I'm Gerald Ashby. I build and lead product organizations that turn emerging technology into portfolios with real business growth and real customer value. Over 15+ years I've grown small teams of PMs into a large org spanning multiple product lines, and I've owned outcomes as a GM, CPO, and platform leader — P&L, pricing, and adoption, not just roadmaps. For the past several years that's meant enterprise AI/ML platforms — core agents, agent frameworks, retrieval, evals, and governance — with a focus on turning a working set of AI capabilities into a true platform: reusable, self-service, and extensible rather than rebuilt by every team that needs it. Currently Director of Product for AI and Platform at Ivanti, after Mastercard, UHIN, MX, Adobe, and LANDESK. Below is the detail — case studies, a career timeline, and essays on how I lead.

A short version of what I actually do, and what I optimize for day to day.
Two threads run through fifteen years of this. The first is technical: take raw, messy data — card transactions, healthcare claims, endpoint telemetry, model output — and turn it into something a business will pay for and a customer will trust. That one runs from security software at LANDESK through Adobe, MX, Mastercard, and now Ivanti.
The second is the one I've come to care about more. I've built the product function where there wasn't one — as CPO at UHIN, standing up the practice and the operating cadence from zero. I've turned an engineering-led org into a product-led one by putting PM, design, and engineering into customer conversations together instead of handing them a backlog. And I've coached product managers through the gap between running a backlog well and owning a strategy, including one who made Director on the strength of the discovery skills he didn't have when we started.
What I lead now is platform work, and platform work is its own discipline. A shared AI capability isn't finished when it works. It's finished when another team can adopt it faster than they could rebuild it — which makes developer experience, golden paths, and self-service onboarding part of the product rather than something you get to afterward. I'm hands-on about it: I'd rather prototype with agentic tooling than describe what I'd like someone to build, and I'd rather let eval evidence settle an argument than a well-made slide. A lot of my recent thinking is about what that changes for how teams work — it's in the writing.
“Empowerment without context isn't trust. It's abandonment with better branding.”
I run teams on the product operating model as Marty Cagan and SVPG describe it in INSPIRED, EMPOWERED, and TRANSFORMED. The last six years have been a test of which parts of it survive contact with AI. Most of them do.
I arrived at Ivanti with no AI strategy and real debate about pace. I didn't start from the technology — I started from insight, and force-ranked every candidate against workflow value, defensibility, and a real path to monetization. Nothing shipped because it was AI. It shipped because a workflow someone already performed got measurably better.
A trio gets the problem and the context, not a feature list — and agentic tooling makes a working prototype cost an afternoon. That quietly changes what a prototype is for: it stops being a delivery artifact and becomes the instrument the team discovers with. I'd rather hand a team a running thing to argue with than a document to agree to.
Value, usability, feasibility, and viability all still apply — they just look different. Feasibility stops being “can we build it” and becomes “does it work reliably enough, often enough.” Viability picks up cost per call and whether governance will actually permit it in a customer's tenant. Answerable questions — but not by opinion, which is why the platform underneath has to make them measurable.
It doesn't change what a product team is for. Using AI to aggregate requests, generate roadmaps, and write PRDs faster doesn't move a team to the product model. It runs the project model at a higher frame rate — Cagan calls that product management theater, and the label is deserved. Outcomes over output survives the technology change completely intact.
It does change the cost of being wrong. When discovery evidence takes an afternoon instead of a quarter, the honest move is to raise how often a team is willing to be wrong in private, not to ship faster in public. Most of what I've built at the platform layer — evals, traces, an agent framework teams don't each rebuild — exists to shorten that loop for everyone else.
It changes where the coaching bottleneck is. Cagan's recent argument is that a foundation model can serve as a personal product coach, and for craft — sharper problem framing, better eval design, an honest critique of a strategy doc — I think he's right, and it's genuinely democratizing. What a model can't supply is strategic context or the organizational cover a PM needs to make a real decision. Nor does it make a team ready to be empowered; empowerment is an outcome of coaching, not a substitute for it. That part was always the leader's job and still is.
“The operating model doesn't change because the product is AI. What changes is how fast a team can find out it's wrong.”
Running that operating model on AI, at three companies, kept producing the same three answers. They're now how I sequence platform work.
Platforms built on guesses solve imagined problems. At Ivanti the first thing out the door was a small natural-language query builder — and the gaps it exposed are what justified the agent framework and the evals layer underneath it. The shared layer gets built against evidence a room full of engineers already agrees on.
For AI products, quality has to be measurable before it's shippable. Pass rates and traces move acceptance left, so teams design against a known bar instead of discovering it during a late review that nobody has time to act on.
Identity, auditability, and reversibility aren't compliance work you bolt on at the end. In enterprise AI the question is never only “can the agent do this” — it's on whose behalf, with what permissions, and whether you can see and undo it afterward.
Put PM, design, and engineering into discovery calls together, reprioritized around what customers would actually pay for — and killed the CPO’s favorite project when the evidence said to.
No AI strategy on arrival. Shipped one small feature first, then used the gaps it exposed to justify the agent framework, evals layer, and governance underneath it.
Led PMs and cross-functional partners on predictive signals from messy transaction data — and resolved a regex-versus-ML standoff by giving each approach the half of the problem it was best at.
Vision and multi-year strategy, empowered team topology, continuous discovery, outcome-based goals, product operations and cadence, PM coaching and career development, standing up the practice where there isn't one.
Core agents and agent orchestration, agent frameworks, RAG and retrieval, MCP-era integration, evals and observability, governance and multi-tenant safety, agentic prototyping.
Developer experience and golden paths, APIs and SDKs, self-service onboarding, reuse and adoption, data pipelines and system-of-record layers, usage- and outcome-based pricing, ROI and willingness to pay.
Cagan and Torres are both arguing for the same thing underneath: decision rights have to move. Where that holds in enterprise B2B, and where it doesn’t.
Teams lose to undecided things far more often than to wrong decisions. Vision concrete enough to settle an argument, strategy tactical enough to disqualify work.
The 1:1, career development, and performance management have different horizons and different owners. Merging them into one meeting degrades all three.
An AI feature without an eval set isn’t untested — it’s unspecified. Why the cases, the grading, and the bar belong in the spec.
I'm always happy to talk shop — moving a team to the product model, what discovery looks like when the prototype is free, agent frameworks and evals, or an AI roadmap you're not sure you believe anymore.