Owls to Employee Experience: Regis Wakefield of Greenhouse

Kristen Felicetti
June 13, 2019

For Regis Wakefield, Greenhouse's Senior Manager of Employee Experience, her path to office management was unexpected, and it all began with a job post that requested a “picture of a badass owl.”

Regis’s educational background is in counseling and therapy. While she has never practiced, she jokes that the counseling skills she learned “come in handy every so often” in her current role at Greenhouse. Upon graduating from the University of New Hampshire, she started her career in the legal department of a financial services company, where she realized the importance of process, accountability, and efficiency. These are all skills she continues to develop through her current work at Greenhouse.

A move to Ann Arbor, Michigan led her to Duo Security, where she applied to be the company’s office manager. It was a normal job application until she got to the end when she was asked to attach a picture of a “badass owl.” This offbeat, amusing request hinted at a company that was relaxed, funny, and didn’t take itself too seriously. They must have approved of the owl she created (a photoshopped picture of Steven SeagOwl, an owl with Steven Seagal’s face), because not only was she hired, but when she left the company to relocate to New York City they printed Steven SeagOwl on a cake as part of her send-off.

Regis’ colleagues from Duo Security put her in touch with Greenhouse, a growing tech company that helps companies optimize how they interview, hire, and onboard the best talent. She began working as the Operations Manager in December 2015. At the beginning of 2017, she was promoted to Senior Manager of Employee Experience.


Prior to her promotion, Regis described her role as half operations and half employee programming. The operations side of things includes repairs, Greenhouse’s food program, office layout and design, and supply management. Regis has made it her mission to automate many of these processes so that they don’t require as much of her attention and time on a day-to-day basis. She credits Managed by Q and other vendors for making this possible and emphasizes the importance of “finding incredible vendors to work with that utilize technology to make your life easier.” Once you find those vendors, she believes it’s equally essential to build and nurture your relationship with them.

Automating some of these processes allows Regis to also focus on employee programming. This includes overseeing the company onboarding program, launching learning and development initiatives, and working with the Greenhouse culture committee. She particularly enjoys this part of her job, because she gets to work closely with her coworkers.

“To put it plainly, the people here are awesome,” she said. "Even when things get stressful, I look forward to coming to the office, because I laugh at work every day.”

She cites planning for an off-site in the Poconos for her team as an especially memorable project. The trip gave her colleagues a chance to bond while playing summer-camp games such as “zombie staredown,” which she documented in an entry about planning team retreats on Greenhouse's blog. When the team returned to the office, morale and camaraderie was high, making Regis feel especially proud.

Through her relationships with her coworkers to vendor representatives, it’s clear that Regis values people, and that appreciation extends to others in her profession. She stresses that office and operations managers don’t have to figure it all out on their own. There are plenty of communities out there to join, whether you connect with other office managers in person or online groups. Regis is a member of OrgOrg, a community and Google Group made up of office managers, administrative assistants, and other human resources professionals. When she has a question, she knows she can turn to the 2,000 (and counting) members for answers, or search the listserv archive.

While the constant demands on an Operations Manager mean there is never a typical day, Regis sets up processes to keep herself organized. She’ll try to get scheduling tasks, like repairs or team moves, taken care of on Monday or Tuesday. On Wednesdays, she strives to clear her schedule of meetings, so there is one day a week where she’ll have significant heads-down time to focus on projects. The end of the week is reserved for wrapping up any loose ends and preparing for the following week.

Regis also has a system for maintaining a balance of accessibility while minimizing interruptions. As a company, Greenhouse fosters a casual, open environment so people often stop by her desk to say hello, suggest a new event, or discuss an initiative they’d like to start. For more routine issues, such as a leak in the bathroom, or a broken light, she has created a Zendesk account where coworkers can submit requests. By streamlining the process and creating a database of open issues, Regis has ensured that she will never miss a request.

When emergencies or last-minute projects come up, “one half of being a great office manager is having the grit, passion, and drive to accomplish something no matter what,” said Regis. She explained that finding an equilibrium between extreme perseverance and preventing unnecessary hassles is a key quality for those working in office management and operations roles. “On the flip side," she mused, "the other half is doing everything in your power to make sure things don’t get out of control in the first place. The best solution is to plan ahead, and foresee challenges to avoid high-stress situations before they happen.”

Photography by Dominick Mastrangelo

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