Landing a Startup Job
The power of preparation and personal initiative
TL;DR
If you want to land a job at a startup, you need to stand out. Hiring managers are time poor and resource constrained people. Make it easy for them by being unreasonably well prepared. Show that you are someone that can add value in every interaction and without much coordination cost. Make yourself the inevitable choice by being introduced from various people close to the company. If you can, suggest that they can work with you as a consultant or on a part-time basis before they hire you.
So you want to get a startup job? Whether you are a person working for <insert big tech evil corp> or someone working for a corporate in a different industry, here are some tips that will help you stand out in your startup job search. Let me warn you this is the opposite of a spray and pray approach. For reference I've both been on the hiring side and on the job seeking side of the equation a few times.
Three Dimensional
In general, when you are changing jobs there are multiple dimensions of change that can occur: industry, function and location. It is not advisable to try to change all three at once. For instance, if you've been a London based lawyer in finance it's going to be hard to become a Singapore based marketer at a startup.
Your first job at a startup might have to be a compromise. What you've done previously (e.g. law), even if you are bored of it, is your best shot when switching to a new industry (e.g. tech). Once you've landed a job with a company, you can gain reputation and credibility to switch the function (long game). So ideally stay focused on roles that are a decent fit to your current functional experience when you are making changes on the other dimensions (industry, location).
Perusing Portfolios
The starting point for your journey is knowing what companies are out there. The startup scene can be a bit more opaque, hence assessing the opportunity space is not super straightforward. A good place for you to look is the portfolios of the Venture Capital funds that you consider reputable. Just Google / ChatGPT a list. They usually have portfolio sections on their website where you can find all the companies that they have invested in. Another approach is checking sites like Pitchbook or Crunchbase for recent investments as some of the portfolio page listings may be outdated.
The startups you pick should depend on what type of experience you are seeking. Wanting to join a company that has roles that are fairly broad and allow you to dabble in many different functions, requires joining a riskier early stage company. So it doesn't make sense to add a bunch of Series B+ companies to your selection.
Stack Ranking Opportunities
You found a bunch of startups you like but haven't really looked at the job pages (the senior jobs are often not on there). How to rank these startups? There are many ways to skin a cat. You know what matters most to you but here a far from comprehensive list of a few factors I like to take into consideration:
Without access to the team
Vision/Mission - if you're into it, it won't feel like work
Potential total addressable market size - if you are interested in upside this is important
Financial health - figure out the last raise, assume a monthly burn and calculate remaining runway
Competitive landscape - how differentiated is the company vis a vis the market
With access to the team
Founder/CEO character - the culture of a startup is determined top down
Work culture and values - work hard, play hard or here for a fun ride
Existing team and dynamics - quality of the team
Development potential - how much can you learn and how much can you move up
Financial upside - valuation of the company and what equity will you get
Find All the Roads to Rome
Now it's time to find multiple angles to the potential hiring manager. Who that is, very much depends on how mature the organisation is. Say you are a lawyer and are applying to a Series A startup. It's fair to assume that the COO/CFO is the right person for you to go to. If it's a Series C startup there is probably already a General Counsel you should try to get to instead. At Seed stage go to the CEO.
You should try to reach out directly but only do so after you've had at least a few people ping your CV over to the hiring manager. LinkedIn hopefully tells you who your connections in common are. Going through VCs or Angels is also a viable option.
Don't underestimate how much of an impact it makes to be mentioned by various different people. It immediately shows the hiring manager a much stronger intent than a random application coming through the job site.
Note I did not suggest that you should reach out to recruiters or the in-house recruitment team of a company. Third party recruiters have incentive systems that as a hiring manager I'm suspicious of so if I get approached by them, I'll take the applicant less serious. Also, someone good should make the effort to find their way to the hiring manager directly. It’s called hustle.
Bypassing the in-house recruitment team is also advisable. In-house recruiters can only say "no". They are not empowered to hire you. So they at best become an intermediary of your story (thereby watering it down) or at worst they shoot you down before you even got started.
Anti-Coffee Meet
NEVER ask for a coffee. Let me say this again NEVER EVER ask for a coffee meeting. Hiring managers can buy their own coffees. They are time poor and busy so they don't want to grab coffee with random people, who think that their time is worth very little.
To stand out among the masses add value to the hiring manager's life. Point them to a relevant news article about the industry or competition. Suggest to introduce them to a contact of yours that could help with a potential business problem. Present them with information you have gathered from a competitor you’ve emailed as a consumer. Be creative!
I remember how one applicant suggested a business development deal including the specific unit economics. I had thought through that type of deal before as it was my job but the fact that this person had figured out so much detail impressed me. In another situation, an applicant sent me a job spec for one of the many roles I was half-assing at the time. They had rightly assessed the business need and written a pretty good spec. Needless to say, I took the meeting.
