Caitlin Bolnick

Caitlin Bolnick


Where To Find Them

Type of Investing


How did you decide on investing?

Caitlyn started with multiple experiences operating startups before falling into investing accidentally. Going to business school presented her with some cool opportunities to try out investing and she eventually found her way to OpenView.

Why do you love investing?

  • The ability to work with lots of different founders going after lots of different problems

Breaking In

How can I break into VC?

  • Get interested in a specific industry or thesis and do tons of research
  • Start sourcing companies in the space and think about why they're interesting to you
  • The best way to become an investor is to start doing the job now

What advice do you have for undergrads?

  • Don't be afraid of risk or failure early on. It's more of a risk not to take risks.

Current Job

What is it like to be fresh at your first investing job?

  • It's like drinking from a fire hose. There is just so much going on that you need to figure out.
  • There will also be some skills that you need to develop, even if that means putting in time on the weekends.
  • The key is to be clear about expectations for your role as well as the KPIs that will be used to measure your success.

What's your most valuable skill as an investor?

  • Empathy. A lot of career investors lack empathy for the founder because they don't have any operating experiences. Her operating experience gives her that empathy, as well as something meaningful to talk about with founders.

How do you think about sourcing?

  • Just be a human in your email when you reach out to founders. Realize that there is a human on the other side of the table.
  • You also need to build a personal brand for yourself and think about where to find the best companies for your specific firm, whether that be Twitter, GitHub, LinkedIn, or elsewhere.

How do you use Twitter?

  • Be authentic
  • Put interesting content out there, but also remember to engage with other people's content

What gets you excited about a company?

  • Caitlyn thinks a lot about company defensibilities, as well as the bottoms-up adoption of products

How do you evaluate a bottom up business?

  • With bottoms up (or freemium) businesses, there is a lag between user engagement and revenue. So whether or not the user engagement is compelling enough to drive significant revenue is something they debate a lot at OpenView.

Career Plans

What does the future hold for you?

  • Keep investing in the B2B software space, and perhaps jump into operating again later