In Depth

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 [email protected] 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 [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Kevin Fishner, Chief of Staff at HashiCorp. As the first business hire at the cloud infrastructure automation company, he previously built out the sales, marketing and product management teams.

Now as chief of staff, he’s focused on building a strong foundation of company-wide systems, now that the team has grown to over 1000 people. In today’s conversation, Kevin shares a detailed look at how they run meetings, set and track progress toward goals, and make decisions through writing at HashiCorp. 

He also shares incredibly tactical advice for making annual planning more effective, including the unique business simulation they run, their scorecard system, and the weekly and quarterly meetings that help them stay focused on important KPIs.

While today’s episode is clearly a must-listen for fellow chiefs of staff and founders spinning up a company from scratch, managers and leaders of all kinds will walk away with several takeaways on how to make their teams more effective.

Because so much of what he shared is so detailed, we’ll be sharing some templates and visuals to go along with Kevin’s interview over on the First Round Review, so be sure to check that out. 

You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with David Lieb, the Director of Google Photos. Previously, he was the founder/CEO of Bump, an app that allowed users to swap contact information by physically bumping phones. Bump was acquired by Google in 2013, and formed the basis for the design of Google Photos, which launched in 2015 and passed the 1 billion users mark in 2019.

In today’s conversation, David takes us through that journey of building a consumer product from scratch and scaling it to over a billion users in just four years. He shares the mistakes they made while building Bump, what he learned from navigating big company politics at Google, and how they pinpointed the problem in the photo-sharing space.

From the precise questions they asked in user interviews, to how they stack ranked for the canonical users, there’s tons of wisdom in here for early product builders. There’s also lessons from operating at Google’s scale as well, including how his approach to planning and org design have evolved.

Learn more about the Spotify “squads’ model that David mentioned in the org design section here: https://medium.com/pm101/spotify-squad-framework-part-i-8f74bcfcd761 

You can follow David on Twitter at @dflieb, and you can learn more about his approach to building products on First Round Review: https://firstround.com/review/cognitive-overhead-is-your-products-overlord-topple-it-with-these-tips/ 

You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Bill Carr and Colin Bryar, two long-time Amazon executives who just published a new book, “Working Backwards,” which provides an inside look at how the leadership principles and business processes that have made the company so successful.

Bill started at Amazon in 1999, and went on to launch and run the Prime Video, Amazon Studios, and Amazon Music businesses before he left the company in 2014. Colin joined Amazon in 1998, as the Director for Amazon Associates and Amazon Web Services Programs. He also spent two years as Jeff Bezos’ technical advisor or “shadow,” and later served as the COO for IMDb.com. 

In today’s conversation, Bill and Colin take us through Amazon’s culture of innovation and the origin stories of the Kindle, AWS, and Prime businesses. From granular details about the “working backwards” process, to an inside look at how players like Jeff Bezos and incoming CEO Andy Jassy operated up close, they share invaluable insights on diving deep and operational excellence.

Whether it’s their lessons on why innovation can’t be a part-time job, or the perils of taking a “skills-forward” approach to exploring new opportunities, or why mechanisms are more important than good intentions, there’s lots of food for thought in here for founders and startup leaders.

Learn more about “Working Backwards” here

You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  

Today’s episode is with Anne Raimondi, Chief Customer Officer at Guru, and independent board member at Asana, Gusto and Patreon. Previously, she was part of the founding team at Blue Nile, spent five years in product marketing at eBay, and led marketing as an early employee at SurveyMonkey, before pivoting to operations as an SVP at Zendesk. 

In today’s conversation, Anne pulls on threads from across her impressive career as a founder, operator, executive and board member to deliver spot-on advice for folks with an eye for the C-suite. From what enables the best executives to scale up, to how she’s approached her own 30, 60, 90-day plans as a brand-new hire — she doles out plenty of prescriptions for getting this critical transition right and avoiding common traps.

She also opens up her playbook for approaching executive recruiting, interviewing and hiring, and when to mine executive talent internally rather than defaulting to external hires. Finally, she opens up about her board work, sharing the essential ingredients for productive, impactful boards across every growth stage. 

Today’s conversation is a must-listen for executives, founders and board members looking to level up their leadership frameworks — and for folks who someday hope to step into these same shoes.

You can follow Anne on Twitter at @anneraimondi and you can learn more about her approach to diagnosing and repairing team trust on First Round Review: https://firstround.com/review/use-this-equation-to-determine-diagnose-and-repair-trust/

You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Jean-Denis Grèze, Head of Engineering at Plaid, which securely connects your bank to your apps. Before joining Plaid, Jean-Denis served as Director of Engineering at Dropbox, and even had a stint in law school and one year as a lawyer under his belt before diving deep into the world of CS. 

