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 in telemedicine due to COVID-19, the company has tripled both their revenue and their team size in the past year, recently announcing $140M in Series C funding and a more than $1B evaluation. We start our conversation by getting into the challenges of building an operationally complex business with a physical or real-world component. Steve shares the lessons he learned from building his first two startups, and figuring out what he was uniquely suited to build. He also shares why they wanted to pick a business that worked with unit economics on day one, walking us through their methodical approach to figuring out if the idea for Thirty Madison would. From their conservative assumptions for each line item, to the unlocks that came from more inventive moves, Steve shares tons of pointers here — including why you should think of your own internal operations as a marketplace, and how unit economics won’t magically fix themselves at scale. In the last part of our conversation, we get into building the team that’s pulling all of this complex work off. We talked about when to hire for industry experience versus a fresh perspective, as well as more granular hiring tactics such as the interview questions he asks to learn about a candidate’s journey as a manager. You can follow Steve on Twitter @stevengoodday, and you can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

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 going through how she applies her playbook in the early-stage startup context — when you’re shipping the first version of your product and don’t yet have the resources to invest in a full research team. We also dig into challenges such as deeply understanding the problem you’re solving, taking on a competitive or a greenfield market, and figuring out willingness to pay. We also get into best practices for prototyping and iterating, as well as some of the common roadblocks startups face later on, including how to build for multiple users and what to do when people aren’t excited about your product or using it frequently. Whether you’re talking to potential customers before you start a company, or are looking to get better feedback from your current users, there’s tons of insights in here for founders, product-builders, and design folks alike. Here’s the book Jane mentioned in the episode: Just Enough Research by Erica Hall. We also recommend checking out Jane’s recent article: What’s the point of a UX research team? You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

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 at work. Alex talks us through the patterns she’s seen across her career and her advice for troubleshooting, including why she loves borrowing techniques from the world of couples therapy.   We also touch on the challenge of getting employees to stick around long-term at startups. From hiring your own boss to navigating tough career conversations, Alex shares helpful tips, as well as more about her own journey rising through the ranks from IC to exec at Flatiron.   Her experiences mean that she’s also seen the growing pains that come with scaling first hand — things like the challenge of “selling” your new role with an elevator pitch when you first join, or the danger of locking into people processes and frameworks too early.   This episode explores so many different facets of what it means to be both a people leader and a long-tenured employee at a fast-growing startup, meaning there are plenty of lessons for managers and leaders in any function.   You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

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 assessing the crowded market. From how he approached segmentation and early customer conversations, to common product/market fit mistakes, there’s so much advice in here for aspiring entrepreneurs.   We also get into what the first version of the product looked like, how they think about adding new features, and how UserLeap’s 3 product principles are used day-to-day. We also dig into how this self-described “product guy” taught himself founder-led sales, including the specific tactics that made the biggest difference and how he’s refined his approach into a repeatable playbook.   From the question he always asks in customer meetings, to the books that have had the biggest impact on his development, there’s tons of really tactical nuggets in here for founders and product leaders alike.   Here are the books Ryan mentioned in the episode: What Customers Want: Using Outcome-Driven Innovation to Create Breakthrough Products and Services by Anthony Ulwick You Can't Teach a Kid to Ride a Bike at a Seminar by David Sandler User Story Mapping: Discover the Whole Story, Build the Right Product by Jeff Patton   You can follow Ryan on Twitter at @ryanglasgow.   You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

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 believes is a massively underrated approach to organizational design. He explains the company’s rigorously approach to regular pruning and shaping the org chart. He also gives us an inside look at their management training and talent development, as well as what Nick calls the fairest performance review system he’s seen.   As Nick tells it, there was a steep learning curve when he pivoted from 15 years at Microsoft to Reddit. He doles out advice for other folks getting their bearings after a big career move. He also explains how Reddit’s mission-driven culture informs his approach to leadership at Twitter.    Finally, with Looker, Nick unpacks his biggest lessons from leading both the product and engineering teams, which offered him a unique perspective on how these two orgs that are often at odds can properly team up.   It’s an incredibly wide-reaching conversation, so there’s something for pretty much everyone. Whether you’re interested in the cultural practices that power some of the world’s biggest companies, or you’re a manager looking to level up, or you’re an engineer with goals to take on leadership, Nick’s got plenty of advice and insider stories to share.    You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

