What startups want from business hires

Lesssons from my first two years at Astranis

Last Thursday was my two-year work anniversary at Astranis. 🚀

It’s been an incredible journey — from Series A to Series C; from three Ops teammates to fifteen (and from Ops to Chief of Staff); from an empty clean room to one with a real-life satellite. So far, it’s surpassed even my most unrealistic expectations heading into startup land.

Pictured: my Ops teammate Will Harden, and our full-scale satellite prototype.

I think constantly about how improbable this entire journey has been. As I explained a few weeks ago, I was initially rejected by Astranis, and subsequently applied to dozens of jobs, all of which rejected (or just ghosted) me in turn. What if just one of them had said yes? I might have ended up at Coinbase (which went public at a a >$50 billion market cap), or Atrium (which went bankrupt), or anywhere in between. I try not to think about the inverse: what would have happened if one more of them had said no.

I’m sure I’ll spend future Outsider editions patting myself on the back, but today, I’d like to focus on what I did wrong that brought me to where I am today — meaning, how I messed up my startup job search so badly. After some soul searching, I think I’ve landed on the root cause:

I didn’t know what startups were looking for in business hires.

I knew precisely what business schools wanted in applicants and what corporations wanted in consultants. But I didn’t know that startups wanted fundamentally different things than did schools or big businesses, and as a result I was presenting my experiences and skills in a way that made it hard for potential employers to appreciate how I would perform at a startup.

Here are a few tips to make sure that you are all better prepared for your startup recruitment journeys than I was for mine.

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#1: Startups want operators, not “leaders.”

“Step one: let’s find some freshmen to do our work for us.”

The prototypical career advice for future business people is to acquire as much “leadership experience” as possible. In practice, this often means becoming the President of a club on campus or taking a first job in a “leadership rotation.” (There are literally hundreds of leadership rotation programs in the US; whether that’s the cause or effect is left as an exercise to the reader.)

The trouble, however, is that startups need people who can get stuff done themselves, and highlighting your “leadership” skills in an interview can rub people the wrong way. There’s simply too much work to be done, and most new hires, particularly at early-stage startups, will be asked to do both the management (i.e., strategy, planning, communication) and the execution (i.e., doing the actual work) without the support of a team.

Being a successful business person at a small startup requires the humility to admit that yes, of everyone on the team, you may be the best one to take out the literal trash. It also means you need to be the person who relentlessly gets shit done — and does so quickly without sacrificing (too much) quality.

✨Pro-tip: In your application, don’t highlight the times that you sat above a project and directed the troops — highlight the times that you rolled up your sleeves and did the dirty work yourself.

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#2: Startups want to see results, not experiences, on your resume.

The resume bullet reads: “Tasked with important mission for the future of humanity, given multi-million dollar budget and many direct reports.”

My (brilliant, talented, stunning) fiancée is a former consultant, and secured a spot at a top-tier business school and a highly-coveted job in Big Tech by telling compelling stories from her consulting days. One of her favorites went something like this:

“I was tapped for a highly-selective role that many people at the firm wanted. Over many months, I personally interviewed nearly every Partner at the firm, and used those inputs to re-shape our whole organization’s operating model.”

This story is perfect for normal corporate interviews: it shows that she was a great networker, that people knew who she was, and that she was entrusted with a significant amount of responsibility. The bummer, however, is that some stories that crush in big-business interviews aren’t directly applicable to startup life.

Startups pride themselves on being anti-hierarchical, so political success isn’t very highly valued. Similarly, working with super senior people doesn’t always have a direct analog to a startup role, where principal actors are more often than not just part of the team. And, finally, claiming membership on a important team is far less important to startups than you, personally, completing important work. (One common pitfall is when folks early in their careers overstate their ownership of massive projects where they were just one of many analysts, which can come across as dishonest!)

✨Pro-tip: Talk about smaller projects (or subsets of projects) that you owned end-to-end in your interviews.

