Vice President of Investment

Gemspring Capital 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.

About Gemspring Growth Solution (GGS)

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.

alongside management teams.

Position Description

GemSpring is seeking a Vice President to join the GGS Software investment team. The VP will play a central role in originating proprietary deal flow, leading investment diligence, and supporting portfolio companies post‑investment. This is a highly entrepreneurial position that blends business development with deep investment rigor. The ideal candidate has a strong foundation in software investing, a proven ability to build relationships with founders and CEOs, and the drive to help build a differentiated growth equity platform from the ground up.

Key Responsibilities

Origination & Business Development

• Drive proprietary deal sourcing through direct outreach to software company founders, CEOs, and management teams across target verticals
• Develop and execute thematic market mapping across software sub‑sectors to identify high‑quality investment targets with attractive growth profiles
• Manage and mentor junior investment professionals, providing direct sourcing guidance and support to drive new deal pipeline
• Report on business development activity and performance, in collaboration with the broader software team and business development teams
• Lead end‑to‑end due diligence on prospective investments, including detailed financial analysis, KPI evaluation, market assessment, and competitive benchmarking
• Build and oversee comprehensive financial models incorporating SaaS/recurring revenue metrics (ARR, NRR, CAC, CLTV, churn, cohort analysis, unit economics)
• Prepare and present investment memoranda and recommendations to the investment committee
• Structure and negotiate transaction terms, working closely with legal counsel and third‑party advisors
• Coordinate and manage cross‑functional workstreams throughout the deal process, ensuring efficient execution
• Partner with portfolio company management teams and GemSpring operating partners to drive strategic and operational initiatives
• Support portfolio companies in evaluating and executing add‑on acquisitions, market expansion strategies, and product roadmap development
• Monitor portfolio company performance and provide ongoing analytical and strategic support

Team Development

• Mentor and develop junior team members, including Associates and Analysts, providing guidance on deal execution, analytical best practices, and professional growth
• Contribute to building the GGS platform’s processes, tools, and culture as the team scales

Qualifications & Requirements

• Bachelor’s degree required; MBA or CFA designation is a plus
• 5–8+ years of progressive experience in growth equity or private equity and software‑focused investment banking with meaningful exposure to software and tech‑enabled services.
• Demonstrated track record of proprietary deal sourcing and relationship‑driven business development with founders and management teams
• Deep understanding of software business models, including SaaS metrics (ARR, MRR, NRR, CAC, CLTV, churn), product‑led growth, and unit economics
• Advanced financial modeling, valuation, and analytical capabilities with experience underwriting growth equity and minority investments
• Excellent written and verbal communication skills, with the ability to present complex investment theses clearly and persuasively to internal and external stakeholders
• A highly motivated, self‑directed professional with an entrepreneurial mindset and comfort operating in a lean, fast‑paced environment
• Strong interpersonal skills and executive presence, with the ability to build trusted relationships with C‑suite management teams, board members, and industry participants

GemSpring offers a highly competitive compensation package commensurate with the qualifications and experience required for this role, including base salary, annual performance bonus, and carried interest participation. The firm also provides an excellent benefits package.

5 Days / Week In‑Office Model

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.