All Episodes
In Depth — 185 episodes
The fastest way to learn is to run two competing bets | Jay Parikh (EVP CoreAI, Microsoft)
What startups get wrong about enterprise | Lindsey Scrase (COO, Checkr)
How Gamma pulled off their AI pivot | Jon Noronha (Co-founder and CPO of Gamma)
Why Plaid’s COO cold-calls new hires | Eric Sager (COO of Plaid)
How Supabase became the essential infrastructure for the AI era | Paul Copplestone (Co-founder, CEO)
How to build a beloved tech brand | Sheila Joglekar Vashee (CMO, Figma)
Why old-school sales work still wins in the AI era | Graham Moreno (Head of GTM, Parallel)
Why founders should bet on first-time executives | Praveer Melwani (CFO, Figma)
Why great product leaders should stop obsessing over the roadmap | Diya Jolly (CPO & CTO of Xero)
Inside Artemis' "AI vs AI" war | Shachar Hirshberg & Dan Shiebler (Co-founders, Artemis)
Scaling DoorDash to market dominance | Christopher Payne (Former COO, DoorDash)
The most politically dangerous role in the C-suite | Katie Burke (COO, Harvey)
What nobody tells engineers about becoming a CEO | Jay Kreps (Co-founder and CEO, Confluent)
The product wisdom every CPO should ignore | Jeremy Epling (CPO, Vanta)
Building Zipline: From launch disaster to drone-delivery giant | Keller Cliffton (Co-founder, CEO)
Snowflake’s first sales hire on scaling from $0 to $3.5B | Chris Degnan (Former CRO, Snowflake)
Why 90% of CROs will fall behind in the next 2 years | Stevie Case (CRO, Vanta)
Figma is not the source of truth | Ryan Lucas (VP of Design, Rippling)
Executive Function: Building systems that can make decisions without you | Jeanne DeWitt Grosser (COO, Vercel)
Building Meter for decades, not an exit | Anil Varanasi (Co-founder and CEO)
How Harness runs 16 “startups within a startup” at scale | Jyoti Bansal (Co-founder and CEO)
How to build a company you’ll run forever | Zack Kanter (Founder and CEO of Stedi)
Go hard early: How lessons from Verkada shaped Serval's AI agents for IT teams | Jake Stauch (Founder and CEO)
The pivot that paid off: How fal found explosive growth in generative media | Gorkem Yurtseven (Co-founder and CTO)
From dorm room to life-saving AI | Prepared’s story | Michael Chime (Co-founder & CEO of Prepared)
Saying yes to everything: How customer obsession built Samsara | Kiren Sekar (CPO)
Starting an education giant in a “bad market” | ClassDojo’s story | Sam Chaudhary (Co-founder and CEO)
From Chrome extension to $5B platform | Postman’s journey | Abhinav Asthana (Co-founder & CEO)
How Canva leveraged unconventional growth levers to grow to $42B | Cameron Adams (Co-founder & CPO)
Twitter's former CEO on rebuilding the web for AI | Parag Agrawal (Co-founder and CEO of Parallel)
Ignoring Silicon Valley advice to build a $3B fintech unicorn | Immad Akhund (Co-founder and CEO of Mercury)
Inside the ex-YC partner’s $15B self driving car company | Qasar Younis
What Braintrust got right about product-market fit | Ankur Goyal (Founder and CEO)
How Gusto built a $9.5 billion company by identifying a burning problem
How rejecting conventional wisdom grew Sentry to a $3 billion company | David Cramer (Co-founder and CPO)
Inside Linear: Why craft and focus still win in product building | Karri Saarinen (Co-founder and CEO)
How Wes Kao coaches founders to influence, lead, and get what they want | Wes Kao (Executive coach, co-founder of Maven)
From reluctant founder to $2B valuation: The story of Persona | Rick Song (Co-founder and CEO)
How a weekend hack became a multimillion-dollar AI startup | Adit Abraham (Co-founder & CEO at Reducto)
1Password’s growth story | How they went from bootstrapped to $6B company | Jeff Shiner (CEO)
Scrappy tactics and a huge post-COVID pivot | Owner’s unconventional journey to product-market fit | Adam Guild (Co-founder and CEO of Owner)
What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Head of Global Product at Stripe)
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)
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)
Inside Clay's unconventional path to $1.25B: Rethinking GTM, pricing, and enterprise sales | Varun Anand (Co-founder and Head of Operations)
Building a 4 billion dollar data platform: Inside dbt Labs’ unconventional path | Tristan Handy (Co-founder and CEO, ex-RJMetrics, Squarespace)
How Figma taps into taste, simplicity, and storytelling | Yuhki Yamashita (CPO at Figma, ex-Uber, Google, Microsoft)
How to find customers in the Dept of Defense: From prototype to the Pentagon | Steve Blank (Hacking for Defense)
