Dear Hiring Manager: How To Hire Entrepreneurs

Nowadays, there’s a lot of talk from companies both big and small about how much they want to hire entrepreneurs. Reid Hoffman recently extolled the benefits in a piece for The Financial Times:

To innovate successfully requires entrepreneurial talent, which is not simply being creative, smart and flexible. What sets entrepreneurs apart is that they envision a future that defies conventional wisdom, then assemble (and reassemble) the plans and resources needed to make it a reality.

Oh Reid, I’m blushing!

Earlier this year, I sold a company I had been working on for the last ~3.5 years (Fetchnotes). The team wasn’t part of the deal, so I had to figure out what I was going to do next: start another company, join someone else’s, or move back in with my parents and watch reruns of Boy Meets World all day. Eventually, I ended up joining a mobile computer vision startup called Occipital in San Francisco.

Unfortunately, 95% of the companies I spoke with about their self-described “entrepreneurial culture” had zero idea what they were doing when it came to hiring entrepreneurs. It was just their way of saying they want creative, smart, and flexible people.

Understanding the unique aspirations, pet peeves, and personality quirks of an entrepreneur is a non-obvious problem for most hiring managers, so I wanted to offer some advice on how to hire slightly insane, excessively ambitious, and occasionally arrogant people like me.

Note: This is not saying hiring managers should change their process because entrepreneurs should get special treatment. This is simply saying that if hiring entrepreneurs is a priority for your company, you need to rethink the way your process works.

Entrepreneurs (myself included) tend to have an irrational amount of self-confidence. This means that the question for us is not, “Where can I get a job?” but “Who do I want to work for?” We’re not really going to jobs websites, we’re not working with recruiters, and we definitely will not have “available” posted anywhere on our LinkedIn (often for practical reasons, like impending M&A or hiding a failure from the press). Rightly or wrongly (usually wrongly), we believe ourselves to be in the driver’s seat of the discussion.

So how do we find you? Well, there were 3 things I did to learn about opportunities:

1) Looked through my phone/Chrome bookmarks for what apps I (or my business) regularly use. I want to work on things I’m passionate about, so if I use your product there’s a good chance I’m interested in the problem you’re solving.

2) Looked through the portfolios of respected venture capital firms and accelerators (especially ones to which I had connections). This is a great source for interesting companies that have some legitimacy behind them already.

3) Talked to friends. Sometimes this meant asking people I respect about the places they work to see if I might like it, and sometimes it was simply asking friends what companies they were excited about.

In any case, we’re building a list of companies BEFORE we know anything about your job openings. First we need to buy into you as a company, then we can talk about the role itself. “Mission-centrism” vs. “role-centrism” is the easiest difference hiring managers often overlook.

This brings up another important point about hiring entrepreneurs and why we’re hard to hire — we’ve done a little bit of everything, but we haven’t honed our skills at anything in particular. Over the last several years, I had built meaningful experience in sales, biz dev, fundraising, engineering, product management, growth/marketing, PR, recruiting, culture-building, office management, operations, and even getting 21-year-olds to clean up after themselves. When I started interviewing, I was being considered for roles as diverse as:

  • Product Manager
  • VP of Marketing
  • Managing Editor
  • VC Associate
  • Developer Evangelist
  • Freelance Writer

The list goes on and on. Hell, I think I applied to be CFO by accident once. The point is, this should be an early sign that we are bad “role-players” — we’re ADD and don’t know how nor want to box ourselves. You should be aware that every time we apply to a job, we’re going through a personal identity crisis:

The Circle of Angst engendered by reading your job posting for a Product Manager role.

If you are actually committed to hiring entrepreneurs, consider offering an option to interview as a generalist, where the emphasis is simply on better understanding each other and assessing whether or not current any openings are a good fit. I was able to do this informally with a few companies, and it made me think highly of the company even when there wasn’t a good fit.

Note: This takes more time, and usually there is not a good fit.

