How the design team behind Twilio Engage came together

Kwasi Twum-Acheampong
Segment Design + Research
7 min readNov 4, 2021
Twilio CEO, Jeff Lawson, unveiling Twilio Engage at the Signal conference

*Record scratch* *Freeze frame* You’re probably wondering how we got on the stage at Twilio’s customer and developer conference, Signal… and before I get into the story of how a team of superstars unlocked Twilio’s latest and greatest offering: a marketing automation tool built on top of the #1 customer data platform (CDP), allow me to introduce myself... I’m Kwasi and I have the pleasure of leading the aforementioned product design team of superstars. I’ve managed the team from when it was only a few designers to where we are today but more on that later. Okay, let’s get back to it! *Resume track*

There are only a few times when a design team has their new product showcased by the CEO as part of the keynote of their annual conference to tens of thousands of attendees. There are even fewer times when that team makes me cry tears of joy from the beautiful customer experiences they designed and meaty challenges they masterfully navigated (jk, that happens all the time because they’re so wonderful 🥲 ). But all of that is EXACTLY what happened recently when our new flagship product, Twilio Engage, was revealed at Signal.

What is Twilio Engage?

Twilio Engage is a growth automation platform, built on Segment as the CDP and natively on Twilio’s communication APIs. This exciting new omni-channel marketing tool will allow marketers to understand their customers more deeply while providing a way to deliver personalized messaging. And all of this began with a couple of design sprints and a handful of sketches of the new journey orchestration tool (seriously… check it out below!), which is the foundation by which a marketer can craft their customer workflow to deliver campaigns across multiple channels.

Early sketch of what will become Journey orchestration

Forming to Performing in 1.3 seconds flat

As we progressed on this journey to build Twilio Engage, we grew from 3 to 10 designers and added 2 brilliant researchers. We initially set out to provide marketers a visual no-code means of orchestrating journeys so that they can deliver targeted campaigns in their marketing tools without being dependent on their engineer partners. However, once this team launched Journeys in less than three months we realized that our ambitions of building an in-house marketing automation tool was very achievable. Very quickly there was a need to spin up a team that would build a messaging tool for marketers to build/launch campaigns and another team to focus on surfacing valuable analytics as to how those campaigns were doing. The excitement around this product attracted designers from all over:

  • Designers interviewed internally to move to the team
  • Sendgrid designers that brought a wealth of messaging expertise
  • A group product manger even that transitioned into design to work on it!

With the brilliant product, engineer, and design minds working on Engage, it was obvious that technical problems weren’t going to be our biggest challenge. Rather with a constant stream of new faces, people problems were going to be the biggest hurdle — new teammates that don’t know each other’s communication style, role, collaboration preferences, etc. This is totally expected because team was just forming after all.

“Forming” is the first of four stages that psychologist Bruce Tuckman defined teams go through on their path towards high performance. During forming, individuals are unsure of the team’s purpose, their role, or if they’ll work well with each other. In the storming stage, there is typically friction as established boundaries are pushed and the team’s mission is challenged. Over time, teams start to resolve their differences and value each other’s strength as they move into the norming stage. Lastly, the team moves into the performing stage and reach a flow state where goals are achieved efficiently. The big question for this new team was how we were going to get from forming to performing as quickly as possible.

Phases of Team Development created by psychologist Bruce Tuckman

In order to ship, you must first RELATIONship

As a firm believer that the best work happens among people who have invested time into building and nurturing relationships, the Twilio Engage design team decided to do exactly that from the start. I started this effort off by designing a team kickoff workshop where we could come together to not only learn more about each other on a personal level but also shape the way we work and what we value TOGETHER. With designers coming together for the first time, we wanted to ensure we took the best of what each has previously experienced to build our new culture as a team. The workshop (done in FigJam) went like this:

  1. Expectation setting

As with any workshop (and especially so with new teammates), it’s important to clearly to explain why we are having it, share the agenda, and get buy-in on the ground rules before beginning. This will have everyone on the same page and will emphasize the fact that it is a safe space for all voices to be heard.

2. Player cards

Inspired by Figma’s player card & Josh Silverman’s “User manual for me”, I created templates for everyone to fill out and share. These player cards allowed us to quickly share information like our working preferences, aspirations, superpowers, and much more! This not only allowed the team to get to know each other on a personal level but also demystifies the assumptions we build in our heads as to how we like to work. For instance, I personally like it when people schedule meetings with me immediately after others so that I can create bigger blocks of focus time but it’s easy to assume that I’d like time between meetings to recoup.

3. How we work brainstorm

We then brainstormed, clustered, and prioritized how we’d like to operate as a team. This was focused across three categories: (1) our principles and values, (2) how we communicate to each other, and (3) processes and ops that will set us up for success.

4. Synthesis and share-out

The final step was to document the synthesis of the workshop to share for final buy-in and easy access. We now have one artifact that hosts our user manuals, team principles, and ops for new/existing designers can reference. This artifact however, is not meant to be final but rather a living document that evolves to reflect our team’s changing needs as we mature.

Snippet of the synthesized outcomes of the workshop

The dream team

Step aside 1992 USA men’s Olympic basketball team. There’s a new dream team and they go by the 2021 Twilio Engage designers. Even before the kickoff was done, new teammates were pairing up to design needed workshops for the rest of the organization. The next two weeks were filled with many cross-functional workshops driven by this dream team that progressed alignment around product vision, identity, information architecture, taxonomy, and needed research. More importantly, they continued to bring the necessary cross-functional partners to have hard discussions that ultimately brought us closer to a successful launch with each succeeding engagement.

Fast forward to today and this melting pot of a team is working seamlessly in the middle of a pilot of our exciting new product launch. We are iterating on customer feedback, planning our next year with an energizing line up of roadmap items, and designing awesome new swag for the broader team (which is arguably the most important). The amount of collaboration happening both within the team and cross-functionally does not cease to impress me. From weekly design critiques, stand-ups, hangouts, and ad-hoc design jams we always find ways to come together.

One team. One Opportunity. To seize everything you ever wanted.

We’re excited to continue to build on our culture, the way we work, and we’d love for you to be part of that endeavor… we’re hiring! On this team everyone is an owner and empowered to make a real impact. Professional and personal development is incredibly important as well as a continued conversation. You have the power to craft your future (and I will be there every step of the way to support). Meet the faces of the incredibly fun and talented Twilio Engage design-research team who are already doing so:

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