Managing VC Director @ Fifth Star Funds in Chicago, IL

Fifth Star Funds

Fifth Star Funds is a venture philanthropy fund fighting to close the racial funding gap where only 1% of venture capital is awarded to Black tech founders today. We accomplish this by investing in Black tech founders in Chicago at the early stage “Friends & Family” round. We believe the funding gap at this stage is the most critical to address, as centuries of inequity have prevented these potential entrepreneurs from having the initial capital to start their businesses.

Anyone can contribute to the fund as a tax-deductible donation, and 100% of all returns from successful investments are reinvested into the fund to support future generations of Black founders. We employ rigorous, objective processes to evaluate founders to remove the racial biases that exist in the traditional venture landscape. In our first 2 years, we have accomplished an incredible amount:

  • Invested Friends & Family capital into 21 wonderful Black-led startups and the portfolio has raised millions of dollars in follow-on funding since our initial investments.
  • Built our community fund with donations from local business leaders, VC firms, foundations, and corporations such as Salesforce and Goldman Sachs.
  • Expanded our organizational structure to include full-time team members in addition to the co-founding team’s support.
  • Created a robust rubric and objective processes to remove the biases that exist in the traditional venture landscape in the evaluation of founders.
  • Formed a recognized brand that has garnered awards and national attention from media outlets such as TechCrunch, Axios, WGN TV, Crain’s, and Chicago Inno.

The Chicago flag features four stars that represent pivotal events in our city’s history; we contend that the Fifth Star belongs to underrepresented founders and the extraordinary impact they will have on our city’s future.

Position Summary

Fifth Star Funds is seeking a Managing Director to lead the organization, build upon the foundation that has been established, and continue to scale our impact in Chicago and beyond. Reporting directly to the Advisory Board, this leadership position offers an exciting opportunity to build on the momentum of the fund and create a more inclusive tech ecosystem.

The Managing Director will oversee the primary pillars of Fifth Star Funds – Fundraising, Investing, Portfolio Support, Marketing, and Operations. The Managing Director will also assist in setting the strategy for the fund as well as hiring the organizational structure to implement the fund’s vision. Fifth Star is one of the premiere tech initiatives of Chicago and candidates will gain the opportunity to connect with key partners / leaders in the Chicago tech community and ultimately change the venture landscape of our city and new geographies in the future as we scale.

Objectives & Responsibilities

The Managing Director is responsible for overall programmatic operation, all fundraising and financial sustainability of the project, as well as supervision of all employees and volunteers. Within that, the Managing Director performs the following responsibilities:

  • Vision / Strategy – help define and communicate the near term and long term vision of Fifth Star Funds as we build on our momentum and maximize our impact in Chicago and expand to new regions in the future. Draft the strategy to scale our operations to invest Friends & Family capital into more Black tech founders.
  • Org Structure – define, recruit, and hire the positions necessary to implement Fifth Star Funds defined mission and support across our primary pillars (Fundraising, Investing, Portfolio Support, Marketing, and Operations).
  • Team Culture – maintain and build upon the high standards of how we interact with all entrepreneurs we meet with (seeking to remove/address all biases) while also uplifting the cultural values of the internal team. Set the tone for appropriate work standards, ensure an equitable and healthy work environment, and foster a spirit of collaboration, trust, and team building.
  • Fundraising – create fundraising strategy to receive donations to the fund from both new donors and existing donors. Lead pitch meetings and help build pitch collateral as well as impact reporting on the success metrics of the fund.
  • Investing – work with Fifth Star’s Venture Associate and Fifth Star’s Co-Founders to interview Black tech founders to invest in. Continue to iterate on our rubric and processes to ensure we are removing any and all biases that exist in the evaluation of founders. Build processes to increase our throughput to interview more entrepreneurs.
  • Portfolio Support – iterate on our strategy to ensure our portfolio of startups are properly supported in reaching their next milestones beyond our investment. Put in place capacity to support our portfolio as it grows in number.
  • Marketing & PR – create marketing strategy to reinforce Fifth Star Funds as the premiere fund fighting for racial equality in the technology industry. Put in place capacity to handle Fifth Star’s social media and content marketing as well as coordinate community events. Serve as a spokesperson with external stakeholders, including policymakers, funders, partners, and the media. Participate in speaking engagements and be the external representative of Fifth Star in the tech leadership community.
  • Operations – work with Fifth Star’s Operations Lead to continue our focus on operational excellence and ensure our backend operations (Finance, Accounting, etc.) are handled effectively. Maintain clear communication with the Advisory Board and consult with them when appropriate.
  • Fiscal Sponsorship – serve as the Project Director for our fiscal sponsor, Tides Center. Ensure compliance on rules and regulations, assess potential risks related to new organizational initiatives, and take action on all notices and changes in project procedures. Ensure that day-to-day operations are in accordance with processes and procedures defined by Tides Center.

