Making the Leap: Big Company to a Small Startup

A few months ago, I decided to leave the comfort of my cushy corporate gig (I was one of the EMEA Sales Directors at Salesloft) and make the move to a startup. I know, ballsy.

With that move, I left the wonderfully designed office (which I did with Modus and Kontor if anyone is looking to get their own place), the predictable hours and flexible working, the endless supply of snacks, the corporate card, the multiple benefits… and the frustrations that come with working in a PE-backed company.

Maybe you too are chasing the dream of working in a cool, innovative environment, with less processes and more flexibility. Well, let me tell you, you’re in for a wild ride.

But don’t worry, it’s not all chaos and 18-hour workdays (well, mostly). Moving from a big company to a small startup is a big adjustment, but it also is one of the most rewarding experiences of your career. The learning curve is steeper than the caffeine spike in your bloodstream at 10am, but worth it.

Here’s what you can expect.

You’ll Wear More Hats than a Royal Wedding

In a big company, you probably had one job. Maybe even one job title. You knew exactly what your day looked like: a little email here, a meeting there, a lot of coffee in between. In a startup, everyone does everything. Your title might as well be “Chief of Stuff,” because you’ll end up doing anything from SDRing, AEing, Sales Engineering, Product visioning, printer fixing and, of course, culture building.

The good news is that you’ll develop skills in areas you never even knew existed. The bad news? You’ll have to figure out what “growth hacking” is, and no, it’s not an illegal activity.

You’ll Feel Like The Adults Have Left The Room (Wait, that’s my decision to make??)

If you’ve spent most of your career in a big company, you’re used to rigid structures: meetings, KPIs, quarterly reports, and the ability to complain about decisions made, in the total safety of not having to make them yourself.In a startup, those structures are more like... suggestions. Your calendar might say “Team Sync” at 10 a.m., but that could easily get pushed to 11:30 a.m., when the CEO has managed to get out of an intro call, fixed a product bug for a key customer and remembered he now has a team to manage.

While it can be liberating to have the freedom to work how you want, it can also feel like trying to find your way through a maze but blindfolded. “Who’s in charge of this project? Oh, it’s everyone. Great. Cool. Got it.”Don’t wait for someone to come up with the strategy, the comp plans, the territories, the fields, and stages in your CRM - this is now all yours to decide on and implement. It’s a little bit like having your first kid (what do you mean I am the parent now? That just feels wrong, who would think it’s a good idea to have me in charge?)Worth noting that if you are not happy with the decision made, there is very little complaining and finger-pointing that can be done.

Everything You Do Will Be a Big Deal

In a large company, you might have spent weeks preparing a report that only five people will read. In a startup, your every move is under the microscope. You updated the website? Celebrate. Did you answer an email that stopped a crisis? You're a hero. Have you launched a new feature? Get ready for your “Employee of the Week” mug (even if the CEO is also the intern).

The pressure is real, but the rewards? Also real. You’ll find yourself going home every day thinking, “Did I just save the company? Or did I accidentally delete all the files? Wait, let’s not check.” Either way, everything is high-impact. You can’t hide in a cubicle here, because you're literally the one making the changes.

The Learning Curve Is Like Climbing a Very Steep, Very Slippery Mountain

In a big company, you’re used to having plenty of resources. If you need something, there’s a whole department to help: HR for benefits, IT for your slow computer, and Legal for that one contract you never understood. In a startup? You are HR, IT, and Legal. And you still have your actual job to do.

You’ll learn new things faster than you ever thought possible, and probably stumble a few times along the way. “Wait, we’re supposed to be doing what by 5 p.m.? Sure, let me just invent a new marketing strategy, launch a product, and sign a couple of deals. No biggie.”

But here’s the thing: you’ll learn. And you’ll grow. You’ll leave the office at night feeling like you’ve just taken a crash course in everything, and somehow, you’ll survive (even though you didn’t know half of what you did two weeks ago).

Be Warned - It’s Not For Everyone.

Moving from a big company to a startup is like jumping off a cliff and hoping you’ve packed a parachute - except the parachute might just be your determination to figure it out as you go. It’ll be messy, stressful, and occasionally chaotic. But if you can embrace the uncertainty, the chaos, and the weird-but-wonderful team dynamics, you’ll come out the other side with more experience and stories than you ever thought possible.

Whatever you do, the experience is worth living and you’ll only learn and grow. Good luck anyway.