Regista — Product & AI strategy advisory
Someone has to set the tempo.
25 years leading product in PE-backed vertical SaaS — Vista, Roper, Luminate, Francisco Partners
In soccer, that's the regista — the deep-lying playmaker who orchestrates the game without ever crowding the goal. In a company, that orchestrator is the product organization. I help investor-backed and founder-led software companies make the high-stakes bets that decide where R&D capital compounds instead of leaks — and I leave their teams able to keep making those bets without me.
01 — The problem
The problem I see
Most product organizations play like defenders. They react — to the loudest or most recent customer escalation, to the next big deal on the table, to whatever the last board meeting surfaced. Effort gets spread evenly across everything, which feels responsible but never produces differentiation.
That was survivable when building the actual software was the constraint. It isn't anymore. Engineering capacity expanded materially in late 2025 — AI reduced the cost of building and decreased the time to ship. Almost no product organization retooled its decision-making to match. The result is a company that can now build twice as much of the wrong thing, twice as fast. That gap is where R&D capital leaks, quietly and quickly.
AI has raised the stakes on every product bet, and introduced three failure modes I now see consistently:
Teams automate their own judgment.
In the rush to put AI everywhere, product teams quietly and unintentionally hand the decisions that used to define their product over to a model — and lose the very thing that made them distinct.
Teams automate the customer's decision.
Sometimes the judgment you're removing isn't yours to remove. Automate a choice the customer wanted to keep and you don't save them work — you take away their ability to differentiate, and they feel it.
Teams let variable cost become the conversation.
When a customer starts scrutinizing the token consumption, that's the tell: the value isn't landing. Priced and delivered right, the variable cost of an AI capability never comes up — because what it produces is obviously worth more than what it consumes. Get any of these wrong, and you don't just lose your differentiation — you take it from your customer too.
Underneath all three is the same operating-model gap: knowing which bets matter, sizing their feasibility, usability, viability, and value honestly, and refusing to spread effort evenly across every bet. Get that right and R&D spend compounds. Get it wrong and it leaks — and nobody sees it on a P&L until the growth rate does. The player who makes the biggest impact in compounded value is the regista — by reading the whole field and deciding where the play goes. That is what I do.
02 — How I work
How I work
I work as an embedded product operator, not a framework. I work alongside your team, not over it. I'm not known for building features. I'm known for making product organizations decide better and faster — which is where R&D dollars either compound or leak. What changes outcomes is someone who has personally made these calls, working directly with your team, making them again, and building the durability for the team to make the next one alone.
Discover
Understand the business, the bets on the table, and how consistently the product organization is making them well today.
Diagnose
Find where judgment is being spread thin, handed off too early, or lost.
Design
Define how the team decides: which bets, in which categories, weighed against feasibility, usability, viability, and value.
Deliver
Work alongside the team, and transfer the capability so it sticks. Making durable bets isn't just better product — it's the difference between R&D that compounds into enterprise value and R&D that quietly leaks.
COMING INTO FOCUS
The Durable AI Capability Index (DACI)
A focused diagnostic taking shape — built to evaluate how a product organization makes its highest-stakes AI-era bets, across strategy, org structure, process, tooling, and talent, and hand back a clear, prioritized view of where durable capability exists and where it's missing. A small, well-defined engagement — enough to know if it's worth going further. If that sounds like where you are, let's talk directly — the engagement gets built around your specific problem, not a fixed template.
03 — Who I work with
Who I work with
I'm most useful to software companies at an inflection point in how their product organization operates — often investor-backed and many times founder-led, sensing that the operating model behind their product decisions won't carry them through the next stage. Growth and margin both run through that operating model. A Rule of 40 company doesn't become a Rule of 70 company by spending more on R&D. It becomes one by investing R&D on better bets, more quickly.
Operating partners at PE, venture, and growth-equity firms
who need a senior product operator embedded in a portfolio company — someone who does the work and builds the team and its leaders, not someone who shouts advice from the sideline. Especially useful where the firm doesn't carry a dedicated product bench, or where a platform has grown by acquisition and now runs four product teams with four operating models and no way to allocate R&D across them.
CEOs and founders
whose product organization has outgrown its operating model and who know the next set of bets are too big to get wrong.
Product leaders
who want a peer who's actually sat in the seat — through scale, through change, through exits — to think and act right along with them.
04 — About
About
I'm Jon, and REGISTA is how I do this work now.
For more than 25 years I led product at vertical SaaS companies, almost entirely private-equity backed — Vista, Roper, Luminate, and Francisco Partners lineage. Most recently I was Chief Product Officer at JAGGAER, Vista's procurement platform, where the mandate was AI transformation across the product organization.
I've been the executive responsible for strategy, for the roadmap, and accountable for the bets that determined whether the business grew or stalled. I've taken companies through scale and through multiple successful exits. I've made the hard call, convicted by the data, to sunset a product line to concentrate the roadmap where differentiation actually compounds. I've rebuilt decision-making in teams that were automating their own judgment without realizing it. I've sat in the rooms where a single high-stakes bet reshaped the company. And I've built teams that kept making good bets after I moved on.
The regista — the deep-lying playmaker who sets the tempo — is the role every great product organization plays on behalf of their company. It's the one I play for the companies I work with. You get a senior operator directly. Not a brand-name firm that bills senior and staffs junior. Just me, 25 years of having actually done the job, and the commitment to build the operating model that outlasts me. I take on a small number of engagements at a time.
05 — Let's talk
Let's talk.
If your product organization is making bets too big to get wrong, let's talk about them directly. No pitch deck, no process — just a conversation about what you're deciding, where your R&D is actually going, and whether I'm the right person to help.