Executive Hiring for Startups From the Author of Startup CEO

Bolster CEO Matt Blumberg began his career as a management consultant and then worked in venture capital. “Those two things taught me a ton about business,” he says. “One of the things they taught me is that I wanted to be an operator, not someone on the outside. Advisor [and] investor were both really interesting, but I wanted to build something.”

In 1995, Matt went to work for an ad-supported, interactive telephone service called Moviefone that allowed people to buy movie tickets over the phone. He served as the general manager of that company’s internet business for several years. “Those were really formative years for the commercial internet as we know it today,” he says. “It was great. I woke up one day at age 24 or 25 or whatever it was, and I was running a top 25 internet property, which I kind of had no business doing. But it was a great experience.”

Moviefone was eventually sold to America Online. Matt then co-founded an email marketing business called Return Path and helped build that company into a $100 million business with 500 employees in 20 years. He sold Return Path in 2019, and in 2020 he co-founded Bolster with seven other people who had worked with him previously.

Bolster offers a marketplace that connects executives with startups and scale-ups. It can meet a wide variety of needs, including interim work for startups that are between executives, fractional executives for ongoing consulting projects, advisory and coaching for startup leaders, and boards of director candidates for companies expanding their board independence.

“We are building … a really interesting and very impactful and hopefully somewhat disruptive business in the talent space,” Matt says. “We're a marketplace that connects founders and startup CEOs with senior executives. We believe that there's got to be a better way to access executive talent than the way it works today, which is either very ad hoc, like you know someone or you know someone who knows someone, or it's very expensive and very slow. You hire a search firm, it costs a lot of money, it takes a long time. You end up with a very expensive person.”

While this approach may work for more established companies, it doesn’t work for a lot of startups. “The needs of startups are really, really different from the needs of larger companies or even middle-market companies,” he says. “Being able to get good executive talent on demand if you need someone for an hour for a project, for a day a week, or a day a month, this is a better way of doing that. And if you need someone full-time or you need someone to be on your board, it's a much lighter-weight process that we go through … Bolster makes it a lot easier to do that, a lot more comprehensively, a lot faster, [and] a lot cheaper.”

Matt says one of the things that gets him up in the morning is the opportunity to make other startups more successful by helping them find the right talent.

“We as a team [are] really energized and motivated around the topic of talent and of scaling and of leadership development,” he says. In that regard, Bolster applies a lot of lessons learned from scaling Return Path and from mentoring earlier-stage or first-time founders. “If you think about the successful ingredients of a startup, it's money, product, and talent,” he says. “There's plenty of money out there … and I think there are some tools out there around helping founders find product-market fit. But the talent area was the one that really had us the most excited about ways to have an impact on the startup ecosystem.”

Scaling is a continual challenge for startups, and Bolster helps founders meet that challenge. “The thing that founders struggle with the most is how to scale a leadership team … how to scale themselves as a leader, as a CEO, and how to scale their board,” he says. “The common ingredient in all of those things – [the] leadership team, mentoring and coaching, and board – is … experienced senior executives. We realized that the model was just kind of broken. The way that people access senior talent – there had to be a better way.” 

Bolster’s investors include some top-tier venture capital firms like Foundry Group, Union Square Ventures, and Costanoa Venture Capital. Bolster also has partnered with the business-to-business studio High Alpha and Silicon Valley Bank. “At the end of the day, we want tens of thousands of founders using Bolster and hundreds of thousands of executives in it,” Matt says. “We're well on our way, but it takes a village.”