Today’s episode is with Dharmesh Shah, the co-founder and CTO of Hubspot. In today’s conversation, we deeply explore some of the marquee moments along the 15-year journey building Hubspot. To start, Dharmesh unpacks the very specific way he and his co-founder Brian Halligan approached evaluating their compatibility as co-founders. He’s got tons of advice for other potential founding pairs to increase the likelihood of success and smoother sailing. Next, he points to some of the foundational buil...
Dec 02, 2021•54 min•Ep. 45
Today’s episode is with Zach Kitschke , CMO of Canva, an online design and publishing tool. Since launching in 2013, Canva has grown from an Australian startup to a global company, with 60 million monthly active users, over 2,000 employees, and a $40 billion valuation. Zach was one of Canva's first employees, leading comms efforts around their initial launch and fundraise. But since then, he’s done everything from answering support tickets and cooking the team lunch, to serving as a product lead...
Nov 18, 2021•1 hr 1 min•Ep. 44
Today’s episode is with Hareem Mannan, who was a product design leader at Segment for nearly four years, and joined Twilio as a Senior Director of Product, Enablement & Design following the company’s acquisition of Segment. In today’s conversation, we deeply explore Hareem’s three pillars of what makes a great designer. To summarize, they are a product quality ambassador, serve as the glue across product areas, and intricately understand the go-to-market motion. We peel back the layers for e...
Nov 11, 2021•1 hr 4 min•Ep. 43
Today’s episode is with Max Mullen, co-founder of Instacart. He started as a generalist, running everything from product to payroll, but as the company has grown over the years, he’s come to focus on one particular area: culture. Since Max is also an active angel investor, he’s also been able to partner with tons of founders and help them think about architecting their own culture at the early stages — which is exactly what we dive into in today’s episode. In the first half of our conversation, ...
Nov 04, 2021•1 hr 2 min•Ep. 42
Today’s episode is with Alisa Cohn, an executive coach with nearly 20 years of experience working with companies like Etsy, Venmo, InVision, The Wirecutter, Google and IBM. Her new book, From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business , just came out this week. In our conversation today, we focus on what founders and startup leaders can learn from Alisa’s experiences as a coach. We start by getting into self-awareness, and how tough it can be for executives to get truly can...
Oct 28, 2021•1 hr 1 min•Ep. 41
Today’s episode is with Gretchen Howard, COO of Robinhood. Gretchen joined Robinhood in early 2019 as the company’s COO and just its second executive hire. She climbed aboard the Robinhood rocketship after 5 years building CapitalG, Alphabet’s investment fund. In today’s conversation, we dive really deep into what she’s learned about executive hiring. To start, she explains how to align the hiring profile to the trajectory of the business to make sure you’re investing in the right places. She al...
Oct 21, 2021•1 hr•Ep. 40
Today’s episode is with Giancarlo 'GC' Lionetti , the former CMO of Confluent and VP of Self-Serve Growth at Dropbox. (GC also previously spent 6 years at Atlassian, as a sales engineer and product marketing manager for developer tools.) He describes his career as more of a maze than a ladder, and this functional diversity combined with his deep experience at standout B2B companies gives him a unique perspective. In today’s conversation, we dig deep into why he advocates for a hybrid go-to-marke...
Oct 07, 2021•1 hr 6 min•Ep. 36
Today’s episode is with Sandr Oh Lin, founder and CEO of KiwiCo, which creates hands-on learning kits for children. Sandra started KiwiCo over ten years ago, after a career with executive positions at PayPal and eBay. She was looking for ways to give her own kids more hands-on projects to exercise their creativity, which led her down the path to become an entrepreneur and create KiwiCo. Today, KiwiCo has expanded to include 8 different lines of crates that are shipped out monthly. In the first h...
Sep 30, 2021•58 min•Ep. 38
Today’s episode is with Maya Spivak, the Head of Marketing at Mux, which is an API for developers to build video experiences. Maya recently joined Mux after five years at Segment, where she was the company’s second marketer and its Head of Global Brand Marketing and Communications, as well as a stint at Wealthfront as a marketing director. In today’s conversation, she takes a magnifying glass to the core components of a startup’s marketing org. She starts by breaking down the three pillars of ...
Sep 16, 2021•57 min•Ep. 37
Today’s episode is with Archana Agrawal, CMO of Airtable, a low-code platform for building collaborative apps. Archana joined Airtable last year after 7 years at Atlassian, where she eventually became the company’s Head of Enterprise and Cloud Marketing. She also sits on the board for MongoDB and Zendesk. We start today’s conversation by dissecting some of the messaging challenges facing horizontal products like both Airtable and Atlassian, and her tips for narrowing in on the right persona. She...
