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 the Director of Analytics for Obama’s first presidential campaign. In today’s episode, we discuss: Rew...
Sep 14, 2023•1 hr 6 min
Sprig is an AI-powered user insights platform that has raised over $88m. Today’s discussion features two key individuals in Sprig’s journey so far: Ryan Glasgow, Sprig’s CEO and founder; and Kevin Mandich, Sprig’s Head of Machine Learning. Before Sprig, Ryan was an early PM at GraphScience, Vurb, and Weeby (all of which were acquired), and Kevin was an ML Engineer at Incubit, and a Post-Doctoral Researcher at UC San Diego. In today’s episode, we discuss: Key lessons from the Sprig founding story...
Sep 07, 2023•1 hr 17 min
Saumil Mehta is the GM of Square’s flagship point-of-sale business, as well as CRM, Square Staff, and Square Online. Before Square, Saumil was the Founder and CEO of LocBox, which raised over $5.1M, and helped offline/local businesses run multi-channel marketing campaigns, all from one universal dashboard. Saumil has now been a leader at Square for 8+ years, and has overseen many complex re-orgs. These experiences have shaped Saumil into an all-round org-design expert. In today’s episode we disc...
Aug 31, 2023•1 hr 15 min•Ep. 103
Kellan Elliott-McCrea is a Head of Engineering at Adobe, overseeing Frame.io , a newly acquired video review and collaboration platform. He is known for his experience and expertise as an engineering leader. He was previously a VPE at Dropbox, and CTO at Etsy where he built and led a team of 300 people, from tech and platform reboot through to IPO. Kellan also built and scaled teams at Flickr, and has a coaching and advising practice for companies looking to supercharge their engineering teams. ...
Aug 17, 2023•1 hr 13 min•Ep. 102
Alex Kracov is the CEO and Co-Founder at Dock, and the former VP of Marketing at Lattice. Alex joined Lattice as the first marketer and third employee, and he helped to grow the business from seed to 1850+ customers. Prior to Lattice, Alex was a consultant at Blue State Digital — the team that elected President Obama and orchestrated projects at Google. Since leaving Lattice in 2021, Alex co-founded Dock, a B2B platform that has streamlined the customer buying experience for clients like Loom, O...
Aug 10, 2023•1 hr 4 min
Anique Drumright is the COO at Loom, a video communication tool for streamlining workflows. Loom has raised over $200M, and was last valued at $1.5B. Anique has a proven track record across product development, executive leadership, and building high-performing organizations. Before joining Loom, Anique was the VP of Product at TripActions, where she scaled the team over 8x globally, and she has also held multiple roles at Uber. In today's episode, we discuss: Best-practice product management Ho...
Aug 03, 2023•1 hr 2 min
Noah Desai Weiss is the Chief Product Officer of Slack, and has an accomplished track record inside and outside of the company. He started Slack’s Search, Learning, and Intelligence division, led the Self-Service (SMB) Business, and led the Expansion and Virtual HQ product areas (responsible for Huddles, Clips, and more). Before joining Slack, Noah was the SVP of Product Management at Foursquare (raised over $390m), and was a Product Manager at Google. In today's episode, we discuss: When to use...
Jul 13, 2023•1 hr 18 min
Jack Altman is the co-founder and CEO of Lattice, a people success platform for building engaged, high-performing teams. Lattice has raised over $330M, and was last valued at $3B. He is an expert in building company culture, and wrote a book on the topic, titled: “People Strategy”. In today's episode, we discuss: The importance of self-awareness and how to develop it The value of difficult conversations and advice for having them Common mistakes when scaling a company How to approach firing deci...
Jul 06, 2023•1 hr 18 min
Tara Seshan is the Head of Product at Watershed, a climate platform that companies use to measure, report, and reduce their carbon emissions. Before joining Watershed, Tara was Head of Product at Stripe throughout the launch of Stripe Billing and Stripe Treasury. As a Thiel Fellow and experienced multi-product builder, Tara brings a wealth of experience with 0-1 SaaS products. In today's episode, we discuss: The different types of multi-product strategies. Stories from Stripe’s multi-product suc...
Jun 22, 2023•56 min•Ep. 97
Our guest today is Melissa Tan , GM of Self-Service and Head of Growth at Webflow and formerly Head of Growth and Monetization for Dropbox Business. In today’s conversation, she unpacks the nuances between the two PLG businesses and how growth strategy changes for a more complex product like Webflow, including: Designing and structuring a growth org The right way to tackle goal-setting How Webflow’s pricing and packaging has evolved How to calibrate pricing feedback You can email us questions di...
