In Depth

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.

David Lieb, Director of Google Photos and former CEO of Bump, shares insights on scaling a product to over a billion users. He discusses the evolution from Bump to Google Photos, emphasizing the importance of targeted user feedback and team dynamics. David reflects on past mistakes, corporate challenges, and the need for clarity in product vision. He also highlights how Google Photos transformed from mere storage to a tool for reliving memories, providing valuable lessons for aspiring product builders.

Bill Carr and Colin Bryar, former Amazon executives, share insights on Amazon's culture of innovation, including the origin stories of the Kindle, AWS, and Prime businesses. They discuss the importance of full-time focus on innovation, customer obsession, diving deep, and developing controllable input metrics. They also explore the significance of balancing customer interests, transparent policies, and Amazon's structured interviewing process.

Anne Raimondi, Chief Customer Officer at Guru and board member at companies like Asana and Patreon, shares her extensive leadership experience. She reveals key traits that successful executives possess, such as adaptability and humility. Anne emphasizes the importance of a structured 30, 60, and 90-day plan for new executives to build trust and engage their teams. She also discusses effective executive recruiting strategies and the significance of inclusivity in board dynamics, providing invaluable insights for current and aspiring leaders.

Jean-Denis Grèze, Head of Engineering at Plaid and former Director of Engineering at Dropbox, shares insights on leadership, pragmatism over perfection, team motivation, KPI tracking, and fostering ownership mentality in engineering. He emphasizes prioritizing technical debt, aligning team performance with business goals, and hiring strategies for engineering roles. A must-listen for technical leaders looking for actionable advice.

Dave Girouard, CEO and co-founder of Upstart and former President of Google Enterprise, shares insights on starting and growing Upstart, the challenges of fundraising, the successful pivot, and his management philosophies. He emphasizes the importance of believing in the product, shares helpful frameworks for startup leaders, and discusses managing the executive team.