"Help me with this."

CTO Deep Dive

90 minutes. One problem. Worked through until you have a decision.

You've been going back and forth on a decision for weeks. Maybe months. You've read the blog posts, asked ChatGPT, polled your network. Everyone has an opinion. Nobody has context.

You need 90 minutes with someone who has made this call before.

Book a Deep Dive, $600

Not sure this is the right fit? Book a free 20-minute diagnostic call first.

What You Get

90 Minutes on Your Problem

No group. No slides. We work through your situation, with your constraints, and come out with a plan.

Experience, Not Theory

27 years of building, breaking and fixing systems. Fortune 500s and two-person startups. I've seen what works and what blows up.

A Decision and Next Steps

You leave with a call made and steps you can take on Monday. Not more questions. Not "it depends."

People Book This For

  • Rewrite or refactor? When to push through and when to start over. (Usually push through.)
  • Architecture decisions. Monolith or services, database choices, what breaks at 10x.
  • Technical debt. You have 47 things on the list. Which two matter.
  • Engineering velocity. Why the team is slow and whether the devs are the reason.
  • AI risk. What AI-written code is safe to ship and what will cost you six months later.
  • Hiring. Is this candidate senior? How do you run the interview?
  • Vendors and dev shops. Is this proposal sane? Is this team any good?
  • A second opinion. Before you sign off on something expensive.

$600

One 90-minute session. No ongoing commitment. Pick a time that works.

Book Your Session

Payment handled securely via Stripe at booking.

Decide you want this every week? Start Advisory within two weeks and the $600 comes off your first month.

Have more than one problem, or want me in the room?

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