hacking in a basement to scaling a cross-industry IoT platform. He shares how early customer feedback loops led
Starting an education giant in a “bad market” | ClassDojo’s story | Sam Chaudhary (Co-founder and CEO)
Sam Chaudhary is the co-founder and CEO of ClassDojo, a multi-product education platform used in 95% of U.S. schools and over 180 countries globally to connect teachers, students, and families. In this episode, Sam shares the full arc of building ClassDojo, from early skepticism about education and a failed group-making tool, to creating a communication platform loved by millions.
In this episod
From Chrome extension to $5B platform | Postman’s journey | Abhinav Asthana (Co-founder & CEO)
Abhinav Asthana is the co-founder and CEO of Postman, the world's leading API collaboration platform used by millions of developers and thousands of companies. What began as a personal itch, a simple Chrome extension Abhinav built to make his own API work easier, became a global phenomenon within weeks.
In this episode, we discuss:
Making the leap from India to Silicon Valley
The moment
How Canva leveraged unconventional growth levers to grow to $42B | Cameron Adams (Co-founder & CPO)
Cameron Adams is the co-founder and Chief Product Officer at Canva, the design platform valued at $42B as of July 2025, used by over 230 million people every month.
Before starting Canva, Cameron was a designer and engineer at Google and co-founded Fluent, an email startup. In this episode, Cameron walks through Canva’s earliest days — from the remarkably fast courtship with co-founders Melanie P
Twitter's former CEO on rebuilding the web for AI | Parag Agrawal (Co-founder and CEO of Parallel)
Parag Agrawal is the co-founder and CEO of Parallel, a startup building search infrastructure for the web’s second user: AIs. Before launching Parallel, Parag spent over a decade at Twitter, where he served as CTO and later CEO during a period of intense transformation, as well as public scrutiny.
In this episode, Parag shares what he learned from his time at Twitter, why the web must evolve to
Ignoring Silicon Valley advice to build a $3B fintech unicorn | Immad Akhund (Co-founder and CEO of Mercury)
Immad Akhund is the CEO and co-founder of Mercury, a digital banking platform that’s become the go-to financial infrastructure for startups. Before Mercury, Immad spent nearly two decades founding companies, learning the hard way what separates a good idea from a great business.
In this episode, Immad shares the hard-earned lessons from launching Mercury as his third startup. He unpacks how he
Inside the ex-YC partner’s $15B self driving car company | Qasar Younis
Qasar Younis is the co-founder and CEO of Applied Intuition, a leading vehicle intelligence platform that helps companies develop and deploy autonomous systems at scale. In June 2025, the company raised $600M at a $15B valuation. Before Applied Intuition, Qasar was the COO and a group partner at Y Combinator, and earlier founded TalkBin, which was acquired by Google. He’s also held engineering rol
What Braintrust got right about product-market fit | Ankur Goyal (Founder and CEO)
Ankur Goyal is the founder and CEO of Braintrust, an end-to-end platform for building AI apps. Before that, he founded Impira, a data management platform that was acquired by Figma, where he went on to lead the AI team. Ankur kickstarted his career when he dropped out of college to join the founding team at SingleStore (formerly MemSQL), a formative experience that shaped his views on building for
How Gusto built a $9.5 billion company by identifying a burning problem
Tomer London is the co-founder and Chief Product Officer at Gusto, the payroll and people platform used by over 400,000 businesses. He grew up helping run his dad’s clothing store in Israel — an experience that sparked his mission to build better tools for small business owners. After moving to the US for a PhD at Stanford, he met his co-founders and started Gusto.
In today’s episode, we discus
How rejecting conventional wisdom grew Sentry to a $3 billion company | David Cramer (Co-founder and CPO)
David Cramer is the co-founder of Sentry, the leading open-source error monitoring tool used by over 90,000 companies. A self-taught engineer, he went from 9th grade high school dropout and Burger King manager to building one of the most widely adopted developer tools in the world — by working hard and rejecting conventional wisdom. As of 2022, Sentry is valued at over $3 billion. David now serves
Inside Linear: Why craft and focus still win in product building | Karri Saarinen (Co-founder and CEO)
Karri Saarinen is the co-founder and CEO of Linear, the project management tool built for high-performance software teams. Since its founding in 2019, Linear has achieved a valuation of $1.25B as of 10th June 2025 and now counts companies like OpenAI, Ramp and Vercel as customers. Before founding Linear, Karri led design at Airbnb and Coinbase, and previously co-founded Kippt, a bookmarking tool a
How Wes Kao coaches founders to influence, lead, and get what they want | Wes Kao (Executive coach, co-founder of Maven)
Wes Kao is an executive coach, advisor, and instructor, best known for her newsletter on high-impact communication, and for co-founding course platform Maven and the AltMBA with Seth Godin. Across her career, Wes has helped leaders communicate with clarity and conviction, whether it’s rallying a team, pitching investors, or influencing stakeholders.
