The Well-Crafted Cold Email to a Startup CEO

On a day to basis here at OpenView both myself and the rest of the investment team spend a lot of time with “outbound” activities … essentially trying to connect and get our foot in the door with exciting, expansion stage companies. You learn new techniques through this constant outreach and tend to get a sense for what works and what doesn’t rather quickly.

One area that produces a lot of success is a well-crafted email to an entrepreneur outlining your interest in connecting along with what OpenView brings to the table. If you are the CEO of an up and coming software startup, there is no shortage of inbound interest, as there are more than enough software/tech-focused VCs to go around. The key for me is figuring out how to stand out among all of the other noise in their inbox. Here at OpenView, being able to point to our concrete value add is a great way to kick things off.

After outlining our stage and sector focus I immediately point to the work our Labs team undertakes on behalf of our portfolio. If I were on the other side of the table and pondering whether or not to take on capital, a few key questions come to mind as I am evaluating potential suitors. One of the biggest centers around what kind of support I am able to extract from our partners aside from just a big check and a padded bank account. If my goal is to build something big (which it needs to be if OpenView is going to invest) than there is a lot more to the equation than a check with plenty of zeroes. I am going to be looking for a partner that can help me execute against my go-to-market strategy, build out my management team, etc. Luckily we already have a number of well constructed case studies outlining how we have done so on a number of occasions over the years.

Having an ice breaker such as this goes a long way…


Brian is an Associate at OpenView where he is responsible for identifying and evaluating investment opportunities for the firm. He currently manages the firm’s analyst program and particularly enjoys assessing new markets/technologies and connecting with passionate founders.
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