Investment Associate

Firm Overview

Gemspring is a Westport, Connecticut-based investment firm with $3.8 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.

Position Description

Gemspring is currently seeking an Associate to join the firm’s software investment team. This position will be a key contributor to the investment team, with primary responsibilities in the identification, evaluation, and execution of investment opportunities in the software sector and working directly with portfolio companies. 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.

Job Description

• Conduct detailed financial modeling and company KPI analyses to inform underwriting of potential software investments
• Lead market research, competitive analysis and other qualitative workstreams
• Prepare detailed investment memos and presentations for internal investment committee
• Manage internal, company and third-party stakeholders to ensure effective and efficient deal processes
• Maintain close partnership with portfolio company management teams and internal operating partners to drive financial and operational improvements and execute add-on acquisitions

Job Requirements

• Bachelor’s degree and minimum of two (2) years of professional experience at bulge bracket, middle market investment bank, boutique software investment bank or private equity firm with a strong preference for those with direct experience and interest in software and recurring revenue business models
• Experience in Software is a plus, but not a requirement; however, must have a strong interest in Software
• Advanced analytical capabilities, financial modeling proficiency, valuations, and deal execution understanding
• Familiarity with software / recurring revenue metrics such as ARR, MRR, CAC, CLTV, NRR, Churn, etc. is a plus
• A highly motivated, outside-the-box thinker, who understands how to deliver on short-term frames and is committed to meeting deadlines
• A thoughtful, open, and honest communicator with an ability to communicate effectively and succinctly, both verbally and on paper internally and externally with bankers, lawyers, c-suite portfolio teams, and other third parties
• A demonstrated track record of prioritizing and managing multiple deals and tasks in an organized, solutions-oriented manner

Compensation & Benefits

• Gemspring offers a highly competitive salary that reflects the qualifications required for the role and a full benefits package

In-Office Model (5 days/week)

Gemspring’s work model emphasizes in-office collaboration and apprenticeship-style learning, fostering deep connections among our team members. We believe this approach accelerates learning and integration into the firm. Meaningful interactions that occur in person cannot be replicated in a remote setting, making this model essential for personal and professional growth.