In this episode, Wes and Brett unpack how found
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 founding the company, Rick has scaled Persona into a category-defining leader, rece
How a weekend hack became a multimillion-dollar AI startup | Adit Abraham (Co-founder & CEO at Reducto)
Adit Abraham is the co-founder and CEO of Reducto, which helps leading AI teams extract and structure data from complex documents and spreadsheets in their pipeline. Within 6 months of launching, Reducto went from 0→7 figures in ARR. Reducto has grown to process tens of millions of pages monthly for companies ranging from startups to Fortune 10 enterprises. They just announced a $24M Series A. Bef
1Password’s growth story | How they went from bootstrapped to $6B company | Jeff Shiner (CEO)
Jeff Shiner is the CEO of 1Password, the access management company used by over 100,000 businesses and millions of individuals worldwide. He joined 1Password as CEO in 2012, when the team was just under 20 people. Under Jeff’s leadership, 1Password expanded into B2B, launched a SaaS platform, and scaled from a small family-run operation into a global company. In 2019, Jeff led 1Password through it
Scrappy tactics and a huge post-COVID pivot | Owner’s unconventional journey to product-market fit | Adam Guild (Co-founder and CEO of Owner)
Adam Guild is the co-founder and CEO at Owner, an online food ordering system for independent restaurants. Within a year, Owner went from being about to run out of money to having hundreds of customers. Last year, they raised a $33M Series B.
Adam’s entrepreneurial journey began as a teenager when he built a successful Minecraft server, which led him to drop out of high school to become a founder.
What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Head of Global Product at Stripe)
Eeke de Milliano is the Head of Global Product at Stripe, helping drive innovation and success in the company's product line. Before this role, she was Head of Product at Retool and co-founded Constellate. Eeke previously spent 6 years as Product Lead at Stripe, working with the company during their hyper-growth era.
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In today’s episode, we discuss:
Eeke’s wealth of experience as an executive le
Inside Guideline's mission to modernize 401(k)s | Building from first principles, finding strategic edges, and rewiring retirement | Kevin Busque (Co-founder and CEO)
Kevin Busque is the co-founder and CEO of Guideline, a 401(k) management company revolutionizing the retirement space for small and medium-sized businesses. Prior to Guideline, Kevin co-founded Taskrabbit, where he encountered firsthand the complexity and low participation rates of traditional 401(k) plans—largely due to confusing fee structures.
After launching Guideline to address those problems
Inside Braze’s blitz to $500M in CARR | Building broad, going global, and outfoxing the competition | Bill Magnuson (Co-founder & CEO) and Kevin Wang (CPO)
Bill Magnuson is the co-founder and CEO at Braze, along with Kevin Wang, who joined as employee #8 and serves as the CPO. The two MIT graduates have built Braze into a publicly listed customer engagement platform with a $4.4B market cap. In 2023, Braze surpassed $500M in CARR, and serves over 2,200 customers worldwide. Before Braze, Bill spent time at Bridgewater Associates. Kevin’s academic backg
Inside Clay's unconventional path to $1.25B: Rethinking GTM, pricing, and enterprise sales | Varun Anand (Co-founder and Head of Operations)
Varun Anand is the co-founder and Head of Operations at Clay, a GTM development environment that combines data and AI to help over 5000 companies power everything from CRM enrichment to highly targeted outreach campaigns. Clay recently announced their Series B expansion, raising $40M at a $1.25B valuation. Before Clay, Varun was the Director of Operations at Newfront and the Head of Expansion at C
Building a 4 billion dollar data platform: Inside dbt Labs’ unconventional path | Tristan Handy (Co-founder and CEO, ex-RJMetrics, Squarespace)
Tristan Handy is the Founder and CEO at dbt Labs, a cloud-based data management platform that has raised over $400M to date, and was last valued at $4.2B in 2022. Dbt Labs has grown from just three companies using its free tool in 2016 to an ecosystem of 30,000+ enterprise users. Before founding dbt Labs, Tristan was the VP of Marketing at RJMetrics and the Director of Operations at Squarespace.
