Investment Team Lead

Tributary Group; Chicago (IL); On-site; USD 120,000 - 180,000; Full time

Benefits offered by this job

Base salary

Performance-based bonus

Long-term equity incentive

Job summary

Tributary Group, a long-term holding company focused on profitable software and tech-enabled services, seeks an Investment Team Lead to work with partners across sourcing, evaluating, executing, and supporting acquisitions. You will develop investing judgment, think critically, and take ownership of real work shaping capital allocation decisions.

You will lead identification, due diligence, and post-acquisition portfolio support to drive durable growth and value creation.

Qualifications

• 2–5 years of experience in business development, investment banking, private equity, consulting, corporate finance, or similarly rigorous analytical role.
• Unquestionable integrity and ethics, sound judgment, and comfort operating independently.

Responsibilities

• Source and cultivate potential acquisition opportunities and develop theses on investment themes.
• Lead due diligence efforts and manage relationships with external advisors; design deal structure and closing processes.
• Drive operational improvements in portfolio companies and act on real outcomes, not just analyses.

Skills

Entrepreneurial drive

Tenacity

Integrity

Independent working

Analytical thinking

Communication

Job description

About Tributary Group

Tributary Group is a long-term holding company that acquires and builds profitable, founder-led software and tech-enabled services companies. We focus on enduring businesses with a strong product and runway for sustainable growth, and we actively partner with leaders to achieve that growth. We operate with a small team and high individual accountability. Every person at the firm materially affects our outcomes.

The Role

The Investment Team Lead will work directly with the partners across the full lifecycle of an investment: sourcing opportunities, evaluating businesses, executing transactions, and supporting portfolio companies after acquisition. This role is designed for someone who wants to develop strong investing judgment, not just technical skills. You will be expected to think critically, communicate clearly, and take ownership of real work that directly impacts capital allocation decisions.

Key Responsibilities

Investment Identification / Analysis (60%)

• Source and cultivate potential acquisition opportunities
• Develop theses on investment themes and areas of focus for the firm
• Conduct market and customer research to assess durability and growth potential

Transaction Support (20%)

• Lead due diligence efforts on investment opportunities
• Build and manage relationships with external advisors (lenders, legal, accounting)
• Design deal structure and closing processes

Portfolio Company Support (20%)

• Drive operational improvements to support investment thesis
• Work on real outcomes, not on spreadsheets: hire, inspire talent, lead real change

Who We’re Looking For

• High entrepreneurial drive and tenacity, low ego. This role is an incredible opportunity for those early in their career, but naturally requires a risk-taking mentality and ability to operate outside the bounds of a more typical “laddered” team environment.
• 2-5 years of experience in business development, investment banking, private equity, consulting, corporate finance, or a similarly rigorous analytical role
• Unquestionable integrity and ethics, sound judgment, and comfort operating independently.

Who We’re NOT Looking For

• Spreadsheet experts: this role is real-world investing. Building financial models should be less than 1% of our investment process. We care more about finding and assessing great products and teams, not financial engineering.
• Someone who is looking to be handed work passively: this is an active role. Our firm’s growth is dependent on proactive entrepreneurial drive.

What Makes This Role Different

• You will have direct exposure to decision-making, not filtered through layers
• Your work will influence real investments, not hypothetical exercises
• You will see how deals translate into operating reality after close
• Performance is rewarded with increased responsibility and long-term upside

Compensation & Development

• Competitive base salary and performance-based bonus
• Generous long-term equity incentive tied to firm and portfolio success
• Opportunity to grow into senior investing or operating roles over time