People + Strategy Journal

Spring 2021

Chief of the Company Operating System

Company values and culture make up the underlying operating system of an organization. Leaders must embody and embed values while tracking and refreshing culture.

By Christy Lake, Twilio

Company culture is fluid, dynamic and at times hard to articulate. Companies often draw up lists of values, but those lists don’t capture the full ecosystem of what it feels like to work at the company and how people are expected to interact with each other. 

Through years of working in HR at several companies, I’ve seen what works and what doesn’t. Now at Twilio, a cloud communications and customer engagement company with more than 4,000 employees, we refer to our values and principles as our “operating system.” It’s like your phone’s operating system—it works invisibly in the background to connect your apps and help you get things done. You also expect it to be regularly updated with enhancements, performance improvements and new features. The same is true for company culture. The operating system needs to be updated to ensure that it’s staying current to where the company is and where it’s going.

While every company’s culture should be unique, analyzing our experience at Twilio provides some clear patterns that can provide a guide for building an intentional culture. Our conversations about how to build, reinforce and evolve our culture are constant and methodical, and guiding principles on culture emerge from the steps we take. 

Values Can’t Be Generic 

Values are the architecture of your operating system. The underlying ideas behind your company’s values may be similar to other organizations, but they need to be differentiated in articulation and how they are brought to life, so they are unique and authentic to your company and employees. 

For example, one of Twilio’s values is “Wear the Customer’s Shoes.” We’ve built stories and traditions around this value. We take the age-old saying of “walk a mile in someone else’s shoes” literally. When we start working together, customers will give us a pair of their shoes. We have customers’ shoes on the walls in our offices that are visual reminders of our customers and the stories associated with them. This approach goes beyond simply saying generic statements like “the customer is always right.” You have to find ways to make these ideas pop and make them understandable and memorable. They need to have life behind them.

Our talent team is developing a new program to better train our leaders on what our values—what we call the Twilio Magic—look like in action. What does “Ruthless Prioritization” look like in practice? How does “Draw the Owl” apply when you are leading? The core tenets of Twilio’s values and culture will be integral to how our leaders are trained. In effect, our leadership expectations are not a stand-alone set of behaviors; rather, they are the Twilio Magic, embodied.
In a perfect world, employees, current and prospective, will remember all the company values. That’s likely not the case. What matters more is whether they’re able to answer the question, “What is it like to work at your company?” Ideally, they will describe the environment in ways that align with your values. Put another way, values are the architecture of the operating system, the fundamental structure around which everything else is built. They act as the blueprint for the operating system, which is made up of the policies, programs and behaviors that connect the framework to action. If employees haven’t memorized the blueprint but can describe the final product, that’s a win.

Practice and Lead with Your Values 

All employees are owners of company culture, but the HR team is responsible for building out the programs, practices and policies to reinforce the system we’re trying to create. At Twilio, this includes bringing to life our values at every touchpoint to reinforce culture, including hiring, talent management, recognition systems and exiting employees. Company culture will be reinforced (or not) based on who we hire, advance and celebrate. 

One of our values is “Draw the Owl.” It’s based on the Internet meme that uses only two panels to explain how to draw an owl. The first panel shows two overlapping circles with the caption, “Step 1, draw some circles.” The second panel shows a fully rendered owl over the words, “Step 2, draw the rest of the owl.” The point is to be curious, be a problem solver, seek to figure things out and innovate, rather than looking for a detailed instruction book. We explain what that means in our work at Twilio and we celebrate those behaviors when we see them.

The year 2020 brought many challenges, and one of them has been assimilating new hires into our culture while working fully remotely, without the benefit of the natural osmosis that occurs when colleagues work together in an office space. Our workforce grew roughly 45 percent in 2020 and we created thoughtful virtual experiences for new “Twilions” to learn about our culture. We launched a leadership video series where leaders invited Twilions into their home and shared how they were adapting to their new reality. 

We also kept key traditions alive by bringing them online. For example, new hires gain a deeper appreciation for our company’s builder spirit by creating an application on Twilio and earning a coveted red track jacket after they demonstrate it live to their cohort. New employees still have a chance to build an app and get their track jacket shipped to them as part of virtual onboarding to ensure the same immersive experience when they join remotely. Continuing these kinds of practices helped make incoming employees feel included and connected as we navigated this especially tough year together. 

Putting values into practice as an operating system simply doesn’t work, though, if the CEO and broader leadership team do not role-model the culture. If the CEO thinks it’s a project that somebody else can run, HR leaders must find a way to engage the CEO to help them understand that they are the primary spokesperson for the company, and that the values won’t live unless the leader buys into them.

Our leadership team, led by CEO Jeff Lawson, takes every opportunity to live out our values and principles, and demonstrate what they look like in action. For example, one of our values is “Empower Others,” which is about unleashing human potential inside and outside the company and recognizing our impact on those around us. Recently, a slew of Silicon Valley tech leaders announced that they are moving their headquarters out of the Bay Area, where they raised capital and grew their businesses. Lawson spoke out publicly against the exodus, encouraging his peers to reinvest in their communities when they need it most, a call to empower rather than abandon.   

Measure and Track Cultural Health 

Just like other parts of the business, we must measure and track success. For the people team, this means how employees react to and live our values and culture. There are a variety of standard measures and tools that can indicate organizational health (employee net promotor score, retention, manager effectiveness). At Twilio, we also have a cultural index in our sentiment survey, which includes specific questions about whether and how leaders are living our values. 

A tight connection between words and action is crucial. Without it, you will likely have a high rate of hiring failure or people leaving the company within a couple of months. In exit interviews (regardless of tenure), departing employees will highlight a disconnect and say that leaders are not living the values. 

HR teams should track whether there are challenges with certain populations, teams or locations. Are there experiential differences across different demographics? The Twilio team uses employee survey data to construct a belonging and diversity index, which we break out by gender and underrepresented populations. This allows us to not only review our survey responses as a whole, but look for differences across different groups and ensure consistency.

Intentional employee engagement helps make sure we put these measurements and what we find to good use. Before we pulse survey or collect input from our employees, we ask ourselves—is this question actionable and will what we learn help strengthen our core values? If we can’t answer these questions, it means we need to reframe what we’re asking or cut the question altogether. This framework ensures we’re engaging employees thoughtfully and measuring the criteria that truly matter. 

Continually Refresh the Culture 

Culture is a living, breathing entity and must be treated as such. As with most things in today’s digital age, the need to evolve company culture has accelerated. There was a time when companies would go five to 10 years without doing any review or refresh of values. Now, in order to maintain a relevant and successful culture, a company must keep it current in a much more agile and dynamic way. (Imagine what our laptops and phones would feel like to use if operating system updates were pushed once every five years!) 

Another reason to constantly evolve company culture is that tenure overall has decreased over the last several years, particularly in the tech industry. It wasn’t uncommon 10 years ago that people would stay up to 25 or 30 years with larger companies. Now, people are moving so fast that there must be an active effort to help new employees assimilate into your culture.

There is no perfect formula for building intentional culture that grows with your company, but as you’re developing a strategy, keep in mind the analogy that your culture should function like an operating system. Core values are the architecture and should be authentic to your organization. The best operating systems are actively managed. Company leaders and managers must be role models and enforcers, and it must be embedded in every possible touchpoint.  

Christy Lake is Chief People Officer of Twilio. She can be reached through LinkedIn.