Starting a New Trek

After twenty years making technology decisions — presenting to skeptical boards, managing vendors, a lot of good ones, and some who overpromised, inheriting systems that nobody wanted to touch — I left the corporate world. Not because I was tired of the work. Because I realized I could be more useful on the other side of the table.

The Problem I Kept Seeing

As an entrepreneur and former CTIO at one of the largest BPO companies in the world, I have seen the same pattern repeat across industries: companies making critical technology decisions feeling isolated, under pressure, and without the right support.

Leaders who know their business inside out, but face technology choices that move faster than their teams can evaluate. Boards asking for confidence in decisions that carry real risk. Projects that start with ambition and stall when reality hits. These leaders do not need more reports. They need someone with experience who sits beside them, helps them decide, and stays to make things happen.

Why Trek to Win Exists

Trek to Win (T2W) — was founded on a simple conviction: business leaders deserve technology guidance from someone who has actually done their job. Not someone who studied it. Not someone who researched it. Someone who has sat in the same chair, faced the same pressures, and lived with the consequences of the same kinds of decisions.

The name says it. Building a successful business is not a sprint or a straight line. It is a trek — a deliberate, sometimes difficult journey through uncertain terrain. And the goal is not to survive the trek. The goal is to win.

Your goals, tech-enabled. That is our tagline, and it is also our operating principle. Technology is not the destination. Your business goals are. Technology is what gets you there faster, safer, and with more confidence.

What I Actually Do

I work as a strategic technology advisor for a small number of companies. Not a dozen. Not twenty. A handful — because that is the only way I can be truly present for each one.

What does that look like in practice?

• I continuously evaluate technology trends and filter what is relevant for your business — so you stay informed without the noise
• I help you define technology strategies and landing plans that align with your business goals
• I guide vendor selection and technology decisions — so you choose what fits, not what sells
• I sit in your steering committees and help you ask the right questions before decisions get made
• I help you build business cases that your CFO will actually fund
• I stay through implementation, because that is where most advice falls apart

I do not run six-week discovery phases that tell you what you and your team already know. And I do not send someone else to do the work. When you hire T2W, you get me — from the first conversation to the last. I do produce the reports and analysis your CEO and Board of Directors need to make informed decisions with confidence — because every strategic choice deserves proper documentation that protects the company and its shareholders.

How I Work Differently

Most consulting engagements follow a pattern: assess, recommend, leave. The client is left holding a document full of best practices that nobody knows how to implement in their specific context.

I work differently because my role is not to tell you what to do. My role is to help you decide, walk the path with you, and tackle the issues that inevitably come up along the way — so you can defend every decision to anyone who asks.

Behind every engagement, I apply a structured approach to decision-making that I have refined over two decades. It combines rigorous analysis with practical judgment. It documents reasoning so there is always a clear answer to "why did we choose this path?" And it keeps humans — specifically you — at the center of every decision.

You do not buy a methodology. You experience the results of one.

Who This Is For

T2W is built for business leaders who:

• Need strategic technology guidance but do not want (or need) a permanent CTO or CIO on payroll
• Are facing a specific decision — an AI initiative, a cloud migration, a vendor selection, a security challenge — and want someone in their corner who has been there before
• Value speed over process — you want traction from the first meeting, not after a lengthy onboarding phase
• Want an advocate, not a consultant — someone who empowers your leadership rather than replacing it

If you run a company and technology is part of your growth equation, we should talk.

Starting a New Trek

Every company I have worked with had the same moment: the realization that technology decisions are too important to make alone, and too consequential to delegate to someone who has never made them.

If that sounds familiar, I have been where you are. And I can help you navigate what comes next.

Not with a framework. Not with a report. With the experience of someone who has walked this path before — and wants to help you win.