How To Scale A Founder-Led Culture Through 15 Years Of Rapid Growth with Twilio’s CPO

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The Culture Code

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Scaling a founder-led, start-up culture is the ultimate challenge. However, success yields large results. Reuters’ data shows that the top 400 founder-led companies have registered an average share price gain of 58.4% compared to just a 10% return for the top 400 stocks led by other founder-led companies.

As Karen Wickre wrote in a piece for Wired: “At the four companies where founders played an active role, I had better personal and professional experiences. I was more challenged, worked alongside smarter people, and developed new skills. The culture at a founder company was infinitely more coherent and cohesive than the culture at a successor company.”

For a living, breathing example, I met with the Chief People Officer (CPO) of Twilio, Christy Lake. Despite growing from 3,600 Twilions (employees) to 6,000 Twilions over the last three years, and despite being 15 years old, Twilio clearly operates with a founder-led, start-up culture. Twilio is a customer communications and engagement platform that enables companies to directly communicate with their customers.

Christy Lake, Chief People Officer of Twilio
Christy Lake, Chief People Officer of Twilio

What a Founder-led Culture at Scale Looks Like

As companies grow over time, it can be tough to hold onto the magic of the startup feel. However, at Twilio, it’s still a core part of the company ethos. Lake remarked, “I would describe us as a company full of humble, customer-focused builders. That builder ethos permeates the culture. We’re a startup at scale. After 15 years out, we've still maintained that founder-led feel.”

Twilio Sustains Its Culture with a Value System

Lake and Twilio recently reconstructed the company values. Lake started at Twilio over three years ago when the company had approximately 3,300 employees. Twilio has nearly doubled in size since then. “Culture was one of our obvious focus areas. We needed to figure out how to continue to scale our culture. The actual bones and infrastructure of the culture were confusing as heck. We had this pyramid that had a huge number of values that interplayed with each other. You could not have named all the values or explained the interplay among them.” So, Lake and her team did a lot of work in 2021 to evolve their value set. “You have to have a foundation built from which you can scale and ensure that you have shared language, understanding, and expectations. It all starts with that value system,” Lake emphasized.

Lake and her team established a system with four values:

  • We're builders.
  • We're owners.
  • We're curious.
  • We're positrons.

Lake describes the system’s four concentric circles. “The system acknowledges that our most ideal Twilion lives right in the center, where all four circles come together and you're living and demonstrating each of these values in perfect harmony.” However, the system also recognizes that during any day, period, or quarter, people may be a little light in one or some of the values. Then, the system becomes a framework for coaching and performance conversations.

Why Twilio’s Core Value “Positrons” Is Brilliant

When it comes to company values, there can be genius in simplicity. Values that are too simple and pervasive (every company has them, and all people know they’re important) can feel too generic and therefore unlivable. When a CPO like Lake mentions a value like “positron,” my ears perk up. It’s so unique, and that makes it sticky and, therefore, livable.

“The way we worked the value system is that our founder Jeff Lawson ‘held the pen.’ This is a founder-led company, and we needed to make sure that wherever we landed, Jeff was a thousand percent the owner and champion of these values.”

“You could literally see the flicker in Jeff’s eyes when he came up with this value,” Lake said. “A positron is the positively charged antiparticle of an electron. What it means culturally is that you are not fake happy all the time. It’s about being really genuine, leaning in, and helping. We believe that people are good and that we're here to do good work.”

Track Jacket Program

One thing that great company cultures seem to have in common is that they create unique and inventive rituals. At Twilio, one of these initiatives is named the Track Jacket Program. “Our track jacket program is rooted in the notion that the core Twilio product was a developer-facing product. The premise is that we're all developers. To earn your Twilio track jacket, which is this red track jacket with the company colors and logo, you actually have to code an app on our communications platform. Every single person at every level has to be hands-on keyboard, using Twilio products, and building an actual app.” People proudly wear their jackets, which remind employees how the company began.

Twilio Scaled Coaching to Every Leader

Since research correlates 70% of employee engagement to management, the way a company develops its leaders can be incredibly telling of its culture.

At Twilio, leadership development is something that is measured and scaled:

Measurement – Twilio measures manager effectiveness on a quarterly basis. “Our belief is that the unit of a team is where the magic happens. The more information that we can give the team leader and team members and the more we are able to monitor the health of each team, the better off we'll be.”

Scaling coaching and learning – “All of our managers get dedicated coaches so that they, on their own journey, can up-level their leadership and navigate challenges they encountered while leading their team, having difficult conversations, and during performance coaching. In addition, we started core manager training for newer leaders.” In just two years since launching coaching and learning, Twilio saw a 20-point jump in people manager effectiveness.

Lake’s Advice for CPOs: “Ruthless Prioritization” + “Investing in People Management and DEI Early”

Lake’s advice for someone stepping into a CPO role was two-fold.

  • Ruthless prioritization: Lake said, “I've never gone into any job that did not come with its own version of technical debt. You're going to have a backlog of requests from the business. They want everything, they want it at full maturity, and they want it at full scale, automated, streamlined, and systematized. Ruthless, rigorous prioritization is such an important skill. You don’t have to do it all.”
  • Investing in people management and DEI early: “I would invest in people management capability and diversity, equity, and inclusion (DEI) as early as day two of working with the company. If I could rewind the tapes and start with a leadership philosophy for developing people, which would be fantastic.”
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CEO of LEADx, and NY Times bestselling author, of Great Leaders Have No Rules and Employee Engagement 2.0. Get a FREE demo of the LEADx platform at https://leadx.org/preview.