Experienced technology leadership for your next big challenge.
Fractional CTO services, strategic advising, and hands-on technical expertise for startups and growing companies — without the commitment of a full-time executive.
Situations I help with
Most engagements start with a question that does not have an obvious answer yet.
Leadership without a full-time CTO
You need senior technology leadership to guide the team and set direction, but not necessarily a full-time executive hire.
A roadmap that needs a fresh perspective
Your product and engineering roadmap could benefit from an experienced outside perspective to prioritize and sequence the work.
A high-stakes platform or vendor decision
You are weighing a significant architecture, platform, or vendor decision and want a thorough, independent assessment.
Figuring out where AI fits
You need to understand how AI should realistically fit into your product and business — not as a buzzword, but as a plan.
Preparing for diligence
You are preparing for an investment, acquisition, or technical diligence process and need the engineering story to hold up.
An important project that needs leadership
You have a high-priority technical project that needs experienced leadership to get across the finish line.
Services
Engagements are tailored to the problem. These are the areas where I am most often asked to help.
Fractional CTO
Ongoing technology leadership for companies that need a senior technical voice in the room without a full-time hire — owning roadmap, architecture, and engineering decisions.
Technology Advising
Strategic guidance for founders and executives facing complex technical decisions, from product direction to team structure to platform choices.
AI Strategy & Implementation
Practical AI planning and implementation — identifying where it creates real value, designing the architecture, and shipping working systems.
Architecture & Technical Roadmaps
Systems design and roadmaps that balance speed, scale, and maintainability, with a clear path from where you are to where you need to be.
Technical Diligence
Independent technical assessments for investors, acquirers, and leadership teams — evaluating architecture, engineering practices, and technical risk.
Special Projects
Hands-on leadership for a high-priority technology initiative that needs experienced direction to move quickly and land well.
How engagements work
Every engagement is structured around the problem. Scope can range from a few strategic sessions to ongoing involvement with your team.
Ongoing Advisory
Regular sessions to advise on technical strategy, product decisions, and engineering direction as situations evolve.
Fractional Leadership
Embedded technology leadership — owning roadmap, architecture, and team decisions on a part-time, ongoing basis.
Focused Project
A defined project with a clear deliverable: an architecture review, a technical roadmap, or an AI initiative taken to completion.
Technical Assessment
A structured diligence or assessment engagement that produces a clear, written evaluation of technical risk and opportunity.
Scope can range from a few strategic sessions to ongoing involvement with a leadership or engineering team.
How I work
A simple approach built on clear thinking, practical recommendations, and hands-on collaboration.
Understand the challenge
Start by listening. I work to understand the business context, the technical landscape, and what success actually looks like.
Identify the highest-leverage path
Cut through ambiguity to find the path that matters most — and sequence the work so the most important things move first.
Work alongside the team
Roll up sleeves and work directly with the team — making decisions, unblocking problems, and keeping momentum.
Leave the organization stronger
The goal is not dependence. I aim to leave behind clearer thinking, better process, and a team that can carry the work forward.
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Turning ambiguity into an executable plan
I started Side Quest Works to help companies navigate consequential technology decisions with experienced, hands-on leadership.
My work sits at the intersection of strategy and execution. I help teams turn ambiguity into an executable plan — whether that means shaping a roadmap, evaluating a platform decision, leading a technical initiative, or stepping in as fractional CTO.
I believe the best technology decisions come from clear thinking, direct communication, and a genuine understanding of the business. No buzzwords, no theater — just practical guidance and work that holds up.
Start a conversation
Whether it is a difficult technical decision, a fractional leadership need, an upcoming diligence process, an AI initiative, or a high-priority project — I would like to hear about it.