Aaron Stafford

Aaron Stafford is a Founder and Managing Partner at ROC Venture Group, a Naples-based venture capital firm he established in 2021 that invests primarily in seed and growth-stage technology companies. Prior to founding ROC Venture Group, Stafford co-founded and served as Managing Director of Two39 Ventures in Bonita Springs, Florida, a venture capital firm targeting B2B SaaS companies that launched in 2020.

Stafford brings over a decade of professional experience spanning technology, real estate, and venture capital. He grew up in Shrewsbury, Massachusetts and attended UMass Lowell's Manning School of Business, where he concurrently built and scaled a real estate investment and development company. During his time at UMass, Stafford raised over $4 million for his real estate venture and delivered strong returns to investors, demonstrating early entrepreneurial success. This experience building and scaling a capital-intensive business while completing his education laid the foundation for his career in fundraising and venture investing.

After completing his studies, Stafford joined Gartner, a leading technology research and advisory firm, where he worked as an Account Executive from January 2015 to January 2017. He then transitioned to Salesforce, one of the world's premier SaaS companies, where he served as a Business Value Advisor from January 2017 to January 2019. At Salesforce, Stafford progressed to a leadership role managing consulting operations for Commerce Cloud channels generating over $100 million in annual recurring revenue. Most recently before launching his venture career, he led Business Value Services, a consulting division within Salesforce's Commerce Cloud unit, working with enterprise clients on strategic implementations and value realization.

In 2019, Stafford joined Two39 Group as a partner, bringing his expertise in business growth and fundraising within technology and real estate. He co-founded Two39 Ventures in 2020 to focus on venture capital investments in early-stage B2B SaaS companies, building the Southwest Florida technology ecosystem. In 2021, Stafford founded ROC Venture Group with a unique approach: rather than operating as a traditional VC fund where a general partner exercises full discretion over capital allocation, ROC Venture Group empowers limited partners to take control of their portfolio by making their own investment decisions while leveraging the firm's deal sourcing and diligence. This model gives investors a more active role in shaping their investment strategy while benefiting from institutional-quality deal flow.

Aaron currently resides in Bonita Springs, Florida and focuses his efforts on building the local Southwest Florida (SWFL) technology community and identifying innovative startups with strong leadership teams and large market opportunities.

Aaron Stafford's investment approach spans two complementary strategies across his Two39 Ventures and ROC Venture Group platforms:

Two39 Ventures focused primarily on B2B SaaS companies at the seed stage, targeting founder-run businesses in financial services, fintech, and healthcare sectors. The firm provided early-stage capital to companies headquartered primarily in technology hubs like San Francisco, while sourcing deals with strong unit economics and recurring revenue models.

ROC Venture Group takes a broader technology focus, investing in both seed and growth-stage companies across diverse sectors including:

Stafford's investment philosophy emphasizes:

• Enterprise Applications & SaaS: Business software, productivity tools
• Artificial Intelligence & Cybersecurity: AI/ML platforms, security solutions (e.g., seQure)
• Healthcare & Biotechnology: Medical devices, genetic engineering, immunotherapy (AddImmune, American Gene Technology, LightLine Medical)
• Infrastructure & Networks: Digital infrastructure, fiber optics (Harbor Link)
• Consumer & Marketplace: Food tech, agricultural marketplaces (GrubMarket, Artie)
• Fintech & Real Estate: Financial services, real estate platforms (Upfront, Cadre)
• Education Technology: Educational services (Crimson Education)
• Founder-led companies: Backing strong leadership teams with domain expertise
• Large addressable markets: Targeting companies addressing significant market opportunities
• Technology-enabled disruption: Supporting startups leveraging technology to transform traditional industries
• Investor empowerment: At ROC, enabling LPs to make their own investment decisions from a curated deal pipeline
• Geographic flexibility: While based in Florida, investing nationally with a focus on high-growth tech hubs