Loy O'Kelley — senior program manager and transformation delivery leader. Enterprise program rescue, PMO design and governance, SAFe Agile transformation, AI-augmented delivery, and program risk management across government, financial services, and healthcare.

Senior Program Manager · Transformation Executive

Delivering
what others
struggle to finish.

I help stabilize, govern, and deliver complex programs when timelines compress, stakeholders misalign, and failure starts becoming expensive. Two decades across U.S. Army leadership, a technology consultancy I founded and sold, and Big Four transformation delivery.

Read the Insights → View select work → Download resume ↓

Army Engineer Officer (Ret.) · Founder — Exited · Big Four Delivery · MBA + MS Finance · PMP · SAFe ACSM · LSS Black Belt

Government · Financial Services · Healthcare · $75M+ delivered · 20M+ end users

Loy O'Kelley, Senior Program Manager, Transformation Executive at KPMG US and retired U.S. Army engineer officer
Senior Program Manager, Transformation Executive · KPMG US
$75M+
Enterprise programs delivered
20M+
End users impacted
0 → Exit
Consultancy founded & acquired
20+
Years operational leadership
What I Solve

When the program is drifting, I bring it back under control.

Programs behind schedule

Rebuild the plan against reality, sequence the critical path, and put named owners on every slip.

Dates leadership can defend

Reporting that hides reality

Replace negotiated green with one executive report that tells the truth weekly — built from the system of record.

Decisions made on facts

Stakeholders moving in different directions

Map the decision rights, reset the forum structure, and hold alignment where misalignment actually starts.

One direction of travel

Vendors operating without discipline

Dependency choreography, release-train discipline, and escalation paths vendors actually respect.

Accountability across the seam

PMOs producing noise instead of decisions

Strip the theater: RAID that matters, KPIs that drive action, cadence that ends in decisions — not minutes.

Governance that gets used

Teams drowning in status and meetings

AI-augmented reporting and RAID upkeep — machine-drafted, human-signed — to give delivery hours back to delivery.

Reduce noise, expose truth

Field Notes

Running programs with AI in the loop.

Data Discipline · Jun 2026

Garbage in, gospel out

AI doesn't fix a dishonest system of record — it launders it into confident, polished fiction.

 Accountability · Jun 2026

When the agent does the work, who signs?

You can delegate the labor. You cannot delegate the signature.

 Governance · May 2026

The AI-augmented PMO: what actually changes

The 20% of the job AI can't absorb was always the entire job.

All field notes →

Every note is narrated · Listen on Spotify

Field Notes

One note a week, every week since May 2026.

Governance, reporting, program risk, and where the machine stops and judgment starts. Written from live enterprise programs. No pitch, no course, no funnel — just the writing.

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I learned program management before I had the term for it. As a U.S. Army leader — first an enlisted Infantryman (11B), later a commissioned Engineer Officer (12A) — I ran concurrent operations where the deliverables were people, the stakeholders were governments, and the variance you tolerated was zero. Two combat tours in Afghanistan taught me what an operating tempo really looks like.

After the Army, I founded Sapper Coding — a technology consultancy I bootstrapped from zero, ran for three years across multiple industry verticals, and exited through acquisition. Sapper, in the Army, is the soldier who clears the obstacles so the formation can move. That's still the work.

Today, I'm a Manager in KPMG's Transformation Delivery practice carrying director-scope accountability — concurrent multi-million-dollar engagements across government, financial services, and healthcare. I'm engaged by clients when programs are over-budget, over-deadline, or under-governed — when someone needs to walk in on day one, build the RAID log, run the PI Planning, set the cadence, and get the train moving.

That's the brand. Disciplined, plain-spoken, accountable for outcomes. No theater. No shelfware. Just programs that finish.

Now
Program rescue · AI-augmented delivery · Venture building
The Current Mission
2021 — Present
Senior Program Manager, Transformation Executive
KPMG US
2018 — 2021
Founder & CEO
Sapper Coding · Acquired 2021
2005 — 2018
Engineer Officer (12A) · Prior Enlisted Infantry (11B)
U.S. Army · Honorable Retirement
The Sapper Method

A simple operating model for programs that can't afford to drift.

Named for the Army discipline of clearing obstacles ahead of the main force. Diagnose the terrain, stabilize the system, deliver the mission — built for programs already in flight.

PHASE 01

Diagnose

Find the real failure points: governance gaps, stakeholder friction, unclear decision rights, schedule risk, vendor issues, and reporting noise. Day-one RAID build, stakeholder map, dependency audit — a written read of where the program is actually breaking, inside fourteen days.

PHASE 02

Stabilize

Reset the operating rhythm: governance cadence, executive reporting that tells the truth weekly, risk burn-down with named owners, escalation paths, and scope discipline. The program stops bleeding before anyone talks about acceleration — nothing accelerates inside chaos.

PHASE 03

Deliver

Drive execution through clear priorities, measurable progress, decision discipline, and transparent leadership. Release-train cadence, dependency choreography, accountability for outcomes — programs leave on schedule, under their resource plan, with the next leader trained on the runway.

Apply the Sapper Method to your program →
Select Engagements

Programs that moved the needle.

01 / 05
Financial Services
Merrill Lynch

Zero-downtime enterprise migration across 8+ vendor teams.

Orchestrated a platform migration impacting 2M+ end users. Coordinated release-train dependencies and rollback protocols across multiple vendor partners. Delivered ahead of schedule, under resource plan.

