Mid-market technology leaders face unique pressure — board expectations, technology debt, transformation mandates, and limited peer networks. Tim works directly with CIOs and CTOs as a trusted advisor and sounding board, bringing 13+ years of real-world experience to your most complex technology decisions.
This is not a vendor relationship. It's a peer-level partnership built on candor, accountability, and genuine investment in your success.
Learn more →Whether you're a business owner asking "where do I even start with AI?" or a CIO managing a full-scale deployment, TIMIT brings structured, practical guidance to every stage — process readiness, data preparation, team alignment, and hands-on deployment leadership.
We move at your speed, stay personally involved, and measure success by real business outcomes — not deliverables.
Explore this path →TIMIT Solutions listened to us and provided a timely holistic assessment and recommendations that helped us put the right people in place and deliver the changes our business and IT needed to deliver results.
Itransition reached out to TIMIT for help with business growth in our US market. TIMIT has a great network and worked with us to jointly close our first multi-million deal in our first year working together.
We engaged TIMIT consulting services to help us in our planning activities for a key business initiative. They kept to schedule and provided valuable help with our analysis and planning for our applications and PMO.
These testimonials reflect earlier engagements. New testimonials being added as current work matures.
An AI readiness assessment evaluates whether a company's processes, data, and team are prepared to deploy artificial intelligence successfully. For mid-market companies ($10M–$500M in revenue), it identifies the top AI opportunities, gaps in data quality or process documentation, and the organizational changes needed before deployment begins. TIMIT's AI readiness assessment covers process readiness, data preparation, team alignment, and produces a prioritized action plan tailored to the company's specific operations.
A fractional CIO advisor provides executive-level technology leadership without the cost of a full-time hire. For mid-market companies ($100M–$1B in revenue), this means a trusted peer who can pressure-test technology decisions before they are made, support board-level communication, evaluate vendor relationships, and lead transformation initiatives. TIMIT's CIO/CTO advisory is a peer-level partnership — not a vendor relationship — built on candor and genuine involvement in execution.
Mid-market AI consulting ($10M–$500M in revenue) focuses on practical, outcome-driven deployment rather than large-scale enterprise programs. Mid-market companies typically lack a dedicated AI team, have more constrained data infrastructure, and need advisors who can span both strategy and hands-on execution. TIMIT builds AI roadmaps around each company's specific processes, existing data, and available people — rather than applying enterprise frameworks that do not fit the scale or speed of a mid-market business.
TIMIT Solutions has worked across 8 industries. Founder Tim Montgomery has held CIO leadership roles in manufacturing at GE and The Stanley Works and in insurance at Cigna, and has led global IT services organizations serving mid-market and large insurance and healthcare companies. TIMIT brings direct executive experience — not third-party research — to clients in manufacturing, insurance, healthcare, and IT services, with broader mid-market consulting across additional sectors.
AI readiness is the evaluation phase: assessing whether a company's processes, data, and team are prepared to adopt AI. AI deployment is the execution phase: implementing AI tools and workflows into live business operations. TIMIT addresses both. The AI Readiness service identifies gaps and opportunities. The AI Deployment service provides hands-on leadership through process redesign, data preparation, team alignment, and production rollout — with TIMIT staying personally involved through execution, not just planning.
A business is ready for AI when its core processes are documented, its relevant data is accessible and reasonably clean, and its leadership team is aligned on the business outcomes AI should deliver. Most mid-market companies are partially ready — strong in some areas, with gaps in others. TIMIT offers a free 10-minute AI readiness review that identifies your top three opportunities and where the gaps are, with no sales pitch and no obligation.
When evaluating an AI consultant, look for: hands-on deployment experience across multiple industries (not just strategy work), familiarity with your company's scale and sector, involvement through execution rather than just delivering a report, and a track record of measuring success by business outcomes. Mid-market companies should specifically seek consultants with experience at the $10M–$500M scale, since enterprise AI frameworks often do not translate to organizations at this size.
TIMIT Solutions was founded in January 2012, giving the firm more than 13 years of experience in technology consulting, AI advisory, and CIO/CTO coaching for mid-market companies. Founder Tim Montgomery brings additional decades of corporate IT leadership, including executive roles at GE, The Stanley Works, and Cigna, and experience leading global IT services organizations with teams of 7,000 employees and P&Ls of $500M.
Most business leaders don't know what they don't know about AI. The TIMIT AI Assessment gives you a clear, honest picture of your top three opportunities — and a practical path to act on them.
Takes 10 minutes · Results are private · No sales pitch