For startup founders and CEOs
Product and engineering leadership for startups going AI-native.
I help founders and CEOs build with AI, scale with it, and make the company AI-native. I also run AI enablement for the team you already have, and cover open leadership seats while you hire.
I've held the IC seats in product and engineering, up through the executive seat.
What I do
Three ways to work with me
For startup founders and CEOs
AI-native product and engineering leadership
Strong product and engineering leadership that leans into AI: building with it, scaling with it, and making the company AI-native.
- Lead product and engineering as a player-coach: execution, people, the release bar, and judgment on the hard calls.
- Build with AI and scale with it, in the product and in how the team works.
- Help turn the company AI-native, starting with the people and workflows you already have.
For existing teams
AI enablement for the team you already have
I help the people you already have work faster with modern tooling, and get the company's people and workflows AI-native, without standing up a whole new AI organization.
- Help the people you already have work faster with modern tooling.
- Grow how the team uses AI while the current work still ships.
- Get the company's people and workflows AI-native.
For companies with an open seat
Interim seat coverage while you hire
You keep the search. I cover the seat you've posted so the work does not stall, then I hand it to your hire.
- Technical Program Manager
- Head / VP of Product Engineering
- Engineering Manager
- Product Manager / Head of Product
- AI lead
Running a critical software build and hiring a TPM for it? I’ll send a sample delivery timeline for your build: the milestones that protect your date, what each one depends on, and how I’d keep it on track. It is a sample of the work before any engagement. Request a sample delivery timeline.
How I use AI
AI does the middle. I own judgment, people, and the outcome.
- AI does drafting and synthesis. Status, synthesis, handoffs, first drafts.
- A person signs off on anything that goes out. Nothing goes out on AI alone.
I lean hard on AI in how the work gets done.
Longer field notes live on AI Agent Management, a separate publication.
Where I’ve sat
I work across engineering, product and program at once.
My approach is to empower the team so dependency never grows on me.
- Now
- Currently leading AI enablement as a product and engineering executive.
- Previously
- Allergan Data Labs, Ruggable, Cypress Creek Renewables, ADP, Syncromatics, Cornerstone OnDemand and Kareo: IC seats in product and engineering, up through the executive seat.
- Results
- Promoted senior engineers into lead, staff and manager roles. Stabilized and grew an engineering team while cutting critical application disruptions. Brought an external contracting team in-house and rebuilt a monolith as Node.js microservices on Kafka. Brought predictability to a multi-product cloud ERP-integration program.
- Education
- UCLA, BS Computer/Electrical Engineering.
- Recommendations
- What people I've worked with say, on LinkedIn.
Who this is for
- Startup founders and CEOs who want strong product and engineering leadership that leans into AI.
- Teams that want AI-driven productivity gains without funding a whole new AI team. I help the people you already have work faster with modern tooling.
- Mid-market companies with a critical software initiative underway — a migration, a replatform, a new platform build, a funded program — where an open seat slows delivery or costs budget.
- Companies outside tech, or only lightly technical, building their first real technical systems and teams. I've held that seat about three times.
- Written for the owner, founder, VP or head with the budget.
Who this isn’t for
- Companies that only want another full-time employee and have no appetite for coverage.
- Organizations already funding a full greenfield AI team and leadership as their main path.
I take a small number of engagements at a time.
How it works
Every engagement starts with an email
You email me
What you are building or which seat is open, where the team is today, and any hard date.
We talk
Advice first: what's slipping, the initiative behind it, and what it is costing you.
A time-boxed trial
A clear window, one plain success check you already care about, and what I need from you: access, intros, time.
Continue, or stop cleanly
If it works, the work continues on agreed terms. If it does not, it stops cleanly.
Questions
All questionsWho do you work with?
Startup founders and CEOs first, on product and engineering leadership that leans into AI. Then existing teams that need AI enablement, and companies with an open leadership seat.
Do we have to stop our search?
No. You keep searching. I cover the seat in the meantime.
Is this a full-time hire?
No. It's coverage while you hire. I take a small number of engagements at a time.
What does it cost?
We work it out in the first conversation, scoped to the work.
How do we start?
Email rick@datasaa.com with what you're building or the seat that's open, the initiative behind it, and your date.
Do you work remotely?
Yes. I'm based in Irvine, CA, and work with US startups remotely. Core hours are 1–9pm PT (Pacific).
How do you use AI on our work?
AI does drafting and synthesis. A person signs off on anything that goes out.
Start with an email.
Building with AI, scaling with it, or turning the company AI-native? Tell me where you are. If a seat is open instead, tell me which one.
Subject: “Product and engineering leadership - via datasaa.com” (the link above fills it in).
Include
- what you are building, or the seat that is open (and the job post link, if it is posted)
- where the team is today and what is slipping
- any hard date (launch, migration cutover, board, hire)
- who owns the budget for it
I reply by email within one business day. Core hours 1–9pm PT (Pacific). There is no form and no booking link.