Darryn Cooke

Technical Program Manager who builds AI people can trust.

I run $1M–$10M+ technology programs across a four-hospital health system, and I design and ship AI products of my own. My focus is the gap between "the AI can do it" and "we can rely on it."

Darryn Cooke smiling, in front of a neon synthwave sunset
  • 20years enterprise delivery
  • $1M–$10M+programs
  • 500+system integrations
  • 3AI reports in production

About

I've spent 20 years where technology meets the business: running client implementations for a compliance software company, selling enterprise software, and now leading Workday, UKG, and StrataJazz programs across a four-hospital health system. The common thread is getting complex systems live, with people who don't report to me, against deadlines that don't move.

In 2026 I started building with AI myself. Not to become an engineer, but to learn what it takes to make AI dependable enough for finance, healthcare, and compliance work. ReportForge is the result. You get a program manager who has shipped AI hands-on and knows where it breaks.

Off the clock, I've spent 15 years officiating high school and college basketball: fast calls, under pressure, with everyone watching.

Work

Case study 1ReportForge

Problem
AI can write a financial report in seconds, but it will sometimes invent a number. In finance, one made-up figure ruins trust in the whole report. That's the main thing holding companies back from using AI for real work.
What I built
A reporting product where every number the AI writes is checked against the source data before the report goes out. Each figure passes four checks: is it sourced, is anything missing, is the math right, are the names right. Numbers that can't be verified get flagged or blocked, and each report gets a 0–100 trust score instead of a black-box pass/fail.
Keeping it honest
I built a test harness that deliberately tries to trick the AI into making things up. If the trust score drops, the build fails.
The product call
I first built it to handle dozens of report types. Once the verification engine was proven, I cut the scope to three finance reports done well: flux analysis (why numbers changed), budget vs. actual, and price-volume-mix (what drove revenue up or down). Narrowing it was the hardest and best decision on the project.
How it was built
Solo, with AI as the developer and me as product manager. That meant a ticketed backlog, a Strategist → Critic → Planner review step for big design decisions, roughly 3,000 automated tests, and security reviews.
Built with
  • React
  • Node
  • Supabase
  • Claude API
  • Vercel + Railway
Visit ReportForge →

Case study 2AI Job Evaluator

Problem
A serious job search is a pipeline problem: dozens of postings, each needing an honest fit assessment and tailored materials.
What I built
An open-source tool that helps job seekers use AI to evaluate postings honestly instead of applying to everything. You set your criteria once. AI then scores each job on fit and odds, explains its reasoning, and splits the requirements into what you meet, what you don't, and what you could close. It drafts tailored materials for the roles worth pursuing.
Why it matters
I've run my own search through it, 37 roles so far. It's the pattern I bring to any team: define the rules clearly, let AI handle the volume, keep a human on the final call.
View on GitHub →

How I can help your team

Run your AI rollout like a program

Scope, risks, adoption, and the executive story that keeps it funded.

Prototype fast, then make it dependable

Build a working version to prove the value, then scope the real build with engineering.

Put guardrails on AI output

Add verification and review steps, so teams in regulated work can trust what AI produces.

Experience

Senior Technical Program Manager

Albany Medical Center 2023–present

Lead concurrent enterprise programs, $1M–$10M+, across a four-hospital health system, and was given larger, higher-risk programs each year.

  • UKG Workforce Management: leading 7 of 11 workstreams, 150+ participants, seven-figure budget.
  • StrataJazz Cost Accounting: 200+ integrations across four hospitals, delivered on schedule.
  • Workday Supply Chain & Finance: took over 90+ integrations as a new hire, including the highest-risk ones, and drove them to a clean go-live.
  • Epic Willow: authored a seven-figure business case that leadership adopted.
  • Run the operating rhythm: plans, risk and issue logs, decision records, and executive status reporting.
  • Coordinate clinical, IT, finance, HR, supply chain, and vendors, none of whom report to me.

Technical Support Manager / IT Operations

MyComplianceOffice 2014–2020

  • Led global support and client implementations for a compliance platform used by banks and investment firms.
  • Managed a team of 5 across the US, Ireland, and Hong Kong, with 96%+ client satisfaction.
  • Built the client portal, documentation library, and training program from scratch.

Enterprise Software Sales

IgniteTech & Uzabase 2021–2022

  • Worked enterprise deals end to end with executive, legal, and technical stakeholders. It taught me the buyer's side of every implementation I've run since.

Digital Marketing & CRM Leadership

2002–2014

  • Led full Salesforce and Microsoft Dynamics implementations, from requirements through user adoption.

Education · BA, Economics, UC Irvine

Skills

Prefer to blast them? Each one comes with proof.

Program delivery

  • Enterprise program management
  • Multi-workstream delivery
  • Risk, issue & dependency management
  • Executive reporting
  • Business cases
  • Vendor coordination
  • Agile & waterfall

AI & building

  • AI product delivery
  • LLM applications (Claude API)
  • AI verification & guardrails
  • Test harnesses
  • AI-assisted development
  • Rapid prototyping

Platforms & tools

  • Workday
  • UKG
  • StrataJazz
  • Salesforce
  • Microsoft Dynamics
  • Jira
  • Smartsheet
  • MS Project
  • Confluence
  • Supabase
  • Vercel

How this site was built

I designed this site with Claude as my product and design partner, and Claude Code wrote and deployed every line. This is how I work now.

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