From MBA Intern to EIR: Creating a Career Path in VC

Written by Emma Lawler, our new EIR. Read ‘How working in VC has make me a better entrepreneur’ on her Substack here

A career in venture capital is an entrepreneurial winding path. Finding a job opening and getting hired is like discovering a rare gemstone. Once you’re hired, there’s no hand-holding or guaranteed path to partnership. It’s a high-risk, high-reward endeavor – just like the act of investing in early-stage companies. 

My journey from product design to venture capital

I started my career in San Francisco as a product designer at Fitstar, which was acquired by Fitbit just 9-months after I joined. Fitbit went public a few months later. Two years into my career, I had seen the full upward trajectory of tech entrepreneurship.  

San Francisco was buzzing with creative energy. I was surrounded by engineers, designers, entrepreneurs, and venture capitalists who were constantly hustling to make the next big thing. In this world, taking ambiguous risks with no clear reward was expected and celebrated. 

After leaving Fitbit, I co-founded Moonlight – a platform for software engineers to find remote work and get paid for completing weekly milestones. We bootstrapped to profitability, then raised venture capital to pursue subscription growth. Then the pandemic hit in 2020. Remote work was becoming mainstream, but it was a bad time to close a second round of funding. Moonlight was acquired by Google-backed PullRequest, and the platform continues to exist under their umbrella today. 

Last summer, I was planning my move from Brooklyn to Chicago to start the full-time MBA at Chicago Booth. I did a quick search on Twitter – ‘best VC firm Chicago’. The top post was from Steven at Chicago Ventures:

It seemed like a great opportunity to get experience investing while I decided what my next startup would be. I spent the next week applying for the role, doing successive case studies, and interviewing with the team. I was ecstatic when they offered me the position – MBA Intern. 

Turning my business school internship into an entrepreneur in residence position

I was getting meaningful experience as an MBA intern at Chicago Ventures. I managed weekly sourcing, researched and analyzed through due diligence, took pitch meetings, created a new deal flow process, and anything else that supported the team. I sought out every opportunity to take initiative and add value. The more time I spent with the team each week, the more experience and ownership I gained. Most importantly, weekly partner meetings offered the best education I could get on decision-making, deal structure, and fund strategy. 

A few weeks ago, CV partners Jackie and Peter pitched me the idea of a new position – Entrepreneur in Residence. This role aligned incentives. It would keep me activated at the fund for the next year while I started my next company (read about my startup journey here). I took the next week to do research, talk to EIRs at other funds, and put together a proposal on how this should work. We agreed on terms and I was excited to accept the new position. 

The value and structure of an EIR program

Venture capital funds are often small teams with limited room for process, mentorship, or management. Chicago Ventures is currently a team of 6. There are two general partners, two investment partners, one platform partner, and now me (the intern turned EIR). We are excited to bring on two new analysts starting this summer – but it will still be a lean operation.

​​When a fund adds a new program outside of their traditional structure, there needs to be a good reason for the added overhead. The program should support the core business activities of finding deals (network or sourcing), picking the right investments (due diligence), and making those startups successful (expert advice). 

In my research, I discovered a few different program types and structures.

Entrepreneur in Residence: An EIR is looking for time away from an operational role in a company to discover or build their next idea. They’ve started a company in the past or are a seasoned executive. They may leverage their network for deal flow, support due diligence for companies in the pipeline, and contribute to decision-making. The end goal for the EIR is to start a VC-backable company. In some cases they may end up  joining a portfolio company, or finding a role in VC. 

Venture Partner: Firms have an engaged community of founders, angel investors, and executives. The venture partner role is about access to sourcing. They support the firm’s ecosystem but don’t have as much time to spend at the fund. They keep a pulse on new startups, get access to angel investing opportunities, and contribute during due diligence. Read a more detailed article about this role from CV partner Lindsay here.  

Operating Partner: Usually an industry executive who is plugged into companies. Operating partners can help with deal flow, due diligence, and also work directly with companies on specialized activities like sales, recruiting, or product. The goal here is to increase the value of the company with access to experienced talent that may not be in a position to join full-time. 

Venture Studio: In this hands-on model, funds bring in experienced entrepreneurs or operators to launch a startup together. The fund takes a higher percentage of equity ownership in exchange for early investment, supports the team with employees or contractors, and takes a more active role in developing the company. Note: This program type doesn’t fall into the same category as the three positions mentioned previously as it requires a very different fund strategy and approach. 

Compensation: I found a range of compensation arrangements depending on the entrepreneur’s background and relationship with the firm.

  • Unpaid: Access to an office, email address, partner meetings, and deal flow. Community building and flexibility to contribute in whatever ways are most valuable. 
  • Stipend: Covers a set number of hours working on fund-related activities like sourcing, pitch meetings, due diligence, and other projects for the firm. 
  • Funding: Investment to get the business off the ground. Makes sense for venture studios or when there’s an existing relationship in place and the idea is further along. 
  • Carry: Some funds give carry to impactful executives who can sit on boards or invest. This is rare and compensates for a more long-term commitment to the firm’s success. 

Terms: Setting the timeline upfront is important for alignment on both sides. Funds understand how long they’ll have resourcing support, and entrepreneurs or executives get a deadline to work against for defining their next role. This means setting a clear timeline of 6-18 months, defining a list of responsibilities, and creating a clear line of communication or process.  

This is the first time Chicago Ventures has supported an EIR program. We opportunistically piloted the role through my internship position, then decided to make it official. 

My role is time-boxed to a set number of hours per week. I manage a weekly automated sourcing process, run 6-week focused research sprints, and take first calls with founders. When there are companies relevant to my background, I support on due diligence and decisions. Additionally, the partners are supporting me with advice and feedback as I develop my next startup. 

I’m grateful for this continued opportunity at Chicago Ventures, and hope to see more funds try out similar programming to support the founder ecosystem. 

Lindsay Knight


Posted On

April 21, 2022


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