One of the most critical factors for startups to grow, thrive, and scale is their ability to attract the right talent. The effects of the pandemic, the Great Resignation, and a host of other factors have made the competition for candidates more intense than ever before. Emerging companies are pitted against more established, larger companies that have greater resources and ability to compensate. Bolster is a talent marketplace for startups that matches them with executive talent for fractional, interim, advisory, board, and full-time roles. Unlike other recruitment platforms, Bolster works directly with a founder-centric framework that looks at recruiting as a part of leadership and company development versus merely hiring resources, offering software-driven mentorship modules. With the flexibility in the types of roles that it covers, the platform enables CEOs to quickly and cost-effectively implement the resources required to scale. The company offers a number of different options for companies looking for talent ranging from a free self-search to full-time sourcing that comes in at $20K per hire. Since its launch in the Fall of 2020, Bolster has worked with 1000+ leadership teams and boasts 7000+ registered senior executives looking for their next opportunity.
AlleyWatch caught up with CEO and Cofounder Matt Blumberg to learn more about how the founding team’s experience with Return Path laid the foundation for Bolster, the state of the startup recruitment market, the company’s strategic plans, latest round of funding, which brings the total funding raised to $13.8M, and much, much more.
Who were your investors and how much did you raise?
We announced our Series B round of $11M led by Foundry. This latest round also includes participation from all existing investors; SVB Financial Group, the parent company of Silicon Valley Bank, High Alpha, Union Square Ventures, and Costanoa Venture Capital, as well as new investors Capital Factory and Alumni Ventures.
Tell us about the product or service that Bolster offers.
Bolster helps startup CEOs scale themselves, their leadership teams, and their boards. The Bolster marketplace matches startups with executives for interim, fractional, or advisory roles, board appointments, and full-time jobs. Bolster also offers robust mentorship and advisory services. Since its launch in September 2020, almost 7,000 curated senior executives have joined Bolster as Members, and over 1,000 founders and CEOs have joined Bolster as Clients, a testament to the growing workforce trend of on-demand, flexible work opportunities that exploded with the pandemic and the mainstreaming of remote work in 2020 and 2021.
What inspired the start of Bolster?
I used to run a technology company called Return Path for over 20 years, which is where all of Bolster’s founders worked as well. Return Path was one of the first companies to establish a “people-first” culture where the circle of life for a high-growth, highly scalable business began with employees at the forefront; anchored in values of equity, parity, flexibility, and an intense focus on investing in employee development. This was back in 1999, before it was in vogue. Our focus on people first led to better customer outcomes, which led to better business outcomes. As a result, we invested a lot in people – including a substantial investment in growth mindset learning and development. One testament to the success of this approach was that at the point of our 2019 exit, the leadership team was filled with people who had been promoted into these roles after growing their skills at the company throughout the years.
After exiting Return Path, we wanted to do for others what we did for each other as a seasoned executive team. We wanted to know: How could we help other CEOs, executives, and boards bolster themselves to go the distance and scale with their organizations? While the founding team was exploring potential business opportunities that allowed us to make a bigger impact on the world, Silicon Valley Bank and High Alpha Innovation were together envisioning a platform to help VC-backed portfolio companies more effectively navigate the complex world of executive talent needs. When our three groups came together, we realized we shared a vision to build a company that puts people first in all aspects to drive high-growth businesses.
How is Bolster different?
Bolster is a “by founders, for founders” approach to scaling talent. Together, we’re building a business that helps CEOs scale their companies differently… and that starts with talent. Bolster’s marketplace connects executives with startups and scaleups to match a wide variety of needs: Interim work for the in-between executives. Fractional opportunities for ongoing, consulting work. Advisory and coaching opportunities to help leaders receive the development we sought to provide our own colleagues at Return Path. Board of Director opportunities for companies expanding their board independence. We know the tone for a diverse and inclusive business starts at the top, which is why we ensure that we provide diverse slates of candidates for all roles. And the unique suite of tools we are building for CEOs unlocks incredible potential for a new way of developing leaders and scalable businesses, leveraging data, not anecdotes.