Sep 09, 2021•56 min•Ep. 36
Today’s episode is with Tara Viswanathan, co-founder and CEO of Rupa Health. Tara started Rupa Health in early 2018, but the product vision today looks very different from what she first built. As she’ll talk about over the course of today’s interview, she went through plenty of sometimes painful pivots on the path to finding product/market fit for Rupa. Tara is incredibly candid about all of the things she had to learn the hard way as a first-time founder going from zero to one. For the first h...
Sep 02, 2021•57 min•Ep. 35
Today’s episode is with Steve Gutentag , the co-founder and CEO of Thirty Madison , a healthcare company focused on widening access to specialized care for chronic conditions. After previously starting two other companies with his co-founder Demetri Karagas, they launched Thirty Madison in 2017 with Keeps , a men’s hair loss solution. The team has since gone on to launch several new brands, including Cove (for migraines), Evens (for GI issues), and Picnic (for allergies). With the acceleration i...
Aug 19, 2021•1 hr•Ep. 34
Today’s episode is with Jane Davis , the Director of UX Research and UX Writing at Zoom. She previously led UX Research and Content Design at Zapier, and managed the growth research team at Dropbox. Throughout the episode, Jane tackles the thorniest customer development questions and walks us through the end-to-end research process in incredible detail, covering everything from clarifying your goals and asking the right questions, to selecting participants and synthesizing insights. We start by ...
Aug 12, 2021•1 hr 4 min•Ep. 33
Today’s episode is with Alex Buder Shapiro , the Chief People Officer at Flatiron Health, a company that focuses on accelerating cancer research and improving patient care. Alex first joined Flatiron back in 2016, after an 8-year stint on Google’s People Operations team. Before her promotion to Flatiron’s executive team this past March, Alex previously ran the HR business partner and employee relations team as the startup rapidly scaled. We kicked things off by talking about resolving conflict a...
Jul 29, 2021•58 min•Ep. 32
Today’s episode is with Ryan Glasgow, the founder and CEO of UserLeap, a product research platform that helps PMs, user researchers, and growth marketers launch microsurveys to uncover customer insights faster. Before founding UserLeap in 2018, Ryan was a PM and early team member at Weebly (which was acquired by Square) and Vurb (which was acquired by Snapchat). We start by rewinding the clock back to the 6-month period before Ryan started the company — when he was validating his idea and assess...
Jul 22, 2021•1 hr 5 min•Ep. 31
Today’s episode is with Nick Caldwell, VP of Engineering at Twitter. Previously, Nick was at Microsoft for 15 years, eventually becoming GM of Power BI. Nick has also held roles as Reddit’s VP of Engineering and Looker’s Chief Product and Engineering Officer. Between Microsoft, Reddit, Looker, and now Twitter, Nick’s worked for companies with vastly different cultures. And in today’s conversations, we comb through the biggest lessons from each of these orgs. With Microsoft, we unpack what Nick b...
Jul 15, 2021•59 min•Ep. 30
Today’s episode is with Sam Taylor, VP of Sales and Success at Loom. Previously, Sam was Dropbox’s first enterprise sales rep, and also served as Quip’s first sales leader. In today’s conversation, we dig into the key learnings from each stop in Sam’s career so far. Starting with his earliest experience at Dropbox, he walks us through his aha moment that sales is an insight driver — which includes his lessons on pricing and packaging, as well as plotting the feature roadmap as Dropbox moved up m...
Jul 08, 2021•1 hr 2 min•Ep. 29
Today’s episode is with McKenna Quint, who was most recently the Head of People at Plaid and also built and led the people team at Cruise Automation. Currently, she’s co-founder and general partner at Quint Capital, a seed-stage fund. In today’s conversation, we focus on the people challenges that inevitably crop up when you’re going from a couple dozen employees to a couple thousand. We start by discussing when startups should draw from established playbooks in the people space versus when to s...
Jun 24, 2021•1 hr 6 min•Ep. 28
Today’s episode is with Waseem Daher, co-founder and CEO of Pilot, a company that specializes in bookkeeping, tax prep, and CFO services for high-growth startups. In addition to Pilot, Waseem co-founded two other startups with the same group of co-founders, including Ksplice, which was acquired by Oracle in 2011, and Zulip, which was acquired by Dropbox in 2014. In today’s conversation, we pay particular attention to the earliest days of Pilot. Waseem takes us behind the scenes of the ideation s...
Jun 17, 2021•1 hr 7 min•Ep. 27
Today’s episode is with Shannon Brayton, a Silicon Valley veteran with more than two decades of experience shaping corporate narratives and leading teams at companies like LinkedIn, OpenTable, eBay, Yahoo!, and Intuit. She recently joined Bessemer as the venture capital firm’s first-ever CMO. In today’s conversation, Shannon shares the comms and leadership lessons she’s picked up along the way. In addition to sharing her broader philosophy around the role of comms and her thoughts on why it’s on...
