Leaving Your Big Company Job for the Startup Ecosystem: Three Essential Strategies

So you’re sick and tired of working for the big, boring company that doesn’t let you do anything interesting anymore. Maybe you used to be the person who was hands-on, but the Peter Principle kicked in and now you’re managing the people who manage the people who actually do things. You’re itching to try something new – or maybe go back to something you remember fondly in your early career.

SHOULD I leave my job for a startup?

Answer: absolutely yes. Startups are where it’s at. With the world changing as fast as it is, startups are the only institution that can plausibly claim to be bringing the benefits of change directly to the people who need it. Getting involved with startups gets you closer to making an positive difference in the world than pretty much any other option. [See below]

That said, it won’t necessarily be easy. Here’s why:

  • Working for startups is not a shortcut to fame and glory. We see a lot of entrepreneur glorification in the press. Read Fast Company or Wired and you’ll see lots of rockstar entrepreneurs talking about how brilliant they are. The dirty secret is that rockstar entrepreneurs, like real rockstars, are extremely rare. Most toil in obscurity and never reach rockstar status. Even most rockstars actually toiled in obscurity before they became rockstars. But people with true entrepreneur souls (like true rockstars) would happily do what they do whether they make it big. If you think you’ll join a startup and retire rich in six months, you won’t last long. But if you’re doing it for the right reasons you’ll do fine.
  • Working for startups is different than working for big companies. The lifestyle choices and expectations of big companies are so fundamentally different from those in the startup world that most employees can’t (and shouldn’t) make the transition. (Most big-company people think they can, but most are wrong.) Early-stage startup life is hard, unpredictable, and risky. You never have the budget or the people or the time you really need. The pay cut and hours may be invigorating at first but become harder to sustain over time. You’ll miss your expense account, travel budget and leisurely quarterly reviews. Abject failure is always around the corner – which means your portfolio, your kids’ college tuitions, and your regular vacations will all be at serious risk. That said, if you go into this with eyes wide open it can be the most rewarding profession you can imagine.

HOW do I leave my company for a startup?

First let’s talk about how not to do it.

  • Don’t just treat it like a job hunt. Applying cold to an early stage company isn’t easy. Startups are – quite correctly – suspicious of people with big company backgrounds (for the reasons mentioned above), so the cold candidate applying for a job will be at a disadvantage – your big company background may actually do you more harm than good. More importantly, since chemistry and cultural fit are critical for senior-level hires, it’s better for you and the company to know each other a bit before committing. That means expanding your connections and experience with the startup ecosystem before making the big leap.
  • Don’t think you know what working for a startup is really like. Take the time to do some research and extend your network, then get to know the people actually in the trenches. Odds are good if you’ve spent time in big companies your personal network extends to other people in big companies: fix that first. Start by joining the online startup communities, making yourself a profile, and reaching out to companies already in the space. Some places to start:
    • Gust.com. Mostly for startups raising angel money, but a good place to get listed and start getting to know startups who might be good fits.
    • AngelList. Also largely a fundraising site, but with a good (and powerful) tool for you to approach startups you’re interested in working for.
    • MosaicHub. A site catering to startups and the people who advise them. Offer services as a consultant in your specialty or industry and dive in.

But all this is just the start. Here are three long-term strategies for taking the plunge:

Strategy 1. Work your way down.

The idea here is to wean yourself off the big-company world over time, massaging your resume as you go. Apply for positions with companies 10%-25% your current company’s size, work for them for a year, then go work for one 10%-25% of *that* size. After a while you’ll have a resume that relegates your big-company experience to prestigious “background” status, while proving (to yourself and others) that you can thrive in a small-company culture. This will also let you add earlier-stage people to your network. If at any time you find it’s not worth it, you can chicken out and go back to your parking space and lifeless corporate tool existence.

Strategy 2. Become a startup advisor.

Odds are you’d make an impressive one for companies interested in the industries you know. Engage deeply and volunteer to be hands on. This gives you the opportunity to expand your network and get comfortable with startup culture. You don’t really have to leave your job to do it.

These days, every major city seems to be building its own startup ecosystem. Google “startups [your city name]” and plug in. You know how to network: attend lots of events, meet lots of people, and be helpful and engaged with people you come across. Boston (my home town) is lucky to have a vibrant startup community – we often joke that you could attend an event every night if you chose to. Here are some places to start around here:

  • Mass Innovation Nights. A monthly event featuring a handful of active Massachusetts-based startups launching innovative products. A stalwart feature of the startup scene and a good place for people exploring the community to start
  • Open Drinks Meetup. A good broad-spectrum, general-purpose meetup group.
  • Mass Challenge. The premiere accelerator in Boston. Events are always well attended and good for meeting people
  • PitchClubBoston. One of my side projects (shameless plug). Good place to pick up the startup vibe and meet interesting early-stage entrepreneurs.

Strategy 3. Found something.

This is the riskiest but most rewarding path. The risk is basically twofold: not only could your company fail, but you may not be cut out for a deep-end-of-the-pool immersion in startup life. That said, although they will (correctly) be suspicious of your ability to survive the early-stage world, a background of respected big-name companies will be appreciated by investors. Assembling or joining a team with a balance of early- and big-company people should neutralize this concern. Remember that specialization is anathema to startups. Everyone does a bit of everything, and everyone works on the product. Always be willing to water the plants.

Finding founders is not easy, of course. It’s very very much like dating. Luckily, founder dating is a thing. Approach them the same way dating is done these days: connect online, then go out a few times to see if there’s chemistry.

  • FounderDating.  A bit self-absorbed and not very community focused, but still a useful place for making connections to potential founders.
  • CoFoundersLab.  Similar to FounderDating but more open.
  • F6S. Another founders site but with an international focus.


* A note on changing the world.

Leaving your job and volunteering at a soup kitchen or a refugee camp will make a difference in the world too. But your influence will be limited to the individuals you come in contact with, and will always be subject to the whims of donors, foundations, or governments. A perfectly viable, effective nonprofit can still be shut down because a distant foundation threw a bad fundraising event. Startups, by contrast, are in the business of solving problems experienced by many people in an economically sustainable way. A viable and effective startup can keep doing what it’s doing forever. If you want to have impact, go join a startup.

Michael Sattler

With a career spent in founding and technical leadership roles with new and enterprise-level organizations, Michael Sattler is a veteran in technology strategy, operations, and product management. He’s spent decades in B2B and B2C SaaS product development, software and application design, engineering operations, new venture creation, and innovation practices.

He has scaled and managed technical teams from 2-50+ across three continents, led large-scale cross-functional program management, and founded or co-founded six companies.