The Friday Night Experiment That Changed Everything
Laura Schaffer had no team, no engineering resources, and a company full of people who believed asking developers anything during signup would tank conversion. So she did what any good growth leader would do: she shipped it anyway.
It was 7 PM on a Friday. Schaffer and Andre Crowe, an early Twilio employee, slipped four questions into the signup flow and turned on an A/B test. The questions were simple: What language are you coding in? What product do you want to use? What's your use case? Are you a developer?
Schaffer expected the numbers to drop. She was already drafting her defense—ready to argue that the data they'd collect would be worth the hit to conversion. Then the results came in.
We start to get the data for this thing. I'm like getting an improved conversion. Like we, there's no personalization, nothing past it, just the questions. It improved conversion by like 5%. Like just improved signups. And it was one of those like, what? Like, okay, this, like, what is going on here?
— Laura Schaffer
Why New Users Are Looking for the Bogeyman
Schaffer dug in. She talked to customers who had gone through the new flow. What she found wasn't about friction at all—it was about fear.
When users sign up for a new product, they're anxious. They're expecting it to be hard. They're waiting for the moment they won't be able to figure it out. Schaffer calls it "looking for the bogeyman."
The questions didn't add friction. They added comfort. Selecting "JavaScript" or "SMS" told users: you're in the right place. This product speaks your language. You can do this.
The psyche of the user is so, so critical, right? Like that's just as important as understanding your product and the broader market you're applying to and all those things like. Just the psyche of users, new people doing things for the first time in your user flow, like understanding that is powerful.
— Laura Schaffer
The takeaway wasn't just about Twilio. It's about any signup flow, any front door. Users don't just want simplicity—they want reassurance. The questions didn't just help Twilio segment users and prioritize product work. They calmed nerves.
Carve Your Own Path (Your Manager Can't Do It for You)
Before Schaffer joined Twilio, there was no growth team. When she left, she'd built the growth product and engineering org from scratch. She didn't wait for a job req. She created the role.
Her method: get closer to customers than anyone else in the company. At Bandwidth, her first real job, she was in sales. She noticed she was repeating the same answers over and over. She pitched the GM on building a self-serve e-commerce flow. He said yes. She moved into a new role.
At Twilio, she started writing a Voice of the Customer report. She shared insights from customer conversations. People asked to be added to the list. It turned into a quarterly session for all of product. CEO Jeff Lawson started attending. Within months, she'd built enough trust to pitch—and get approval for—Twilio's first growth team.
Your executive team and executive teams at companies are often very sharp, but the nature of their day-to-day just does not link them with customers. And so that means that over time, especially as a company grows, they often lose access to some of the best insights.
— Laura Schaffer
The pattern: don't wait for your manager to advocate for you. Build your own brand. Share what you know. Ungate your insights. Make yourself the person executives think of when they need someone who understands the customer.
The Career Framework That Doesn't Depend on One Person
Most people try to grow by working hard in their current role, keeping a spreadsheet of wins, and hoping their manager notices. Schaffer thinks that's limiting.
You're constrained by your manager's ability to advocate for you. You're constrained by the explicit trajectory of your role. And if your manager leaves, you start over.
Her framework: take power back. Get to know customers better than anyone. Share those insights widely. Build a reputation as someone who solves problems outside your job description. When leaders need something new, they'll think of you.
At Twilio, Schaffer cracked the top 50 employees by tenure. She didn't do it by waiting. She did it by making herself indispensable—not just to her manager, but to the company.
And if you're not sure where to start? Talk to customers. Get insights. Share them. Schaffer's advice is simple: there's no executive who won't be excited to hear valuable customer insights that highlight problems they're not seeing. Use that.
Source Episode
Career frameworks, A/B testing, onboarding
Lenny's Podcast · 81 min
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