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 market. Next, he reflects on his time at Quip, including what sticks with him from working closely with its CEO Bret Taylor and COO Molly Graham. He also digs into his tested tactics for selling in a competitive market where you’re going up against plenty of established players, like Google and Microsoft. We then turn our attention to his current role at Loom, and how he’s threading all of those experiences together. He pays particular attention to his partnership with Loom’s product leaders, and how they’re teaming up to achieve what he jokingly calls “total Loom domination.” If you’re in sales, you won’t want to miss Sam’s insights he’s picked up over the course of multiple startup success stories. And folks that work for other functions at product-led growth companies will come away with a greater understanding and appreciation for how sales fits in. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

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 start from first principles. She also dives into the details of bringing her data mindset to the people space, including designing a sophisticated attrition model.   Next, she tackles some of the questions she most often gets from startup founders, including whether the company should introduce levels, what to look for in your first people leadership hire, and how to approach performance reviews.   Finally, we dive into a larger conversation about the roles that companies play in today’s employee experience. From the company cultures that most inspire her, to the evolution of uncomfortable conversations in the workplace, and what pieces of the Google cultural revolution she’s ready to leave behind.   Today’s conversation is a must-listen for HR leaders of course, but also for folks at startups across the org chart that want an inside look at what’s top of mind for people leaders today — and the systems behind the scenes that powers startups to reach new heights.   Let My People Go Surfing: https://www.amazon.com/Let-People-Surfing-Education-Businessman/dp/0143037838   Management Lessons from the Mayo Clinic: https://www.amazon.com/Management-Lessons-Mayo-Clinic-Organizations/dp/1260011836   Let’s Not Kill Performance Evaluations Yet: https://hbr.org/2016/11/lets-not-kill-performance-evaluations-yet   You can follow McKenna on Twitter at @mckmoreau   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

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 stage for what would eventually become Pilot, and how the founding team gained conviction to actually start building. He also explains why Pilot landed on its human plus machine model, with a software component in addition to employing full-time accountants and tax preparers to partner with customers.     Next, we talk about building out Pilot’s ICP, and how he started getting the product into the hands of paying customers. He’s got some great tips for framing conversations with potential customers to make sure you’re building a must-have product that solves hair-on-fire problems, not a nice-to-have. Finally, he looks out to the horizon and shares how he prioritizes which offerings to add to Pilot’s product suite.    Today’s conversation is an absolute must-listen for founders and folks that have goals to one day become founders. Product pros also won’t want to miss learning from Waseem’s playbook honed over the course of building three companies.    You can follow Waseem on Twitter at @waseem. For more startup real talk from Waseem, you can subscribe to his Substack: https://waseem.substack.com/    You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

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 one of the more underappreciated functions, Shannon gets into the tactical weeds on everything from killing stories and creating new categories, to her frameworks for building relationships with reporters. There’s plenty of career advice as well, from how she approaches selecting companies to work for, to what the transition from head of comms to CMO was like, to what she’s learned from mentors and bosses like Jeff Weiner.   Here’s the reverse mentoring post Shannon mentioned on how she approached taking on the CMO role: https://www.linkedin.com/pulse/how-i-tackled-first-100-days-my-new-role-reverse-brayton/    You can follow Shannon on Twitter at @sstubo.   You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson

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 with Colleen’s explanation of why she designs for the 80% and focuses on clarity, context, and consistency when building people organizations and crafting culture. She walks us through some really tactical examples of that work, including how her team approaches compensation at Credit Karma and the reason they do promotions quarterly.   Colleen also shares why she views the Chief People Officer not as the CEO of culture, but rather the product manager of the systems and tools that run the company. She gives a detailed look at how she approaches many of those systems, from how rewards and recognition were incredibly different at Zynga and Credit Karma, to why career growth isn’t just about a promotion. Colleen also shares her take on whether we should double down on strengths or focus on correcting weaknesses when it comes to performance.   Given her experience as a 4X Chief People Officer, today’s episode is a must-listen for first-time founders and early people leaders looking for a roadmap as their startups scale.   You can follow Colleen on Twitter at @Chiefpplofficer, and you can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.