Positive Sum Research Analyst

At Positive Sum, we invest in companies where we believe entrepreneurs are doing their life’s work and addressing a large or exploding market. We’ve raised over $300M of capital across two funds and have several dozen active investments in our portfolio. 

We invest in a variety of markets, typically lead rounds, and run a concentrated portfolio.

Research is the foundation on which so much of this work is built, and we’re constantly looking for ways to share what we learn with our portfolio companies, founders we meet, and other investors. 

The Role

As a research analyst at Positive Sum, you’ll be joining our research director in deeply understanding and communicating the market context around the investments we spend time on. This usually involves a mix of the following:

  • Understanding the competitive landscape around a company. 
  • Tracing the history of the market and products that have been successful (or not).
  • Estimating the size of the market opportunity for the company’s business.
  • Identifying the critical risks the company will need to navigate now and in the future. 

Most of the time, it’s not obvious how to get the information we need. The company may be in a fast-moving technology space, opportunity size may be unclear or changing rapidly, or significant domain expertise can be required to understand a specific go to market strategy. 

Here’s what you’ll own as we tackle these things:

  • Finding the right questions to ask. When faced with an unknown, our first questions are often shallow and uninteresting. You quickly bootstrap yourself to a place where you start asking the questions that a subject matter expert would - the questions that are often most important to answer when evaluating an investment.
  • Forming an opinion on what matters. The markets, products, and people we evaluate are wonderfully complex, yet it’s critical that we learn about them as quickly and deeply as possible. You accomplish this by identifying and only leaning into the most important aspects to understand as an investor.
  • Pulling the story out of the data. Good research describes what something is: the size of the market, the performance of public competitors. Great research explains why something is: why does the market look the way it does? Why did previous companies in the space fail and why would this time be different? Your research has a well-reasoned conclusion backed by evidence. You present this conclusion with an exceptional level of clarity, so others can understand it and how you got there.

Finally, we’ve seen over and over again that genuine curiosity is behind every great piece of research. When you want to understand how and why a market, product, or business works, the questions you ask and answers you find tend to be the important ones.

If you know you’ll bring that curiosity to any market we look at, and our research philosophy resonates, we’d love to hear from you. 


We bring a growth mindset to the table. Our commitment is to help you grow in your career, and our expectation is that you’ll help us grow, too. We are excited to shape the role around your level of experience and skill set, but we’ll be looking for these foundational skills:

  • At least 2 years’ professional research experience in investment (especially venture), academia (e.g. MS / PhD), journalism, consulting, or similar. Basically, we’re looking for a track record taking the lead in cracking open ended research questions.
  • Proficient collecting and working with data to answer quantitative questions using, e.g. spreadsheets.
  • Exceptional oral and written communication skills.
  • Can set and meet deadlines by scoping work appropriately.
  • Comfortable shifting focus quickly as our investment pipeline updates.
  • Ability to self-start as well as work closely with the rest of the investment team.
  • A strong plus is familiarity with the startup environment - from experience as an employee, founder, or at another venture firm.


This is an in person position, out of our Greenwich, CT office (our headquarters, a short train ride from New York City). In exceptional cases we will consider a candidate based in Seattle or SF. We expect team members to be in at least 3 days a week on average, though we often come in more frequently. 

How to Apply

Please use the form below to apply. We ask that you provide a sample of previous work you’ve done (or something new, if you’d like) that showcases how you tackle a research problem. The topic itself doesn’t matter; what we want to see is that you have the curiosity to fully “map” some space or topic and present a coherent conclusion on it. We’d welcome a note that addresses why this job interests you and why you are a perfect candidate for it. Please also share a normal resume or your LinkedIn for us to quickly understand your background.