How to Break into a Senior Business Position at a Growing Startup

You’ve got a great resume. You went to top schools, trained at a prestigious bank/consulting firm/etc, and you’ve succeeded in the corporate world doing some important and impactful stuff. Now you want to take that skillset over to the startup world and you’ve got a lot to offer. You can bring some serious business chops to a company that is going up and to the right but needs to take it to the next level.

Unfortunately, there are a few hurdles in your way:

1) It’s very difficult from the outside to identify which companies are for real—and also which are at the stage you’re looking for, which is out of the “might not be around next year” stage, but not already a unicorn.

2) You’re not a specialist—so a company at that stage would be hard pressed to hire you as a head of sales or marketing, for example, because there are plenty of people out there who already have that specific skill set with startup leadership experience behind it.

3) You’re at a point in your life and career where you’re not about to chance things on a company that might not be around in six months for zero salary.

These are all reasonable points—but the difficulty is that you’re part of a marketplace of talent where you’re in the mix with lots of other people with, at first glance, similar backgrounds. They’re willing to take a lot more risk for earlier stage positions, getting into companies before anyone has a chance to see if they’re going to make it, leaving very few opportunities open by the time they get to a stage you’re more comfortable with.

Still, these kinds of positions do open up occasionally—opportunities to lead new business units as General Managers, Heads of Business Development, COO’s, etc. The key is to be “nearby” to the opening when it comes up—to somehow be a known and trusted quantity, not just a resume. As investors, we do make these introductions to companies, but we do it with people that we can vouch for.

Accomplishing that means understanding how the key stakeholders, like founders and investors, spend their time. These folks are super busy and have learned to have a really high bar for 1:1 meetings. They’re not just grabbing coffee with any random former McKinsey consultant who wants to “get into the startup world”. If they did, they could fill their schedule with just that—that’s how many such requests they get.

You’ve got to bring something valuable—like talent, money, or visibility.

If you start making introductions to founders based on openings they have, that’s going to get you in the door. I mean, what’s the point of having a Harvard MBA if you can’t connect someone to the very best professionals. Same goes for business opportunities. If your classmates are running various groups within the kinds of companies these people want to work with, you can be an invaluable resource.

Why stop at classmates? If you know that someone from your school or extended network is a lot more senior to you and is seriously influential in a company that lots of startups would want to work with—why not host a meal or event for them to showcase what they’re working on.

Who wouldn’t accept an invite to “A networking breakfast where 7 midstage startups will be able to give short demos to the CEO/COO/Head of Business Development/etc for Big Interesting Company X that has huge reach/distribution/userbase, etc.” Maybe make it sector focused and bring in a bunch of such contacts. You could ask a bunch of VCs who would be relevant for those companies—and only ask that you bring Series A/B and beyond companies to the mix.

Now you’re offering value ahead of making asks for your own career—and doing it in a way that doesn’t require me to have to go for coffee (or in my case, tea) ahead of time with someone I feel like I’ve met a bunch of times before resume-wise.

Money works this way, too—and it’s a way to get in with VCs, especially smaller funds. Smaller funds are always looking for limited partners and co-investors in their deals—so starting an angel group or just being willing to make such introductions in your network goes a long way. You could run the same kind of group suggested above on a regular basis as a way to network with investors.

The point is, you’re aiming to build trust and show that you’re willing to offer value before asking for it. That’s what a founder and investors want to see with a senior businessperson before seriously considering them for positions. They want to know if this person can leverage their network in interesting and smart ways to create opportunities for the company.

Media is a great opportunity for companies as well. For those that want to also create visibility for themselves in the process as a smart and connected executive, how about creating a podcast or video interview series about “Hires that took the company to the next level” or “The next Unicorn”—i.e. the types of companies you want to be talking to. The secret to asking people to interviews is that they largely don’t care what kind of following you have—because they can always link to the interview in front of their following. So, worse comes to worse you’re just an outsourced segment producer for their content—and eventually with enough links, you will have that following. That’s basically the story of the 20 Minute VC—a random 20ish year old just started asking VCs to be on a podcast and, yada yada yada, a couple of years later he’s out with his own fund. The best part about this format is that you don’t actually need to be an expert—you just need to be able to ask good questions.

What this does for you is that it accomplishes the filtering mechanism as well. Instead of asking people “Who should I network with” which people really don’t have time to think about, you’re asking “Who would be interested in this opportunity I have—it’s only open to companies with at least X number of employees, funding, stage, etc. and we’re really trying to bring impressive up and comers to the table.”

Of course, you don’t have to take any of this advice. You could just e-mail me and other investors with your resume attached, request my time to help you (a one way street), and ask which companies are likely to be near riskless, high upside opportunities for you to get lots of employee options in.

Good luck with all that.