Jun 10, 2021•59 min•Ep. 26
Today’s episode is with Colleen McCreary, the Chief People Officer at Credit Karma. With more than 20 years of experience in HR, operations, recruiting and M&A, Colleen has headed up the people function at companies such as Vevo, The Climate Corporation, and Zynga. She’s also seen the early-stages and scaled through multiple IPOs and acquisitions, which means she has a great perspective on the people problems founders tend to run into as their businesses grow. We kick this conversation off w...
Jun 03, 2021•1 hr 8 min•Ep. 25
Today’s episode is with Irving Fain, founder and CEO of Bowery Farming. Bowery is a modern farming company that grows produce indoors, free from pollutants and using significantly less water and space. Just this week, the company announced a $300 million Series C round, the largest private fundraise to date for an indoor farming company. Bowery’s mission to democratize access to fresh, locally grown food. It’s no doubt an extremely complex problem, so it might surprise you that its founder, Irvi...
May 26, 2021•1 hr 8 min•Ep. 24
Today’s episode is with Kelly Watkins, CEO of Abstract, a platform for structure and transparency in the design process. In joining Abstract last year, Kelly is one of very few folks from a marketing background to take on the CEO seat. She brings a wealth of experience leading incredibly high-performing marketing teams for Slack, Github, and Bugsnag. In today’s conversation, we start by reflecting on her first year as CEO. She shares her alternative to yearly planning, borrowing from famed milit...
May 20, 2021•1 hr 3 min•Ep. 23
Today’s episode is with Rick Song, the co-founder and CEO of Persona, a platform that enables companies to create the ideal identity verification experience for their customers. Before founding Persona in 2018, Rick was an engineer at Square for 5 years, and an early team member at Square Capital. Rick is at an exciting inflection point in his journey of building from zero to one — just last week, Persona shared that they’ve raised a $50 million Series B round. The company plans to double the te...
May 13, 2021•58 min•Ep. 22
Today’s episode is with Eric Berg, CEO of Fauna, which is an adaptive operational database platform. In joining Fauna as its CEO in the summer of 2020, he brought a wealth of experience as a product leader. Most recently, he was the Chief Product Officer at Okta, scaling the company from 10 employees and zero customers to its eventual IPO in 2017. He started his career in product at Intel, working under the legendary Andy Grove, as well as a five-year stint as a product leader at Microsoft. In t...
May 06, 2021•1 hr 2 min•Ep. 21
Today’s conversation is with Elliot Shmukler, founder and CEO of Anomalo, which is a platform that validates and documents all of your data. Elliot founded Anomalo after a storied career as a product and growth leader at some of the most interesting companies around. Most recently, he was Instacart’s Chief Growth Officer, driving fast and profitable growth and geographic expansion. His jam-packed resume also includes stops at Wealthfront as the VP of Product and Growth and as a product leader at...
Apr 29, 2021•1 hr 5 min•Ep. 20
Today’s episode is with Kate Taylor, who recently joined Notion as their Head of Customer Experience. Previously, Kate spent 8 years at Dropbox, leading their SMB revenue and scaled sales operation before leaving in 2020. Prior to that, she started her career as a sales rep at Salesforce. In today’s conversation, Kate shares a wealth of advice for building out product-led growth and self-serve motions. She shares tons of nuances around going up market, competing with sales and product planning, ...
Apr 22, 2021•57 min•Ep. 19
Today’s episode is with Mark Frein, the Chief People Officer & Head of Alumni Programs at Lambda School. Previously, Mark served as the Chief People Officer at both InVision and Return Path. He also ran his own leadership development consultancy and taught on HR topics as an adjunct professor. Mark has an invaluable perspective and tons of advice to share after setting up several people orgs in a range of different companies. In this conversation, Mark shares his approach to the CPO role and...
Apr 15, 2021•1 hr 7 min•Ep. 18
Today’s episode is with Marco Zappacosta, co-founder and CEO of Thumbtack. He’s spent the last 13 years building the company into a billion-dollar business — and it’s his first and only job after graduating college. In today’s conversation, Marco dives into the company milestones that require a return to first principles versus pulling from a tested playbook, and the mental models he leans on when parsing through the mountains of advice he gets as a first-time founder and CEO. He connects these ...
Apr 08, 2021•1 hr 8 min•Ep. 17
Today’s episode is with Tido Carriero, the Chief Product Officer at Segment, a customer data platform which was recently acquired by Twilio. Before that, he built out the engineering teams that worked on the core product and the initial business product at Dropbox. Tido started out his career in 2008 as an early member of the Facebook ads engineering team, and went on to become an eng manager on the Pages team, a transition from IC to leadership that he talks about in this episode. In today’s co...
Apr 01, 2021•58 min•Ep. 16