Shifting Career Altitudes: Insights from a CPO’s Journey Leading in Nearly Every Function | Anneka Gupta (Rubrik, ex-LiveRamp)
How to find and pull startup growth levers | Matt Lerner (Founder and CEO at SYSTM, Author of Growth Levers)
How to find — and keep — product-market fit | Bob Moore (Co-founder and CEO at Crossbeam, ex-RJMetrics and Stitch Data)
Rebooting Intercom: Eoghan McCabe on Defying Silicon Valley Orthodoxy | Co-founder & CEO
Inside marketing at Stripe, OpenAI and Retool | Krithika Muthukumar (VP of Marketing at OpenAI, ex-Stripe, Retool, Dropbox, Google)
Developing technical taste: A guide for next-gen engineers | Sam Schillace (Deputy CTO at Microsoft, creator of Google Docs)
How to build and scale winning marketplaces | Casey Winters (Eventbrite, Pinterest, Grubhub)
Lessons from Sentry on scaling DevTools and finding product market fit (again) | Milin Desai (Sentry, VMware, Riverbed)
How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple)
Timeless lessons on running software companies that endure | Alyssa Henry (Square, Amazon, Microsoft)
Building products that delight customers | Adam Nash (Daffy, Wealthfront, LinkedIn, eBay, Apple)
A masterclass in founder conviction | Eilon Reshef (Co-founder and CPO at Gong)
Essential lessons for building and scaling DevTools | Dennis Pilarinos (Unblocked, Apple, Amazon, Buddybuild, Microsoft)
Scaling and selling AI products for enterprise | May Habib (Co-founder and CEO of Writer)
The secret lever Replit pulled to scale ahead of its competition | Amjad Masad (Co-founder and CEO)
Lessons from Gusto & Square on finding your product wedge | Michael Cieri
A customer success masterclass | How to design, build, and scale a CS org | Stephanie Berner (LinkedIn)
The human side of world-class engineering leadership | Michael Lopp (Apple, Palantir, Slack)
Clay’s path to product-market-fit: Building vertical, creating power users, and understanding founder psychology | Kareem Amin (Co-founder and CEO)
Inside Figma’s early days: How to build a world-class sales org | Kyle Parrish (VP of Sales)
The new PLG playbook | Arming the next generation of product-led companies | Oliver Jay (Asana, Dropbox)
Mastering modern entrepreneurship | Building lean, starting young, and studying customers | Steve Blank (Author of The Four Steps to the Epiphany)
Winning with open and closed source products | Neha Narkhede (Co-founder at Confluent and Oscilar)
The Bard blueprint | Creating value, shipping fast, and advancing AI ethically | Jack Krawczyk (Google)
A masterclass in engineering leadership from Carta, Stripe, Uber, and Calm | Will Larson (CTO at Carta)
How goal-setting and planning is different for AI products | Anastasis Germanidis (Co-Founder & CTO at Runway)
How Vercel found extreme product-market fit by focusing on simplification | Guillermo Rauch (Vercel's CEO)
The business of growing and monetizing an open source product | Ashley Kramer (GitLab CMO/CSO)
How to leverage intuition, customer support, and raw effort | Colin Zima (Omni & Looker)
Building Zapier from first principles | Contrarian takes on growth, hiring, fundraising | Wade Foster (Co-founder & CEO)
How young outsiders changed the shipping industry by finding product-market fit again and again | Laura Behrens Wu (Shippo)
AI Hot Takes and Unusual Twitter Fundraising Strategies with Dan Siroker (Rewind AI)
A guide to building product in a post-LLM world | Ryan Glasgow and Kevin Mandich from Sprig
An org-design masterclass from a Square GM | Saumil Mehta
How to supercharge your engineering org | Kellan Elliott-McCrea (Adobe, Dropbox)
The zero to one B2B marketing playbook | Alex Kracov (Lattice, Dock)
Lessons from Loom on product strategy, organizational leadership, and cross-functional performance | Anique Drumright (COO at Loom)
Lessons from Slack on decision making, product-led growth, and taking big swings — Noah Desai Weiss
Lessons in leadership | Scaling an org, developing yourself, and tactical management advice | Jack Altman (Lattice)
Lessons from Stripe on adding new products - Assessing ideas, structuring teams, and tactics for product reviews | Tara Seshan (Watershed, Stripe)
How to design a high-impact growth org for a PLG startup — Webflow & Dropbox’s Melissa Tan
Why is the transition from IC Engineer to Manager so tricky (and how to get it right)? — Marcel Weekes, VP of Product Engineering at Figma
How to pull off the ‘zoom-in pivot,’ and other lessons in early-stage building with Luminai’s Kesava Kirupa Dinakaran