What market does Bolster target and how big is it?
Bolster works most closely with CEOs of venture-backed startups that are looking to add leverage to their leadership teams and boards. Our business taps directly into the growing trend of flexible work even at the most senior levels of business. Last year alone, over 10,000 startups in the U.S. received external venture funding, and if you ask VCs what they need to accelerate the growth of these businesses, the answer is always the same: Talent. Through our marketplace model and programmatic way of addressing mentorship and advisory work at any stage of business, Bolster is infinitely scalable to meet the needs of startup CEOs more quickly and cost-effectively than any alternative solution.
What’s your business model?
Bolster is free for executives who are looking for on-demand work and free for VC and PE firms that use our platform to collaborate with their CEOs on key executive and board searches. Any client can create an account and browse our marketplace free of charge – including meeting prospective candidates for open roles at your organization. We charge only when you successfully engage a member for a placement. The pricing structure is a markup fee for most on-demand searches, but we also offer a variety of supplemental higher-touch services, such as assisted searches, and full-time and board placements.
Bolster is free for executives who are looking for on-demand work and free for VC and PE firms that use our platform to collaborate with their CEOs on key executive and board searches. Any client can create an account and browse our marketplace free of charge – including meeting prospective candidates for open roles at your organization. We charge only when you successfully engage a member for a placement. The pricing structure is a markup fee for most on-demand searches, but we also offer a variety of supplemental higher-touch services, such as assisted searches, and full-time and board placements.
What are your post-COVID office plans??
We founded Bolster in April 2020, right at the first peak of the pandemic, and have operated as a remote-first business from day one. This flexibility has enabled us to hire the best people from all across the country. Today, our employees span three major geographies: New York, Colorado, and Indianapolis. We’re still working through what each geographic cluster of employees need in terms of facetime and office space, but I imagine it will include a blend of occasional synchronous in-office time and regular remote work. For example, in New York City, our colleagues regularly cowork together out of the Grand Central Tech space in midtown, and it’s been wonderful to have access to this network and community. One important tenant to our business is to regularly convene our executive team on a quarterly basis so we can get through strategic problem-solving together. This fall, we also held our first all-company offsite for the entire organization, and we intend to follow suit in years to come.
What was the funding process like?
We are incredibly lucky to have the support and advocacy of such a strong investor syndicate from the beginning. High Alpha and SVB helped us start the company, so they’ve been with us from Day 1. Nearly all of our board members from the Return Path days have recommitted capital into Bolster, and when they found out what we were working on, they latched on immediately to the massive opportunity we are chasing with this business. In all of my years of raising capital, I can honestly say that this was the most straightforward process I’ve ever run. When Foundry offered to lead this latest round, it felt like a natural fit and so well aligned with their thesis around strong networks. I believe this is a testament to the spike in early traction we’re seeing in just over a year since our marketplace launch, combined with some of the visionary stuff we’re going to be announcing in how we support early-stage founders even more. And in a network business like this, we were excited that Alumni Ventures and Capital Factory, two large networks themselves, got our vision and also wanted to participate.
What are the biggest challenges that you faced while raising capital?
