Connecting the Chicago Ventures Portfolio Community: 4,510 People (and Counting)

Introducing CV Portfolio 1-on-1s

Chicago Ventures
Published in
3 min readMar 4, 2020

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Update 3/16/20: We launched this initiative on 3/3/20, assuming some of these meetings would be done virtually. We now imagine that at least the first match in April will be virtual, and perhaps in May as well. We imagine you’re craving connection more than ever and hope you find this a small way to stay engaged and energized.

We believe in the power of Community.

So much so that we started building our Platform function in 2014, with an emphasis on connecting the teams of our portfolio companies to help each other skill up and scale up. While we have lots of love for the founders in our portfolio, we also know that the first engineer, marketer, or people ops exec can be a lonely spot.

For six years we’ve curated workshops, meetups, connections and collaboration amongst our 50+ portfolio companies. We’ve seen companies share candidates, mentor each other, and become each others’ customers. We’ve facilitated lots of 1-on-1 meetups, and have heard from our portfolio company employees that an opportunity to connect with, learn from, and maybe struggle through something with someone outside of your company is a valuable experience.

Today, we’re launching a monthly 1-on-1 matching program for employees at Chicago Ventures portfolio companies to tap into the power of the community, connecting them with others in similar roles.

If you’re a CV portfolio company employee and would like to participate in monthly 1-on-1 matching, you can sign up here until April 1.

Signed up? Good. Starting in April, here’s how it’ll go:

  • Each month, over six months, you’ll receive an email introducing you to someone at another portfolio company in a similar role to you (founders and CEOs are welcome too!).
  • We’ll suggest that you spend 1 hour with your match that month. It’ll be up to you and your match to find a time to meet in person, or do a video or phone call.
  • We’ll do our best to match you to someone local, but please expect a few matches with people who aren’t in your city.
  • We’ll do our best to facilitate peer-to-peer matches, but please be open to some matches with people who are at a different point in their careers.
  • We won’t set expectations for you: we hope you use this hour each month to ask questions and share best practices. You can keep it casual, or come prepared with topics you’re working through that an unbiased third party could have perspective on.

If you’re a CV portfolio company employee and have questions, reach out to me (lindsay (at) chicagoventures.com).

Thank you for being a part of the Community!

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Lindsay Knight
Chicago Ventures

Director of Platform @chicagoventures. Kauffman Fellows Class 23. Chicago Blend + Lookingglass Boards. Triathlon junkie.