Best Stedy Podcasts (2026)

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Health plan design with Caroline Loy 48:54

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1M ago48:54

48:54

Caroline Loy is Principal Product Strategist at Turquoise Health. In this episode, she explains what health plan design is, the decisions employers make when designing or buying plans, and how plan design affects care. (00:00) - Intro (00:15) - What is health plan design? (01:35) - Who decides plan design? (02:32) - What are self-funded vs fully in…

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Building Meter for decades, not an exit | Anil Varanasi (Co-founder and CEO) 1:14:53

1M ago1:14:53

1:14:53

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 mu…

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How Harness runs 16 “startups within a startup” at scale | Jyoti Bansal (Co-founder and CEO) 1:05:17

2M ago1:05:17

1:05:17

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 …

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How to build a company you’ll run forever | Zack Kanter (Founder and CEO of Stedi) 1:24:09

2M ago1:24:09

1:24:09

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,…

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Go hard early: How lessons from Verkada shaped Serval's AI agents for IT teams | Jake Stauch (Founder and CEO) 1:23:01

3M ago1:23:01

1:23:01

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 …

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The pivot that paid off: How fal found explosive growth in generative media | Gorkem Yurtseven (Co-founder and CTO) 59:18

3M ago59:18

59:18

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 shar…

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From dorm room to life-saving AI | Prepared’s story | Michael Chime (Co-founder & CEO of Prepared) 1:09:07

3M ago1:09:07

1:09:07

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, disrup…

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Saying yes to everything: How customer obsession built Samsara | Kiren Sekar (CPO) 1:08:57

4M ago1:08:57

1:08:57

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…

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Starting an education giant in a “bad market” | ClassDojo’s story | Sam Chaudhary (Co-founder and CEO) 1:12:29

4M ago1:12:29

1:12:29

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 communic…

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From Chrome extension to $5B platform | Postman’s journey | Abhinav Asthana (Co-founder & CEO) 1:06:20

5M ago1:06:20

1:06:20

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 …

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How Canva leveraged unconventional growth levers to grow to $42B | Cameron Adams (Co-founder & CPO) 1:04:26

5M ago1:04:26

1:04:26

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 rem…

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Twitter's former CEO on rebuilding the web for AI | Parag Agrawal (Co-founder and CEO of Parallel) 1:05:35

5M ago1:05:35

1:05:35

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 …

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Ignoring Silicon Valley advice to build a $3B fintech unicorn | Immad Akhund (Co-founder and CEO of Mercury) 1:01:52

5M ago1:01:52

1:01:52

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 M…

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Inside the ex-YC partner’s $15B self driving car company | Qasar Younis 1:00:25

5M ago1:00:25

1:00:25

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 …

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What Braintrust got right about product-market fit | Ankur Goyal (Founder and CEO) 1:10:04

6M ago1:10:04

1:10:04

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 formativ…

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How Gusto built a $9.5 billion company by identifying a burning problem 55:01

7M ago55:01

55:01

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 a…

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How rejecting conventional wisdom grew Sentry to a $3 billion company | David Cramer (Co-founder and CPO) 1:41:24

7M ago1:41:24

1:41:24

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, Sen…

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Inside Linear: Why craft and focus still win in product building | Karri Saarinen (Co-founder and CEO) 1:33:04

7M ago1:33:04

1:33:04

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…

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How Wes Kao coaches founders to influence, lead, and get what they want | Wes Kao (Executive coach, co-founder of Maven) 1:19:34

8M ago1:19:34

1:19:34

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…

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From reluctant founder to $2B valuation: The story of Persona | Rick Song (Co-founder and CEO) 1:14:59

8M ago1:14:59

1:14:59

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 sc…

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How a weekend hack became a multimillion-dollar AI startup | Adit Abraham (Co-founder & CEO at Reducto) 1:00:02

9M ago1:00:02

1:00:02

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 ent…

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1Password’s growth story | How they went from bootstrapped to $6B company | Jeff Shiner (CEO) 1:08:08

9M ago1:08:08

1:08:08

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 glob…

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Scrappy tactics and a huge post-COVID pivot | Owner’s unconventional journey to product-market fit | Adam Guild (Co-founder and CEO of Owner) 1:23:29

10M ago1:23:29

1:23:29

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 h…

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What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Head of Global Product at Stripe) 59:59

10M ago59:59

59:59

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. – In today’s episode, we discus…

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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) 1:24:49

11M ago1:24:49

1:24:49

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. A…

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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) 1:23:07