Jun 08, 2023•1 hr•Ep. 91
Our guest today is Marcel Weekes , VP of Product Engineering at Figma and former VP of Engineering at Slack. In today’s conversation, he unpacks why most startups get it wrong when they uplevel someone from IC engineer to eng manager and unfurls what stellar engineering management looks like at high-growth companies, including: Setting appropriate expectations and goals Turbocharging the team’s effectiveness Delivering high-impact feedback Going from a peer to a manager What leaders risk when th...
May 25, 2023•1 hr•Ep. 95
Todd Jackson is back on the mic to guest host another product-focused episode. This time, he chats with Kesava Kirupa Dinakaran , co-founder and CEO of Luminai, a B2B software tool that helps automate any manual process down to just one click. Dinakaran’s personal and professional story is one that you do not want to miss. A former Rubik’s Cube champion and back-to-back Hackathon winner, Dinakaran’s foray into the world of building software products is anything but conventional. The founders stu...
May 18, 2023•59 min•Ep. 94
Our guest today is Douglas Hanna , Chief Operating Officer at Grafana Labs. Grafana Labs is an observability stack built around Grafana, a leading open-source technology for dashboards and visualization. Douglas is a seasoned revenue leader, previously leading operations and GTM strategy at Zendesk. At Grafana Labs, Douglas has been instrumental in scaling GTM at the open-source company — building up both team headcount and its revenue model. In our conversation today, Douglas dives deep into th...
May 11, 2023•1 hr 5 min•Ep. 93
Today’s conversation is with Jessica McKellar , co-founder and CTO of Pilot , which is the largest accounting firm for startups. She’s been working on Pilot for the last 6 years with her two co-founders, Waseem Daher and Jeff Arnold. But what makes this founding trio super unique is that they’ve stuck together in not just one, but three different startups. As repeat founders, the Pilot team has learned a ton from their first two ventures, K Splice and Zulip, and both netted some positive outcome...
May 04, 2023•56 min•Ep. 92
Our guest today is Artem Kroupenev, VP of Strategy at Augury. Augury is a leader in a category they helped to define known as “machine health.” The company sells products that combine hardware, AI, and SaaS within industrial manufacturing. Artem joined the team at the very beginning of its journey and helped shape strategies for how the team measured product-market fit, go-to-market, and eventually, a strategy for designing a brand new market category they could compete in. In our conversation t...
Apr 27, 2023•55 min•Ep. 91
Our guest today is Jeanette Mellinger , Head of UX Research at BetterUp and our User Research Expert in Residence at First Round. In today’s conversation, Jeanette unspools her tested playbook for high-quality customer interviews, with particular advice for founders in the very early days of validating an idea, including: The three-step framework for a thorough user-research process The biggest mistakes she’s noticed after working with dozens of early-stage companies Specific advice for structur...
Apr 20, 2023•1 hr 11 min•Ep. 88
Our guest today is Claire Hughes Johnson , former COO of Stripe and author of the new book, “ Scaling People: Tactics for Management and Company Building .” Claire joined Stripe as its COO back in 2014 and, over the course of her nearly seven years in the company’s executive suite, she oversaw rapid growth as Stripe scaled from under 200 employees to over 7,000. Prior to Stripe, she spent 10 years at Google leading various high-impact business teams. In today’s conversation, In today’s conversat...
Apr 13, 2023•1 hr 16 min•Ep. 89
Our guest today is Rachel Hepworth, Head of Marketing at Notion. Rachel currently runs growth marketing at Notion, and sees her job as bringing process and control to all of Notion’s different marketing channels. Before joining Notion, Rachel launched the first growth marketing team at Slack, laying down the tracks for a well-oiled go-to-market strategy that could be measured easily. Much like Slack, Notion has made a name for itself largely through customer love and a powerful word-of-mouth rec...
Apr 06, 2023•54 min•Ep. 86
Our guest today is Nadia Singer, Chief People Officer at Figma. Nadia joined Figma in 2020 and has seen explosive growth in her own career alongside the collaborative design platform’s. Before Figma, Singer was a talent expert who has hired hundreds of talented folks at places like Quora, Facebook and Google. In our conversation today, we dive deep into what makes someone a terrific talent evaluator. Nadia opens up her own recruiter playbook and shares: Her personal recruiting trick, which is to...
Mar 30, 2023•49 min•Ep. 87
Todd Jackson is back on the mic to guest host another product-focused episode this week with Christina Cacioppo , the co-founder and CEO of Vanta . Vanta is the leading automated security and compliance platform, with thousands of businesses relying on the product to get compliant (and to stay that way). After toying with some initial ideas, like a voice assistant for biologists, Christina started building Vanta to solve a problem that didn’t really exist at the time. The company started out in ...