The go-to-market guide for open-source companies — Douglas Hanna, COO Grafana Labs
What this 3-time founding team did differently to find product-market fit faster — Jessica McKellar, CTO of Pilot
How to measure product-market fit with the REV model — Artem Kroupenev
The early user research playbook for founders — Jeanette Mellinger’s expert advice for validating your idea with high-quality interviews
Claire Hughes Johnson on being a “learning organism” during Stripe’s growth, and more scaling advice for leaders
Notion’s Head of Marketing on building a growth marketing engine at a PLG company — Rachel Hepworth
What makes someone a truly remarkable talent evaluator — Nadia Singer, Figma’s Chief People Officer
How Vanta’s founder bet big on startup security and found product-market fit — Christina Cacioppo
Lessons from Notion on building a thriving decentralized community — Ben Lang
From a narrow ICP to a wide-open market – Lessons from Webflow’s Bryant Chou on using customer empathy to get product-market fit
How to lead with transparency amidst adversity — Don Faul, CEO of CrossFit and former Google, Facebook & Pinterest exec
From kickoffs to retros and Slack channels — Stripe's documentation best practices with Brie Wolfson
Why comms deserves its own spot on the exec team — Aaron Zamost’s lessons from Square
What founders need to know about acquisitions: Shopify’s Daniel Debow on M&A lessons from selling three startups
How to build your culture like a product — Lessons from Anna Binder, Asana’s Head of People
How to scale your career alongside your startup: Mike Boufford’s lessons after 10 years at Greenhouse
Founders: Here’s how to get your sales pitch in ship-shape — Peter Kazanjy
Deepak Rao on how X1 pivoted, launched, built a +600K-long waitlist and fundraised in tough times
How to lower barriers to change when building and selling products — Jonah Berger’s advice for founders
How Retool reached $2M in ARR before launch by focusing on developers — David Hsu
How to approach GTM with an engineering lens — Rich Rao’s advice from Google & Meta
What startups can learn from enterprise corporate messaging — Sara Varni’s lessons from Salesforce & Twilio
Finding product-market fit twice — Alma’s Harry Ritter on pivots and staying close to customers
Why everything we’ve been taught about quitting is wrong — Annie Duke
How to scale your co-founder relationship alongside your startup — Manu Sharma & Brian Rieger of Labelbox
A crash course on founder-led customer success — Sydney Strader’s lessons from Catalyst & InVision
The founder’s guide to making your first few hires — Steven Bartel on recruiting at Gem & Dropbox
From product roadmapping to sprint planning: How to ship software at scale — Snir Kodesh
The 5 phases of Figma’s community-led growth — Claire Butler
Airtable’s path to product-market fit — co-founder Andrew Ofstad on building horizontal products
Operations vs. Algorithms: Advice for scaling startups, from Opendoor CTO Ian Wong
Want to go totally asynchronous? Repeat founder Sidharth Kakkar on building a remote team & autonomous culture
Why COO is the most fluid role in the C-Suite — Sara Clemens, former COO of Twitch & Pandora
From PM to VP of Product: Jiaona Zhang’s career advice from Webflow, Airbnb & Dropbox
“When They Win, You Win”: Russ Laraway unpacks his new guide for the modern manager
Building a highly-technical enterprise product? Essential advice for product leaders — Nate Stewart of Cockroach Labs
Building & selling a product into government is tricky — Phaedra Ellis-Lamkins shares critical advice for getting it right
The art of starting a startup — Gagan Biyani’s advice for generating, validating, and executing on ideas
How to handle comp challenges at every startup stage — Kaitlyn Knopp’s advice from Pequity, Instacart, Cruise & Google
A crash course on comms for founders — Nairi Hourdajian’s early-stage advice from Figma & Uber
How founders can get executive hiring right from startup to scale — advice from Lattice’s Jack Altman
IC? Manager? Technical Founder? How to chart your engineering career path — Stripe & Cocoon’s Amber Feng
Never done sales before? Meka Asonye shares GTM playbooks from Stripe, Mixpanel, and backing founders at First Round
The startup playbook for expanding internationally — Advice from Faire CEO Max Rhodes
Usage-based? Hybrid? Tiered? Which pricing model is right for you? — Stripe’s Jeanne DeWitt Grosser
