In Depth

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. 

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, Irving, didn’t have any background in agriculture before starting Bowery. He was previously the CEO and founder of CrowdTwist, a loyalty and analytics solution that was eventually acquired by Oracle, and helped build iHeartRadio.    But looking back on the early days of Bowery, Irving believes his naivety was in fact an asset. Coming in with no preconceived notions about how to solve the problem, he committed to approaching agriculture with a wide aperture and going unreasonably deep. In today’s conversation, he walks us through his multi-pronged approach to developing the idea for what would become Bowery, which includes paying just as much attention to the doubters as to the folks who believed in the vision.      Next we switch gears and talk about assembling Bowery’s small-but-mighty team of five, which Irving kept deliberately small and sought out folks that didn’t have vast agriculture experience and could approach problems from first principles. Whether you’re a founder yourself or have long-term career goals to make the leap, today’s episode is packed with equal parts inspiration and tactical takeaways.    You can follow Irving on Twitter at @ifain   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson    To learn more about Bowery Farming and its most recent fundraise, https://techcrunch.com/2021/05/25/indoor-farming-company-bowery-raises-300m/amp/

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 military strategist John Boyd. Kelly also walks us through Abstract’s most recent product launch, and how it clearly crystallized her leadership point of view to constantly optimize for trade-offs, rather than clear-cut right and wrong.    Next we switch gears to talk about some of the lessons from her storied marketing career. She unpacks her jobs-to-be-done approach for crafting a product story when there’s loads of competition. She also takes us behind the scenes in developing Slack’s “where work happens” tagline, and crossing the chasm from a passionate early adopter customer base to the ubiquitous product it is today.    Today’s conversation is a must-listen for marketing folks, who will surely appreciate the peek behind the curtain. But all sorts of leaders with goals to more effectively collaborate with the org will come away with a deeper understanding of marketing’s art and science.    You can follow Kelly on Twitter at @_kcwatkins   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson    To learn more about Kelly’s advice on hiring your first head of marketing, read her Medium article: https://medium.com/hackernoon/how-to-hire-your-first-head-of-marketing-67c43dd2cd73 For more on the jobs-to-be-done framework, check out this article on the Review: https://review.firstround.com/build-products-that-solve-real-problems-with-this-lightweight-jtbd-framework

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 team this year to keep up with revenue that’s surged more than 10x and a customer base that’s grown to include big logos like Square, Postmates, and Gusto. In today’s conversation, one theme stands out: Rick is somewhat obsessed with the idea of pre-mortems, or figuring out why things might not work out. From all the ways a candidate might fail, to why a customer won’t want a product, to how a commonly-used framework might not be a good fit, Rick brings this mindset to every aspect of running Persona.  From hiring lessons to go-to-market strategies, Rick offers up some counterintuitive thinking, including why his engineers sell and cold-email prospects, and why he doesn’t try to convince candidates that Persona is a company that will change the world. Today’s episode holds tons of insights for anyone who’s a founder or thinking about starting a company one day, but there’s also plenty in here for engineering leaders and hiring managers. You can follow Rick on Twitter at @rickcsong and learn more about Persona at https://withpersona.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 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 today’s conversation, he opens up his executive playbook as he weaves together each of those experiences — and covers a lot of ground along the way. He starts by talking about early go-to-market lessons and the keys to honing in on an ICP to get Okta off the ground. He also dives into the often-maligned “messy middle,” particularly when it comes to moving upmarket and developing a pricing and packaging model that, when done well, takes a company to new heights.         We then switch gears and discuss more broadly about team building and company building — particularly the cultural lessons that stick with him from his tenure at each stop in his career. His biggest learnings include hiring folks up and down the org chart with the right ego to talent ratio and the tactical steps he takes to implement a “disagree and commit’ value so it’s not just a long-forgotten team motto. Finally, we touch on the biggest surprises as he approaches one year of sitting in the CEO seat.    Today’s conversation is a must-listen particularly for product folks, as well as others who want to more deeply understand the trade-offs that nearly every great company faces on the path to scale.    You can follow Eric on Twitter at @ericberg.   You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

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 LinkedIn and eBay.    In today’s conversation, we pull on threads from his newest role as a founder of a startup going from zero to one, including his biggest surprises in the transition from executive to CEO. We also touch on how he prioritizes his time at a startup still in the earliest stages of company-building, and how to avoid wasting your time on prospects that are not all that interested in actually buying.    Next, we turn our attention to his history of picking incredible companies to work for — from the questions he asks as a candidate to the decision-making frameworks he borrows from his poker playing. Finally, we end with his biggest lessons from the best CEOs he’s worked with, including habits that set the best communicators apart from the pack, and the tactics for keeping office politics at bay so the best ideas are able to surface.    All sorts of folks will find something worthwhile in today’s conversation — whether you’re a founder still in the early phases of customer discovery, an executive with long-term goals to start your own company, or someone earlier in their career that wants to get better at spotting the next unicorn.    You can follow Elliot on Twitter at @eshmu.   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson   To learn more about how Elliot uses A/B testing as a management framework, check out this article on First Round Review: https://review.firstround.com/how-a-b-testing-at-linkedin-wealthfront-and-ebay-made-me-a-better-manager   And check out “The Goal,” which Elliot cited as the most influential management book he’s ever read: https://www.amazon.com/Goal-Process-Ongoing-Improvement/dp/0884271951

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, offering up tactical advice that any founder, product or go-to-market leader can learn from.   Kate also gives us a detailed look at how they approach product prioritization at Notion, including their system of 700 tags and examples of tradeoffs they’ve had to navigate. We also get into pricing and packaging, from specific experiments at Dropbox to why interestingly Notion’s trial isn’t time based.    We also chat about how to handle a wide range of use cases, as well as the “front door” customer experience her team is trying to build. From why customer service shouldn’t be focused on getting customers off the phone faster, to the questions she asks to find more signal in their product feedback, Kate shares some counterintuitive thoughts here.   Finally, we wrap up by talking about her approach to leading teams, including why she hires for curiosity, how she tries to teach her team to ride the ups and downs of startup life, and how working for three very different CEOs — Marc Benioff, Drew Houston and Ivan Zhao — has impacted her own leadership style.   Kate isn’t on Twitter, but 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 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 his philosophy around the function more generally, including why he thinks at its core, it’s a data and analytical function and how to match the employee experience to your company’s competitive positioning.   He also gets incredibly tactical on a wide range of topics, from how to hire with empathy and advice for approaching skip-levels, to gathering employee feedback and driving career conversations.   Today’s conversation is a must-listen for both founders and early-stage people leaders trying to thoughtfully scale this function, as well as for current and aspiring managers hoping to hone their leadership and development chops.   You can follow Mark on Twitter at @freintime, and 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 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 dots to how he manages Thumbtack’s board so those quarterly meetings are a critical resource, not just a time suck — and why he shares the board deck with the entire company.   He also candidly reflects on Thumbtack’s COVID-related layoff last year, and what he specifically did as CEO to make sure the folks that remained still had confidence in the company and his leadership moving forward.    Finally, he opens up his playbook for choosing what to spend his time on as a busy CEO with only so many hours in the day — and perhaps more importantly, how he stays accountable for these priorities.   Today’s conversation is a must-listen for company-builders across all industries and growth stages, as well as folks that have hopes to someday occupy these same seats.    To learn more about how Marco and Thumbtack approach executive hiring, check out the article on First Round Review: https://review.firstround.com/assembling-an-executive-leadership-team-is-daunting-let-thumbtacks-ceo-help   You can follow Marco on Twitter at @mlz.   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson