November 24, 2021

Inside Smartcar: Why I keep joining startups

Victor Black

Head of Customer Success

Hey there, I’m Victor and I’m the Head of Customer Success at Smartcar. As the title of this post alludes, I wanted to share my experiences at startups and why I’ll make the same choice over and over again. Are you thinking about working at a startup? I hope this gives you more understanding of what to expect from that journey and if it’s a journey you want to take.

I first heard about Smartcar when a former coworker reached out to invite me to lunch. What I thought would be a delightful catch-up session with an old friend over sushi and sake ended up with me getting snookered into the best job of my life.

The deal was sealed the moment I learned Smartcar encompassed all three of my favorite things —  cars, startups, and APIs. I joined just under a month later as its Head of Success.

Titles, of course, are always deceptive at a startup. More often than not, you end up experiencing things beyond the job description you signed up for. That’s actually my favorite part of it all.  

My ability to make an impact here doesn’t just stop at the borders of Customer Success. In my (almost) two years here, I’ve helped create our company’s first-ever usage dashboards, laid the foundation for a  new company wiki, and created the first of many iterations of our Customer Success playbooks.

There’s never a shortage of problems to solve, and I’m currently working on scaling up the Success team to serve our ever-growing customer base.

It’s an easy choice for me

Given the choice of joining a startup versus a larger corporation, I’ll always pick the startup.

Forgive the sweeping generalizations I’m about to make, but given how I need to keep this post short and sweet, I’ll try to cut to the essence of that statement as succinctly as I can.

Had I wanted to become the very best at a defined set of skills, I would have chosen the path of being at a large company. I believe there’s no better way to pick up deep expertise than by learning from the very best teams, which are often found at companies at the top of their games. Working for those experts is a great way to observe and soak up all of the excellent reflexes they’ve developed over the years.

But here’s my problem — I don’t want to be an expert at any one thing.

I’d rather learn as many things as I can and piece them all together in new and interesting ways for excellent out-of-the-ordinary outcomes. Thus, startups. Join any small company that’s either taking on an incumbent or trying to define a whole new market, and you’ll find yourself solving new problems from angles you’ve never even thought of, all in the spirit of staying alive by being different.

What happens when you work with the best problem-solvers?

The best part of joining a startup is that I’m constantly surrounded by people with similar enthusiasm and diverse experiences in their own domain of expertise. Regardless of our different strengths, we’all bound by that same desire to solve the next problem, and the next, and the next, and the…..well, you get the point.

Mistakes are encouraged. After all, the faster you make a mistake, the faster you can get to the part where you don’t make the same mistake twice. The sheer breadth of knowledge you pick up in just one year at a startup is enough to boost your career path several years ahead.

But hold your horses. Before you jump ship for a startup, I should mention that this lifestyle of mine doesn’t come without some level of risk.

Join a large company and you can usually expect a defined career path and sometimes more stable financial options (again with the generalizations, I know). Join a startup, and you trade some of that immediate stability and upfront cash for the potential of an outsized future reward.

That said, here’s my advice if you’re making a decision to join a startup just for the money.


Do it for the skills you’ll learn. For the friends you’ll make. And especially for the experiences you’ll have when bonded in the trenches of solving that next problem.

Speaking of joining a startup, have I mentioned that we’re hiring? I’ve been in the Valley for a decade now and I haven’t found a single place that I’ve enjoyed more than Smartcar. Join us, and surround yourself with incredibly kind, talented people determined to learn as much as they can while helping you learn as much as you can.

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