Kelley Systems Group Fractional Technology Leadership

About

Caleb J. Kelley

I am often the first real technology leader a growing company works with. I walk into an under-instrumented business running on spreadsheets and leave it with systems, data, automation, and a team that outlasts me.

How I got here

I joined a private aviation and travel firm in operations. The company had almost no operational data. I proposed the Salesforce platform it now runs on, built it, and trained every employee on it.

When the VP of Engineering left, I absorbed his remit after a single one-hour handoff and expanded the charter to cover every system in the company. Over eight years and three promotions I built business intelligence and engineering into standalone departments, developed the leader for each one internally, and handed both functions off. I stood up an offshore engineering team in Bangalore, traveling there three times to train the engineers in person. I led the company's adoption of AI, including an enterprise agreement for Claude and a hybrid on-premise and cloud inference stack.

Through all of it I kept consulting clients on the side, most of them for about four years. By 2026 the practice had outgrown what a side commitment could serve, so it went full time. That employer retained it as a client.

What I actually do

Strategy on Monday, building in the platform on Tuesday. I am not a strategist who hands you a deck and leaves, and I am not an administrator who waits for tickets. The value is in being the same person who decides what should happen and then makes it happen.

Delegate and elevate

I work the EOS model deliberately: build the capability, develop a successor, hand it off. I have done it twice with named successors. A good engagement should make me progressively less necessary, and I would rather tell you that up front than have you discover it.

On tools

I spent years under a mandate to prevent platform sprawl while the company grew sixfold. Consolidating and integrating beats adding. The answer to most problems is not another subscription.

Scope and scale

6
Engineers led, split between the US and Bangalore
$300K
Annual systems budget owned, with every vendor contract
4
Offices worldwide supported
40 of 200
Candidates personally interviewed to build the India team
2022
Awarded the company's highest honor

Capabilities

Leadership

  • IT and engineering department leadership
  • Distributed and offshore teams
  • Strategy and budget ownership
  • Hiring and talent development
  • Vendor management, SOPs, SLAs
  • EOS

Salesforce and data

  • Platform ownership and architecture
  • Flow automation and Apex development
  • Classic-to-Lightning migration
  • Sandbox-to-production release management
  • Data governance and migration
  • Reporting, dashboards, KPI design

Systems and AI

  • System architecture and integration
  • Platform consolidation
  • Enterprise AI adoption and LLM integration
  • Hybrid on-premise and cloud inference
  • Zapier, Certinia, Jamf, Jira, Asana
  • Google Workspace, Slack, 1Password

A note on certification: I am self-trained through Trailhead rather than certified. The depth is in the work, 100+ Flows in production, Apex development, a Classic-to-Lightning migration, and release management. Certification does not cover Apex. If a certificate is a requirement for you, I would rather say so now than waste your time.

Where vision meets the system.

If your technology grew faster than anyone planned for, that is a solvable problem and a common one. Thirty minutes is usually enough to tell whether I am the right person for it.

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