Fractional CTO · Milwaukee, WI

Senior Technology Leadership — Without the Full-Time Hire

Now including AI Strategy & Governance

Growing organizations need strategic technology leadership, not another vendor. I embed as your CTO — assessing risk, building AI-ready roadmaps, and guiding execution — so you make confident decisions at every inflection point.

20+
Years of technology leadership across startups, SMBs & enterprise
$6MM
ARR built as co-founder & CTO of a logistics SaaS startup in 3 years
3x
Founder in transportation, logistics & software development
100%
Engineering team retention — culture and execution both matter
20+
Years Technology Leadership
3x
Startup Founder
SMB
to Fortune 500 Experience
T&L
Transportation & Logistics Depth
AI
Strategy, Governance & Adoption
The Value of a Fractional CTO

What changes when you have experienced leadership in the room.

These aren't edge cases. They're the decisions that define whether an organization scales smoothly or pays an expensive technology tax for years.

Scenario · Transportation & Logistics
A freight brokerage selects a TMS without a technology strategy in place.
TMS selection is one of the highest-stakes technology decisions a logistics company can make. The wrong platform — or the right platform implemented without proper integration planning — locks you in for years, creates data silos between your TMS, load boards, and accounting systems, and forces your team to work around the software instead of through it. The cost isn't just the license fee. It's the operational drag, the custom workaround development, and eventually the painful migration.

A fractional CTO brings vendor-neutral evaluation, integration architecture review, and real-world implementation experience — before the contract is signed.
Without CTO Guidance
TMS selected based on sales demo and peer recommendation
No integration assessment. No evaluation of carrier connectivity, load board APIs, or accounting sync.
With CTO Guidance
Structured vendor evaluation with weighted scoring across 12+ criteria
Integration map built before selection. Implementation risks surfaced and mitigated early.
Cost of a wrong TMS decision
$250K–$500K+ over 3 years
Without CTO Guidance
6-month implementation overrun, data inconsistencies, manual reconciliation
Operations team spending 30–40% of time on workarounds.
With CTO Guidance
Phased implementation plan with clear milestones and rollback criteria
Vendor held accountable. Team trained. Go-live on schedule.
Revenue per headcount impact
Measurable within 90 days of go-live
Scenario · All Industries
An organization deploys AI tools across the team without a governance framework.
AI adoption is accelerating faster than most organizations' ability to govern it. Teams experiment with ChatGPT, Copilot, and dozens of other tools — often without leadership visibility into what data is being shared, what workflows are changing, or what the liability implications are. The risk isn't that AI is dangerous. The risk is that undirected AI adoption creates inconsistency, data exposure, and a patchwork of tools that don't integrate with your core systems.

A fractional CTO builds the governance framework first — defining acceptable use, data handling, vendor evaluation criteria, and a strategic adoption roadmap — so AI works for the organization, not around it.
Without CTO Guidance
5–10 different AI tools in use, none integrated, no usage policy
Sensitive client or operational data entered into consumer AI tools. No audit trail.
With CTO Guidance
AI governance framework with clear acceptable use and data handling policies
Approved tool list. Enterprise agreements where needed. Audit-ready posture.
Average time to meaningful AI ROI without a plan
18–24 months of trial and error
Without CTO Guidance
AI investment fragmented across departments, no strategic alignment
Budget spent on tools that duplicate existing capabilities or create new integration debt.
With CTO Guidance
Prioritized AI adoption roadmap tied to business outcomes, not vendor hype
Use cases ranked by impact and feasibility. Quick wins identified in 30 days.
Productivity gains from structured AI adoption
15–30% in targeted workflows
Scenario · Growth-Stage SMBs
A growing company decides to build custom software instead of buying — or vice versa.
The build-vs-buy decision is one of the most consequential a growing organization makes. Build too early and you're maintaining custom software before you've found product-market fit. Buy the wrong platform and you're locked into a vendor relationship that becomes a strategic liability. Most organizations make this decision under time pressure, with incomplete information, and without someone in the room who has made it before.

