In Depth

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 

Tido Carriero, Chief Product Officer at Segment, previously built teams at Dropbox and was an early Facebook ads engineer. He discusses the challenges of transitioning from individual contributor to leadership, the importance of iterative product development, and achieving product-market fit. Tido shares valuable insights on fostering open communication in teams, the need for clear accountability, and how to effectively recruit top talent. His experiences highlight the balance between engineering goals and business objectives in tech organizations.

Today’s episode is with Russ Laraway. After starting out in the Marine Corps, Russ made his way into the world of startups, joining Google in 2005 where he led teams for 7 years and was recognized as one of the company’s best managers. Russ then went to Twitter, where he founded and ran the SMB advertising business. Afterwards, he teamed up with Kim Scott to co-found Candor, Inc to help people implement the concepts from Radical Candor and have better relationships at work.  In 2018, he joined Qualtrics as the Chief People Officer, a position he stepped away from this past January to focus on helping the company’s customers think differently about employee experience. Russ also has a book on this topic coming out soon — and we can’t wait to read it. In today’s conversation, we dig into how startups can drive employee engagement and develop high-quality managers. Russ reaches across his career to serve up some incredible wisdom, whether you’re a first-time manager or a seasoned leader. He starts by sharing his direction-coaching-career framework, along with his thoughts on where companies go wrong on OKRs. He also gets really tactical, sharing the typical phrases he relies on when delivering feedback, his go-to questions for soliciting what folks on his team really think, and underrated questions to include in employment engagement surveys. Finally, Russ gives us 13 recommendations for leadership reads for managers. For more of his thinking on talent development, we recommend reading his article from a few years ago in the First Round Review: https://review.firstround.com/three-powerful-conversations-managers-must-have-to-develop-their-people  You can follow Russ on Twitter at @ral1 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 Jeff Lawson, co-founder and CEO of Twilio. He’s spent the last 13 years building and running the company, including leading through a successful IPO in 2016.    In today’s conversation, Jeff looks back on some of the peaks and valleys in Twilio’s journey, and his own evolution as the CEO. He dives into some of the initial wins, like going against conventional wisdom to launch a second product in the early days of Twilio. He’s equally game to unpack some of the mistakes along Twilio’s path — like when one of their biggest customers, Uber, significantly scaled back their investment in Twilio’s products.    Jeff also opens up the pages from the playbook he pulled from his time at Amazon, chiefly Twilio’s “write it down” company value, and makes his case for why PowerPoint is a terrible decision-making tool. He takes us inside Twilio’s C-suite, including why they do post-mortems when things go right — not just when they go wrong. He also sketches out his “aha” moment that his executive team needed to argue more.    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.    Jeff’s new book is titled “Ask Your Developer: How to Harness the Power of Software Developers and Win in the 21st Century.” https://www.amazon.com/Ask-Your-Developer-Software-Developers/dp/0063018292   To learn more about how Twilio approaches company values, check out this article on First Round Review: https://review.firstround.com/draw-the-owl-and-other-company-values-you-didnt-know-you-should-have   You can follow Jeff on Twitter at @jeffiel.   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 Leah Sutton, SVP of Global HR at Elastic. Leah’s been in the HR space for over 20 years, and now leads everything from HR operations to recruiting and employee engagement for Elastic’s fully-distributed employee base, which includes over 2,000 spread across 40 countries and 48 states.  In today’s conversation, we look closely under the hood of what Leah calls Elastic’s “distributed by design” company DNA. She walks us through her learnings tackling challenges companies now are paying close attention to — including how to interview for leaders that can manage well remotely — and even dives into the nitty-gritty details about payroll and compensation across regions. She also outlines a few of the tactics Elastic has leaned on to smooth over some of the language and cultural barriers that often trip up global leadership teams. Leah zooms out even further to discuss Elastic’s source code, which she describes as not so much a traditional list of values but more the things that make Elastic, Elastic. Finally, she sketches out her pitch for why companies should talk about operational debt as much as they do technical debt. Today’s conversation is a must-listen for HR leaders and founders — and for folks on the hunt for a more systematic approach to the new challenges of distributed work.   Learn more about Elastic’s source code here: https://www.elastic.co/about/our-source-code   You can follow Leah on Twitter at @leahesutton   You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Kevin Fishner, Chief of Staff at HashiCorp, discusses how they run meetings, set and track goals, and make decisions through writing. He shares tactical advice for annual planning, including business simulations and scorecard systems. The episode provides valuable insights for managers and leaders on making teams more effective.