Doug Rosenstein

## PROSPECT INFORMATION: Name: Doug Rosenstein Title: Managing Partner Fund: Uplift Investors Background: Doug Rosenstein is the Managing Partner and Co-Founder of Uplift Investors, a purpose-built services investment firm based in Darien, Connecticut, launched in January 2025. He founded the firm alongside long-term partners Will Hausberg and Bradley Skaf, with whom he has invested for over a decade. Uplift utilizes a "5-5-5 Framework" focusing on the intersection of specific business models and service sectors, specifically targeting microsectors where the team has deep pattern recognition and repeatable value-creation playbooks. Current Focus and Projects: Doug is currently focused on operationalizing the Uplift platform and managing its first platform investment, Orion Legal MSO. Orion is a managed services organization providing non-legal infrastructure (AI enablement, marketing, finance, and technology) to plaintiff law firms. He emphasizes a "people-first, alignment-driven culture" and the integration of senior functional operating talent (CTO, CMO, etc.) directly into the investment team from the start. Background: Prior to founding Uplift, Doug spent nearly a decade at Gridiron Capital LLC (2015–2024), where he rose to the rank of Managing Director. His earlier experience includes serving as an Associate at Sterling Partners and an Analyst in the Consumer Group at Bank of America Merrill Lynch. He holds an MBA from The University of Chicago Booth School of Business (2015) and a B.S. in Finance from the Indiana University Kelley School of Business (2009). Key Skills: Private Equity, Mergers & Acquisitions, Financial Modeling, Valuation, LBO, Due Diligence, Strategy, and Business-Model-Centric Investing. Recent Activity and Post Quotes: March 5, 2026: Doug reposted a culture-focused update, stating: "Focus matters. We concentrate on microsectors, the intersection of specific sectors and business models, where we have real pattern recognition and a repeatable value-creation playbooks." February 6, 2026: Discussing the role of technology in legal services, he posted: "The real shift isn’t about replacing lawyers, it’s about which firms have the operating maturity to turn AI into a durable advantage. Data visibility, workflow discipline, and the ability to reinvest matter more than any single tool." January 22, 2026: Announcing the official launch of his new firm: "I’m thrilled to announce the launch of our firm alongside Will Hausberg and Bradley Skaf and our first investment: the formation of Orion Legal MSO... This milestone reflects an incredible amount of hard work from the entire team." November 15, 2023: While at Gridiron Capital, it was officially announced that "Doug Rosenstein, and Bradley Skaf have been promoted to Managing Director." October 18, 2023: Doug shared news of a major milestone: "Gridiron Capital Closes Fifth Fund Above Target at $2.1 Billion." May 2, 2019: Early in his career at Gridiron, he shared: "Excited to announce our latest partnership in the professional training space and looking forward to working with the outstanding team at Colibri Group!" Fund details: - Description: Uplift is a purpose-built, business-model-centric, services investment firm dedicated to scalable success and lasting partnerships. We seek opportunities to catalyze competitive advantages for companies operating at the intersection of five business models and five services sectors where we can excel. - Website: https://www.upliftinvestors.com - Location: Darien, Connecticut, United States - Lead qualification: Research: - Query: =Uplift Investors Doug Rosenstein recent investments fund thesis - Answer: Doug Rosenstein leads Uplift Investors' investment committee; the firm focuses on micro-sectors at the intersection of business models and services; Rosenstein's recent investments emphasize legal service tools.