Jonathan Barrett.
An executive’s experience. A buyer’s perspective. Your technology advisor.

Jonathan’s perspective was built inside the organizations he now advises. Over more than 25 years in technology, his work has spanned IT operations, fintech implementation, national contact center leadership, digital product strategy, and the executive responsibility of a banking Chief Information & Digital Officer. He understands both the systems a business depends on today and the decisions that determine where it can go next.

At Citizens Bank, he directed technology services for more than 1,200 contact center users across six locations, with 24/7 support, before moving into digital strategy across wealth management, credit cards, and mortgages. At Andera, he brought bank executives, marketers, technologists, and compliance teams together to deliver digital account-opening projects. Later, reporting to the Chairman and CEO of Home Loan Investment Bank, he led IT and marketing transformation across ten locations—from cybersecurity and regulatory examinations to a core banking provider change, digital banking services, and a three-year technology roadmap.

That experience shapes Bear IT Group, which Jonathan founded in 2023. His advice considers what a decision means for the budget, the people delivering it, the customers using it, and the risks the business carries—not just the platform being purchased. Today, he provides ongoing vCIO guidance for SMB and midmarket organizations, alongside focused contact center, conversational AI, network transformation and technology sourcing services for enterprise leaders and organizations with existing IT leadership.