✨Bonus pro-tip: Remember to have a real, operational conclusion to every bullet on your resume. “I was given responsibility” isn’t helpful unless the end of the bullet is “and it worked out!”

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#3: Startups want people, not business robots.

Nobody wants to work 9am-9pm with a robot.

In the corporate and academic worlds, you’re often evaluated by professional interviewers — folks like in-house recruiters and admissions staff. While a more personal approach can work with those folks, it’s risky; in my experience, big enterprises and schools generally optimize for professionalism over personality (in deed, even if not in word).

At a startup, you’re likely to be interviewed by the people that you’ll actually work with day to day — and that means that you should act like the real person that you’ll be in the office, rather than a robot optimized to acquire job offers.

As I’ve said before, be careful about over-polishing yourself for a startup interview. If you get the offer, you might be stuck pretending all day every day for your entire tenture at the company.

✨Pro-tip: Don’t be afraid to be enthusiastic! Folks often seem to dull their edges for interviews, but being an energy-giver rather than an energy-taker is a superpower in startup life.

✨Bonus pro-tip: Take time to research the company’s culture. Are they collegial or professional? More like a team, or more like a family? What are the words they use to describe their values? You can often figure out if startups are a good fit for you just by reading their websites.

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#4: Startups want people who are ready to work hard.

In preparing for this piece, I talked to about a dozen folks that work at startups today — and nearly all of them mentioned the need for businesspeople to prove they’re willing to work hard. From a startup’s perspective, however, this can be one of the most challenging attributes to assess about a candidate. How do you know they are actually a hard worker, versus just a great resume-bullet writer?

There are a few tells that I’ve learned over time — were they frustrated by how slow a process was moving? (Great!) do they have a rich intellectual life outside of work? (Great!) — but none are perfect, which makes things hard for companies and candidates alike.

Ultimately, the best way to prove that you’re willing to work really hard in the job is to work really hard in preparation for the interview. If a candidate walks into an interview with me not only having read our company website, but also the websites of a few of our competitors, my Linkedin biography, and this article — the codeword you’ve earned by reading this far is 🐨 koala 🐨, future Astranis interviewees — that’s awesome.

Such favoritism for people who can spend time on interview prep isn’t easy (or, debatably, fair) for interviewees, particularly those with existing full-time jobs. But it’s some of the best data we get as interviewers, so you should know that’s what you’re up against if you can’t dedicate too much time to your application and interview prep.

✨Pro-tip: If they give you a take-home project, don’t be afraid to bend the rules and spend more time on it than they recommend.

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#5: Startups want people who are prepared to tackle the limitations of startup life.

Cash and time are both constantly in high contention.

As much as they like to pretend otherwise, and as much as the popular image of the cash-laden unicorn seems to contradict, startups simply aren’t equipped with the same resources as big businesses — there are fewer people-hours and fewer dollars to go around. As a result, solving problems in startup land often means being scrappy: moving fast and getting things “good enough,” rather than perfect.

For example, if you’re moving from a corporate role that has the world’s best software tools, a massive Wiki full of “how to” guides, and a huge data analysis team to help you with SQL, what will you do when you land at a startup and have no such crutches? Will you be still be able to do your job effectively if it’s just you, with no additional people or dollars?

(You should be honest with yourself about whether such a prospect is energizing or scary. If scary, you might want to join a later stage startup that has more resources at its disposal.)

✨Pro-tip: Make sure to acknowledge the startup-y limitations that will affect you in your new role; if you don’t mention them, your interviewers might assume you don’t know they exist.

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✨Final, shameless pro-tip: Apply to Astranis. We’re hiring!

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Thanks for reading!

My name is Christian, I’m the Chief of Staff at Astranis, and I’m a native Midwesterner. If you enjoyed this piece and want to join 300 folks in getting an email from me every Monday, I’ll help you understand Silicon Valley using normal-human words.