Program Management Insights
Notes on program management from 19+ years leading enterprise programs at Intuit, Atlassian, Adobe, Salesforce, Roku, and Apple. AI adoption, compliance governance, and growth strategy.
Leveling Up When You Already Use AI
If AI still feels slow or generic, the fix is usually habits and measurement, not a new model. How I build skills, what to focus on, and how to tell if AI is actually helping.
Setting Up an AI Executive Assistant
How I set up a personal AI executive assistant when I was new to the tools: context files, prompt structure, starter templates, and a first-week plan that actually sticks.
What Good Looks Like at the Staff TPM Level
Staff TPM is not a title. It is a set of behaviors that are visible before the promotion happens and that continue to compound afterward.
Program Health Versus Project Health
A program can be on time and still be unhealthy. The difference is in what you are measuring and at what level.
Working With Legal on Technical Programs
Legal reviews that happen at the end of a program are a tax on bad planning. The TPMs who get clean launches involve legal at the right points earlier in the process.
Running a Responsible AI Governance Program
Responsible AI is not an ethics exercise. It is a program management problem: getting AI products through internal review, external audit, and regulatory scrutiny without slowing the teams building them.
What Running a Payment System Migration Taught Me
The Roku payment gateway migration to Adyen was the hardest program I have run. The lessons are specific enough to be useful beyond payments.
Building the Business Case for an AI Program
How I translate model capability into dollars, risk reduction, and time saved so finance and product leadership can fund the program past the pilot phase.
Influencing Without Authority at Senior Levels
Influencing a VP or a C-level sponsor without a direct reporting relationship requires a different toolkit than influencing a peer team. The stakes and the dynamics are different.
When AI Fails in Production: A TPM Playbook
Hallucinations, latency spikes, and policy violations need the same discipline as any production incident. Here is how I run AI incident response without panic or cover-ups.
Building Institutional Knowledge as a TPM
The programs that survive turnover have their knowledge written down. The ones that don't restart from scratch every time someone leaves.
My First 30 Days on an AI Program
What I map, who I meet, and which decisions I force in the first month on a new AI initiative so the program does not build on the wrong assumptions.
Growing From Senior to Staff TPM
The jump from senior to staff is not about doing more of the same work faster. It is about a fundamentally different relationship to scope, ambiguity, and organizational influence.
Embedding AI in Workflows People Already Use
The fastest path to AI adoption is not a new app. It is meeting users inside Slack, Jira, CRM, or the admin console they already open every day.
The Program Charter: What Belongs In It
A program charter is not a scope document or a project plan. It is the contract between the program and its stakeholders about what is being built, why, and how success is defined.
Evaluating AI Vendors, Models, and Build vs Buy
A TPM framework I use to compare foundation model vendors, integration partners, and in-house builds before the organization commits to a date.
Running a Pilot Before Full Rollout
A pilot is not a soft launch. It is a structured experiment designed to answer specific questions before the answers become expensive to change.
Phased Rollout for Enterprise AI Features
How I sequence AI feature rollouts from internal dogfood to general availability without losing control of risk, telemetry, or executive confidence.
Managing Technical Debt as a Program
Technical debt managed as a list of tickets goes nowhere. Technical debt managed as a program with scope, milestones, and executive visibility gets funded and resolved.
How to Scope a Multi-Year Roadmap
A multi-year roadmap is not a twelve-month plan extended. The further out the horizon, the more the document is about principles and bets, not milestones.
Onboarding a New Team Mid-Program
Adding a new team to an active program is one of the more disruptive things that can happen to a timeline. Done well, it accelerates. Done poorly, it costs more than the capacity it adds.
Security Program Management
Security programs fail not because the security requirements are wrong but because they are treated as a track separate from the engineering program. Integration is the job.
Running a Privacy Engineering Program
Privacy engineering is not a legal exercise. It is a program management problem: getting engineering teams to design for data minimization before the feature is built, not after the audit.
The Portfolio Review That Helps Leadership Decide
Most portfolio reviews are program status reports stacked on top of each other. A review that helps leadership decide something looks completely different.
