Who We Serve

Built for mid-market leaders who are serious about AI and technology transformation.

TIMIT works best with companies and leaders who want a real partner — not another vendor, not another report, not another framework that sits on a shelf.

$10M – $1B Revenue US-Based · Global Reach Manufacturing · Healthcare · Financial Services · Technology · and more
You're a great fit if...

This is built for you.

  • You're a business owner, CEO, CIO, or CTO at a $10M–$1B company
  • You know AI matters but aren't sure where to start or how to deploy it effectively
  • You want a partner who stays personally involved — not a team of junior consultants
  • You've been burned by consultants who delivered reports and disappeared
  • You want candid, peer-level input — not someone who tells you what you want to hear
  • You're ready to move from thinking about AI to actually deploying it
  • Your technology is holding your business back and you need a credible path forward
Probably not the right fit if...

We'd refer you elsewhere.

  • You're looking for the lowest-cost option — TIMIT is not the cheapest and doesn't try to be
  • You want a large team with multiple workstreams — TIMIT is intentionally small and focused
  • You need a purely technical implementation team — we lead strategy and deployment, not development
  • You're not ready to commit to the process — real transformation requires real involvement from your side too
  • You're looking for a quick fix — sustainable results take time and honest effort
"I'd rather tell you upfront that we're not the right fit than take on work where I can't deliver the outcomes you need. That honesty is part of how I work." — Tim Montgomery
Who we work with

The leaders TIMIT is built for

01
The Business Owner / CEO
$10M – $50M

You built something real and now you're watching larger competitors move faster with technology. You know AI is a genuine opportunity but every conversation about it either goes over your head or sounds like a sales pitch. You need someone who can translate the complexity into a clear business case and then actually execute it alongside you.

  • AI readiness assessment to identify your top 3 deployment opportunities
  • Process and data foundation work before any AI is introduced
  • Hands-on deployment leadership from planning through live implementation
  • A partner who speaks your language — business outcomes, not technology jargon
02
The CIO / CTO
$50M – $1B

You carry accountability for technology outcomes across the entire organization. The board wants AI progress, your team is stretched, and you have limited peers inside the business who truly understand the tradeoffs you're navigating. You need a trusted, confidential sounding board — someone who will push back, challenge your assumptions, and help you make better decisions.

  • Peer-level advisory relationship with direct access to Tim
  • Technology strategy, AI roadmap, and investment prioritization
  • Board and executive communication support on technology initiatives
  • Confidential pressure-testing of decisions before they're made
03
The Executive Sponsor
$50M – $500M

You're a CFO, COO, or division president who owns a major transformation initiative. Technology is central to your mandate but you're not a technology specialist. You need someone who can bridge the gap between business strategy and technical execution — and help you hold your technology team accountable for real outcomes.

  • Business Process Management (BPM) analysis to identify transformation opportunities
  • AI deployment roadmap aligned to your specific business unit objectives
  • Program oversight and accountability for technology execution
  • Clear, non-technical communication for executive and board audiences
Industry experience

Deep roots across 8 industries

Financial Services
Industry served
Insurance
Industry served
Non-Profit
Industry served
Field Services
Industry served
Retail
Industry served

Industry experience matters because AI deployment challenges are rarely purely technical — they're operational, cultural, and regulatory. Having seen these dynamics firsthand across different sectors means faster diagnosis and more relevant recommendations.

A note on fit

Not every engagement is the right engagement.

TIMIT works with a deliberately small number of clients. That's how personal involvement stays real. It means I'm selective about who I take on — not because of size or prestige, but because I need to believe I can genuinely move the needle for you.

The AI Assessment is the best first step. It takes 10 minutes, it's free, and it gives both of us a clear picture of where you are and whether TIMIT is the right fit for where you want to go.

Free · 10 minutes · No obligation

Sound like the right fit?
Let's find out.

Start with the AI Assessment for a clear picture of your opportunities, or book a direct conversation with Tim if you already know what you need.