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How Figma taps into taste, simplicity, and storytelling | Yuhki Yamashita (CPO at Figma, ex-Uber, Google, Microsoft)
Yuhki Yamashita is the Chief Product Officer at Figma, leading the product and design teams. Previously, he was a product and design leader at Uber, where he orchestrated the redesign of the rider and driver apps. Yuhki was also a product manager at Google (YouTube iOS app) and Microsoft (Hotmail). Additionally, he has taught introductory computer science at Harvard University.
In today’s episode,
How to find customers in the Dept of Defense: From prototype to the Pentagon | Steve Blank (Hacking for Defense)
Steve Blank is an Adjunct Professor at Stanford University, where he co-created the "Hacking for Defense" curriculum for the Department of Defense. As a consultant to top defense and intelligence organizations, Steve brings cutting-edge strategies to the national security sector. Before entering academia, Steve built eight different startups. He helped launch the Lean Startup movement with his May
Shifting Career Altitudes: Insights from a CPO’s Journey Leading in Nearly Every Function | Anneka Gupta (Rubrik, ex-LiveRamp)
Anneka Gupta is the Chief Product Officer at Rubrik, a cloud management and data security company with a US$6B market cap. Before Rubrik, Anneka spent 11 years leading various teams at LiveRamp, including product, go-to-market, and operations.
In today’s episode, we discuss:
How LiveRamp went from $30M to $200M ARR in 3 years
Anneka’s jack-of-all-trades career
Why specialist hires can backfire
How to find and pull startup growth levers | Matt Lerner (Founder and CEO at SYSTM, Author of Growth Levers)
Matt Lerner is the Founder and CEO at SYSTM, a startup coaching consultancy that helps high-potential companies grow their business. Matt also authored the book “Growth Levers”, which shares his framework that's helped over 200 seed-stage startups grow as much as 100x. Previously, Matt was on the early growth team at PayPal, a partner at 500 Startups, and a guest lecturer at Stanford Business Scho
How to find — and keep — product-market fit | Bob Moore (Co-founder and CEO at Crossbeam, ex-RJMetrics and Stitch Data)
Bob Moore is the co-founder and CEO at Crossbeam, a “LinkedIn for data” platform that helps companies find overlapping opportunities with their partners. Crossbeam has raised US$117M to date and recently acquired Reveal in 2024. Bob previously cofounded RJMetrics (now part of Adobe Commerce Cloud) and Stitch Data (acquired by Talend). He is also the author of Ecosystem-Led Growth.
In today’s episo
Rebooting Intercom: Eoghan McCabe on Defying Silicon Valley Orthodoxy | Co-founder & CEO
Eoghan McCabe is the CEO and cofounder at Intercom, an AI customer service platform. Intercom has raised over $240M, and was last valued at $1.3B in 2018. After spending 9 years building the company, Eoghan left Intercom in 2020, but he’s since returned, reshaping Intercom and pioneering its pivot to an AI-first service. This episode highlights his unabashed takes on leaning into your intuition as
Inside marketing at Stripe, OpenAI and Retool | Krithika Muthukumar (VP of Marketing at OpenAI, ex-Stripe, Retool, Dropbox, Google)
Krithika Muthukumar is a marketing veteran. She is currently the VP of Marketing at OpenAI where she was the first marketing hire. Before that, she was Head of Marketing at Retool. Her longest tenure was at Stripe where she was hired as the first marketer and scaled with the company over nine years, from a 60-person team to 7500+. She began her career in Product Marketing at Google and Dropbox.
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Developing technical taste: A guide for next-gen engineers | Sam Schillace (Deputy CTO at Microsoft, creator of Google Docs)
Sam Schillace is the CVP and Deputy CTO at Microsoft. Before Microsoft, Sam held prominent engineering roles at Google and Box. He has also founded six startups, including Writely, which was acquired by Google and became Google Docs.
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In today’s episode, we discuss:
Sam’s advice for future engineers
What’s next for AI
How to develop technical taste
The importance of asking “what if” questions
How to build and scale winning marketplaces | Casey Winters (Eventbrite, Pinterest, Grubhub)
Casey Winters is a legendary advisor on scaling, product and growth. He’s worked with companies like Airbnb, Faire, Canva, Whatnot, Thumbtack, Tinder, and Reddit. Until recently, Casey was the Chief Product Officer at Eventbrite, and has also led growth and product teams at Pinterest and Grubhub.
