VC Associate @ Chicago Ventures in Chicago, IL

Chicago Ventures invests in early-stage enterprise and consumer software companies in the middle of the country. We believe innovation is unbounded by geography. Structural conditions like higher concentrations of talent and customers are accelerating the rise of non-coastal markets. Nonetheless, early-stage institutional capital remains heavily concentrated on the coasts. We fill the gap.

We are hiring an Associate and Analyst on our Investment Team to help us fulfill our mission of serving as the leading partner to founders building companies in non-coastal markets. Both of these roles will span a number of functional areas within the firm, including deal sourcing, portfolio support and fund operations. We are looking for self-directed individuals who can both adapt and bring clarity to unstructured environments.


With over $100M under management, we’ve invested in 86 companies across healthcare, financial services, insurance, supply chain/logistics, manufacturing, education and more. Our team is made up of former startup founders and operators, and we function much like the companies in which we invest. We are self-directed, hard working, resourceful, ego-less and personally invested in what we do.

CV’s portfolio includes high-growth companies like SpotHero, G2, project44 and Cameo. We lean on our operating backgrounds to take a hands-on, partnership-based approach to working with our portfolio companies, providing operational support in the form of business development, talent acquisition, follow-on investment partners, peer mentorship and industry expertise.

Analyst and Associate Responsibilities

The reality of venture is that most functional responsibilities are shared. We all source new investment opportunities. We all help our founders build great companies. We all update the CRM.

How our Analyst and Associate allocate their time across the core functional areas of the business (described below) will differ. Whereas our Associate will be expected to spend the majority of her or his time fueling our sourcing engine, our Analyst’s priorities will, at least initially, revolve around fund operations. Nonetheless, our expectation is that both candidates will move seamlessly across these functions as they familiarize themselves with our operating model.

  • Find and process new investment opportunities. Finding elite founders to partner with is the lifeblood of our firm. Investment Team members are expected to surface new investment opportunities, drive due diligence efforts and build cases for new investments.
  • Support portfolio companies. Our success is determined by the success of our portfolio companies. To that end, Investment Team members are expected to reactively and proactively provide impactful operational support to our portfolio, from connecting founders to prospective customers to driving M&A processes.
  • Manage internal fund operations. Every member of our team plays a role in managing and improving our fund operations. Responsibilities will range from limited partner reporting to intern hiring and management to portfolio construction analysis.

Both our Associate and Analyst will report directly to our Principal but will work closely with all members of the Team.


Venture capital is an apprenticeship business without an ideal prerequisite. We don’t expect either Associate or Analyst candidates to have fully-formed skillsets perfectly suited for their respective roles. Rather, we are looking for competencies that we believe correlate with success in these roles.

A few qualifications included in the cost of admission are a demonstrated interest and respect for entrepreneurship, exceptional analytical, communication (written and verbal) and project management skills, high aptitude for building strong relationships and working autonomously, a team-first mentality, and an inherent sense of accountability.

Candidates should be Chicago-based or willing to relocate. We expect Associate candidates to have 5+ years of professional experience. Analysts are expected to have less.

To Apply:

Send an email with the subject line “Associate Role” or “Analyst Role” to with your resume and a written answer to the following question: If you had to put all of your future earnings into one, non-public, pre-Series B company, which would it be and why?

We look forward to hearing from you.


to be alerted