Data-Driven Program Reporting
Status reporting based on vibes and verbal updates tells leadership what the team believes. Reporting anchored in data tells them what is actually happening.
Setting Up a Program Office From Scratch
A new program office is a blank sheet and a political minefield simultaneously. The first 90 days determine whether it becomes infrastructure or overhead.
Building Trust With Engineering Leads
Engineering leads extend trust to TPMs who understand the technical constraints and protect the team from noise. Everything else is secondary.
How to Handle a Missed Deadline
Missing a deadline is a recoverable event. How you handle it in the first 48 hours determines whether it stays recoverable.
Multi-Region Launch Management
Launching in multiple regions is not launching once and repeating. The complexity is in the differences, and the differences are almost never obvious until you're in them.
Vendor Management for Technical Programs
Vendors are not internal teams and cannot be managed the same way. The patterns that work for internal dependencies fail with external partners for structural reasons.
Retrospectives That Actually Drive Change
Most retrospectives produce a list of things to do differently and change nothing. The format is not the problem. The follow-through is.
Managing a Program Through a Reorg
A reorg mid-program is not an exception. It is a recurring condition. The programs that survive them have a few things in common.
How a TPM Uses the RFC Process
Most TPMs sit outside the RFC process and wait for the output. The ones who influence technical direction are inside it, asking the right questions at the right time.
Cross-Functional Alignment Without Authority
TPMs get things done through people they do not manage. The influence toolkit that actually works looks nothing like what they teach in leadership courses.
How to Write an Executive Brief
An executive brief is not a summary. It is a decision document. The distinction changes how you write it and what it produces.
Building a Tiger Team
A tiger team is not a task force. It is a small, named group with a specific problem, a deadline, and authority to decide. Here is how to stand one up and wind it down.
The Workback Plan Done Right
A workback plan built from a launch date backward tells you whether the date is real. Most TPMs build them forward and miss what the plan is trying to tell them.
How to Run a Program Kickoff That Actually Works
Most program kickoffs produce a shared calendar invite and little else. Here is how to run one that produces shared understanding.
What 19 Years Across Seven Companies Taught Me About Programs
Intuit, Atlassian, Adobe, Salesforce, Roku, Apple, and a startup. The patterns that held true everywhere, and the one that surprised me.
Saying No: Scope Control as a Core Skill
Every program accumulates scope it never agreed to. Protecting the outcome means saying no well, and often.
The Critical Path Is a People Problem
The textbook critical path is about task sequencing. The real one runs through which people can actually decide and deliver.
Dependencies Across Eight Engineering Teams
Lessons from running the Einstein AI portfolio at Salesforce across eight research and engineering teams on different clocks.
Program Health Dashboards: What Belongs on Them
A dashboard that shows everything shows nothing. Here's what earns a spot and what should be cut.
How to Scope an Ambiguous Executive Ask
"Make us faster" isn't a program. Turning a vague executive ask into something deliverable is half the job.
Risk Registers People Actually Use
Most risk registers are written once and never opened again. A living one looks different and does real work.
Managing Up: How to Partner With a C-Level Sponsor
A senior sponsor is the most powerful lever a program has, and the most commonly wasted. Here's how to use one well.
The Weekly Operating Rhythm That Scales
Programs don't fall apart in the planning. They fall apart in the weeks between. Here's the cadence that holds them together.
Onboarding Onto a Compliance Portfolio Without Slowing Engineering
Taking over a regulatory portfolio means getting fluent fast without becoming the bottleneck you were hired to remove.
Aligning Two AI Roadmaps: Rovo and Gemini
Integrating with another company's AI framework is a program problem wearing a technical disguise. Notes from aligning Rovo with Gemini.
Scaling a Candidate-Matching Platform to 65 Million Records
Founding TPM lessons from building a recruiting platform that scored 65M candidates in under ten seconds across 50,000 clients.
Real-Time Data: Moving 100+ Attributes Off the Nightly Batch
Batch processing quietly caps what a product can do. Moving tax attributes to real-time publishing at Intuit removed that cap.
