How to Know It’s Time to Pivot Your Startup

Stella Garber knows when it’s time to pivot—she’s done it. Recognizing that her company’s decision-making software was stuck with sluggish growth, she and her team made the difficult decision to halt its development and turn their attention to an AI-based task management app called Hoop. In this essay, the third in her series on business frameworks, Stella reflects on this decision and how she and her team figured out what’s next, and offers guidance to founders who sense they’re at a crossroads with their companies.—Kate Lee

Was this newsletter forwarded to you? Sign up to get it in your inbox.

We had spent the nine months prior building an app that helped teams of people make better decisions faster at work. Employees could pose questions to one another and independently chime in to reach a decision without biasing each other with responses. The problem was that, while many individuals liked our app, they struggled to get their coworkers on board. As a result, we weren’t growing at the rate we needed, and as the CEO, I was worried that my own team was starting to lose morale.

In the spirit of practicing what we preached—making better decisions faster—we had to be honest with ourselves: It was time to pivot.

Fast forward a year. Our new product is called Hoop, an AI-first task manager. Many of the people we surveyed when we were building our initial product were overwhelmed by everything going on at work, between endless meetings and active Slack workspaces. They worried about missing important tasks and didn’t have consistent ways of staying on top of them. Hoop solves this by automatically capturing tasks across meetings, Slack, and email. You connect Hoop to your tools—your work email, calendar, and Slack—and tasks automatically populate in a to-do list where you can manage everything in one spot. No more missing tasks, writing things down frantically during meetings, or marking messages as “Unread” in Slack for later.

On September 10, Hoop had a successful ProductHunt launch, scoring as the top AI product of the day. Our customers say they can’t imagine going back to life before Hoop because they’re more focused, have less anxiety about missing important tasks, and are generally able to be more productive at work.

So how did we go from one extreme to the other—from stagnation to user love? How did we pivot with conviction, taking what we’d learned and accelerating our path to product-market fit in the next iteration of our product? And how were we able to leverage new technology, in this case AI, to solve age-old problems?

Here’s the story, along with a framework for other founders in the same situation as myself, who might be feeling similarly frustrated and unsure of how to proceed.

A framework for pivoting

It may seem like we knew exactly what we were doing, but we were figuring it out on the fly, doing the best we could given our collective experience. Luckily, that experience was relevant: Most of our distributed team of six had worked together previously across the product, design, engineering, and marketing teams at Trello, where we built and scaled one of the most popular task management apps.

We knew that in moments of uncertainty, figuring it out on the fly never involves guesswork, but begs for structure and organization. To guide our thinking, we developed a framework based on the following questions:

Become a paid subscriber to Every to unlock this piece and learn about:

• A structured approach to pivoting
• Leveraging AI for age-old problems
• A "warm pivot" into familiar territory