The bottom line is if you don't care, ask for a coffee meeting. If you do, then give it your best shot.
Love Their Babies
Startup life is intense and usually the lives of employees especially if they are more senior are dominated by their work. As such, sometimes for better or worse their self-worth is bound up with the startup. So don't go in and start criticising their company. You can never have a good enough understanding from the outside to credibly criticise.
If a random person walks up to you and your baby and tells you it's not cute, you'll be pretty upset. However, if you double opt into getting feedback on whether your baby is really cute or not, then honesty is a good policy. So unless they ask for feedback, stick to the cute stuff. In other words, figure out what you love about the company and convey that to the hiring manager as you communicate with them. Parents like hearing that their babies are cute.
Break the Box
The most infuriating moments of my career have been when I see people wasting an opportunity. If you manage to work your way to an interview with the hiring manager, don't half-ass it.
Showing up to an interview without having consumed the public material available about the company is half-assing it. Not knowing everything there is to know about the people interviewing you is half-assing it. Not knowing broader industry trends and competitive dynamics in the relevant domain is half-assing it.
It makes such a big difference to sit across a prepared person in an interview compared to someone who hasn't put the work in. It's actually much harder to reject someone (even on an emotional level) who has done the work. To improve your odds, be that person. You may get rejected because of timing (I interviewed with the hiring manager at Foursquare one year before I got the job) or other reasons out of your control but at least you gave it your best shot.
The best people who I've rejected asked me for specific intros to other companies. If they were their best selves in the interview with me, I would gladly make the intro. A good rejection can actually be a door opener to other opportunities.
Trade Items of Unequal Value
To stand out from the crowd or improve your odds consider how to make hiring you more appealing. Startups are cash poor and can't pay high salaries. Can you live with a lower salary and instead ask for more equity? This is a contentious point, because affluence makes this trade off easier but I appreciate wanting more equity and thereby being long-term aligned with the business' success.
Sometimes the hiring manager has many jobs at the same time and can't imagine finding time to onboard you. Half-assing seems less painful than training someone new, even if shortsighted. Spend time to deliver a thoughtful work product that proves you don't need much supervision and can immediately add value. I remember a Head of Talent candidate sending me a redraft of our whole jobs page and every job spec. She also sent me a few articles/videos about what her philosophy around interviewing and talent assessment was. This conveyed alignment to me, which meant less time having to calibrate and easier onboarding.
Sometimes joining part-time or for a project, gets you a foot in the door. Coordinating with a consultant that requires a lot of communication and alignment is prohibitive. So the type of projects that work best are research focused with a clear output. For instance, figure out the early go to market hacks of the most successful B2B companies and suggest MVP project experiments. While this example is fitting for a Seed stage startup, a later stage equivalent might be an analysis of a client vertical or a new market. Remember that you are trying to show independent work competence and relevant judgement, so don’t incessantly ping the hiring manager with decisions they are trying to outsource to you.
Conclusion
So, there you have it – some hopefully useful insights to navigate the startup job market. Remember, transitioning to a startup job is more than just a career move; it's about aligning your aspirations with the right opportunity. It's about understanding the unique dynamics of the startup ecosystem and positioning yourself as a valuable asset. From assessing startup viability to making yourself stand out to getting to hiring managers, every step is crucial and therefore has to be thoughtfully planned.
Keep in mind that startup culture is vastly different from corporate environments. It's faster, often more demanding, but also incredibly rewarding for those who thrive in such settings. Make sure you are ready for such a life.
If there is one thing to take away from this post, it is the power of preparation and personal initiative. The most successful candidates are those who go beyond the basics, demonstrating a deep understanding of the startup's mission, its market, and its challenges. They are the ones who bring not just skills, but also specific ideas and authentic passion.
In this journey, remember that rejections are not the end but rather stepping stones. Each interaction, each interview, is an opportunity to learn, grow, and network. The startup world values resilience and creativity, so use every experience to build a stronger, more compelling case for yourself.
ADDENDUM
This is a bonus tip for those among you who are not looking for an early stage job but are looking for a sidekick. First and foremost remember that finding a co-founder is similar to finding a husband/wife. A divorce in a childless marriage might be easier than breaking up your co-founder relationship (hyperbole for dramatic effect), so what is important to assess beyond the basic chemistry fit and interest in building something together is value alignment. Many of the breakups I've witnessed are around the fact that there is a mismatch in terms of willingness to sacrifice one's own needs to make the business work. There are many other questions you should cycle through that are not in the scope of this post but Y-Combinator has a good list.
You can find a co-founder through programs like Entrepreneur First or by hanging out at enough networking events. The more advanced approach is to headhunt a co-founder by seeking out someone with the right industry knowledge or technical skillset. It's best to approach folks who already have well-paying jobs at the right time (not 9 months into a new job but probably post their 4 year vesting cliff).