The Product Strategy Playbook that Powered Growth at Tinder & TripAdvisor — Ravi Mehta
After building hundreds of startup brands, Arielle Jackson shares 6 early marketing missteps to avoid
Buy or build? Focus on the core product or innovate? Zendesk CTO Adrian McDermott's advice for scaling
The biggest lessons from building Hubspot, from co-founder harmony to engineering the culture — Dharmesh Shah
The story of why Canva worked: Zach Kitschke shares his lessons from early hire to current CMO
Take your design org from good to great with these principles from Segment to Twilio — Hareem Mannan
Instacart co-founder Max Mullen gets tactical on crafting company values and intentionally building culture
Growing from founder to CEO: Executive coach Alisa Cohn on how to get better feedback
Executive hiring is incredibly difficult to get right — Robinhood COO Gretchen Howard shares her playbook
Building a hybrid go-to-market motion — GC Lionetti’s lessons from Confluent, Dropbox & Atlassian
Creating physical products and getting feedback from toddlers — KiwiCo’s Sandra Oh Lin
How to hire the right marketer at the right time for your startup — Mux & Segment’s Maya Spivak
From developer to CMO — Archana Agrawal’s marketing lessons from Airtable & Atlassian
How to pivot your way to product/market fit & other 0-1 lessons — Rupa Health CEO Tara Viswanathan
Building an operationally-intensive business and avoiding upside down unit economics — Thirty Madison’s Steve Gutentag
Don’t have a UX research team? Jane Davis’ tips from Zoom, Zapier & Dropbox to get you started
Getting startup employees to stick around & learning from couples therapy — Flatiron’s Alex Buder Shapiro
How to find product/market fit before you start building — UserLeap’s Ryan Glasgow
Nick Caldwell on the engineering cultures that power Microsoft, Reddit, Looker & Twitter
“Everyone wants a silver bullet” — Selling lessons from Sam Taylor, of Dropbox, Quip & now Loom
The do’s and don’ts of scaling from dozens of employees to thousands — McKenna Quint
A look at one repeat founder’s frameworks for validating ideas — Pilot’s Waseem Daher
Killing stories and creating categories — Comms tips from Shannon Brayton’s 25+ years in tech
People leaders aren’t the CEO of culture, they’re product managers — Credit Karma’s Colleen McCreary
Go unreasonably deep on complex problems and build with naivety — Bowery Farming’s Irving Fain
The story behind Slack’s marketing and the leap from marketer to CEO — Abstract’s Kelly Watkins
Ask why it won’t work — Rick Song’s lessons from Square and building from 0 to 1
Product Pitfalls From 0 Customers to the Messy Middle and IPO — Eric Berg on Okta, Intel & Fauna
After leading product & growth teams at Instacart, Wealthfront & LinkedIn, Elliot Shmukler is tackling zero to one as founder & CEO of Anomalo
A deep-dive into product-led growth & self-serve strategies — Notion’s & Dropbox’s Kate Taylor
Setting up the people function and training for empathy — Lambda School’s Mark Frein
How Thumbtack CEO Marco Zappacosta Parses Through Mountains of Advice as a First-Time Founder
Building engineering orgs and new products at Segment, Dropbox & Facebook — Tido Carriero
Essentials to engaging employees & developing high-quality managers — Qualtrics’ Russ Laraway
CEO Jeff Lawson Reflects on the Peaks and Valleys of Twilio’s Growth Story
Treat Operational Debt like Tech Debt — Leah Sutton on Elastic’s Distributed Work Playbook
“My product is the company” — Kevin Fishner on how startups can build better systems
Growing a consumer product from scratch to 1 billion users — Google Photos’ David Lieb
An inside look at the system that will outlast Bezos—Bill Carr & Colin Bryar on lessons from Amazon
From exec roles to board seats — Anne Raimondi’s leadership lessons for the startup C-Suite
Plaid & Dropbox’s Jean-Denis Grèze’s playbook for building an engineering culture of ownership
Upstart just went public — CEO Dave Girouard shares why it isn’t a typical success story
Unpacking all the non-consensus moves in Atlassian’s story — Jay Simons
Partnerships lessons from Stripe & Notion — Cristina Cordova on creating win-win deals
Start with the story — Drift’s David Cancel on lessons he’s learned as a 5X founder
Lessons from a first-time CEO — Steve El-Hage on learning everything the hard way
Product lessons from Cash App & Carbon Health — Ayo Omojola on going “unreasonably deep”
Molly Graham’s management lessons from Google, Facebook, Quip & Lambda School
Preview of In Depth from First Round