The right answer depends on your competitive differentiation, your team's technical capacity, and your integration landscape — not on which vendor has the better demo or which developer is most excited about the project.
Without CTO Guidance
Custom build initiated based on developer enthusiasm and feature gap
No TCO analysis. No evaluation of existing platforms. 18-month timeline becomes 36.
With CTO Guidance
Structured build-vs-buy analysis with total cost of ownership modeling
Market landscape evaluated. Build only when differentiation justifies it.
Average custom build cost overrun
2–3x original estimate
Without CTO Guidance
Vendor selected based on price alone, contract signed without SLA review
Data portability not addressed. Exit costs emerge at renewal.
With CTO Guidance
Vendor contract reviewed for SLAs, data ownership, and exit provisions
Negotiating leverage preserved. No lock-in surprises.
Typical vendor negotiation savings
10–25% on multi-year contracts
Scenario · Member-Based Nonprofits & Associations
A nonprofit's technology investments don't align with their mission or member experience.
Member-based organizations face a unique technology challenge: limited budgets, high member expectations, and mission-critical data that can't be treated like a typical commercial enterprise. AMS platforms, member portals, event management systems, and communication tools all need to integrate and serve members effectively — often with a small staff and minimal IT support.

The risk is spending on technology that doesn't move the mission forward. The opportunity is using a strategic assessment to identify where technology can actually improve member value, reduce administrative burden, and free staff to focus on what matters.
Without CTO Guidance
AMS selected to match a peer org's platform, poor adoption by staff
Member data fragmented across 4 systems. Event management still handled manually.
With CTO Guidance
Member-first technology assessment identifies integration gaps and quick wins
Unified member view. Automated workflows. Staff time recaptured.
Typical staff time recaptured via integration
5–10 hours/week per staff member
Without CTO Guidance
Technology budget allocated reactively to immediate fires
No multi-year roadmap. Board questions ROI of technology spending.
With CTO Guidance
3-year technology roadmap presented to board with clear mission alignment
Investment prioritized by member impact. Technology strategy included in annual plan.
Budget confidence gained
Board-ready technology strategy in 8–10 weeks
AI Strategy & Governance

AI is not a feature.
It's a leadership decision.

Every organization is being sold AI. Few have a plan for it. The organizations that capture real value from AI aren't the ones that adopt the most tools — they're the ones that adopt the right tools with the right governance, tied to specific operational outcomes.

AI strategy is now a core part of every engagement I do. Whether you're a freight brokerage evaluating route optimization tools, a nonprofit exploring member engagement automation, or a manufacturer looking at predictive maintenance — the questions are the same: what's worth pursuing, what's the risk, and how do you govern it?

🗺️
AI Readiness Assessment
Evaluate your current AI posture: what tools are in use, what data you have, where the risks are, and where the highest-value opportunities exist. Built into every Technology Assessment.
Assessment Package
🏛️
AI Governance Framework
Acceptable use policies, data handling standards, vendor evaluation criteria, and audit posture — so your organization can adopt AI confidently without exposing itself to unnecessary liability.
Roadmap Package
📋
AI Adoption Roadmap
A prioritized, phased plan for AI adoption across your organization — with use cases ranked by impact, feasibility, and alignment with business goals. Not vendor-driven. Business-driven.
Roadmap Package
🔧
Microsoft 365 & Copilot Strategy
Most organizations already pay for Microsoft 365. Few are extracting the AI value embedded in it. I help organizations plan and deploy Copilot and Power Platform capabilities that actually stick.
Advisory Retainer
🚛
AI in Transportation & Logistics
Route optimization, freight pricing models, carrier matching, predictive capacity planning — I evaluate AI tools in logistics with the domain depth to separate genuine capability from vendor marketing.
Industry Specialty
🛡️
Ongoing AI Oversight
As part of an advisory retainer, I provide ongoing oversight of AI initiatives — monitoring for governance drift, evaluating new tools as they emerge, and keeping your AI strategy aligned with business goals.
Advisory Retainer
A note on AI hype: Every vendor is calling their product "AI-powered" right now. One of the most valuable things I do is help organizations distinguish between tools that create genuine operational leverage and tools that are marketing first, capability second. You deserve a technology partner who will tell you when something isn't worth it — not just when it is.
Services

Clear offerings.
Fixed fees. No ambiguity.

Four named packages. You know exactly what you're buying and what you'll receive. Pricing discussed on your discovery call.

