An Entrepreneurial Feedback Loop

Anne Lewallen ’06 founded OnLoop to build better teams

Anne Lewallen '06, CEO of OnLoop, in the company's office space in midtown Manhattan. OnLoop is an AI-driven mobile app that helps teams set goals and capture feedback on progress automatically through integrations with other tools like the messaging app Slack.
By Kayla Voigt ’14Photography by Karsten Mora
January 7, 2022

A classic (and often dreaded) interview question most recent grads face: What are your strengths and weaknesses? For many of us, it’s difficult to articulate.

“As a leader, I want to always feel like I’m supporting my team and building those habits to make them better,” said Anne Lewallen ’06. “The reality is, so many of us go through our days with no concrete data to show what we’ve done or what our blind spots are.”

For many students, entering the workforce means leaving behind the world of clear-cut feedback like grades and transcripts. Soft strengths like curiosity, willingness to learn, or attention to detail can easily go unnoticed in the real world, especially when getting up to speed on new technologies, processes, or industries. How can you identify those strengths and continue to improve on any gaps?

Building Better Feedback Loops with AI

Anne Lewallen ’06 cofounded OnLoop in June 2021 to help teams answer that question — and to help managers deliver better feedback to their employees. “We built this aspirationally, so we can create a more-just and less-anxious world through deliberately developing teams in a meaningful way,” said Lewallen. “It was a real pain point for me as a manager, and I was tired of feeling like there was nothing I could do to help my team.”

The AI-driven mobile app helps teams set goals, capture feedback on progress automatically through integrations with other tools like the messaging app Slack, and surface that feedback into themes and action items. From there, personalized analysis gives team members and managers alike better insight into how they’re doing. “This is the app I always wanted as a leader,” said Lewallen. “It makes feedback easy to incorporate into your day, with the AI compiling insights about superpowers and blind spots and recommending personalized content.”

That means making sure teams celebrate their wins more often—and pay more attention to where they can improve. Said Lewallen, “One of our goals is to normalize constructive feedback, and to take out the assumptions people make. It’s not just about giving feedback, but receiving it in a non-defensive way.”

The team uses AI not only to effectively capture real-time feedback from video calls, emails, and instant messages, but it also gives concrete advice on how to deliver that feedback in an effective way through the most advanced natural language processing available today.

An Entrepreneurial Spirit within the Liberal Arts

Using AI to power stronger feedback loops and to help students grow is just the latest technology investment made by the College. Colby launched a partnership with OnLoop during the summer of 2021 through three different departments: International Student Programs, Diversity, Equity, and Inclusion, and DavisConnects. 

“We’re partnering with Colby in a few different ways,” said Lewallen. “Colby is on the forefront of AI and using our cutting-edge technology to build better teams internally, but also to help students stay connected and collaborate with one another.”

One such program already making the most of OnLoop’s technology is Colby’s DEI mentorship programs through the Pugh Center for Diversity, Equity, and Inclusion. “We’re here to establish a sense of belonging,” said Masi Ngidi-Brown, director. “We do this through peer-to-peer cohort groups, where first-years learn from older students.”

Ngidi-Brown works with a team of student leaders, fellows, and mentors that help facilitate the program for first-year students. “OnLoop becomes an instrumental tool within that structure to build a sense of team,” he said.

“It’s also creating a student culture where we can be thoughtful in our interactions, and mindful of how we can improve. It’s a new way of thinking.”

Said Lewallen, “An important pillar for Colby is to lead with AI, and I think what’s so innovative about that is they’re adopting technology like OnLoop and really using it to make their own staff and students that much better.”

OnLoop Pays it Northward

What does this look like in action? Just ask recent grad Patrick Sopko ’20, who sees this firsthand as a sales associate for OnLoop, one of several Colby graduates Lewallen hired as part of DavisConnects’ Pay It Northward program. 

“The nature of the work is very motivating,” said Sopko. “We’re building a completely new software category, and constantly improving yourself is something that really strikes a chord with me. It’s been really cool being one of the people that puts those pieces together.”

The government major never expected to join such a fast-paced startup so quickly. After trying a few different positions after graduation, he feels like he’s finally found a place to learn and grow. Said Sopko, “If there’s one thing I learned at Colby, it’s that there are multiple solutions to the same problem. I felt like at Colby, I could take classes in philosophy or East Asian studies or economics, and I can apply all of those to what I’m doing now, just not in the way that I thought.”

Lewallen also attributes Colby’s liberal arts education to helping her make the leap from leader to founder. “Entrepreneurship in many ways is just creative problem solving,” she said. “You can’t rely on what you know because every company is different. At Colby, I had the opportunity to learn about so many different things, and draw connections between them, which is what entrepreneurship is all about.”