We are incredibly fortunate to not have hit many roadblocks while raising this round of funding. My bigger challenge was deciding who to bring on as our next independent director to coincide with this funding round. I’m a big believer in adding independent directors as early as possible, as this is a great way to diversify the perspectives you get around the board room table. As it turned out, we had such strong profiles of candidates for our independent seat that I couldn’t pick just one! That’s why we ended up bringing on two independents with this financing: Andrea Rice and Rory Verrett. Andrea is currently managing director of Management Leadership for Tomorrow (MLT), helping drive the organization’s Black Equity at Work Certification program, having spent the bulk of her career as founder and president of CareerCore, a platform for enterprise professional development and coaching. She serves on the boards of the International Tennis Hall of Fame and the Washington Tennis & Education Foundation (WTEF) and is an internationally ranked competitive tennis player. Rory is currently CEO of Protege Search, a retained executive search and leadership advisory firm focused on diverse talent, which he founded in 2016 after a career in executive search that included Russell Reynolds Associates, Spencer Stuart, and head of talent management and public affairs for the National Football League. This now brings our board to a total of three independent directors, including Cristina Miller, who is the COO of Goldbelly and a long-time online marketplace executive with companies including 1stDibs and Gilt Groupe. We’re also in the unique position that our investors Fred Wilson from Union Square Ventures, Brad Feld from Foundry, and Greg Sands from Costanoa Ventures, have each taken on observer seats on our board in order to make room for more independents and also offer these new directors their mentorship and advice.
My bigger challenge was deciding who to bring on as our next independent director to coincide with this funding round. I’m a big believer in adding independent directors as early as possible, as this is a great way to diversify the perspectives you get around the board room table. As it turned out, we had such strong profiles of candidates for our independent seat that I couldn’t pick just one!
What factors about your business led your investors to write the check?
All of the investors around the table are incredibly bullish about the power of network effects in any marketplace business. One of the things we speak about a lot internally is how we can unlock the flywheel effect to really open the floodgates and let the marketplace work for itself. Even in such a short time, we’re already seeing early signs of what Bolster’s long-tail flywheel might look like. At its core, you might see Bolster as a marketplace between CEOs looking to hire and executives looking for job opportunities. But the reality is that we’re building deep engagement mechanisms for three audiences: CEOs, executives, and VCs. When our investors saw the scope of what we’re setting out to accomplish, they knew that we had landed on not just a better way to hire executives, but an entirely new paradigm for company-building.
What are the milestones you plan to achieve in the next six months?
We’ve spent most of this past year building the foundation for a pretty big house. This year, we’re going to see a lot of this work come to fruition in a really big way. Some of what you can expect include expanded marketplace features for CEOs and members, a streamlined way for CEOs to collaborate with their close advisors and investors on any key search, and some really exciting support structures and mentorship modules that we’re building out for early-stage business leaders. At the end of the month, we’ll be announcing two of these newest initiatives back-to-back. I can’t share more about these just yet, but you’ll want to check back in with me on February 1.
We’ve spent most of this past year building the foundation for a pretty big house. This year, we’re going to see a lot of this work come to fruition in a really big way. Some of what you can expect include expanded marketplace features for CEOs and members, a streamlined way for CEOs to collaborate with their close advisors and investors on any key search, and some really exciting support structures and mentorship modules that we’re building out for early-stage business leaders
What advice can you offer companies in New York that do not have a fresh injection of capital in the bank?
There are so many benefits to building a business in New York City. Even during the pandemic, New Yorkers keep moving. We’ve been lucky enough to land a few seats at the coworking space, Grand Central Tech, part of Company’s building in midtown, and we’ve been blown away by the level of community and support in place for early-stage businesses. There are dozens of accelerators, peer communities, and meetups (including virtual) that take place every single week in the city. The most entrepreneurial founders I come across are those who haven’t lost the New York hustle, despite the uncertain external circumstances. More so than ever before, it’s important for founders to find communities for themselves to help them acquire the connections, capital, and advice they need to level up to the next stage. This is part of what inspired us to build some additional structural elements and supports for early-stage startups through two new initiatives, which we will be rolling out later this month.
Where do you see the company going now over the near term?
We are excited to continue to prepare company leaders and executives for a new era of working in a flexible-first atmosphere. Last year we helped venture-backed companies hire nearly 150 executives and board members for their business. We’re just getting started.
What’s your favorite outdoor dining restaurant in NYC?
If you’ve never dined in a yurt, it’s certainly worth the experience to book an outdoor heated yurt at The Garden at The Standard in the East Village. Don’t miss the cheese fondue.
