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Rebecca Goberstein
UX & interaction designer who codes. Tells @menu_stories, loves movies, takes photos. Once upon a time: made @terrapnapp, product marketing @#JnJ. @UM_SPH alum.
Image from solsenseyoga.com

Finding the Right Job: How to swim to safety in the curious journey from former founder to startup employee

This past year, I thought the hardest career hurdle I was going to experience was shutting down my startup. Instead, I found that looking for the right job after this entrepreneurial adventure would turn out to be the toughest professional learning I’ve gone through in a long time.

After taking a couple months to unwind and freelance, I knew I wanted to work at a small-medium sized startup. I was also open to larger companies and wasn’t picky about the market, as I was thinking of this next step as a growth opportunity. I figured finding a job would be pretty easy. And at first, it was! Before even launching into a job search, an offer more or less fell into my lap. Bingo.

I was soon reminded the easy path nearly always leads to the wrong destination. Doing your own startup is hard, but finding a job is a different kind of hard — a process where very little is in your control and where many decisions are based on subjective first impressions. Finding the right job — the right role with the right team that’s the right fit for both you and the company right now — is even harder. It turns out building your own startup is no preparation for what you’re about to face in the gauntlet that is looking for your first job in tech.

It can be tempting to jump at the first shiny opportunity that comes knocking. And if you’re like how I was this past summer — an exhausted former founder coming off a startup failure — you’re all the more vulnerable. After all, you’ve been swimming in a rough ocean by yourself and you just want to find a damn raft.

But, with this temptation comes danger — especially when startups have seemingly few windows into their inner workings. Trust these windows can be found, if you learn to ask the right questions and look for the right clues.

But what could go wrong?

The farther you get into your career, the fewer opportunities you have to take a wrong turn. Joining the wrong company can negatively manifest in many different ways. You could end up being treated with a lack of professionalism or even subjected to harassment. You might find you get little to no trust or respect from your colleagues or the founders. You might get little to no freedom to do what you do best. You might not get paid fairly for the work you do. You might find people who dismiss you based solely on who you are or what you look like. You might become very unhappy.

Any one of these scenarios relentlessly chips away at your self confidence. When a company doesn’t want or need your skills, doesn’t create a path for you to do your job well, and ultimately doesn’t deserve your talent, you are actively being blocked from being your best self and delivering your highest-quality work. Startups face a stormy ocean every day and the last place you want to be is on a ship with the wrong crew.

Asking the right questions

After the easy path took me down a wrong turn, I took some time to think. I was actively reminded by friends in and out of the tech community that the interview process is a two-way assessment.

I identified three things I wanted to get out of my next opportunity: Great culture, high probability of success, and, most importantly, the chance to work against a steep learning curve that would force me to stretch. The following questions helped me uncover whether I was heading toward the right job that would hopefully fulfill all three desires:

Desire 1: “Great culture”

Silicon Valley spends a lot of time bloviating about culture (as of today, a search for “startup culture” on Google returns 67 million results). I’m in my 30s and have worked at some great places with talented people who were excellent managers, so good culture to me means more than a charade of entertainment and free food. For me, a company with great culture is one led by effective leaders who respect the people they hire.

  1. Has the interview process been straightforward and generally pleasant/reasonable? 
    Based on what I’ve seen, many startups ask you to do an unpaid project to see how you work. My personal take: if this project takes longer than a couple hours, you can get a sense for how well this startup respects and treats its employees. A better solution some companies follow is a trial period where you’re paid for a few hours of work and have a chance to really work with the team (though this might not work for everyone — especially if the company forces you to do this trial period during work hours, a privilege many cannot afford). In all cases, though, you should have a general sense of how long the process lasts, from start to finish, and who you’ll meet along the way before a decision is made. And if there’s no real interview process at all (at a company with more than 20 employees), consider this a red flag.
     
    Ideal answer: Yes.
  2. Have the founders had past work experience that would have exposed them to opportunities that prepare them to lead a startup? 
    Being a good startup CEO requires being more than a great sales person — it requires the ability to manage administrative tasks and influence other people to do great work. Founders often have to give up being the star performer to allow their team to shine. 
     
    Ideal answer: Yes.
  3. Is the team diverse (in all senses of the word)? 
    Diverse teams produce better results. The end. 
     
    Ideal answer: Yes (and hopefully this applies to the founding and leadership team, as well as the rest of the staff).
  4. Could I understand what they do and why in a few seconds? 
    Clear communication runs all the way to what’s visible on the company’s website. 
     
    Ideal answer: Yes.
  5. How is the organization structured? It is structured, right…? 
    A wise friend and venture capitalist recently shared with me: “Too many companies spend time innovating their org structure, when they should really be focusing on their product. Usually, an ‘innovative’ structure serves no one except the founders.” So, if the answer is along the lines of “we’re totally flat” or “we don’t have real roles or titles,” I would run — nay, sprint — in the opposite direction. As Jo Freeman writes, “contrary to what we would like to believe, there is no such thing as a structureless group.” (See also: Lord of the Flies). Having little hierarchy can be highly beneficial and enable companies to move fast, but it has to be done well and that can prove to be difficult. It’s important for individuals to know their general role and how this role fits into the structure of the broader team. Structure follows strategy and, in a startup with no structure at all, it’s likely no real strategy exists. Too often, companies that sell themselves as “totally flat” are, at worst, in the business of being dishonest with their employees, or at best, drinking too much of their own Kool-Aid. Neither scenario ends well. 
     
