For SMB & midmarket organizations
Technology leadership on demand
Roadmap · Budget · Security
vCIO & Trusted Technology Advisory
Accelerate Your Transformation
CIO leadership and trusted advice to align IT with your goals, strengthen security, and make smarter investments in cloud, communications, and AI.
Expertise
Two ways to put CIO experience to work
For teams with existing IT leadership
Better technology decisions
Contact center · AI · Sourcing
Four connected advisory practices
One advisor, four disciplines — each engagement draws on the practices your priority needs.
vCIO & Technology Leadership
Senior technology leadership for your roadmap, budget, priorities, and executive decisions—working alongside your IT team without a full-time CIO role.
Explore practiceCustomer Experience & Contact Center Advisory
Transform customer experiences through AI-powered service, contact center modernization, and digital channel optimization that drive measurable efficiency and satisfaction.
Explore practiceAI Enablement & Governance
Practical AI enablement that delivers measurable value—from customer service automation to operational efficiency and sales enablement.
Explore practiceTechnology Sourcing & Vendor Advisory
Translate your strategy into well-considered technology choices across managed services, contact center, AI, connectivity, cloud, communications, and cybersecurity—with capability, fit, and terms in focus.
Explore practiceHow engagements work
Start with a complimentary assessment.
Up to four weeks, at no cost — our way to find real opportunities and earn your trust. If we continue, you choose how you pay: hourly or fixed price, for either service.
- 01 · Start hereNo cost
Complimentary assessment
Identifying opportunities and building a partnership grounded in trust.
Week 1Up to week 4- Review current spend, contracts and renewals
- Map opportunities against your priorities
- Share findings and a recommended path
02 · Then, if it fits — priced hourly or fixed
Hourly or fixedOngoing advisory
Leadership, reviews and decisions as needs arise. Ongoing, agreed cadence.
- Senior advisor on call
- Regular review cadence
- Scale up or down as needs change
Hourly or fixedDefined project
A roadmap, provider evaluation or sourcing effort. Scope agreed in writing.
- Deliverables agreed up front
- Clear finish line
- Handover to your team
Opportunities are evaluated, not guaranteed. Scope, price and terms are agreed in writing before any paid work begins.
Meet your advisor
Executive experience, applied to your next decision.
Jonathan Barrett brings technology, banking, and contact center leadership experience to organizations seeking ongoing vCIO guidance or focused enterprise advisory.
- Technology experience
- 25+ years
- Former CIO
- 2016–2023
INSIGHTS / 2027 BUDGET PLANNING
Before you finalize your budget, let’s find the savings.
A fresh look at recurring technology costs could make room for what comes next.
From advice to action
Client Outcomes
Education & Learning
Education Organization: From AI Ambition to Enterprise-Scale Voice Agent Deployment
Bear IT guided an education organization through the decisions behind an enterprise-scale Intelligent Voice Agent initiative, from evaluating the opportunity and developing the business case through selecting and supporting deployment of the Poly.ai voice agent.
Contact Center Advisory · Deployment Advisory
Read engagement storyLaw Firms & Professional Services
Law Firm: Strategic Technology Leadership & Vendor Accountability
Bear IT Group provides ongoing vCIO services and IT governance for this law firm, overseeing vendor relationships and leading technology changes that included a Zoom communications deployment, a managed service provider migration, a NetDocuments migration, and Microsoft Intune adoption.
vCIO · Technology Advisor
Read engagement story1–2 / 10
Anonymized, Bear IT-authored engagement narratives. Modeled benefits are not measured results; scope and outcomes vary by engagement.
Ready to discuss your technology leadership needs?
Discuss your priorities, current challenges, and which advisory practices could support your next decisions.