01 / Entry Point
Technology Health Check
"Get clarity in one day."
Includes AI posture review
  • Full-day on-site assessment with leadership
  • Technology Health Check Report
  • Top 5 prioritized recommendations
  • Risk scorecard & AI readiness snapshot
  • Delivered within 5 business days
Schedule a Call to Learn More
02 / Deep Dive
Strategic Technology Assessment
"Know exactly where you stand."
Includes full AI readiness evaluation
  • Systems, integrations & vendor review
  • Security & team capability evaluation
  • Architecture diagrams & integration map
  • Risk register, gap analysis & AI assessment
  • Stakeholder interviews included
Schedule a Call to Learn More
03 / The Plan
Digital Roadmap & Strategy
"A plan your team can execute."
Includes AI strategy framework
  • Prioritized multi-year technology roadmap
  • AI adoption roadmap & governance framework
  • Vendor evaluation & recommendations
  • Investment estimates & initiative sequencing
  • Executive presentation to board/leadership
Schedule a Call to Learn More
04 / Ongoing
Strategic Advisory Retainer
"CTO-level leadership, fractional commitment."
Includes ongoing AI oversight
  • ½–2 days/week, scales with your needs
  • AI governance & tool evaluation
  • Vendor selection & security oversight
  • Monthly status + quarterly strategic review
  • Month-to-month with 30-day notice
Schedule a Call to Learn More
Most Popular Engagement
Assessment + Roadmap Bundle
The complete engagement: deep-dive today, executable plan tomorrow. Includes full AI strategy framework. Bundled engagements receive preferred pricing.
Get Bundle Pricing
Who I Work With

Built for organizations that are serious about technology — and serious about growth.

I work best with SMBs under 100 employees, nonprofits, and growth-stage organizations across the Midwest making real technology decisions without a full-time CTO in the room.

🚛
Transportation & Logistics
Freight brokerages, carriers, and last-mile operations navigating TMS decisions, system integration, carrier connectivity, and AI-driven pricing tools.
The $500K TMS mistake is real. I've seen it from the inside.
🤝
Member-Based Nonprofits
Associations and employer organizations managing AMS platforms, member portals, digital transformation, and AI readiness on nonprofit budgets.
Technology should serve your mission — not drain it.
🏭
Manufacturing & Industrial
Midwest manufacturers modernizing operations, evaluating ERP and OT systems, and developing technology strategy for the next decade of growth.
Legacy systems + ambitious growth plans = my wheelhouse.
📈
Growth-Stage SMBs
Companies under 100 people that have outgrown their technology setup and need a strategic plan — not just more tools and more vendors.
You've hired great people. Now they need a real system to work in.
How It Works

From first call to strategic execution.

A clear, predictable path. No scope surprises. No endless retainers before you see results.

Step 01
Discovery Call
A focused 45-minute conversation to understand your situation, goals, and where the pressure points are. No pitch — just honest listening.
Free · No obligation
Step 02
Health Check or Assessment
We establish a clear baseline — what you have, what's working, what's at risk, and where the highest-priority opportunities are. Includes AI readiness review.
Health Check or Assessment Package
Step 03
Roadmap & Strategy
A prioritized, multi-year plan built on real findings — not generic best practices. Includes AI adoption roadmap and governance framework.
Roadmap & Strategy Package
Step 04
Ongoing Advisory
Strategic technology leadership on a monthly retainer — present for the decisions that matter, at the level of engagement your organization actually needs.
Advisory Retainer
About Kevin

Founder first.
Strategist always.

I've built and sold a software development firm, co-founded and scaled a logistics SaaS startup to $6MM ARR as CTO, and spent 20+ years leading technology across organizations ranging from early-stage startups to large enterprise engagements in manufacturing, government services, and consumer products.

Three of my companies were in transportation and logistics — so when a freight brokerage asks me about TMS selection, carrier connectivity, or AI-driven pricing tools, I'm not consulting from a textbook. I've made those decisions, lived with them, and learned what actually matters.

Today I work as a solo fractional CTO based in Milwaukee, Wisconsin, serving growing organizations that need experienced strategic leadership at a scale that makes sense for their size and stage. I work with freight brokerages, member-based nonprofits, manufacturers, and growth-stage SMBs — organizations that are serious about technology and ready to make it a competitive advantage.

🚀
Co-Founder & CTO, Logistics SaaS Startup $6MM ARR in 3 years · 100% engineering team retention · transportation & logistics domain
🏗️
Founder, Software Development Firm Built and sold a firm specializing in logistics and operations technology
🏢
Enterprise Technology Leadership Cloud architecture, digital transformation, and AI governance across manufacturing, federal services, and industrial clients
🤖
AI Strategy Practitioner Microsoft 365 / Copilot deployments, AI governance frameworks, and adoption roadmaps across industries
🎙️
Recognized Technology Leader Featured in the C-Suite Series by SafeNet Consulting · Guest on the "How We Innovate" podcast

Ready to see where your technology actually stands?

Start with a free 45-minute discovery call. No pitch, no pressure — just an honest conversation about your situation and whether I'm the right fit to help.

Schedule a Free Call