For leaders and procurement teams
Executive technology advisory
Customer experience · Network · Transformation · Sourcing
Executive Technology Advisory
Accelerate Your Transformation
Senior, independent advice on customer experience, networks and digital transformation, plus buyer-side sourcing and vCIO leadership when you need an executive at the table.
Expertise
Senior advice for the technology decisions that shape your business
For SMB & midmarket organizations
vCIO & technology consulting
Roadmap · Budget · Oversight
Four connected advisory practices
Each engagement draws on the practices your priority needs, in whatever combination the decision calls for.
Customer Experience & Contact Center
Modernize how customers reach you: contact center, CCaaS and conversational AI decisions grounded in real service journeys and agent experience.
Explore practiceDigital Transformation & AI
Move from legacy systems to cloud and AI-ready operations, with practical use cases, data readiness and governance that keep transformation tied to results.
Explore practiceTechnology Sourcing & Procurement
Buyer-side sourcing and network transformation: connectivity, SD-WAN and carriers, plus UCaaS, CCaaS, data center and co-location, and AI solutions, for leaders and procurement teams alike.
Explore practicevCIO & Technology Consulting
Fractional CIO leadership and practical technology consulting: roadmap, budget, security priorities and provider oversight, delivered alongside your team.
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 storyGrowing & Regulated Organizations
Business Services Organization: Putting Conversational AI to Work at the Front Door
Bear IT helped an established business move from interest in AI to a practical receptionist solution on Zoom, focused on its incoming telephone experience.
Technology Advisory · Implementation
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.