Mar 23, 2023•47 min•Ep. 86
Our guest today is Ben Lang , Head of Community at Notion. Since joining the company in 2019, Ben has had his hand in several high-impact projects at Notion that has grown its tight-knit community of passionate Notion evangelists into millions of users today. But before he was doing this as a full-time job, Ben was already spreading his love for Notion in his free time as a voracious product user. After discovering the tool on Product Hunt, he became obsessed. He got on the company’s radar after...
Mar 16, 2023•44 min•Ep. 85
Todd Jackson is back on the mic to guest host another product-focused episode this week. He chats with Bryant Chou , co-founder and founding CTO of Webflow, a no-code visual web design platform built with freelance designers and developers in mind. Today, Webflow is valued at over $4 billion and has millions of users all over the world. More than 200,000 freelancers, agencies, small businesses and enterprises use Webflow to help design and power their websites at businesses large and small. But ...
Mar 09, 2023•56 min•Ep. 84
Our guest today is Don Faul , CEO of CrossFit. Don has a fascinating background where he’s been able to find success in environments as different as a combat zone and a corporate board room. After spending 8 years as a platoon commander in the U.S. Marine Corps, Don had stints at some of the most vaunted companies in tech, including Google, Facebook and Pinterest, the latter of which he served as the Head of Operations. It’s a really unique set of leadership experiences spanning very different c...
Feb 23, 2023•1 hr 10 min•Ep. 83
Our guest today is Brie Wolfson . Brie spent nearly 5 years at Stripe, where she worked on bizops and launched Stripe Press, followed by a stint at Figma where she worked on education. She then started her consultancy, named The Kool-Aid Factory, to share her lessons on building team cultures. And now she’s operating as a first-time founder building Constellate, a new productivity and communications tool for teams. In today’s conversation, we’re focused on company culture. A decade or so ago, co...
Feb 09, 2023•54 min•Ep. 82
Our guest today is Aaron Zamost . After a comms career at Google, Aaron joined Square in 2011 to lead corporate communications. He went on to join the exec team, reporting directly to Jack Dorsey and leading the comms strategy for Square’s IPO in 2015. In an interesting move, he also took on leading the people organization as well, running both orgs up until he left in late 2020. In addition to lecturing at UC Berkeley's School of Law, Aaron now runs Background Partners, a communications consult...
Feb 02, 2023•1 hr 6 min•Ep. 81
Our guest today is Daniel Debow , a VP of Product for Demand at Shopify. Daniel is a three-time founder and a seasoned M&A pro. Daniel oversaw the process of all three of his companies’ acquisitions and has helped continue to grow them at scale inside larger corporations. His most recent startup, Helpful, was acquired by Shopify in 2019. Before that, he co-founded Rypple which was acquired by Salesforce in 2011. His first startup, Workbrain, was acquired by Infor in 2007. In our conversation...
Jan 26, 2023•1 hr 4 min•Ep. 80
Our guest is Anna Binder, Head of People at Asana. We go back to the earliest days when Anna first took on the role, starting with how she prioritized the initial things to tackle as a new People exec and combing through a slew of opinions that bubbled up from other folks at the company. Next, she shares her tactical playbook for creating a culture of feedback for not just low-performers, but high-performers, too. Anna also unpacks her methodology of conscious leadership, and how the best leader...
Jan 20, 2023•1 hr 5 min•Ep. 79
For our first episode of 2023, our guest is Mike Boufford , CTO of Greenhouse , an applicant tracking system and recruiting platform. Mike has a unique career as an engineering leader. He wrote the first line of code at Greenhouse in May 2012, and he’s still there — over a decade later. This isn’t the typical path of non-co-founding engineers, who usually get layered or leave to start their own ventures. In our conversation today, we focus on how founders build an environment that makes early em...
Jan 12, 2023•1 hr 2 min•Ep. 78
Our guest is Peter Kazanjy, co-founder of Atrium and author of “ Founding Sales: The Early Stage Go-to-Market Handbook .” As an early-stage founder, there’s something comforting about the build stage. You’re tinkering with the nascent product, honing your MVP and dreaming up the possibilities of how much folks are going to love what you create. But once you get out of that comfort zone of quietly building and start trying to sell, things tend to get infinitely more complicated. In today’s conver...
Dec 15, 2022•1 hr•Ep. 77
Todd Jackson is back on the mic to guest host another product-market fit focused episode this week. He chats with Deepak Rao , co-founder and CEO of X1 , a consumer fintech startup that’s building a credit card for a new generation. Just last week, X1 announced a $15 million funding round . But we’re here to rewind the clock and unpack how the startup got to this point. As you’ll hear in today’s conversation, the path required a dramatic pivot. Here’s a preview of what Deepak shares: The emotion...
Dec 08, 2022•56 min•Ep. 76
