Ross Freedman is the Co-Founder and Managing Director of 367 Ventures, a Chicago-based investment firm known for advising, mentoring, and investing in visionary founders of early-stage companies. Ross fundamentally believes that every company—regardless of its industry or product—must adopt the mindset of a technology and data-driven organization or be prepared to completely reinvent itself. It’s not just a strategy; it’s an essential mindset. At 367 Ventures, the emphasis is on partnering with companies that strategically use technology and data to establish a lasting competitive edge in their markets.
Ross began his career as a software developer in the Advanced Technology Group at Arthur Andersen, where he worked with global businesses and government agencies to solve complex technology, process and operational challenges. In 1999, he co-founded Wired Matrix, a Chicago-based systems integration firm focused on designing and implementing software solutions for middle-market companies. Wired Matrix later merged with Andersen spin-off, West Monroe, where Ross co-led the Customer Solutions practice, helping clients develop customer engagement strategies and execute successful digital transformations.
In 2007, Ross co-founded Rightpoint, a digital consultancy that started as a two-person venture and grew into an award-winning global firm with nearly 1,000 employees across 12 offices worldwide. Rightpoint specialized in transforming customer and employee experiences by combining strategy, design, and technology capabilities to create world-class digital experiences for large enterprises. Under Ross’s leadership, Rightpoint expanded its offerings through a strategic private equity investment that led to several acquisitions, making the company one of the largest independent digital consultancies in the United States. In 2019, Rightpoint was acquired by Genpact (NYSE: G), a global professional services and business transformation company. The acquisition marked a major milestone in Rightpoint’s journey and further solidified its reputation as a leader in digital innovation.
Throughout his career, Ross has led digital transformation initiatives for many of the world’s most recognized brands, including General Motors, Goldman Sachs, Hulu, 3M, Abbott Labs, and Southwest Airlines. His work has consistently focused on aligning business strategy with emerging technologies, leveraging artificial intelligence, data analytics, and cloud modernization to drive measurable outcomes.
Ross is also the Founder of Badgers in Tech, a national network of local industry-focused communities that connect University of Wisconsin students and alumni in the technology sector. The organization fosters career opportunities, mentorship, and commercial partnerships to support Badger graduates and strengthen Wisconsin’s presence in the tech industry across the country.
Ross’ fundamental belief is that every company is either an experience company today or will need to reinvent themselves to become one. A pioneer and a visionary in creating breakthrough digital experiences, Ross continues to drive creativity and tech innovation with an eye towards the future of digital. In 2015, Ross was the winner of the EY Entrepreneur of the Year Award in the Midwest region. Ross has a Bachelor of Business Administration from the University of Wisconsin-Madison with a specialization in Computer Science.