Want To Ditch The Job You Have And Work For A Startup? Here’s How

Forget the Googles and tiny tech companies of the world. Instead, aim for the middle.

Want To Ditch The Job You Have And Work For A Startup? Here’s How
[Hitchhiking Image: Maridav via Shutterstock]

Bankers, consultants, and lawyers are flocking to startups, and for good reason. It’s mighty bleak where they’re coming from.


The legal industry is jittery after recent layoffs and pay cuts at white shoe New York law firm Weil, Gotshal & Manges–described by a Weil executive as a response to the “new normal,” a world that can’t afford to pay lawyers what it used to.

And finance, of course, is living its “new normal” with the mass layoffs starting in 2009. Meanwhile, 2013 is no better, with first half layoffs nearly tripling those of 2012.

Because of what my company does (publishes content on startups and runs a large startup hiring event), I hear from someone in my network nearly once a week who wants to leave one of these careers and work at a tech startup.

These folks describe to me some combination of “wanting to make a difference.” or “wanting to have real responsibility,” or to “feel good about going to work.”

This is good news for tech startups. These are generally smart people, and with a little rewiring can be quite useful. The problem is that so few of them are going about their search correctly.

They’re focused on the very small companies (“my friend is thinking about starting an Airbnb for X”) or wondering if they should try to go to Yahoo! for a couple of years and then join a startup.


In other words, they’re anchored on the small fries and the behemoths–but are missing the honeypot of opportunity in the middle.

The small fries represent the startup fantasy. You join a team of five, get in early, have a huge exit, and head to the beach or something. Of course the reality is that the company probably won’t make it–but more immediately, the reality is that these teams probably don’t need you in the first place, unless you can code or design or have mastered earned marketing and user acquisition. (The outside world seems to think that there are tons of small startup teams just dying for someone to come in and do everything else while they build product. Not true: They probably have it covered–or at least think they do.)

Even if AirBnB for X does work, it’s almost certainly in for an ulcer–inducing a slog through the “Trough of Sorrow,” “the Wiggles of False Hope,” and the “Crash of Ineptitude” that make up Paul Graham’s Startup Curve. And the postfinance-consulting-law you is not likely ready for the personal finance adjustment required for you to make it though this stretch–which often includes layoffs or a few missed paychecks.

As for the behemoths, this is actually a sufficiently good route, assuming you get around to the startup part. Get a job at Microsoft or Yahoo! and you’ll add skills so that you’re more relevant to digital companies. But you are not joining a startup–and there’s risk getting sucked in there, too.

So why the middle?

By the middle, we’re talking, loosely, about the companies that have 20 to 300 people, are on a growth trajectory and probably aren’t household names nor are they darlings of the funding-and-exit obsessed tech press. Of course, this is an imperfect boundary–this is a world where a six-person company can be valued at $1 billion.

There’s almost an inexhaustible number of companies that qualify. In New York alone, examples include Meetup (150 employees), food-and-drink media company TastingTable (40), Urban Compass (brand new but targeting 150+ by year-end), luxury site Istdibs (150), and journalist marketplace Contently (25). Meetup’s probably the closest to a household name, but how many people know how many employees they have?


These are the companies that have figured out what they’re doing. They’ve also started to formalize by function–real marketing, account management, sales departments are in place. This is critical for the career changer, because you can latch on to one specific piece of the business and learn how to contribute there, rather than floundering in a team of five trying to do everything.

Finally, companies in the middle probably don’t have robust HR functions. Which means you can go to them, and they’re more likely to welcome the help.

So what to do? How do you find them?

Matt Meeker, cofounder and CEO of Bark & Co (and a founder of Meetup previously), has this advice, “I would skip the normal channels altogether. Start with the products and services you already use.”

In other words scan your browser history, inbox, and phone apps for the technology and products you use. Then dig in to the companies behind them and see which ones are in the middle. Even if you don’t have the most relevant skills, you can at least start with an informed conversation about the company.

“We’ve hired a lot from our customer base,” Meeker said. “We get these emails where people say ‘I’m a fan of BarkBox. Here’s what my current job is. Is there any way I can help?”


Meeker says he’s hired more than one person who took that approach–often starting them on moonlighting projects where they’ll work in the off-hours on one specific thing, like developing the Barkbox affiliate program. He’s also hired people who connected initially by being regular commenters on Facebook.

After exhausting the list of companies products you know, it starts to get manual. You’ll have to troll the tech news, dodging all the funding and acquisition noise, and also finding events that feature several of these companies. It was at one such event–a startup job fair called Uncubed put on by our company–where it became clear to me how profoundly hidden the companies in the middle are. People who knew the startup landscape well weren’t familiar with more than a third of the 75 or so companies in attendance. This prompted us to launch our daily email, which features one startup a day, many of those falling in the middle.

Career changers have to seek out this content–finding other sources for their community like New York’s Mapped in NY, a site built by the city that currently shows 1,352 hiring startups. And because not much of it is purpose-built for this, the manual part is sifting through to find those in the middle.

And then, just like the example from Barkbox’s Meeker of those offering to work in the off hours, you’re going to show you’ll do just about anything to contribute. Particularly if you don’t have skills that directly and immediately translate to their business (like code, design, SEO, digital marketing).

Paraag Sarva knew it was time to leave Goldman Sachs (previously he had been a Policy Advisor to the Office of NYC Mayor Michael Bloomberg). So he zeroed in on startups in the middle–wanting a mix of responsibility and growth potential, but also some stability–and he told them he’d work for free.

“I told them they didn’t have to pay me for three months,” Sarva said, in hopes that this would offset the fact he didn’t yet have directly translatable skills.


It generally worked, he said, although “[a few people] were turned off by it, saying they thought I was signaling that I wasn’t valuable.”

Sarva was able to land a gig with experience-dating platform HowAboutWe (50 employees) without the pro bono introductory period–he’s now the Head of Partnerships there.

The existence of the middle is great news for the career changers like Sarva. You can join a startup now, which is good because you probably shouldn’t (or can’t) join the small fry, and the behemoth may simply be another trap. But to benefit from the middle, you’ll have to do the legwork, connect with products, and maybe even work for free for a spell. Most of all, you’ll have to recognize that nothing is traditional at startups–there’s no standard path to finding a job, there’s no standard way to connecting with these companies.

To underscore that unpredictability, even the referral currency can be unusual. Meeker has swapped tattoos for referrals to Barkbox. “I told Jonathan Basker [of Betaworks] I’d buy him a tattoo for every hire he sent me. He sent us two or three people–I guess I owe him a couple tattoos.”

In a startup world where that’s possible, you’ve got to create your own opportunity to change careers. Just go for the middle–and think different.

About the author

Chris Johnson is an entrepreneur and writer in New York City. He's the co-founder of Wakefield, which publishes an entertaining daily email on startups and produces Uncubed, the largest tech startup hiring event in the country