If you’re looking to hire Brian Sierakowski for a job, don’t.
“I’ve never been that great of an employee,” said the TeamPassword cofounder. “I get a lot of meaning out of building something I have ownership in.”
Sierakowski’s resume reads like the greatest hits of the Baltimore tech community: a stint at OrderUp and then a few years running client services at SmartLogic.
“Those are the best two jobs you could have; super flexible, super cool projects to work on, and cool people,” he said. “But I’m not super fulfilled in that, and it makes me antsy when I’m not building something.”
The next logical step was to crank it up all the way.
So recently Sierakowski left SmartLogic to work full-time at TeamPassword, the company he cofounded in 2012 at a Startup Weekend competition.
“I had always had this password management problem throughout my entire career,” Sierakowski said. “Every company I worked at had some version of a spreadsheet with passwords and it sucked. The company started with the idea that this problem is easy to solve so I should solve this problem.”
Initially TeamPassword was more of a pet project than a money-making proposition, Sierakowski said. But after nearly four years of incremental growth and an expanding customer base, he wanted more.
“We made a concerted effort to be more deliberate in the amount of time we spent and we grew a lot,” he said of TeamPassword. “So that is what motivated us to spend more time, because of the correlation. The next logical step was to crank it up all the way.”
All the way meant going all-in.
Sierakowski was already making the biggest time commitment to the company by handling support, writing some code and working with the marketing and sales teams. He said he felt comfortable leaving his position at SmartLogic because TeamPassword was a company with a full list of customers eager to pay for the service.
But now that he’s in the job he’s treating the company like it’s at square one.
“Now I have time to talk to customers and see the competitive landscape, so I think of it as a brand-new company that is lucky enough to have some revenue,” Sierakowski said. “As a part-time job it made sense to do incremental progress but now that it’s my full-time position I’m taking a step back and thinking, ‘What are the things I can do that would yield a 1,000 percent increase.’”
Part of that ramp-up is determining the company’s mission and then building a team around that one focus. He’s ready to experiment and knows he might not hit it out of the park on the first try.
“Maybe it’s unsuccessful and we see nobody has that need but that’s the goal,” Sierakowski said. “It’s not to manage 10 times more passwords, that might happen but I suspect it’s not going to be the explicit goal.”
He’s investigating funding opportunities but says the first priority is trying to get people to stop calling the company a password manager. A term Sierakowski called “boring.”
“I’d like to do what HubSpot did,” he said of the company that coined ‘inbound’ for its marketing automation software. “They invented a word for what they do and they found this thing that really worked for them.”
Sierakowski hasn’t found his “inbound” yet, but the company says something is in the works.
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