11M ago1:23:07

1:23:07

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…

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Inside Clay's unconventional path to $1.25B: Rethinking GTM, pricing, and enterprise sales | Varun Anand (Co-founder and Head of Operations) 1:02:31

12M ago1:02:31

1:02:31

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 Ope…

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Building a 4 billion dollar data platform: Inside dbt Labs’ unconventional path | Tristan Handy (Co-founder and CEO, ex-RJMetrics, Squarespace) 55:21

1y ago55:21

55:21

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 RJMetric…

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How Figma taps into taste, simplicity, and storytelling | Yuhki Yamashita (CPO at Figma, ex-Uber, Google, Microsoft) 1:09:52

1y ago1:09:52

1:09:52

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 …

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How to find customers in the Dept of Defense: From prototype to the Pentagon | Steve Blank (Hacking for Defense) 34:08

1y ago34:08

34:08

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 he…

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Shifting Career Altitudes: Insights from a CPO’s Journey Leading in Nearly Every Function | Anneka Gupta (Rubrik, ex-LiveRamp) 1:09:53

1+ y ago1:09:53

1:09:53

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-t…

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How to find and pull startup growth levers | Matt Lerner (Founder and CEO at SYSTM, Author of Growth Levers) 1:05:57

1+ y ago1:05:57

1:05:57

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 Startu…

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How to find — and keep — product-market fit | Bob Moore (Co-founder and CEO at Crossbeam, ex-RJMetrics and Stitch Data) 1:18:32

1+ y ago1:18:32

1:18:32

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 th…

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Rebooting Intercom: Eoghan McCabe on Defying Silicon Valley Orthodoxy | Co-founder & CEO 1:15:20

1+ y ago1:15:20

1:15:20

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…

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Inside marketing at Stripe, OpenAI and Retool | Krithika Muthukumar (VP of Marketing at OpenAI, ex-Stripe, Retool, Dropbox, Google) 1:08:04

1+ y ago1:08:04

1:08:04

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 car…

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Developing technical taste: A guide for next-gen engineers | Sam Schillace (Deputy CTO at Microsoft, creator of Google Docs) 1:05:26

1+ y ago1:05:26

1:05:26

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. – In today’s episode, we discuss: Sam’s advice for future engineers What’s next for AI How to develop technical tast…

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How to build and scale winning marketplaces | Casey Winters (Eventbrite, Pinterest, Grubhub) 1:13:29

1+ y ago1:13:29

1:13:29

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. – In today’s episode, we discuss: What every marketp…

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Lessons from Sentry on scaling DevTools and finding product market fit (again) | Milin Desai (Sentry, VMware, Riverbed) 58:01

1+ y ago58:01

58:01

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 soft…

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How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple) 1:15:40

1+ y ago1:15:40

1:15:40

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. — In today’s episode, we discuss: Lessons …

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Timeless lessons on running software companies that endure | Alyssa Henry (Square, Amazon, Microsoft) 1:16:55

1+ y ago1:16:55

1:16:55

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. — In today’s episode, we discuss: Lessons from …

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Building products that delight customers | Adam Nash (Daffy, Wealthfront, LinkedIn, eBay, Apple) 1:16:19

2y ago1:16:19

1:16:19

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. — In…

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A masterclass in founder conviction | Eilon Reshef (Co-founder and CPO at Gong) 43:49

2y ago43:49

43:49

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, Webcol…

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Essential lessons for building and scaling DevTools | Dennis Pilarinos (Unblocked, Apple, Amazon, Buddybuild, Microsoft) 58:50

2y ago58:50

58:50

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. — In today’s episode, we …

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Scaling and selling AI products for enterprise | May Habib (Co-founder and CEO of Writer) 40:21

2y ago40:21

40:21

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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The secret lever Replit pulled to scale ahead of its competition | Amjad Masad (Co-founder and CEO) 53:46

2y ago53:46

53:46

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. — In today’s e…

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Lessons from Gusto & Square on finding your product wedge | Michael Cieri 59:08

2y ago59:08

59:08

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…

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A customer success masterclass | How to design, build, and scale a CS org | Stephanie Berner (LinkedIn) 1:11:07

2y ago1:11:07

1:11:07

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 custo…

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The human side of world-class engineering leadership | Michael Lopp (Apple, Palantir, Slack) 1:04:46

2y ago1:04:46

1:04:46

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 G…

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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) 54:16

2y ago54:16

54:16

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. — In today’s episode, we discuss: Creating…

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Inside Figma’s early days: How to build a world-class sales org | Kyle Parrish (VP of Sales) 1:07:58

2y ago1:07:58

1:07:58

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 Sa…