AI Advisory

The pilot ran. Nothing changed.

Most companies have already started: Copilot seats, a chatbot demo, an agent somebody built over a weekend. Few can say what any of it did for the business. I'm a senior engineer who builds with these tools every day. On retainer, I tell your team which few bets are worth making this quarter, then help you ship them.
Month to month, from $5,000. Both tiers are priced below.

The tools work. Choosing is the hard part.

The models get better every few weeks. Deciding where they belong in your business doesn't get easier: which workflows to rebuild, what to buy, what to build, and what quietly breaks when the model is wrong.

That takes someone who has shipped AI into production and cleaned up after it: one senior person your team can bring a hard question to, any week, and get a straight answer with the reasoning behind it.

What you get every month

Both tiers include all six. Embedded adds a weekly cadence and hands-on work in your repos.
01

The opportunity map

In month one I learn how your teams actually work and hand back a ranked list: where AI saves real time, what it costs to get there, and what it puts at risk. Expect most of the list to be things you decide not to do.

02

Working sessions

Scheduled time with your engineers, your leadership, or both, on whatever is live. Architecture reviews, build-or-buy calls, model selection, the agent design nobody is sure about.

03

Async access

Ask between sessions and get an answer from me, usually the same day. The questions that matter tend to show up on a Tuesday afternoon, not in the monthly meeting.

04

Vendor and tool calls

Copilot or Claude Code, which agent platform, whether that vendor's demo survives your data. I take no reseller margins or referral fees, so the answer isn't for sale.

05

Guardrails before scale

Where your data goes, which keys live where, what an agent is allowed to touch. The unglamorous controls that keep an AI feature from turning into an incident.

06

A path to building it

If the map says build, I can build it at a fixed price, scoped separately, in your repos. Or take the map to your own team. Either way, it's yours.

Two retainers, priced in public

Month to month. No annual contract, no termination fee, thirty days' notice either way. For scale: a full-time senior hire who can do this runs $250K+ a year before equity, and takes months to find.
For teams that need direction

Advisor

$5,000/ month

You have capable engineers. What you're short on is someone who has already made the expensive mistakes with these tools and can tell you which bets are worth making.

Every month:

  • The opportunity map in month one, revisited as things change
  • Two working sessions with engineering, leadership, or both
  • Async access between sessions, answered by me, usually same day
  • Vendor, model, and build-or-buy calls

Month one is the map. If it says you don't need a retainer, I'll tell you and we stop there.

For teams putting AI into the product

Embedded

$9,000/ month

AI is going into what your customers touch, and a wrong architecture call costs you quarters, not sprints. This is the forward deployed engineer tier.

Everything in Advisor, plus:

  • Weekly working sessions instead of twice a month
  • Priority async access, in your Slack if you want me there
  • Hands-on review in your repos: PRs, agent design, evals
  • Pairing with your engineers on the hard paths
  • Roadmap work with leadership on the next twelve months

Larger build work is quoted separately, at a fixed price, once we know what it is.

Need it built? SaaS MVPs and custom software are quoted at a fixed price. Need someone shipping inside your team? Forward deployed engineering.

How it works

Thirty minutes to find out whether there's anything here.
01

The call

Thirty minutes, free. Tell me what your teams ship and what you've already tried. If I can't help, I'll say so and point you at someone who can.

02

Month one: the map

How your teams work today, where AI makes them faster, what it costs, and what it breaks. Ranked, with a recommendation.

03

The rhythm

Working sessions and async access, with the cadence set by what your team needs rather than what a contract says.

04

Month to month

Thirty days' notice either way, no termination fee. Every month is a decision you get to make again.

For / not for

Good fit

  • You've tried AI and can't point to what it changed
  • You have engineers, or a vendor, who can do the work once the direction is clear
  • Leadership wants a straight answer, including "don't"
  • AI is headed into the product and the architecture has to hold

Not a fit

  • A strategy deck with no follow-through
  • Someone to sign off on a decision that's already made
  • A ten-person build team on day one
  • Skipping the data and security basics to get to the fun part

Advice from someone who ships it

I'm Matt Wagner. I've built software professionally since 2008 and founded or co-founded eight products. I build and run them with Claude Code, MCP servers, and agents every day, which is the same stack I'll be advising you on.

The advice comes from running these tools in production, on my own products and on client work, every week.

No resale margins, no referral fees, no bench to keep busy. If the honest answer is a $20-a-month tool, that's the answer.

Full background and resume
18+
Years building software
8
Products founded or co-founded
15+
Years of military service
Matt has been an invaluable partner as a fractional CTO — leading complex CRM integrations, building custom programs that enhanced our operational efficiency, and contributing to cost-saving initiatives that positively impacted our bottom line.
Tim Madden
CEO & Founder, Executive Career Upgrades

FAQ

How much does AI advisory cost?

Two tiers, both month to month. Advisor is $5,000 a month: two working sessions, async access, and the opportunity map. Embedded is $9,000 a month: weekly sessions, priority access in your Slack, and hands-on review in your repos. No annual contract and no termination fee; thirty days' notice either way.

What's the difference between Advisor and Embedded?

Advisor fits a team with capable engineers who need direction and a second opinion. Embedded fits a team putting AI into the product itself, where a wrong architecture call costs quarters. The step up buys cadence and depth: weekly instead of twice a month, and review in the actual code instead of on a call.

How is this different from a fractional CTO?

A fractional CTO covers the whole technology function: hiring, vendors, security, roadmap. AI advisory is narrower: where AI belongs in your business and how to ship it without regret. They're priced on the same two tiers, and plenty of clients need a bit of both. The retainer goes to whichever matters that month.

What if the map says we should build something?

Larger build work gets its own fixed-price quote once we know what it is. I can build it, or you can hand the map to your own team or another vendor. I'd rather scope a build honestly when it's real than pad a retainer against work that might not happen.

What if we don't need a retainer after month one?

Then I'll tell you, and we stop there. Some teams need the map and a clear set of next steps, not an ongoing advisor. That's a fine outcome.

Do you work remotely?

Yes, remote-first. Red Leg Dev is based in Lakeland, Florida, so in-person whiteboard days in Tampa, Orlando, and Central Florida are easy when they help.

Thirty minutes. You'll know in ten.

Tell me what your teams ship and what you've already tried. If I'm not the right person for it, I'll say so and point you at who is.
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