Read the case study →

$10M+ Follow-On
02 / 05
Government · State of California
CA Employment Development Dept.

$25M multi-year platform modernization serving 18M+ residents.

Agile delivery lead across security remediation, operational transformation, and UX improvements. Managed a 20-person distributed team and stood up the governance cadence the program had been missing.

Read the case study →

Multi-Year Expansion
03 / 05
Government · State of Florida
FL Agency for Health Care Admin.

$20M+ CMS-compliant Medicaid platform overhaul.

Led modernization across 10+ workstreams and 15+ stakeholder organizations. Stood up complete governance infrastructure compliant with Centers for Medicare & Medicaid Services (CMS) standards. Zero critical defects at go-live.

Read the case study →

Zero Critical Defects
04 / 05
Founder · CEO
Sapper Coding

Founded, scaled, and exited a technology consultancy.

Bootstrapped a technology consultancy from zero across a three-year run. Full P&L ownership across delivery operations, business development, and team growth. Delivered to clients across multiple industry verticals before exiting through acquisition in 2021.

Founder · Acquired
05 / 05
KPMG Advisory · Portfolio
Enterprise Governance Frameworks

Standards adopted across the broader engagement portfolio.

Established program governance standards, RAID frameworks, KPI dashboards, and Agile delivery playbooks that were adopted as standards across the broader KPMG engagement portfolio.

Portfolio Adoption
Areas of Practice

The work I'm known for.

Five disciplines that recur across every program I've carried — and how each one actually gets done.

PRACTICE 01

Fractional Program Director

Director-level delivery leadership on programs that already have a plan and still aren't moving. A weekly operating rhythm, executive reporting that tells the truth, and decision escalation that ends in decisions.

  • Weekly operating cadence
  • Executive reporting
  • Delivery team coaching
PRACTICE 02

Enterprise Program Rescue

End-to-end recovery of distressed multi-stakeholder programs. RAID frameworks, executive reporting, dependency mapping, and delivery accountability from day one.

  • Day-one diagnostic
  • Governance reset
  • Outcome accountability
PRACTICE 03

PMO Design & Governance

Building PMO infrastructure from the ground up — or maturing existing delivery functions. Governance playbooks, KPI frameworks, delivery standards, and executive reporting cadences that actually get used.

  • PMO charter & operating model
  • KPI dashboards & reporting
  • Delivery standards that stick
PRACTICE 04

SAFe Agile Transformation

Embedding Scaled Agile Framework (SAFe) inside enterprise organizations. Program Increment (PI) Planning facilitation, Agile Release Train (ART) standup, and coaching for waterfall-to-Agile transitions.

  • PI Planning facilitation
  • ART standup & RTE coaching
  • Team-of-teams enablement
PRACTICE 05

AI-Augmented PMO

Practical AI inside the delivery organization — reporting automation, RAID upkeep, and prompt libraries with governance built in. AI drafts; humans govern and sign.

  • AI workflow audit
  • Reporting automation
  • PMO prompt library & playbook
Also Building

Building while delivering.

Outside the day job I run Legion Implementation Group, an AI adoption and delivery-automation practice, and Atlas Moon Publishing. I've written The Claude Method, The 365 Method, and a series of practical AI field guides — same discipline, different surface.

Stack & Tooling

The instruments I run programs on.

Delivery & Reporting
Jira Confluence MS Project Power BI
Frameworks
SAFe PMBOK Lean Six Sigma
AI & Automation
Claude Microsoft Copilot Power Automate Make n8n
Certifications
PMP SAFe ACSM Six Sigma Black Belt
Recognition

Awards, badges, credentials.

Military · Decoration

Combat Infantryman Badge

U.S. Army

Military · Decoration

Meritorious Service Medal

U.S. Army

Military · Qualification

Air Assault · Airborne

U.S. Army

Leadership

David L. Clark Leadership Award

National Leadership Institute

Certification

PMP · SAFe ACSM · Six Sigma BB

PMI · Scrum Alliance · Six Sigma Academy

Education

MBA & MS Finance

Texas A&M University

Education

Executive Education

Harvard Business School

Military · Technical

Prime Power School Graduate

U.S. Army (52-Week Program)

Selected Feedback

In the words of the people I've delivered for.

The rare officer who could hold a complex operation together without burning the team out doing it. Plans like a staff officer, executes like a platoon leader, tells you the truth before you ask. The discipline travels.
Maj. Jacob L. · U.S. Army
Served under Loy when he was a platoon leader. The man's straight to it — no theater, no excuses, just the work. Soldiers knew it. Chain of command knew it. Whatever he's running now is in good hands.
SSG Ronald B. · U.S. Army (Ret.)
Briefing Documents

Take the file with you.

PDF · 2 pages

Executive Resume

Full record — Army leadership, founder exit, Big Four delivery, education, certifications.

Download Resume ↓ PDF · 1 page

Program Rescue Brief

Warning signs, the Sapper Method, representative results, engagement modes.

Download Program Rescue Brief ↓ PDF · 1 page

AI PMO Brief

What actually changes, engagement deliverables, stack experience, the operating rule.

Download AI PMO Brief ↓
Contact

Get in touch.

I read everything that comes in — notes on the writing, questions about how a governance problem was solved, or anything else worth a conversation. Fully remote, U.S.-based.

loy@loyokelley.com