How I Help

I help startup leaders shape, prioritize, and execute their AI strategy. Three focused offerings, depending on where you are.

A bit about me. 20+ years in ML, PhD from MIT, 2x startup CTO. I've shipped AI in travel, digital rights, fintech, health, and insurance, and lived every failure mode along the way. More about how I got here →

Fractional Head of AI

AI leadership without the full-time hire. Strategic sounding board, roadmap and feasibility checks, staffing guidance, and investor support, embedded with your team.

What's Included

  • ✓ AI/ML strategy, roadmap, and architecture design
  • ✓ Hands-on guidance for building ML or GenAI-powered applications (agents, evals, prompt design)
  • ✓ Translating the latest ML & AI research into what matters for your team
  • ✓ Team coaching and unblocking
  • ✓ Board and investor prep
  • ✓ Hiring strategy for AI roles

Best For

  • → Teams building GenAI applications for the first time
  • → Startups without a senior AI leader
  • → Engineering teams that need clearer AI direction
  • → Founders preparing for fundraising
  • → Companies where AI experiments haven't shipped
Discuss This Option

AI Strategy Sprint

5 weeks

5 weeks to a clear AI strategy. Stakeholder discovery, competitive review, and a written strategy document your board and team can rally behind.

Deliverables

  • ✓ Written AI Strategy Document
  • ✓ AI opportunity assessment
  • ✓ Roadmap of product enhancements and new bets
  • ✓ Decision-making framework for evaluating AI opportunities
  • ✓ Board and investor-ready narrative

Best For

  • → Teams that need clarity before committing
  • → Founders prepping for a fundraise
  • → Companies exploring AI for the first time
  • → Boards asking "what's our AI strategy?"
Book a Sprint

Executive Coaching

Limited openings

1-on-1 coaching for technical founders and leaders, grounded in what I've learned as a 2x AI/ML CTO and from coaching CTOs through the hard moments. We work on the things that actually take up your headspace: the people decision you've been avoiding, the patterns that are making you grumpy, when to push and when to nudge, leading through tech and markets that won't sit still. You'll leave each session with more clarity, less noise in your head, and a couple of concrete things to try this week.

What We Work On

  • ✓ The hard people calls and tough conversations
  • ✓ Delegation, and building trust
  • ✓ Founder stress and the stories that drive it
  • ✓ Setting clear success criteria and building teams that consistently ship
  • ✓ Knowing when to ship an experiment vs. kill it

Best For

    I
  • → CTOs growing into the role
  • → AI/ML leaders whose roadmap depends on tech that's still moving
  • → Leaders looking for a perspective shift from someone who's been there

I take on a very limited number of coaching clients.

Inquire About Coaching

Frequently Asked Questions

What industries do you work with?

I'm vertical-agnostic. Current and recent work spans B2B SaaS, consumer marketplaces, and early-stage startups. The common thread is companies where AI is becoming central to product direction or fundraising.

What stage companies do you work with?

Seed to scale-up. At this stage, AI decisions have outsized impact, and the wrong direction can burn months of runway.

Do you write code?

Sometimes, but that's not the primary value. I focus on strategy, direction, and making sure your team is building the right thing in the right way. When needed, I can get hands-on with architecture and technical decisions.

How do we get started?

Book an intro call. We'll talk about where you are, what you're trying to accomplish, and whether there's a fit. No pitch, just a conversation.

Can we start with a Sprint and then move to Fractional?

Absolutely. Many clients start with a Sprint to get clarity, then continue with fractional engagement for execution. It's a natural progression.

What Clients Say

Founders and technical leaders I've worked with.

“Diana was a trusted advisor on a generative AI project where our team didn't yet have deep experience in the space. She set up our evaluation infrastructure, helped us think clearly about RAG, and coached our engineer through to a successful POC.”

Matt

CEO, Masterpoint

“I trust Diana as an advisor on the most difficult technical problems I encounter. She's a rare triple threat in terms of: the fundamentals and mental horsepower of a researcher, the pragmatic craft of a consummate engineer, and expert communication with a high content-to-word ratio.”

Gautam

Co-Founder and CTO

“Diana's empathetic approach to coaching made Diana a partner who helped me to be a confident leader by understanding and resolving technical, people and self-made blockers. Her understanding of management and technical skills helped us to navigate all types of challenges together.”

Balazs

Head of Engineering @ Superlinked

“Diana's biggest impact was introducing me to two mental models: One that I use daily to make high-stakes decisions, and the second that has helped me run a tighter execution cycle with my team. She stands out in her ability to introduce frameworks that dovetail with the context presented to her rather than merely cargo-cult or anchor to her past experience.”

Kao

CTO, Coverbase

Feeling stuck with your AI direction or execution?

Book some time to chat. No expectations, I'd love to hear about your situation.

Book an Intro Call