Bolster
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The New Way to Scale an Executive Team

As we wrote in our Founding Manifesto, Bolster was started in part to create a new way for startup and scaleup CEOs to think about growing their leadership teams.

Why do CEOs need help with this?

CEOs of any company have too many things to do at all times. This is even more true at startups and scaleups, which by definition are more fast-paced, dynamic, CEO-driven, and thinly staffed. All those challenges point directly to the specific challenge CEOs have with their leadership team.

Think about the journey of a company from a founding team to 50 employees. My long time friend and former board member Greg Sands once compared the phenomenon of companies growing out of the startup stage to cell development in small organisms. Amoeba or paramecia consist of one cell, and that cell has to do everything: eat, move, sense its surroundings, and respond accordingly. When the cell divides, the new cells still need to do everything – they’re just attached to other cells. As organisms grow more complex, individual cells need to specialize. And when things get really complex, you need a liver, a spleen, a stomach, and a pancreas. By and large, startups work the same way. In the early stages, you have to hire generalists who are both willing and able to take on dozens of tasks at once. Your developers will have to speak with potential customers; your accountants will have to give advice on product direction; and the born salesperson on your team will need to put the phone down a few hours a day and set up a new employee’s computer. That’s a really different team than when you need functional managers on top of engineering, sales, etc. – not to mention needing strategic leadership of those functions as the company grows from 50 to 100 to 250 to 500 employees.

That’s the journey that startup and scaleup CEOs are on. It’s less of a journey and more of a roller coaster ride. Jason is running HR today…but tomorrow, the job of “head of HR” will be different, and Jason might or might not be capable of it. Then your VP Finance Sally gets lured away by an even hotter and sexier new startup and leaves a sudden, gaping hole on your team. Then cracks start to show up with the job Jamie is doing as your marketing director and you lose confidence that your upcoming product launch is going to be a success. Every time one of these events happens - whether it’s an actual event, or just an “aha moment” for you as CEO, you add something to your plate. You add tasks to take over work yourself. You add the task of finding a new person. You add stress from having to deal with one more critical thing.

Leveling up a leadership team is probably the hardest part of the CEO’s job.

Why don’t current solutions meet the CEO’s needs? Well, of course they do, sometimes. The problem is that the current solutions either aren’t tailored to the needs of startup or scaleup CEOs, or they’re ad hoc and inefficient. Executive search is slow and expensive, and it produces expensive full-time executives. And no matter how good an executive search firm is, I’ve never met a CEO who has a better than 50% success rate in hiring new leaders from the outside. Ever. Add all that up - expensive, slow, medium success rate, and perhaps most important for a startup CEO, leaving you with expensive full-time headcount in multiple areas of your company - that is not a recipe for startup success when you’re sweating your burn rate.

Frequently, the CEO just taps her network for execs or for on-demand executives like the ones Bolster places – that could be asking board members or friends or advisors for suggestions. Quite frankly, those suggestions stand a better chance of success than transactional executive search since the candidate referral source is usually somewhat of an insider. But those searches are really disorganized or one-off. When a CEO turns to their network for spot help, they often aren’t running a comprehensive process, creating a serious job spec, seeing a broad set of candidates for comparisons, and the like.

Our job at Bolster is to make all of this easier and lighter weight. The rise of the gig economy means that startups no longer need to rely on the painful binary choice of “the person/opening I have today” and “the expensive full-time exec coming in from the outside.” The new way to scale an executive team is with a mix of interim executive talent to quickly fill gaps, fractional executive talent to provide strategic oversight and guidance to a team, part-time, functional mentors/coaches/advisors to advise a less experienced functional leader, project-based consultants to fill in specific holes, and yes, the occasional full-time outside hire, possibly via a search firm (or if your fractional CXO loves your company and joins full-time!).

With Bolster, you have a network of all those types of talent, well curated and well profiled, available for near-instant matches and near-instant start dates - and a suite of tools and services designed to help you proactively identify your needs across all your functional areas so you’re never scrambling your way out of a tight spot.

What about the existing team? If you’re a leader inside a startup or scaleup, Bolster is ALSO created for you. The painful binary choice CEOs face that I wrote above is particularly painful for you if you’re no longer scaling quickly enough. Frequently, promising junior people are layered or shuttered aside because the CEO doesn’t have the time, or the functional expertise required, to coach or mentor the person to success. Bolster creates an easy mechanism for CEOs to help pinpoint the areas in which you need growth and development as well as an easy way to find either temporary leadership or a function-specific advisor/mentor/coach to help you grow with the role and with the company.

The best startup CEOs I know are the ones who are already using multiple types of on-demand talent at the same time to help their companies along that journey from single-cell to complex organisms. I believe three years from today, the frequent usage of this kind of talent will move from the realm of early adopters to mainstream. The ones who embrace it first will have a competitive advantage.

– Matt Blumberg, May 11, 2020