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In today’s episode, we discuss:
What every marketplace founder should think about
Why marketplaces
Lessons from Sentry on scaling DevTools and finding product market fit (again) | Milin Desai (Sentry, VMware, Riverbed)
Milin Desai is the CEO at Sentry, an application monitoring tool for developers. Sentry has recently passed two key milestones: 100K customers and over $100M in ARR. Before Sentry, Milin was a GM at VMware and scaled their cloud networking into a billion-dollar business. Prior to stepping into leadership roles, Milin was a PM at Riverbed and a software engineer at Veritas.
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In today’s episode, we
How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple)
Matt MacInnis is the COO at Rippling, an all-in-one HR, IT, and finance platform for businesses, which last raised $500M at a $11.25B valuation. Before Rippling, Matt was the co-founder and CEO at Inkling, a mobile learning platform that was acquired in 2018. He also held several management roles at Apple.
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In today’s episode, we discuss:
Lessons on culture, org-design, and product from Rippling
Timeless lessons on running software companies that endure | Alyssa Henry (Square, Amazon, Microsoft)
Alyssa Henry is the former CEO of Square, a financial services company providing products and services used by over 4 million merchants. Formerly at Amazon, Alyssa led the development and growth of Simple Storage Service (S3) at AWS. Alyssa now serves as an Independent Director at Intel and Confluent.
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In today’s episode, we discuss:
Lessons from Amazon, Microsoft, and Square
“Minimum Remarkab
Building products that delight customers | Adam Nash (Daffy, Wealthfront, LinkedIn, eBay, Apple)
Adam Nash is the co-founder and CEO at Daffy, a platform that makes it easier to donate to charities and non-profits. Before Daffy, Adam was the President and CEO at Wealthfront, where he scaled the company’s assets under management from $100M to over $4B. Adam has also held leadership and technical roles at Dropbox, LinkedIn, eBay, and Apple.
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In today’s episode, we discuss:
Why founders should
A masterclass in founder conviction | Eilon Reshef (Co-founder and CPO at Gong)
Eilon Reshef is the co-founder and CPO at Gong, an AI-powered platform that tracks, records, and analyzes sales calls to drive revenue growth. In 2021, Gong raised $250M at a $7.25B valuation. Gong was one of the fastest SaaS companies to hit $100m ARR, and now has over 4000 customers. Before Gong, Eilon sold his previous e-commerce startup, Webcollage.
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In today’s episode, we discuss:
Why Eilon
Essential lessons for building and scaling DevTools | Dennis Pilarinos (Unblocked, Apple, Amazon, Buddybuild, Microsoft)
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:
Lessons on culture and product from Amaz
Scaling and selling AI products for enterprise | May Habib (Co-founder and CEO of Writer)
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:
Advice for AI
The secret lever Replit pulled to scale ahead of its competition | Amjad Masad (Co-founder and CEO)
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:
How AI is reshaping the softw
Lessons from Gusto & Square on finding your product wedge | Michael Cieri
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 Manag
A customer success masterclass | How to design, build, and scale a CS org | Stephanie Berner (LinkedIn)
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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I
The human side of world-class engineering leadership | Michael Lopp (Apple, Palantir, Slack)
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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Clay’s path to product-market-fit: Building vertical, creating power users, and understanding founder psychology | Kareem Amin (Co-founder and CEO)
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:
Creating a community of power users
How to stay ruthless
Inside Figma’s early days: How to build a world-class sales org | Kyle Parrish (VP of Sales)
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
The new PLG playbook | Arming the next generation of product-led companies | Oliver Jay (Asana, Dropbox)
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 no
Mastering modern entrepreneurship | Building lean, starting young, and studying customers | Steve Blank (Author of The Four Steps to the Epiphany)
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 aut
Winning with open and closed source products | Neha Narkhede (Co-founder at Confluent and Oscilar)
