Investment Associate

Gemspring is a Westport, Connecticut-based investment firm with $5.1 billion of committed capital under management. Our strategy is to partner with talented management teams and take a hands‑on approach to driving revenue growth and operating efficiencies. The goal for each of our portfolio companies is growth, enhanced market leadership, and an increase in the strategic value of the business. We are a small entrepreneurial team without bureaucracy, politics or a large investment committee.

This leads to transparency and an efficient transaction process and, critically, sets up our portfolio companies for success post‑closing. Importantly, we also know when and how to provide appropriate strategic and financial support to our partner companies yet let great management teams continue to operate in the manner that has gotten them to the current point of success.

The Gemspring Growth Solutions platform provides flexible capital solutions, including minority equity, structured equity, and growth capital to companies seeking a value‑added partner without relinquishing control. GGS leverages Gemspring’s broader platform resources, operational expertise, and sector relationships to drive value creation alongside management teams.

Gemspring is seeking an Associate to join the GGS Software investment team. This position will be a key contributor to the investment team, with primary responsibilities spanning direct‑to‑company sourcing, investment diligence and execution, and portfolio company support. The individual selected for this position will be a creative, intellectually curious, self‑motivated, high‑energy professional who can operate in a dynamic, performance‑driven environment. The Associate will work closely with the Vice President and Managing Director to build proprietary deal flow while developing deep technical investment skills in software and recurring revenue business models.

• Support and execute proprietary deal sourcing through direct outreach campaigns targeting software company founders, CEOs, and management teams
• Conduct thematic market mapping across software sub‑sectors to identify and prioritize attractive investment targets
• Develop and maintain a pipeline of prospective investment opportunities through proactive relationship building and CRM management
• Prepare outreach materials, company profiles, and preliminary screening analyses to support sourcing initiatives
• Build relationships with intermediaries, investment bankers, and industry contacts to expand the firm’s deal flow network
• Conduct detailed financial modeling and company KPI analyses to inform underwriting of potential software investments, including SaaS metrics (ARR, MRR, NRR, CAC, CLTV, churn, cohort analysis)
• Lead market research, competitive analysis, and other qualitative work streams in support of investment diligence
• Prepare detailed investment memoranda and presentations for the internal investment committee
• Manage internal, company, and third‑party stakeholders to ensure effective and efficient deal processes
• Assist in structuring and negotiating transaction terms alongside senior team members
• Maintain close partnership with portfolio company management teams and internal operating partners to drive financial and operational improvements
• Support evaluation and execution of add‑on acquisitions and strategic growth initiatives for portfolio companies
• Assist in monitoring portfolio company performance through regular financial and operational reporting

• Bachelor’s degree and minimum of two (2) years of professional experience at a bulge bracket or middle market investment bank, boutique software‑focused investment bank, growth equity firm, or private equity firm
• Strong preference for candidates with direct experience in and passion for software and recurring revenue business models
• Advanced analytical capabilities, financial modeling proficiency, and deal execution understanding
• Familiarity with software / recurring revenue metrics such as ARR, MRR, CAC, CLTV, NRR, churn, and unit economics
• Interest…