For startup founders and CEOs
AI-native product and engineering leadership for startups
Strong product and engineering leadership that leans into AI: building with it, scaling with it, and making the company AI-native.
What I do
- 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.
- Work across engineering, product and program at once.
- Build the team up so dependency never grows on me.
Who this is for
- Startup founders and CEOs who want strong product and engineering leadership that leans into AI.
- 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 founder, CEO, or the head with the budget.
Who this isn’t for
- Organizations already funding a full greenfield AI team and leadership as their main path.
How AI fits
I lean hard on AI in how the work gets done. AI does the middle: status, synthesis, handoffs, first drafts. I own judgment, people, and the outcome. A person signs off on anything that goes out.
Field notes
Longer field notes live on AI Agent Management, a separate publication.
Where I’ve sat
I've held the IC seats in product and engineering, up through the executive seat. I'm currently leading AI enablement as a product and engineering executive.
How it starts
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.
At a glance
- Service
- Product and engineering leadership that leans into AI, for startups.
- Who it is for
- Startup founders and CEOs.
- Engagement
- We start with a conversation.
- Availability
- Open now for new engagements, as of October 2026.
- Location
- Irvine, CA, working with US startups remotely. Core hours 1–9pm PT (Pacific).
- Cost
- We work it out in the first conversation, scoped to the work.
- Contact
- rick@datasaa.com
Questions
What does AI-native mean here?
Building with AI, scaling with it, and getting the company's people and workflows to work that way.
Do you work with companies that aren't technical yet?
Yes. Companies outside tech, or only lightly technical, building their first real technical systems and teams. I've held that seat about three times.
How do you use AI on our work?
AI does drafting and synthesis. A person signs off on anything that goes out.
How does it start?
Email rick@datasaa.com with what you're building and where the company is today. Then we talk.
What does it cost?
We work it out in the first conversation, scoped to the work.
Related
Start with an email.
Building with AI, scaling with it, or turning the company AI-native? Tell me where the company is today.
Subject: “AI-native leadership - via datasaa.com/ai-native-product-engineering-leadership” (the link above fills it in).
Include
- what you are building, and where the company is today
- the team 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.