vCIO & Technology Solutions Advisory
Executive technology leadership and trusted advice for your next decision. We help organizations set direction, hold providers accountable, and move forward with communications, customer experience, AI, and technology investments.
Bear IT advises from the buyer’s perspective: clarifying what your business needs, comparing options across a broad technology ecosystem, and staying involved as decisions turn into results.
“Partnering with Bear IT Group has been one of our most impactful decisions. Jon brought structure, leadership, and strategy to our technology operations — implementing an IT roadmap, security program, and vendor oversight. The transition to Zoom Phone improved communication while cutting costs, and Jon continues to be a trusted technology advisor to our firm.”
How We Help
Part-time executive technology leadership to guide your roadmap, budget, technology priorities, and IT providers.
Already have an IT provider? Bear IT works alongside your internal team or managed service provider—your engagement defines who advises, implements, and supports.
Explore Technology LeadershipExpert guidance for technology sourcing, AI voice agents, customer experience, and practical AI adoption.
Explore Advisory ServicesModernize how customers reach you: contact center, cloud contact-center platform (CCaaS) and conversational AI decisions grounded in real service journeys and agent experience.
Explore practiceMove from legacy systems to cloud and AI-ready operations, with practical use cases, data readiness and governance that keep transformation tied to results.
Explore practiceBuyer-side sourcing for the networks connecting your offices, carriers, business phone and collaboration platforms, cloud contact centers, data center and co-location, and AI solutions.
Explore practiceA virtual Chief Information Officer provides part-time executive technology leadership—helping you plan investments, manage technology priorities, and oversee providers.
Explore practice
INSIGHTS / 2027 BUDGET PLANNING
A fresh look at recurring technology costs could make room for what comes next.
From advice to action
Education organization
Law firm
Business services organization
Scope and outcomes vary by engagement. Modeled benefits are not measured results.
How engagements work
Three clear steps, with scope and terms agreed before any additional work begins.
Step Step 01
We discuss your priorities, the decision ahead, and whether Bear IT is the right fit.
Step Step 02
For qualified opportunities, we may offer a limited complimentary assessment. We agree on the scope, required information, and deliverables before starting.
Step Step 03
The assessment concludes with a concise findings brief and a discussion of priorities and potential next steps. Any additional work is separately scoped and agreed.
A limited assessment may review selected spend, contracts, renewals, or a defined technology question. It does not include comprehensive security assessment, implementation, or an unlimited roadmap engagement.
Ongoing leadership, reviews and decisions at an agreed cadence.
A defined scope, agreed deliverables and a clear finish line.
Opportunities are evaluated, not guaranteed. Scope, price and terms are agreed before additional work begins.
Request a ConsultationMeet your advisor
Jonathan Barrett brings technology, banking, and contact center leadership experience to organizations seeking ongoing vCIO guidance or focused enterprise advisory.
Discuss your priorities, current challenges, and which advisory practices could support your next decisions.