    Ideal answer: We have team leads, our founders are involved in high level decisions, and the hiring manager is Suzy/John.
  6. How is performance measured (for the company and for individuals) and what does this role need to deliver? 
    It’s important to understand how performance will be evaluated and whether high level goals for the company are shared within the company. Even in a small startup, where it’s understood boundaries and roles will be more fluid, it’s critical to get a sense of your specific role and expectations. If there are no clear, measurable goals, it’ll be difficult to decide what to prioritize or gauge how you’re doing (and why). 
     
    Ideal answer: We set quarterly/monthly measurable goals and our managers hold weekly/bi-weekly checkins with direct reports to discuss how things are tracking. We also have a clear sense of our long term/big picture goals for where the company is headed. Your role is going to focus on delivering X, Y, and Z.
  7. After doing “back diligence” on the hiring manager/the founders, what did I find? 
    The term “back diligence” comes from a friend who learned this as a Stanford MBA. Because I can’t find an explanation of this term on the interwebs (it must be a Stanford b-school thing), you’re left with my version of a definition: “back diligence” is essentially “reputation due diligence.” What can you find from former colleagues/classmates of the people in the company you might join? Sidenote: the company is already doing this back diligence on you. Hiring managers in tech do not wait for — or even look at — any references you provide. They use LinkedIn, AngelList, or any other clues to use their network to dig in wherever they see fit to learn all there is to know about your lovely self and there’s no reason for you to not do the same. Just be careful to not hear what you want to hear. 
     
    Ideal answer: People say things about your potential new boss/the founders like “this person is great/amazing/trustworthy/I’d love to work with/for them (again) in the future.”
  8. Do I have a good gut feeling about this place? Could I see myself working here? 
    Hiring can unfortunately be a highly subjective process. But there’s something to that proverbial gut feeling. Look around the office when you’re interviewing and get a sense for the energy in the room. Does it feel like a place where you’d fit in? 
     
    Ideal answer: Yes.

Desire 2: High probability of (mine and the company’s) success

Though I’m quite comfortable with risk, I want to take calculated risks. I’d like to work somewhere that has a strong chance of surviving the unavoidable turbulence of a startup. So, I put on my investor hat:

  1. Does the company have product/market fit?
    If you’re not sure what this is, read Revenge of the Fat Guy by Ben Horowitz.
     
    Ideal answer: Yes: 1a) customers are actually paying for the solution; 1b) you’re joining Stripe/Slack/Snapchat/other S-named rocket ship; 2) there aren’t many (or any) direct competitors; 3) the product/company has a leg up on adjacent competitors for defensible reasons that will buy this startup plenty of time to win; 4) there is enough money in this corner of the market to become highly valuable/profitable in a few years and potentially return bags of money for the company’s investors (and hopefully you!).
  2. Have reputable investors already put their dollars into the company? 
    Bonus: do they have deeper pockets and typically invest in later rounds (creating a faster path to money for the next raise)?
     
    Ideal answer: Yes.
  3. Do the investors who led the last round feature this company on their website, or at least list them in their full portfolio?
    The only exception where it’s completely understandable for the answer to be “no” is if 1) the investment happened yesterday; 2) the investment was unannounced because the startup is either very early/in stealth mode; 3) the investment was outside the firm’s typical stage. Otherwise, the pride the investors show in having a stake in the company will likely match yours in having this company on your resume.
     
    Ideal answer: Yes.
  4. Are customers talking about the company on Twitter and saying mostly (very) good things?
     
    Ideal answer:     Yes.
  5. Do they have positive indicators on Mattermark? 
    Though geared toward VCs (…for now…), Mattermark is the best tool currently available to view aggregated, real results against a set of important KPIs on private companies. I’m never joining a startup again without having looked at their performance in Mattermark. If you have found any other ways of tracking quantitative performance on private companies, please add your thoughts in the comments!
     
    Ideal answer: Things are generally going up and to the right!
  6. Are these positive indicators affirmed with you by the company, openly?
    Sure, some numbers are going to be difficult to share with prospective hires, but, as Startup L. Jackson writes, startups rely on trust and should be transparent with you, where appropriate. If they can’t trust you with even basic cash flow or customer growth metrics at the latest stages of the interview process, you probably shouldn’t trust them either. In the same vein, asking for clarity about the equity compensation they’re offering can reveal plenty. Julia Evans from Stripe wrote an informative post about understanding your options.
     
    Ideal answer: Why don’t you come around to my screen and take a look at our numbers.

Desire 3: Steep learning curve / potential for personal growth

The questions and ideal answers here will greatly depend on your functional area and the stage of your career. Generally:

  1. Will I be working with a team of people who impress me and will force me to be harder/better/faster/stronger?
     
    Ideal answer:     Yes.

Analyzing the answers

That’s a lot of questions. How do you make sense of the data you’re gathering? Something like this helped me process my options (roles, company names, and ratings are completely made up):

Though it should be taken with a grain of salt, adding something like a 0–5 rating (0 is bad, 5 is great) for each of the aspects you want from your next job could help you quantitatively compare different companies on something that might at first seem subjective.

The right job for right now

As you navigate the murky waters of startup interviews, I hope you consider asking the right questions of a company before you decide to give them your time and energy. They’re certainly not fool proof, as you can unfortunately never know what it’s going to be like to work somewhere until you’re already working there. Know that all you’re really looking for is the right job for right now — and hopefully, “right now” will last a long time.

Good luck on your journey and may you have an easy landing (but not dangerously easy…) into the right job for you. 🙌

Resources

I found many of these resources useful on my search:

Originally published at blog.rebeccagoberstein.com.