Chicago Ventures
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Chicago Ventures

A Peek into the CV Portfolio [Or, How We Engage 2,200 Startup Employees]

This piece was originally published by Lindsay Knight on LinkedIn.

Some of our portco workshops, where we bring together employees across people ops, tech, product, sales, marketing and ops.

Since 2012, Chicago Ventures has invested in over 80 startups, which means we’ve worked closely with over 80 CEOs. But across the portfolio, our companies employ thousands of people. Some are startup veterans; some come from big companies, with specific industry expertise; some come from consulting or finance, and can help early stage founders scale their team and operations.

We believe that working with these 2,200 people is part of our responsibility as investors, and know that there’s value in creating a network of employees leading specific disciplines at these companies. An early-stage company might have one marketing person executing customer acquisition while building a brand; or one finance person who’s also leading HR, talent and culture. We all know that being a CEO can be lonely, but it can be lonely being a startup employee too — as the sole product manager, data scientist, or account manager, you might feel like you’re on an island.

For this reason, we’ve spent years building our own version of Employee Resource Groups across the portfolio. We’ve focused on creating community, programming, and access for individuals across People Ops, Marketing, Sales, Tech, Product, and Operations.

For reference, here’s the makeup of our portfolio company teams (an average CV portfolio company has 35.6 people and has raised $12.4M):

We’ve structured this community with the following guidelines in mind:

→ Engage when you want: while we encourage participation, we never force or require it.

→ Always ask: while we might not have an answer for something, we probably know someone who does.

→ Be open to sharing: we’ve had great success sharing talent, ideas and connections across the portfolio. Be open to sharing within the community.

→ Embrace crowdsourcing: community members know best what topics they’re struggling with. When scheduling programming, we crowdsource ideas to make sure we’re building relevant, useful content.

We engage this community through Slack, email, in-person networking events, professional development workshops, and personal 1-on-1 relationships.

We’ve hosted nearly 30 Workshops with hundreds of attendees, all influenced by our “embrace crowdsourcing” guideline. Topics have included:

  • An Intro to Docker
  • Event Sourcing and CQRS
  • Using a Graph Database
  • Defining Your Purpose and Creating a Brand
  • Activities with Outsized Impact
  • Creating Culture
  • Onboarding and Orientation
  • Professional Development and Comp Planning
  • Labor and Employment Law
  • Best Practices for Building a Diverse Team
  • From Vision to Actionable Roadmap
  • Thinking about Product from a Design Perspective
  • Product Operating Model
  • How Marketing and Sales Can Work Together

We kick off our workshops joking that “we can’t force people to be friends” — so it’s been fulfilling to watch collaboration across the portfolio happen organically.

We’ve watched senior People Ops leaders develop their own offline relationships to meet monthly (and take junior professionals under their wing); we’ve seen companies share talent when a person wasn’t a perfect fit for their team; we’ve helped connect senior Customer Success execs to pre-seed companies to help them understand how to build out the function; we’ve seen companies reach out to each other to share or sublease office space; and more. We do our best to track these interactions, but would bet that lots are happening without a nudge from us.

We know that these networks and knowledge sharing will help our companies be successful, and we hope that we’re creating massive networks of startup employees who are learning the ropes for the first, second or third time. They may be in the next generation of great startup founders, or they may take the skills and experience they learned today to another startup tomorrow, bringing their knowledge of operating at scale to a new young team. Either way, we hope that they’ll continue to keep Chicago Ventures in their network.




We believe generational companies can be built anywhere, by anyone. We lead seed rounds before it’s obvious, and serve as active, operationally-involved partners during a company’s earliest days.

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Chicago Ventures

Chicago Ventures

We believe generational companies can be built anywhere, by anyone. We lead seed rounds during a company’s earliest days.

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