Metrics That Matter Versus Vanity Metrics
A number that always goes up and never forces a decision is decoration. Here's how to tell a real metric from a comfortable one.
Bundling Strategy Through a Program Lens
A bundle looks like a pricing decision. Delivering one is a cross-functional program that touches engineering, billing, and GTM at once.
When to Kill a Program
Knowing when to stop is a core program management skill and almost nobody trains for it. Here's how I make the call.
Managing $200M in Discount Allocation
A large discount budget is a system with leverage points. Manage it like one and small changes move large numbers.
AI Governance: Making Compliance Real for ISO, SOC2, and HIPAA
AI features ship fast. Compliance frameworks move slow. The TPM's job is to make them move together without faking either one.
Stakeholder Mapping for Cross-Functional Programs
Knowing the org chart isn't knowing your stakeholders. The map that matters tracks influence, interest, and who can kill your program.
How to Run an Experiment Program That Doesn't Lie to You
Most experimentation programs generate confident, wrong conclusions. Here's how to build one whose results you can trust.
A Six-Hour Migration in Fifteen Minutes
Modernizing a forecast system at Apple turned a six-hour migration into fifteen minutes. The win wasn't speed. It was what speed unlocked.
Cutting Partner Inbound by 90 Percent: Process Design at Roku Pay
When partners flood you with the same requests, the volume isn't the problem. The process that generates it is.
The Pre-Mortem: Finding the Failure Before It Finds You
A postmortem explains a failure after it costs you. A pre-mortem catches it while it's still cheap. The format takes one hour.
Why Most OKRs Fail, and the Fix
OKRs don't fail because the framework is bad. They fail because teams write aspirations and call them outcomes.
M&A Integration Governance: What I Learned in Adobe's PMO
Acquisitions don't fail at the deal. They fail at integration. Notes from running a reconciliation track inside Adobe's M&A PMO.
Growth PM in Practice
The mechanics behind scaling a funded account portfolio 4x: what changed, what broke, and what a TPM actually controls in a growth motion.
Decision Logs: Underrated TPM Tool
Half the meetings on a program re-litigate decisions that were already made. A decision log ends that for almost no cost.
Compliance PM Playbook
How to build a regulatory issue lifecycle framework that sticks, from triage to CCO reporting to 96%+ on-time closure.
Enterprise AI Adoption at Scale
What it actually takes to move AI adoption numbers at enterprise scale, from instrumenting telemetry to navigating the politics of feature rollouts.
Building Escalation Paths With Teeth
An escalation path nobody fears is decoration. Here is how to design one teams actually respond to.
Status Reports Executives Actually Read
Most status updates are written to cover the writer, not inform the reader. Flip that, and a VP will actually read your update.
My First 30 Days on a New Program
A field guide to the first month on an unfamiliar program: what to map, who to meet, and the trap most people fall into.
PM to TPM: What Actually Changes
Moving from project manager to technical program manager? Scope, skills, and day-to-day work shift more than the title. A practitioner's view.
Program Management Tools
A small set of program management tools I offer to the TPM community. They run in your browser with no signup: the RACI Matrix Generator for who owns what, the Program Risk Register for scoring and tracking risk, and the Stakeholder Power/Interest Grid for deciding who to keep close. Each one exports to CSV or print.
For the TPM career path, see the Technical Program Manager salary guide, a set of real TPM interview questions, and a plain-English program management glossary.
Guides
New to the discipline? Start with the complete guide to program management or how to become a technical program manager. Browse the types of programs and projects for migration, launch, compliance, security, and more. For quick role distinctions, see TPM vs project manager and TPM vs product manager.
Advisory & Consulting
Available for TPM Advisory Engagements
Beyond full-time roles, I take selective advisory engagements where a senior technical program manager can accelerate a specific outcome: standing up a compliance framework, unblocking an AI adoption initiative, or restructuring a growth program that has stalled.
If your team needs an experienced enterprise program manager for a defined problem, get in touch.
Contact for Advisory →