Desired Qualifications

  • Deep experience and empathy with the Black tech entrepreneur journey
  • Passionate about creating equity in venture funding for early stage Black founders
  • Executive experience building a tech startup, VC fund, and/or nonprofit
  • Senior management experience setting an organization’s vision and defining / recruiting the team to implement the vision
  • Extensive experience fundraising for nonprofits or startups
  • Robust experience building processes to scale operations
  • Strong personal brand with a deep network of existing relationships with prospective donors, partners, and entrepreneurs
  • Humble, entrepreneurial “figure it out” mindset and willing to take on operational tasks while the organizational structure is being built
  • Able to coordinate and build relationships effectively amongst different stakeholders (Advisory Board, donors, entrepreneur investees, and Chicago tech partners)
  • Highly organized and process oriented project management skills
  • Proven ability to deliver high quality reporting using a range of methods and tools and ability to adapt reporting delivery to specific audience needs
  • Excellent written and oral communications skills
  • Strong marketing, PR, and public speaking skills
  • Previous experience creating and executing complex processes, programs, or events


  • $140,000

Location / What to Expect

The Managing Director reports directly to the Advisory Board. This role is located in Chicago with the expectation that 75% of time will be remote, while the remaining time will be spent attending in-person meetings, conferences, and speaking engagements. Day-to-day communications are handled through Slack, Zoom, and Google Workspace. The Fifth Star Funds team will occasionally meet in person for team meetings and community events in Chicago (deep ties to Chicago are highly preferred for candidates).


  • Mission-focused organization seeking to improve racial equity in Chicago and beyond
  • Opportunity to help close the funding gap for Black entrepreneurs and create wealth generation for Black communities
  • Play a lead role in evaluating and investing in the next generation of early stage tech startups led by Black entrepreneurs
  • Work closely with the 9 co-founders of Fifth Star Funds who are all seasoned tech entrepreneurs from different backgrounds and industries
  • Opportunity to be an integral part of the startup and venture ecosystem and shape its future direction
  • Insurance: Medical, Dental, and Vision Plans
  • Workplace Wellness
  • Employee Assistance Program
  • 403(b) Retirement Plan
  • Basic Life Insurance and Accidental Death & Dismemberment (AD&D)
  • Voluntary Life
  • Voluntary AD&D
  • Short-term Disability insurance
  • Long-term Disability insurance
  • Flexible Spending Account
  • Parking and Transportation Savings Account

Fifth Star Principles & Values

Fifth Star Funds exists to reduce the bias in early-stage venture funding to enable more Black founders to access “Friends and Family” stage capital. We do this with our innovative fund model and process that accounts for the unique challenges and unfair obstacles faced by Black founders. We have core principles that guide how we operate and engage with founders:

  • We are mindful of the power dynamic created in the venture funding process and believe it is a privilege for us to engage with each founder whose potential exit could support us in furthering our mission.

  • The venture evaluation process should be a mechanism to identify and highlight the strengths in founders rather than the weaknesses. In every interview, we should focus on looking for signs of strength in the candidate, rather than signs of weakness.

  • Respect the time and effort founders have dedicated to their venture by asking questions rather than making assumptions or assertions. We should always assume that the founder has more information about their domain of expertise than we do, and we are trying to learn more about that information.

  • Transparency Transparency Transparency. We are transparent with our intentions. We are transparent with our process. We are transparent with our decisions. We tell the truth.

  • We all have biases but it is our responsibility to check them at the door.

Application Process

Fifth Star Funds prohibits discrimination and harassment of any kind. All applicants will be considered for employment without attention to race, ethnicity, color, religion, sex, sexual orientation, gender identity, national origin, citizenship or immigration status, veteran status, disability status, family or parental status, or age. We encourage individuals from all backgrounds, both traditional and nontraditional, to apply.

Apply here and a Fifth Star team member will review your application. Thank you!