If you’re interviewing an entrepreneur, it’s likely you’re interviewing someone who has been CEO or CTO of their own company. Any job we take will technically be a step down on the organizational chart. If you want us to be happy about it, you’re going to have to convince us that even as a product manager, or engineer, or marketer, or whatever, this is a step forward in our career. That might be because of the connections we’ll gain, the skills we’ll build, what we’ll be able to achieve together, or something else entirely. In any case, it’s on you to convince me that I’m going to be able to do something with you that I can’t do on my own.

If you have a company worth joining, then this shouldn’t be a problem.

The corollary to this is that entrepreneurs tend to have an overwhelming need to perceive themselves as unique and “special,” so we’re unlikely to be happy if we’re one of 5 other people doing the same thing on our team.

Entrepreneurs looking for a job.

Note: That doesn’t mean this is healthy, nor that this complex should be encouraged by society as a whole. I never claimed we were a sane or well-adjusted lot.

Partly because we all think we’re special snowflakes, and partly because this is simply what we’re good at, we’re going to try to skip as many steps of your interview process as possible. When reaching out to a company for the first time, I always used LinkedIn to either:

1) Find someone who could introduce me to someone at the company directly and say nice things about me.

2) Find the right person for me to talk to at the company and send them a well-reasoned, personalized email about why I’m excited about what they’re doing and how my experience might be relevant.

Not once did I ever apply through a jobs portal or company website. In fact, it was massively off-putting when people would reply asking me to fill out a form or upload my resume (which I didn’t even have). I’ve dealt with rejection often enough that I assume that if I have to go through the “normal” channel, I’ve probably already lost.

(Being on the other side at a slightly-larger company now, I’ve learned that more often than not it’s just because they want to get you in their applicant tracking system.)

As an entrepreneur I’ve had to hire, fire, recruit, and build application processes from the ground up. I’ve learned what works and doesn’t work the hard way (even if the lesson isn’t 100% generalizable), and I’m judging the shit out of every touch point I have with you. I have at least three, concrete pieces of feedback each about why the email I received from your recruiter sucked, how my on-site interview could have been better organized, and how you could have presented my offer in a more meaningful way. I’ve been on both sides.

Simply asking for feedback goes a long way in making me feel like you care about self-improvement, and that my opinion will be valued if I do decide to join. Sadly, this almost never happens.

This last point, I believe, is amongst the most under-appreciated and misunderstood throughout this process. Entrepreneurs are storytellers — we spend our days weaving narratives to sell investors, employees, reporters, and our friends and family about why they should believe in us. That’s because we don’t think of our work as what we do, but who we are.

Moreover, for years, meeting new people has generally gone like this:

*introductions and pleasantries*

Stranger: “So, what do you do?”
Entrepreneur: “I run a small tech startup.”
Stranger: “That’s so cool! What does it do?”

*15 minute conversation about what your startup does and why it matters*

Transitioning into a new role, we crave a story worth telling. “I work in marketing at an enterprise software company” or “I’m a product manager making ads more targeted” isn’t going to inspire people, and in turn that will make us feel uninspired. When you’re recruiting an entrepreneur, pay special attention to the story you craft — it’s the story we’re going to imagine ourselves telling whenever we meet someone new. In fact, I often asked friends for advice about various companies not because I was unsure, but because I wanted to A/B test the different versions of “my story” if I were to join. Coincidentally, several people told me point blank: “I can tell by the way you talk about these companies which one you’re most excited about.”

So, I joined that one.

Want to work with a bunch of entrepreneurs bringing spatial computing to everyday life? Occipital is hiring.

Have more questions about recruiting entrepreneurs? Drop me a line here.

Bringing spatial computing to everyday life @Occipital. Prior: co-founder @Fetchnotes, VP @Benzinga, and chief opinionator @michigandaily. Go Blue!

Bringing spatial computing to everyday life @Occipital. Prior: co-founder @Fetchnotes, VP @Benzinga, and chief opinionator @michigandaily. Go Blue!