Title: Venture Investor - Associate or Sr. Associate
Reports to: Head of Ventures Team
Location: Chicago, IL or New York, NY (in office)
Heartland Ventures — a venture firm with $100M+ in assets under management — is expanding its investment team to support the deployment of Heartland’s $60M Fund III.
Our uniquely strategic LP base of 150+ industrial business owners is the cornerstone of Heartland’s differentiated approach. By leveraging the expertise, purchasing power, and networks of our LP community, Heartland identifies, validates, and accelerates the most promising early-stage technology companies serving industrial markets (manufacturing, logistics, construction, and real estate). Fund III will extend this proven model.
Heartland is seeking a highly motivated, detail-oriented, relationship-oriented venture investor to join our investment team. As an integral member of the team, you will contribute across all stages of the investment lifecycle — from deal sourcing and evaluation to execution and portfolio value creation. This role offers meaningful career growth and advancement potential within a fast-paced, entrepreneurial environment.
Core Responsibilities
- Deal Sourcing: Proactively identify and evaluate new investment opportunities; build relationships with founders, co-investors and ecosystem builders to generate high-quality deal flow.
- Co-Investor Relations: Build and maintain a network of peers in the Venture Capital ecosystem. Represent Heartland at conferences and key ecosystem events.
- Due Diligence: Lead initial diligence efforts — including market research, financial and operational analysis, customer and reference calls — to inform investment decisions.
- Investment Memos and Presentations: Prepare investment memos, presentations, and all other materials required in the investment, fundraising, and fund management processes. Develop investment theses, conduct market research, and present findings to leadership.
- Negotiations: Support financing and transaction negotiations, working with the team to structure deals and liaise with legal counsel and other advisors as necessary.
- Portfolio Management: Track portfolio company performance, synthesize key metrics, and support ongoing value creation initiatives such as go-to-market expansion or introductions to Heartland’s LP community.
- Value Creation: Support value creation initiatives, such as product market fit, strategic growth opportunities, and founder support.
- Cross-Firm Collaboration: Provide accurate and timely insights that inform LP engagement and support Investor Relations by aggregating and synthesizing portfolio data.
- Community Enablement & Network Activation: Codify and share investment/portfolio insights as actionable enablement for the Community team, including but not limited to; LP one-pagers, activation briefs, target ICP, and talk tracks.
- Additional Projects: Support strategic firm initiatives as needed, including thesis development, process improvement, and platform projects.
Desired Skills and Experience:
- Experience: Minimum of 2-6 years of relevant experience in venture capital, corporate venture, investment banking, consulting, or high-growth startups.
- Relationship-Building: Comfortable engaging with founders, executives, and investors; builds trust quickly and represents Heartland with professionalism and authenticity.
- Education: Undergraduate degree with outstanding academic achievement; business, finance, or technical background preferred.
- Intellectual Curiosity: Genuine interest in technology, venture investing, and how innovation transforms industrial sectors.
- Analytical Rigor: Strong quantitative and qualitative research capabilities; ability to evaluate markets, financials, and competitive positioning with depth and precision.
- Communication: Exceptional written and verbal communication skills; able to distill complex ideas and present them clearly to senior stakeholders.
- Team Orientation: Self-starter who thrives in a small, entrepreneurial, and fast-moving team; willing to “raise a hand” for new challenges.
- Organization & Execution: Detail-oriented with strong project management skills; able to manage multiple workstreams and deadlines effectively.
- Values Alignment: Reliable, authentic, curious, and grounded — embodying Heartland’s ethos and collaborative culture.
Compensation
The compensation package for this position includes a competitive base salary, performance-based bonus, and equity participation. Heartland Ventures also offers full health benefits, 401k matching, and unlimited PTO.
How to Apply
If you wish to apply, please send a resume to lucas@heartlandvc.com