Neha Narkhede is a co-founder at Confluent, a data streaming software that raised at a $9.1b valuation in 2021. Neha later co-founded Oscilar, a no-code platform that helps companies detect and manage fraud. Before building these two companies, Neha was a Principal Software Engineer at LinkedIn where she co-created Apache Kafka. Neha is ranked #50 on Forbes’ list of “America’s Richest Self-Made Wo
The Bard blueprint | Creating value, shipping fast, and advancing AI ethically | Jack Krawczyk (Google)
Jack Krawczyk is a Senior Director of Product at Google, building Bard. Bard is Google’s collaborative, conversational, and experimental AI tool that’s bridging the gap between humans and bots, while addressing ethical considerations around AI. After joining the project in 2020, Jack helped ship Bard in less than four years. Bard sources information directly from the web, and now enables users to
A masterclass in engineering leadership from Carta, Stripe, Uber, and Calm | Will Larson (CTO at Carta)
Will Larson is the CTO at Carta, an ownership and equity management platform that raised at a $7.4b valuation in 2021. Prior to joining Carta, Will was CTO at Calm, founded Stripe's Foundation Engineering org, and led Uber’s Platform Engineering people and strategy. Will also writes extensively about engineering leadership, and has authored two books in this area: Staff Engineer, and An Elegant Pu
How goal-setting and planning is different for AI products | Anastasis Germanidis (Co-Founder & CTO at Runway)
Anastasis Germanidis is the Co-Founder & CTO at Runway, an applied AI research company shaping the next era of art, entertainment, and human creativity. Runway has raised $237m and was one of Time Magazine’s “100 most influential companies” in 2023. Runway has been a persistent viral sensation in recent years, and is behind many of the most famous AI demos online.
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In today’s episode we discuss:
How Vercel found extreme product-market fit by focusing on simplification | Guillermo Rauch (Vercel's CEO)
Guillermo Rauch is the CEO of Vercel, a frontend-as-a-service product that was valued at $2.5b in 2021. Vercel serves customers like Uber, Notion and Zapier, and their React framework - Next.js - is used by over 500,000 developers and designers worldwide. Guillermo started his first company at age 11 in Buenos Aires and moved to San Francisco at age 18. In 2013, he sold his company Cloudup to Auto
The business of growing and monetizing an open source product | Ashley Kramer (GitLab CMO/CSO)
Ashley Kramer is the CMO and CSO at GitLab, a publicly listed DevSecOps platform. Ashley took a unique path into her CMO role. She started out in software engineering before becoming a product leader, and eventually, a marketer. Most recently, Ashley was the CPO and CMO at Sisense, a data analytics company last valued at over $1b.
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In today’s episode we discuss:
How GitLab layered a commercial
How to leverage intuition, customer support, and raw effort | Colin Zima (Omni & Looker)
Colin Zima is the co-founder and CEO of Omni, a business intelligence tool that has raised over $26.9m. Prior to starting Omni, Colin was Chief Analytics Officer and VP of Product at Looker, which was acquired by Google for $2.6b. Colin was an early employee at Looker, and stood up its high-touch customer support arm, which turned into a cornerstone competitive advantage for the company.
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In toda
Building Zapier from first principles | Contrarian takes on growth, hiring, fundraising | Wade Foster (Co-founder & CEO)
Wade Foster is the Co-founder & CEO at Zapier, a platform for building workflow automations without a developer. Zapier was started during 2011 in Columbia, Missouri, and by 2021, it was valued at $5b, having only raised $1.3m. Prior to founding Zapier, Wade had just two professional jobs, and had never managed or hired anyone. He worked as a PM on a web app used by 20k students, and as an Email M
How young outsiders changed the shipping industry by finding product-market fit again and again | Laura Behrens Wu (Shippo)
Laura Behrens Wu is the Founder & CEO at Shippo, a company that has raised $100m+ and was last valued at $1b in 2021. Shippo provides an API and dashboard that makes shipping easy for e-commerce businesses, marketplaces, and platforms. Prior to starting Shippo, Laura graduated from Harvard University, and was heavily influenced by a short internship at LendUp, which exposed her to Silicon Valley a
AI Hot Takes and Unusual Twitter Fundraising Strategies with Dan Siroker (Rewind AI)
Dan Siroker is the co-founder and CEO at Rewind AI, a personalized AI powered by everything you’ve seen, said, or heard. Dan launched Rewind to an emphatic response on Twitter, and used a public pitch video to fundraise at a $350m valuation. Prior to starting Rewind, Dan co-founded Optimizely, which reached $120m ARR before being acquired by Episerver, a content management company. Dan was also th
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