KCKeith Cutcliffe
Available for fractional and project work

Fractional CTO. Hands-on architect.

I spent 15+ years inside companies as their technology leader, often stepping in post-merger, post-acquisition, or mid-transformation. Now I bring that experience to organizations as a fractional CTO. I lead the technology function, and I still design the systems myself: the application, integration, and data architecture underneath the strategy. You get executive leadership and a working architect, without the cost of a full-time hire.

Book a free strategy call See how I help
Keith Cutcliffe in an office
Keith CutcliffeFractional CTO · Solutions Architect
Atlanta-based · Remote-first · Ready to travel
15+
years leading enterprise technology
5→27
person technology org built from the ground up
$3M+
annual technology budget owned
~$2M
in annual licensing costs eliminated

Technology leadership at

  • AWC
  • LabConnect
  • Fusion Connect
  • Protective Life
  • Regions Bank
  • ProAssurance

How I help

For organizations of roughly 100 to 1,500 people that have outgrown informal technology management but don't yet need a full-time technology executive.

I also design and build

Strategy is only as good as the systems underneath it. I started as a developer and still love the architecture work: designing how the code, integrations, and data fit together, and working alongside the people who build it.

Talk about a project

  • Application and code architecture

    Designing distributed systems and modernizing legacy applications, with clear structure, standards, and code teams can maintain after I'm gone.

    Distributed architecture · Application modernization · Azure DevOps

  • Integration architecture

    Connecting ERP, CRM, and line-of-business systems through APIs so data moves in real time instead of by spreadsheet and email.

    Built real-time ordering, pricing, and inventory APIs on Dynamics NAV at LabConnect

  • Data architecture

    Data lakes, master data, and analytics layers designed so reporting is trustworthy and the organization is ready to use AI on its own data.

    Snowflake · Azure · Medallion architecture · MDM

Technology changes stick when people trust the process behind them.

How I approach every engagement

A technologist who leads, and a leader who still gets his hands in it

I started as a developer and grew into running technology organizations: building teams, owning budgets, and reporting to CEOs and boards. I've led through mergers, carve-outs, regulated environments, and the messy middle of transformation.

My background in anthropology and political theory shapes how I lead. Technology changes stick when people trust the process behind them, so I put as much care into governance and stakeholder alignment as into the architecture.

  • ITIL V4 Foundation
  • B.A., UAB
  • Post-grad, University of Alabama

How an engagement works

Most engagements follow the same arc, scaled to what you need.

  1. Assess

    First 30 to 90 days

    A clear-eyed review of applications, vendors, data, delivery, and spend, ending in a prioritized roadmap your executive team can act on.

  2. Install the operating cadence

    Months 2 to 6

    Governance, intake, steering, and reporting that make technology work visible and accountable to leadership.

  3. Lead

    Ongoing

    One to two days a week of executive technology leadership: owning the roadmap, managing vendors, and backing key decisions until you're ready for a full-time hire.

What colleagues say

Keith is an exceptional leader who combines strong project management skills with the ability to build, guide, and motivate teams. He excels at bringing people together, providing clear direction, and keeping complex initiatives moving forward. … Keith brings the leadership, organizational skills, and technical understanding needed to turn technology strategy into successful execution.
Gerardo BlancoEnterprise Architect, AWC, Inc.
On multiple occasions I've turned to Keith for advice on complex and poorly formed data, from working with APIs to bringing together sources that were never designed to fit. What I value most is that he looks at the whole picture, from how information is captured at the start to how it shows up in reporting at the end, and explains his recommendations in plain language. Keith combines real technical depth with practical judgment, and I'd recommend him to any organization trying to get its data under control.
Hanson WatkinsOwner and Operator, Vestavia Hills Consulting

Experience

Industrial services, life sciences, telecom, and insurance, each at a turning point.

  1. 2024 – 2026

    Director, Business Technology

    AWC, Inc.

    Senior technology executive for a multi-division ESOP enterprise. Authored the first enterprise technology roadmap and governed three development groups.

  2. 2020 – 2024

    Director, Enterprise Software Development

    LabConnect

    Built a 27-person technology organization inside an FDA-regulated (21 CFR Part 11) clinical trial laboratory and managed a $3M+ budget.

  3. 2017 – 2020

    Sr. Manager / Director, Application Development

    Fusion Connect

    Directed 16–30 developers and analysts through post-merger systems integration at a telecom and UCaaS provider.

  4. 2012 – 2016

    Sr. Technical PM / Lead Developer

    Protective Life

    Led PMO governance and a $2M+ regulated systems implementation at a Fortune 500 insurer; a SQL Server migration cut about $2M in annual licensing.

Let's talk about where you are

A first conversation is free and usually takes 30 minutes. I work with one or two clients at a time. Atlanta-based, remote-first, and glad to travel.

Prefer email? keith@keithcutcliffe.com
Or connect on LinkedIn