Billy Gallagher·Oct 19, 2023

How to create a Chief of Staff, Biz Ops, or Special Projects role for yourself

Most startups don’t want to hire you.

In 2018, I was graduating from Stanford business school with 2 years of work experience as a VC at Khosla Ventures and wanted to join a startup. Most seed-Series B startups I talked with weren’t interested–they only needed people who could build or sell.

I figured out how to become hireable and joined Rippling before its Series A in a Special Projects role by doing 2 things:

  1. Reaching out to companies regardless of whether they were hiring
  2. Creating job seeker-company fit

This advice tends to skew toward earlier stage companies but the principles apply across all stages. After doing this exercise, you may find you’re a better fit for a different team than the established business operations team. You should lean into that if so.

Many of the best roles are created not advertised

Some awesome companies hire for generalist business roles, but these tend to skew more growth stage and do not encompass every great company.

I will save “how to make your initial list of companies” for another time, but a quick shameless plug: I started Prospect to give job seekers an independent projection of what their startup equity is likely worth. I’m biased, but I think it’s the best place to start your job search.

Once you create your list of companies, search on LinkedIn to see if you have any mutual connections to the company or its investors. A warm intro certainly helps, but elbow grease can dramatically move the needle here.

Bevel founder and Foursquare business development lead Tristan Walker sent Foursquare eight cold emails before the founders responded. He started onboarding businesses to Foursquare to prove the value he would create before Foursquare eventually hired him as their third employee.

Job seeker-company fit

For most roles at a startup, there are clear company needs and job seeker skills. We need engineers to write code and salespeople to sell.

For business generalists, you need to do 2 things:

  1. Show how one to three skills you spike on (are truly excellent at) help solve one of the founders' major pain points over the next 6-12 months.
  2. Show how you are smart and scrappy enough to handle whatever else gets put onto your plate

First Round Capital wrote a great guide "50 Questions to Explore with a Potential Co-Founder." I recommend generalist business hires go through question 13 from the exercise and rank their abilities and interests across these categories:

Skills chart

Some of these are going to be zeroes for both your ability and interest, and can be ignored. I would also go much deeper into the specific skills (particularly industry knowledge) both for yourself and each company.

Before I joined Rippling, I had been a writer for TechCrunch, written a book about Snap, and worked on the investing team at Khosla Ventures. These mapped well to a few top priorities at Rippling: do the grunt work to help Rippling founder Parker Conrad raise our Series A, pitch news outlets to cover us, and write some original content with the marketing team.

I ran other projects that any reasonably smart, hard working person could have run. It was the spikes on specific skills that got me in the door, then a “passing grade” on general ability gave me the opportunity to run those other projects.

Remember founders feel they’ve stumbled across a secret and are trying to convince the rest of the world to see things their way. A smart, driven person who sees things the same way is tough to turn down. But I cannot emphasize the genuine part enough; if you research a startup for 30 minutes and try to act like you care deeply about it, founders will see right through you.

Finally, try to point to something you’ve built before. When interviewing at Rippling, I repositioned my book as a consumer product I had shipped and sold. Obviously the more successful and real this example is, the better, but even talking about a small startup you built during college or a side project can make you stand out from the crowd.

This process takes time and effort but makes you stand out from many undifferentiated candidates.

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