Chief of Staff, Investment Team
United States · Remote
Entry Level +2 · Full time
Posted a year ago


Contrary identifies the world's top talent, and invests in companies they start or join.

We raised our fund from the founders of Tesla, Reddit, Facebook, and many more iconic businesses to build networks and tools that empower people to create great startups.

Ultimately, our mission is to become the layer connecting with and investing in every talented, ambitious, and ethical person nationwide, for life.


We've invested in everything from delivery, to defense, to dog food. Some startups were little more than an idea and a team when we partnered, while others were doing millions of dollars of revenue each month.

We have big plans as we grow our team, and you'll be a core part of making that happen. We’re looking for a scrappy generalist to primarily work alongside Will Robbins.

This role could be considered an “all-access behind the scenes” opportunity. You’ll do everything that Will and the rest of the investment team does: support our portfolio companies, meet new founders, build our networks across different spaces, communicate with LPs, and get in the weeds of nitty-gritty tasks that come with operating a venture fund.

One day you may be helping a startup recruit from our talent network, and another day you may be researching the cardiac rehab software market. This is designed to be the most high-growth role possible with tightly-coupled mentorship.


Contrary is ultimately in the business of identifying stellar people, wherever they come from. You'll work with Will and the investing team to:

  • Meet entrepreneurs raising money. Nothing is too early for us — our goal is to find the most inspired and ambitious individuals we can, and back them before anybody else will.
  • Deeply understand the businesses and markets we're looking at. Early-stage investing is known for "gut feel" decisions, but we insist on having every conversation with a prepared mind.
  • Help us tell the Contrary story to stakeholders such as Venture Partners at universities, and LPs who invest in our funds.
  • Leverage the Fellowship and tools like Startup Search or Startup Fair to meet future founders and help them get off the ground.
  • Prepare investment research to raise capital for our funds.
  • Be a scrappy generalist who does whatever needs doing!


We expect breadth and rigor both intellectually and operationally, but are very amenable to alternative backgrounds. Your education and work histories are far less important to us than what you've personally accomplished.

That said, we've listed a handful of qualities that we think are important:

  • You have tolerance for excitement/intensity, as well as tolerance for boredom. We are fast moving but also get our hands dirty with the startup grind.
  • Technical skills are not required, but our culture is builder-oriented at heart. In any case, you must be fluent enough to work with engineering and design-minded entrepreneurs.
  • The 9-to-5 routine may or may not bore you, but the startup lifestyle will energize you. We work hard. With that in mind, we deeply value relationships and health.
  • You can identify and associate with people who are of excellent character, have diverse backgrounds, and are exceedingly intelligent.

Location: Remote. We will be HQ'd in San Francisco and NYC after the pandemic, but you do not need to move there. The investment team currently spans a few major cities and we'll be distributed for quite some time.

Compensation: You will have a competitive cash salary, plus carry in our fund.


Please apply by emailing with your resume or LinkedIn profile, and a quick sentence or two about why the role interests you.

We'll get back to you within 5 days if there may be a fit — we're quite excited to get rolling, and you'd start as soon as possible!

Contrary is a venture fund backed by iconic entrepreneurs that identifies and invests in the world's top talent.
Size:  101-250 employees
Year Founded:  2016
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