How and why I became a fractional startup executive
My journey to my current job of fractional startup executive was indirect and accidental.
It started three years ago, when I was contacted by a two-sided marketplace startup that had just raised their Series A. They were growing 10% month-over-month, and the team couldn’t keep up. As they added more users to their platform, their customer support was getting backlogged. As they added more employees, their internal coordination was falling apart. The growth was exciting, but it was causing the company to spend more and more time fighting fires, and less and less time actually building. They were contacting me to see if I’d be willing to help.
This company reached out to me because they were interested in my experience at Uber, where I’d spent the previous six years helping that company grow from ridesharing infancy to full-blown Big Tech company. They’d never hired an executive externally before, though, so they wanted to try it out first. They asked if I’d be willing to join as COO, but starting as a part-time contractor working 10 hours per week.
At the time, I was taking a sabbatical and mostly focused, through repeated trial and error, on figuring out how to make the best possible scone (the two keys are proper management of butter temperature and not over-kneading the dough). I wasn’t interested in a full-time job at the moment, but 10 hours a week seemed like a great way to “try on” a company before either of us made a larger commitment.
I ended up working with that team as their part-time COO for 8 months.
During those 8 months, I was able to help the team with a number of key blockers to their scale:
Hiring and managed their customer support team
Building their pricing model
Redesigning and standardizing their customer onboarding process
Coaching the executive leadership team on how to make their teams successful
Acting as the CEO’s right hand on numerous strategic projects
Most importantly, though, I helped set them up for scalable growth. After I left, the company brought on a full-time operations leader, and it now has close to 100 employees, over 10 times the number it had when I joined.
Why the fractional executive setup works
That first part-time COO role taught me that it is possible to make a big impact at a startup without working full-time or even for a very long period of time. Having my hours counted made me and the team be very picky about what I focused on. Whereas in a full-time role a company might naturally load someone up with work and meetings only to have this slow down that employee tremendously, the opposite happened here. Knowing they had 10 hours of my time each week, the company only invited me to meetings they deemed absolutely necessary for my work. Being part-time also meant I was focused on just 2-3 key projects at once, rather than the many initiatives that most full-time employees take on. The same was true for the delivery of those projects. Being part-time meant that work I was involved in had to take more direct paths to completion, avoiding some of the unnecessary steps that often bog down projects at growing startups. My impact per hour of work was very high.
Another key factor in the success of this setup was that I could remain a relatively impartial, but very informed, outsider. 10 hours per week meant I could become knowledgeable about the company, but not be involved in the internal politics that companies inevitably have. I could provide far more informed advice to the CEO than an advisor could, but without the bias that would naturally come from being on the inside 24/7. And with my income coming from multiple sources (more clients eventually replaced scones as my main focus), I could offer more honest guidance and input to the leadership team, with far less fear about losing my job because of it (since that first role I’ve recommended to multiple organizations that they replace me with a full-time COO).
Why a company might be interested in a fractional executive
Fast-growing startups have two conflicting problems: they need experienced leaders to help them keep growing, but they have limited runway to use on hiring those leaders (this has been increasingly true of late). A full-time VP or C-suite leader who has “been there and done that” is costly, and the process to find one is both lengthy and time-consuming. Factoring in salary, equity, benefits, and other typical costs like insurance and payroll taxes, a VP of Operations for a Series A startup can easily cost a company $500,000 per year. And filling that role often takes 4 to 8 months.
A fractional executive can solve both of these problems. So far, with my clients, the average time between their first outreach and Day 1 being part of the team has been 20 days. And since I’m a part-time contractor, clients not only don’t pay me a full-time salary, they also incur no costs related to equity, insurance, taxes, or other benefits. Plus, the contract is month-to-month. All together, companies get help much sooner, while being able to pay far less in cash, hold on their equity, and have zero long-term commitments.
I love what I do
Since 2020, I have served as an operations leader for 10 companies, and an advisor to 5 more. They’ve ranged from 2 employees to 2,000, from pre-seed to Series E. In each of these roles, I have had the opportunity to do 3 things that I get really excited about:
1. Identifying and removing growth blockers by understanding the root causes
Working with more than a dozen companies in half a dozen industries has taught me that no two companies or business problems are alike. But the process of understanding and then solving those problems is one that can be honed and applied time and time again. I love getting to understand the context behind a company’s problems, and then helping come up with deceptively simple solutions that they hadn’t yet thought of on their own.
2. Enabling people to do their best work
If I just came in and did some projects on my own, that would certainly create some value for a company. The much larger impact I can make for that company, though, is helping all the rest of their people be more impactful. Developing a company’s top talent, helping improve or usher out the lowest performers, creating the right project structure and cadence, designing better decision-making and prioritization processes, teaching new people managers and org leaders the basics of making their teams successful – all of these create lasting positive impact far beyond my time with the company. I love being the player-coach who not only gets to do impactful work but also gets to help others do impactful work too.
3. Learning new industries, new problems to solve, and new ways of solving them
Every new client I get to work with creates an opportunity to add more knowledge, know-how, and learnings to my skill set. I’ve always loved learning; now I get to be paid for it! My curiosity to understand how things work has become a value-creating skill that my clients benefit from.
I’d love to chat with you
Is your company experiencing some of the growing pains I described above? I’d love to have a conversation. Meeting great people in the startup world is one of the best parts of my job. Even if there isn’t an opportunity to work together, I’d be happy to spend 30 minutes diving into your company’s biggest challenges and asking the right questions to help you get clarity on the best approach to solving them.