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Two ways we work together — both built on personal involvement.

No junior consultants. No generic frameworks. Tim Montgomery works directly with you — from first conversation through execution and results.

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The TIMIT model

A small number of clients. Deep involvement in each.

Most consulting firms scale by adding headcount and reducing partner involvement. TIMIT works the opposite way. I deliberately work with a small number of clients because I believe in being personally accountable for every engagement.

That means you get Tim — not a team of analysts producing deliverables. Every strategy session, every technology decision, every critical milestone has direct involvement from someone who's seen it work across 13+ years and 8 industries.

For scale on larger projects, I bring in a tight network of trusted implementation partners I've worked with for years. I manage the relationship and the outcome. They handle the execution.

13+
Years delivering technology transformation across mid-market companies
8
Industries served — from Manufacturing and Healthcare to Financial Services and Technology
1
Partner personally involved in every engagement — not delegated, not handed off
CIO · CTO Advisory

CIO/CTO Coaching & Mentoring

For companies $100M – $1B · Where Tim has or builds a direct relationship

Mid-market technology leaders operate in a uniquely difficult environment. You carry board-level accountability for technology outcomes, manage teams under constant pressure to modernize, and often have no peer inside the organization who truly understands what you're facing.

Tim works with CIOs and CTOs as a trusted peer advisor — not a vendor, not a coach with a framework, but someone who has navigated the same decisions across dozens of engagements and will tell you what he actually thinks.

What this engagement covers

  • Strategic technology roadmap development and prioritization
  • Technology investment decisions and vendor evaluation
  • AI strategy and readiness planning for your organization
  • Board and executive communication on technology initiatives
  • Technology team leadership and organizational design
  • Digital transformation planning and change management
  • Risk assessment and technology governance frameworks

How it works

  • Ongoing advisory relationship — regular cadence of sessions plus availability for critical decisions
  • Confidential, candid — a safe space to pressure-test decisions before they're made
  • No deliverables for the sake of deliverables — outcomes over outputs
  • Engagements begin with a discovery conversation to confirm fit

Is this the right engagement for you?

CIO/CTO Coaching works best when there's a direct relationship with Tim and a genuine need for a peer-level technology advisor. Let's have a 30-minute conversation to find out.

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AI Readiness · Deployment

AI Readiness & Deployment

For companies $10M – $500M · Two engagement bands based on company size and needs
Band A

Business Owner & CEO Track

Companies $10M – $50M
  • Full AI readiness assessment — process, data, people, and technology
  • Identification of highest-ROI AI deployment opportunities
  • Process documentation and optimization before AI introduction
  • Data readiness evaluation and remediation planning
  • Team preparation and change management
  • Hands-on deployment leadership through to live implementation
  • Ongoing support as your AI capabilities mature
Band B

CIO & Executive Track

Companies $50M – $500M
  • Business Process Management (BPM) analysis and optimization
  • Enterprise AI strategy development and roadmap
  • AI deployment planning across business units
  • Vendor and technology evaluation for AI platforms
  • Executive alignment and board-level AI communication
  • Program management for complex AI deployments
  • Partner network coordination for implementation at scale

The deployment process

01
Assess
AI Readiness Assessment — understand where you are today
02
Prepare
Process and data readiness — fix the foundation before deploying AI
03
Plan
Deployment roadmap — prioritized, sequenced, and realistic
04
Deploy
Hands-on implementation leadership — Tim stays personally involved
05
Mature
Ongoing optimization — AI capabilities that grow with your business

Not sure where your business stands on the AI readiness curve? The assessment takes 10 minutes.

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Global partner network

Scale without compromising quality

For larger engagements, TIMIT brings in a carefully selected network of implementation partners — global development firms and specialist consultants I've worked with for years. I manage the client relationship and hold accountability for outcomes. They bring execution capacity. You get the best of both: personal involvement and the ability to scale.

Free · 10 minutes · No obligation

Not sure which path is right for your business?

The TIMIT AI Assessment identifies your top three AI opportunities and tells you exactly where to start. It's the fastest way to turn a vague question into a clear next step.

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