Community Profiles

BetterUp’s Lily Roosevelt on Her Quest For Lifelong Learning


When Lily Roosevelt set out to grow her career and develop as a professional, she couldn’t have found a better place to work than BetterUp, a company devoted to making career and leadership coaching more accessible.

After graduating from Colorado College with a double major in English and history, she spent several years waitressing in the state before moving to San Francisco. After a few months of working in Bay Area restaurants she decided she wanted to pursue professional opportunities in the city’s startup tech industry. She had a strong background in hospitality thanks to her waitressing experience, but she didn’t quite know how her experience would translate to a 9-to-5 office setting. She decided to focus on office management roles because felt like they would be a good fit for her background and she landed at BetterUp, where she started as the Office Manager and is now a People Operations Associate.

BetterUp is a mobile-based performance coaching platform that brings personalized expert coaching to employees at all levels. Companies like Facebook, Capital One, Square, and TriNet have all partnered with BetterUp to develop the skills and behaviors necessary to maximize team performance, engagement, and retention.


In addition to their clients and the wider BetterUp community, the company takes extra care to focus on the development of their employees. Like many people in office operations roles, Lily balances multiple tasks daily and works with colleagues on the people and culture, operations, and facilities teams. Given her previous experience, the hospitality side of her job came naturally, whether it was hosting visitors, planning an event, or appeasing her coworkers when something was left out of a grocery run. But when it came to the managerial aspects of the role, Lily had to sharpen her skills quickly as the company experienced substantial growth. She had to learn to organize a whole company at various stages, whether it was 15 people or 50.

“I feel very fortunate, because we really walk the walk here at BetterUp. I got a ton of support in learning the skills and tools that I needed to have to be successful in the role,” said Lily.

One major responsibility that tested Lily’s managerial skills was heading up the office’s move into a brand new space. While tackling an office move is practically a rite of passage for an office manager, BetterUp had started in a coworking space, so she had the extra challenge of renovating and setting up the company’s first permanent space. In their coworking space each team member had little more than their computers and a couple of books. In the new space, as she hung plastic to keep dust from the renovation area away from her colleagues’ desks and shouted over loud sand blasters used to redo the floors, Lily realized she was in over her head. She reached out to Liz Haughton at Managed by Q, who arrived the next day. From then on, Lily credits Q for being an invaluable partner.

“From sourcing appliances to major electronic installs, and regular nightly cleaning services, I would have been so lost without Q,” she said. “Eventually we brought in an interior designer and she helped me flesh out my vision for how to make BetterUp’s culture tangible in the space. Q was a partner in that process too. All the way from installing walls and appliances to eventually staffing our office warming party three months after we moved in.”

With guidance from BetterUp’s executives, Lily, the designer, and Managed by Q worked together to create a space that was on brand and representative of BetterUp’s company culture. It was also an opportunity for the young company, which was founded in 2013, to express their values throughout their space. Many BetterUp team members, including the co-founders are avid readers, so an office library was a must. With the library “BetterUppers,” as they call themselves, can participate in lifelong learning, a key company value, while at work.

When BetterUp committed to supporting their employees’ development, they didn’t neglect physical wellness. The company champions grit and continuously accepting challenges to grow. To represent these values in their office Lily had punching bags installed. A personal trainer named George comes to BetterUp to run workouts every Monday and Wednesday.

“We want to support everybody’s personal development here. We believe that’s the only way you make professional gains,” said Lily. “When one of us is flourishing, the whole team gets stronger. So every decision we made about what to put in the office had those baselines in mind.” Creating spaces for collaboration and giving and receiving support was another requirement for BetterUp’s renovated offices. In the center of the office is a giant sectional couch that can be broken off into many different pieces. When a BetterUpper is struggling with a problem, they can get up from their desk and meet a coworker on a piece of the sectional to hash it out.

Beyond the new office, Lily took on recruiting efforts with Susan Hwang, BetterUp’s Head of People, and created culture initiatives that unite the company. Half the company works remotely, which creates a unique challenge when working to unite their culture. To help support everyone on their team Lily worked with Susan to create anniversary and birthday gifts for all employees, which ensure that everyone is getting the same recognition. The one-year anniversary gift is a branded notebook that lists the person’s top five strengths. The entire company takes time to write notes to the employee based on how they’ve seen his or her strengths shine through in everyday working life.

Another way Lily unifies the culture of BetterUp for both the remote and onsite workers is taking her role in planning for offsite retreats seriously. Retreats can be an innovative way to build team cohesion and strengthen work relationships, especially when they are the only occasions everyone gets to interact face-to-face. BetterUp has semiannual retreats, with this summer’s being held in nearby Santa Cruz. The aim of any culture initiative is to get team members thinking with fresh perspectives and out of their comfort zones. Lily finds that the retreats are a great way to accomplish those things, but also believes she still doesn’t have it all figured out. New proposals are always in the works.

Lily stressed, “How we express our culture and support our employees is ever-evolving. And we kind of hope it stays that way. The worst thing that could happen would be a routine that totally eliminates creativity and divergent thinking.”

Photography by William Perls


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