Wonder what Droplr’s up to? We did. So we wandered down the hall of the 1001 Tech Center to find out straight from CEO Gray Skinner. We’re glad we did. Since Skinner started full-time with the company in September, the startup has seen some change, mostly notably doubling its staff as well as focusing on more enterprise clients.

Droplr now employs eight people, with half of them here and the other half (their dev team) in Northern California. Four of those eight are semi-pro or pro runners or triathletes. That’s by design, says Skinner, himself an accomplished triathlete who qualified for the Kona Ironman on his first try. “These are people who know how to win,” he says. “They set a goal and they go after it.”

He notes that he’s less concerned with pedigreed resumes and more interested in potential hires’ passion and the drive they have toward achieving their aims, athletic or otherwise. (Takeaway: Do not challenge the Droplr team to a race.) It’s a mentality that pairs well with growing startups.

Previously COO of an executive coaching firm, Skinner has expounded before on the link between high-performance athletics and business success. From an article profiling him prior to the Kona Ironman:

He says that business leaders can learn focus and attention from elite triathletes. “Triathletes instinctively plan out their daily training, nutrition and rest to peak for key races. Many adhere to their routines very strictly and realize that they perform best when completely dialed in. One of my favorite phrases that we teach in our program is, ‘if you don’t have a plan for your time, someone else will.'” He adds that executives can learn this same type of focus by zeroing in on a few key objectives and learning to say ‘no’ to demands that don’t fall within those.

Part of the Droplr team including Skinner, middle, and co-founder Levi Nunnick, far left.
Droplr team left to right: Levi Nunnink, co-founder and CTO; Jeremy Tufts, sales director and a pro mt biker; Gray Skinner, CEO and triathlete; Ellie Staker, customer support and pro runner; Nick Bernard, engineer and runner.

The company now counts more than 500,000 users. Droplr has long targeted its file-sharing and communication app toward creatives, finding traction with individuals and small groups inside large companies. Skinner says most recently, the company is moving toward true enterprise clients, in which entire companies are using Droplr.

Not only does that strategy create a more stable revenue stream, but “the value of the product is magnified the more people you have using it,” Skinner says. The company’s most recent innovation is the integration of its screenbot app with Slack, which allows users to easily share screenshots via the ubiquitous chat tool.

The startup initially raised more than $850,000 in investment including from local investors Seven Peaks and Cascade Angels. So what’s the future hold? Skinner reports that they’re cash flow positive and continuing to hire for sales and marketing positions, right here in Bend. The company is exploring additional integration opportunities, meeting users on the communication tools they already use.