In Depth

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 candid feedback. As an expert in the art of conducting 360 feedback, Alisa shares the right questions to ask, as well as tips for getting at the root of what people are actually saying in their feedback. We also dive into what to do with what you hear, from why not every piece of feedback is useful, to her tips on how to actually enact change in your day-to-day routine. Next, we tackle the most common opportunities for growth that she’s seen time and time again in her coaching practice, from communication and decision-making, to how the CEO’s own personality is often unconsciously reflected in the company culture.We wrap up by covering how to have effective conversations about layering and letting people go, as well as the reflection ritual that she recommends every founder incorporate into their daily routine.This episode will be helpful for those who are making the transition from scrappy founder to established CEO, but it’s a great listen for any startup leader who’s struggling to give away their Legos.You can follow Alisa on Twitter at @AlisaCohn. You can email us questions directly at review@firstround.com or follow us on Twitter @FirstRound and @BrettBerson.

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 also unpacks her hiring philosophy as it pertains to Robinhood, including balancing financial industry expertise with an innovative, hands-on mindset that’s critical for startups.Next, she walks us through the executive interview process she’s crafted at Robinhood, including the three traits that are always at the top of her wish list for candidates — including sussing out whether someone has a “knower” versus a “learner” attitude. She also explains her complicated feelings towards certain interview exercises and how she leverages reference checks. Finally, she shares her tips for successfully onboarding new executives so these hires don’t result in what she calls “organ rejection.”If you’re struggling with your executive hiring — whether it’s coming up with the right candidate profile, aligning on culture fit, or finding that your interview process doesn’t seem to be surfacing the best candidates, this conversation is a must-listen.You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettbersonLearn more about how Cocoon makes employee leave easy by visiting https://www.meetcocoon.com/

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-market strategy that brings together more traditional selling with modern product-led growth.We start by mining lessons from GC’s time at Atlassian and Dropbox, including his takes on the differences between their business models and what it takes to make a multi-product go-to-market motion work.Then we dive right into his advice for a hybrid approach, covering everything from his litmus tests for picking the right metrics, to the structure of his weekly meetings. GC explains how he sinks tons of time into understanding the customer journey, mapping out the delta between reality and the ideal vision. He also shares plenty of pro-tips about pricing, packaging, and activation, as well as a broader diagnostic framework that he’s developed to evaluate a company’s go-to-market strategy. We wrap up by focusing on team building for a hybrid go-to-market strategy — from hiring profiles to team structure.It’s a great listen for founders, product and go-to-market leaders, with tons of examples of specific impactful experiments he ran, metrics that did or didn’t work out, and common traps that he sees teams falling into. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

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 half of today’s conversation, we excavate some of the thornier challenges that come with creating a physical product — and Sandra’s biggest aha moments as a first-time founder. She talks about creating the first KiwiCo crate, including the product development process and spinning up a supply chain and shipping department. Sandra also walks us through how KiwiCo approaches new product lines, particularly in the last year when KiwiCo demand skyrocketed. She also discusses how the team gathers quality consumer feedback when your customer is often a toddler. In the second half of our interview, she talks about some of the cultural practices at KiwiCo that all sorts of companies can learn from. Sandra’s a big believer in manager training for everyone from folks that manage just one person, to executives that have been managing for decades. She outlines the specific management training modules they leverage at KiwiCo and makes the case for having everyone at the company fill out a motivations spreadsheet. Finally, she discusses the specific tactics she leans on for creating a feedback-rich environment for herself as a CEO. You can follow Sandra on Twitter at @sandraohlin. 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 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 marketing roles — product, brand, and growth. She explains the leading indicators that your startup is ready to hire folks within each of these pillars — which starts with analyzing your sales motion and sizing up the founders’ strengths and weaknesses. Next, Maya pulls back the curtain on how she architects interview loops for each of these different roles, and the unique capabilities that separate good candidates from great, must-hire folks. Finally, she reflects on her experience as one of the earliest marketing hires at Segment, and how she built the marketing org in the first couple of years to keep up with the shifting needs of the growing startup. Today’s conversation is of course a must-listen for marketers, particularly marketing leaders and hiring managers that are trying to pluck out the best and the brightest to join their org. But there’s a ton for other folks to learn from this interview, which explains some of the nuances of startup marketing you may not fully appreciate. You can follow Maya on Twitter at @papayamaya. 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 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 also dives into the close interplay between product and marketing teams, particularly for product-led growth companies. Throughout our conversation, we talk a lot about organizational design, and how to set your teams up for breaking down siloes and fostering experimentation. She explains how she oversees all the different marketing functions that report up to her as CMO, and the rituals she’s established for keeping the pulse on what most deserves her attention. Today’s conversation is of course a must-listen for marketers, but folks all over the org chart at product-led growth companies will appreciate the insights from both Atlassian and Airtable. As a former engineer-turned-marketer, Archana has an incredibly unique, data-driven perspective as a CMO. 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 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 half of our interview, we pay particular attention to her lessons in finding the elusive startup holy grail of product/market fit. We cover the aha moment that the first iteration of the product wasn’t going to work, and why she thinks hiring a few folks before finding product/market fit was one of her earliest mistakes. We then dive into her decision to create a new product knowing that it wasn’t going to be the thing that ultimately worked — but was bullish that it would lead down the right path. In the second half of our interview, she talks about hiring Rupa’s early team, and her tactics that go against the grain of conventional startup wisdom. For starters, she leaned heavily on external contractors rather than full-time employees on the path to product/market fit — and she thinks more founders should consider doing the same. She also dives into why she hates job descriptions, and what she prescribes instead. As a founder still in the trenches, Tara is game to get super tactical about the things she’s tried along Rupa’s winding journey that did and didn’t work. It’s a must-listen for other founders — or anyone that’s got a burning curiosity about what it’s actually like to be an entrepreneur. You can follow Tara on Twitter at @taraviswanathan. To learn more about the “who” interview, check out the book “Who: The A Method for Hiring.” Be sure to check out the recent coverage of Rupa Health in Forbes. 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 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.