How I Evaluate Career Opportunities

Arches National Park, Utah; photo by the author

This is a post that I intended to write in May 2019 shortly after I joined Brightflag as Chief Customer Officer. But a funny thing happened: what little free headspace I had disappeared quickly. In the intervening time, Dave Kellogg wrote about what to look for in and things to avoid in selecting a job at a software startup. Both posts are insightful, as usual, and I felt there was little I could add to the topic.

After more than a year of recruiting and supporting friends and former colleagues with their own job searches, I’ve changed my mind. It seems that no one can get too much advice on this topic. Plus, it turns out this blog is an effective recruiting tool (thanks, Patty Brooks!), and I’m still recruiting for a number of positions at Brightflag.

Without further ado, here are four things that I keep in mind when evaluating career opportunities. It should go without saying that this post isn’t meant to be exhaustive; rather, I aim to explore a handful of considerations that receive less attention than others.

Startups are hard and there’s a natural cycle to people coming and going. But let’s be honest: many people who want to leave their startup job are fed up. This is because the ideal time for them to move on comes and goes without their noticing. By the time they do notice, they’re past the red line, and that fed up feeling has set in.

A consequence is that, when evaluating career opportunities, they look for the opposite of what they have now. This is a mistake for two reasons. First, once you leave your current job, what you did and didn’t like about it is irrelevant. Your next opportunity should be about your future, not your past. Second, head trash can make what you don’t like about your current job feel a lot worse than it was in reality.

By way of example, one of the reasons that I decided to leave Atypon many years ago was that I’d grown tired of working in the “small” STM publishing industry. So, I took a job in a massive industry. Would you rather be a big fish in a small pond, or a tadpole in the ocean? I don’t think there’s a right or wrong answer and simply will point out that Atypon has created more value in its small pond than the overwhelming majority of venture-backed startups ever will create in the ocean.

One of the things that I liked—no, loved—about Atypon was how passionately we debated each and every aspect of the product. The CEO, VP of Engineering, and I would spend hours in a conference room whiteboarding a new capability in excruciating detail. We were great sparring partners and unquestionably customers and the company benefitted from our obsessive attention to detail. It was disagree and commit to the extreme and the polar opposite of move fast and break things.

I remember one occasion on which we were joined by a new member of the engineering team. In the course of debating a new capability, our conversation turned to discussing names for new database columns, and in particular whether they should be uppercase, title case, or camel case. The new engineer was dismissive: the customer won’t see them, he said, and we aren’t trying to win a pretty database contest. It was exactly the wrong thing for him to have said; clearly, he did not understand what our company valued and how we approached decision-making.

I didn’t realize how much this had contributed to my job satisfaction, and I wound up missing the maniacal obsession with first principles and abstraction when I left. More generally, I missed being closer to product. Some of this was a consequence of my new company’s size, but it also was about culture and the responsibilities of my position. All of which is to say, losing what you don’t like isn’t necessarily more important than keeping what you do.

My friend Amanda Kleha wrote a great post about her own job search, titled Finding Figma. It includes one of my all-time favorite pieces of startup advice, delivered with Amanda’s typical radical candor:

The worst thing was watching good people leave a great company (Zendesk) to go chase a salary at a weak startup, all because they didn’t think through what was most important — does the startup have a chance of making it.

To be fair, this is difficult to evaluate and impossible to know with certainty. Depending on your level, you may not have access to the information most relevant to arriving at a conclusion (think growth and burn rates, etc.), and the information to which you do have access, like recent fundraising and hiring, may be misleading. My suggestion is to engage your network for as much insight into the company as is possible.

Just like a good salesperson will avoid noncommittal prospects, so too should candidates avoid noncommittal hiring managers (which in this context could mean noncommittal on the role or noncommittal on your candidacy for the role). Here are a few indicators of a noncommittal hiring manager, all of which I’ve experienced personally:

  • “Still trying to figure out what we need”
  • Unwilling/hesitant to introduce you to the team
  • Non-responsive for more than 3 days
  • For leadership positions, not treating every interaction with you as if you’re already a member of the team

Throughout my career I’ve benefitted from career advice from many people in my network and would like to return the favor. If you’re considering a career change, feel free to contact me for advice.

Chief Customer Officer at Brightflag. I write about issues relevant to and situations faced by SaaS companies as they scale.

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