While he says becoming a lawyer was a “four-year detour he probably didn’t need,” there’s a lot to be said for how it’s shaped his engineering career and management philosophy. As he puts it, he strongly favors pragmatism over perfection, and it’s something he hammers home within his engineering teams. In today’s conversation, Jean-Denis pulls on threads from across his career to weave together a modern playbook for engineering leadership — and the hard-won lessons that stick with him.

He also shares his insights on why his engineering org doesn’t have titles, the one question he asks every engineering manager candidate, and how his team prioritizes technical debt and keeping the lights on versus sexy, brand-new projects.

Today’s conversation is a must-listen for technical leaders or those who are eyeing the engineering leadership track. From motivating a team to tracking the right KPIs, Jean-Denis has got tons of great tactics and stories from his time at Plaid and Dropbox for you to learn from.

You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Dave Girouard, the CEO and co-founder of Upstart, an AI-powered lending platform that recently went public. Before founding Upstart, Dave was President of Google Enterprise, and spent 8 years building Google's billion dollar cloud apps business.

Here at First Round, we first came to know Dave when we invested in Upstart’s seed round back in 2012, and we’ve found him to be one of the most tenacious and focused founders we’ve ever backed. In today’s conversation, Dave gives us an inside look at how the business was built and what other startups can learn from its early days.

In addition to unpacking the initial idea and subsequent business model pivot, Dave gets into what it felt like flying under the radar of Silicon Valley, why he “sucked at fundraising,” and how he and his co-founders have stuck together for almost a decade. 

From his “Are you Airbnb or Paypal?” test and why you should look at your career in landscape mode, to the three mental models he leans on to manage his psychology as a founder, Dave shares helpful frameworks that any startup leader can learn from. We also dive into his “management by exception” philosophy, what he learned from Google, how he runs his leadership team, and why he leans on references, not interviews, when hiring execs.

You can follow Dave on Twitter at @davegirouard and you can read his First Round Review articles that we mentioned in the episode here: 

https://firstround.com/review/speed-as-a-habit/ 

https://firstround.com/review/how-does-your-leadership-team-rate/ 

https://firstround.com/review/a-founders-guide-to-writing-well/ 

You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Jay Simons, who’s currently a partner at Bond and serves on the boards of Hubspot and Zapier. But before that, he had a long run as the President of Atlassian, which develops software collaboration tools like Jira, Confluence and Trello.

In today’s conversation, Jay dives into Atlassian’s growth story, from what’s misunderstood or not talked about enough, to the strategic choices that went against the grain. He shares an inside look at how Atlassian built a product that can sell itself and deferred short-term openings for more durable long-term opportunity.

In addition to unpacking what he calls their “three-legged stool” of self-service, a global network of channel partners, and eventual enterprise upselling, Jay gives us a deep dive into their pricing strategy and how they thought about exploring adjacent product areas. From spinning the flywheels of a remarkable product and a high-velocity self-service funnel, to building a culture that focuses on first principles, there’s tons of great advice in here — not only for go-to-market and revenue leaders, but for anyone who works at a startup.

This blog post from Intercom has the flywheel graphic that Jay mentioned in the episode. https://www.intercom.com/blog/podcasts/scale-how-atlassian-built-a-20-billion-dollar-company-with-no-sales-team/ 

You can follow Jay on Twitter at @jaysimons.

You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Cristina Cordova, Notion’s Head of Platform & Partnerships. Previously, she was the 28th employee and the first partnerships hire at Stripe, where she cultivated partnerships with companies like Shopify, Squarespace and Apple, built out the BD org, and led their new Corporate Card effort. 

After a decade in partnerships, Cristina has bagged big deals, honed her negotiation skills, built out teams — and made plenty of mistakes she hopes others can learn from. In today’s conversation, Cristina pulls from across her career to share the inside scoop on deals that had an unexpected outsized impact — as well as the ones that went sideways. 

She also shares her playbook for being a startup’s first partnership hire, including the three critical areas to focus on first, and the common traps to avoid. It’s also full of actionable tactics on everything from dealing with partners trying to push you around, to how to hire for partnerships roles and structure the org chart.

Today’s conversation is a must-listen of course for folks currently in or hoping to break into partnerships, platform or BD roles, but Cristina also shares great tactics for getting better at negotiating, as well as some fascinating stories of how Stripe and Notion scaled — meaning there’s tons to learn here for everyone.

You can follow Cristina on Twitter at @cjc.

You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson