In January, I left my job at USV to join a new startup (and USV portfolio company), Bolster. Here’s why I made the leap — and what I’m looking forward to in the years ahead.
For years, while working on the sidelines of great companies and entrepreneurs at Union Square Ventures, I’ve been obsessed with one thing: Team-building. How teams come together, how they fall apart, how, with just the right balance, you can unlock greatness.
As it turns out, building the best team for each unique business is exceedingly hard to get right. Early into my tenure at USV, I was surprised to learn that about 80% of startups in our portfolio experienced some change at the executive level each year. And no matter how many resources we deployed into our network and community efforts, the singular need from our CEOs remained the same, month after month, year after year: “We need more talent.”
If only it were that simple. After all, CEOs don’t just need any talent. They need great talent. And they need it immediately, if not sooner. In a world where every company is just barely edging out its competitors while also delicately avoiding treading on Big Tech business model territory, time is of the essence. When good ideas come easy, it’s good execution that comes with a hefty price tag.
Add to this already complicated formula the scale factor. That’s to say, the team you need to start and lead a company through a Series A may not be the same team you need to go the distance through later funding rounds or an IPO. Not to mention the opportunity cost of onboarding and offboarding new exec-level hires.
For some quick mental math, consider this: A typical, 5-person founding executive team will likely bring on 7 new executives by the time their business hits the 10-year mark. If you assume an average of six months onboarding each new hire, a CEO spends more than three years simply acclimating new people to the organization, and that doesn’t even include time spent recruiting.
But what if there were another way? What if, rather than staff the bench of a rotating crew of full-time hires, you instead use talent to augment the existing team? This, at its core, is the promise of Bolster, and it’s why I’m so excited to be a part of this team and vision.
Drafting the Right Team for the Right Moment
Bolster is building an on-demand marketplace for executives. It’s a new way to think about team-building, one where people aren’t “forever” employees of any one place, but “sometimes” employees of many places at once. CEOs choose a small team of full-time leaders, then bring on interim, fractional, or advisory talent to…well, “bolster” their performance.
This external group of leaders or advisors can change over time. As it should. After all, a Series A startup will need a different profile for a fractional CRO than they might as a Series D, pre-public scaleup. But executive-level changeovers don’t lose nearly as much time on the transition when you’re not dealing with full-time employees.
Rather than spend 4-6 months on a full-time search, you can hire and onboard an on-demand worker in 30 days or less. Some fractional executives I’ve spoken with say they start to add value to the business in just a single week. Talk about a serious business productivity unlock.
While I’ve spent my career in the business and tech worlds, I’ve always had a toe in the theatre industry due to my husband’s role as a sound designer on Broadway shows. One of the things that always fascinated me about the entertainment industry is that, for the most part, people work on projects. Each new show brings about a new team, with a perfectly matched cluster of different functional leads, all with different specializations. A show might carry the same director and music director as a previous show, but have a different choreographer, lighting designer, and costume designer based on the needs of that production.
Rather than get “locked in” to the current state of any single team’s performance, the ceiling of possibility raises considerably when you can bring in new people for each new project. I’ve always wondered what this might look like in the tech sector. And I think I’ve found it.
In a Bolster world, CEOs are constantly optimizing their team in small ways to reach peak performance. They support their current team with seasoned professionals who are experts in the very thing their business needs more of. As those business needs change over time, so does their extended executive bench. This, as it turns out, has more benefits: CEOs can bring on temporary experts without the fear of introducing internal politics or jockeying for power. And the existing executive team grows stronger through learning together.
The Right Time for the On-Demand Economy
If there were any year to start a business for fractional and interim executives, 2020 was it. This, after all, was the year we all went remote, and every person on the planet was forced to ask themselves the question: “What do I want, really?”
With that space to step back, a new professional ethos has crystallized. We’re moving away from cities, opting for a little more space in our lives. And, when we’re all working from home anyway, the shift from full-time to consulting suddenly doesn’t seem quite so scary.
As I wrote here, we’re seeing a meteoric rise in demand for on-demand talent across all sectors. Professional flexibility is becoming the new norm. After all, if you’re going to have your kids on the background on all of your Zoom calls anyway, you might as well schedule your workday around their schedules.
Therein lies the perfect storm. A moment in time when the war on talent has never been more competitive intersecting with a seasoned executive workforce that’s more comfortable than ever working in a freelance capacity.
I believe we will see a lot more “agile team-building” in the next decade. I believe it will be better for business outcomes and also for professional satisfaction. When I first learned about Bolster’s business model last summer, I knew then that it was such an obvious match, that it so acutely solved a pain point I’d seen among so many CEOs, that I had to get involved on the ground floor. Not to mention the fact that the company is run by an absolutely killer team themselves.
I’m excited to see this next decade bring about a new norm of team-building and invite you to participate in it yourself at bolster.com.
Also published on Medium.