Genevieve Sheehan on creating her own path

By following her gut, Dropboxer Genevieve Sheehan carved a path from consulting to product management

Lisa Sanchez
Jun 19, 2014 · 5 min read

Genevieve Sheehan took a winding path to product management. But she wouldn’t have it any other way.

“There’s no one-size-fits-all,” she says, reflecting on her trajectory. “There are all manner of paths, and there’s no way to know where any one thing will lead.”

She remembers participating in STEM education initiatives as a child, but her early interest in technology became more of a hobby during her undergraduate years at Harvard College. There she chose an interdisciplinary major in Social Studies and wrote a thesis on modern European Union politics.

In her first job as a consultant at Bain & Company, Genevieve gained exposure to a broad range of businesses. But after a couple of years, her perspective began to shift.

She remembers, “When I started my first job out of college, I thought, this could be my forever job.

It was a tough transition, she says, realizing that might not be the case and following her interests beyond consulting. She spent the next two years working in private equity, where she discovered a love for the hands-on operations work with companies that made up a part of her role. It was then that she decided to return to her alma mater for business school.

“There’s a healthy skepticism of business school,” she acknowledges, “especially in the tech industry. But for me it was really valuable as a place for self-reflection and as an inflection point in my career.”

She approached business school with a very open mind about what she wanted to do next, exploring everything from retail and consumer packaged goods to marketing and general management.

“But I gravitated to tech really quickly,” she says. “A lot of it had to do with making an impact—both being impact-focused and being able to get to answers quickly and make a lot of changes. Those were really attractive to me.”

Genevieve can be spotted cruising between meetings at the Dropbox office in San Francisco.

She was also drawn to the culture of the industry, which seemed much more informal than consulting and finance.

“I felt like I brought the best version of myself to work and was able to really be my true self in a less formal setting.”

Her career explorations led her to an internship at Zynga, where she worked on Farmville while the game was at its peak. It was her first exposure to the many different aspects of building a product—from engineering to design to quality analysis to customer service to art. She found the process and its accompanying questions invigorating.

“How do you deal with having a product that’s live to millions of users all the time? It was really exciting and really motivating for me, knowing that the work I did made it to users and made a difference in their lives.”

After graduating from business school, she returned to Zynga to work on Farmville 2, before joining Dropbox in January. Early on, she worked with the Dropbox partnerships team as a product manager, focusing on the desktop experience. Lately she’s turning her attention to broader questions of growth and engagement.

“Over time, I’ve gone from more structured jobs to much less structured jobs,” she says, and the things she looks for in a job have changed.

“I don’t think about whether this is my forever job. I think, what can I contribute now?

For Genevieve, Dropbox as a company is a work in progress, “something we’re still really building,” and the opportunities to contribute are endless.

One of the challenges of so much possibility is prioritization. “We have more things to do than we have people,” she says, “but it’s a huge opportunity to make an impact as an individual.”

In her role as a product manager, she maintains a vision for the product and keeps a cross-disciplinary team aligned toward a common goal.

“Part of the product manager’s role is to make sure that the team feels empowered, and that really unleashes a lot of creative energy. Activating the people I work with is something that gets me excited on a daily basis.”

Much of her work lies at the intersection of the needs of the user and the business.

“We look to product managers to be the voice of the user and to be impact-driven for the business. Those two things could be seen as a tension,” she says, “but the best product managers actually make them align. That’s the sweet spot of product management, of creating features and product experiences.”

As she continues to grow in her career, Genevieve says she’s becoming more and more comfortable with ambiguity, seeing it as a freeing force.

“If you want to take big risks,” she says, “you have to be willing to fail. Sometimes things don’t go according to plan. The most important thing there is understanding why and being able to course correct, being able to learn from things that don’t go as we want.”

Genevieve fulfilled a lifelong dream of competing on Jeopardy in 2009.

Her perspective stems in part from her experience as a contestant on Jeopardy in 2009. At a critical moment, she wagered everything, only to lose it all moments later. But if she could do it all over again, she wouldn’t change a thing.

“I’ve learned that ‘safer’ choices in life aren’t necessarily better choices,” she once wrote, reflecting on the experience and looking ahead to her future. “I’ll make the best choices I can in each moment, and I’ll own those decisions without regret.”

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Lisa Sanchez

Written by

Leadership & Executive Coach at Cocoon.

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