Nick Charney Kaye
Operator · San Francisco
// FRACTIONAL CTO · SAN FRANCISCO
Senior technology leadership, above your MSP.
Your managed-service provider keeps the machines running. Nobody is deciding what the business should run, holding the vendors to account, reading the AI pitch before you sign it, or owning the risk when the board asks about it. That’s the seat I take — about two days a month, or embedded a day a week — for companies of ten to a hundred people who can’t justify a full-time chief technology officer and shouldn’t have to. I put AI to actual use in my own business every day, which is the only qualification that counts when the next vendor says “AI.”
Who this is for. The firm whose IT person left with the passwords. The one on three email systems and a shared drive nobody trusts. The one whose cloud bill doubled and nobody can say why. The one that has to move thirty people to Google Workspace or Microsoft 365 without losing a file. The one whose MSP does the help desk and leaves the decisions to whoever’s loudest.
Who it is not for. Anyone who needs a help desk, device management, or 24/7 support — I’ll help you choose the MSP that does those well, and then I sit above it. If you run an MSP: I don’t sell what you sell, so there’s nothing to compete over. I take the strategy, project, and escalation work your base contract excludes, on referral or subcontract.
What you’re afraid of, and what I do about it
- “Every vendor is selling us AI and nobody here can tell what’s real.” That’s the seat. I run my own business on AI in production, so I can read the pitch, the contract, and the data-handling terms before you sign — and tell you plainly when the answer is no.
- “Our staff are using AI tools we never approved.” The health check inventories every tool in use, where its data goes, and what it costs; the Read decides which stay, which go, and what governs them.
- “We’ll modernize and lose something we can’t get back.” Zero-loss cutover is the deliverable, not the aspiration: every mailbox and file accounted for before the move and verified after, and a restore you watched happen on a date you can name.
- “The one person who understood our systems is gone.” A stabilization starts as a Day within the week: the keys found, the risks named, the three things to do first.
- “If we fall behind on this, we fall behind on everything.” Then the retainer is the remedy: someone senior in the room about two days a month, deciding what the business should run and what it should refuse.
The record behind the seat
I’ve been the standing technical lead for a Caltech bioengineering group since 2022 — on-demand GPU infrastructure, reproducible results, a development practice the team didn’t have before. On the World Cup program I cut key page-load times by more than six times and put Datadog monitoring in front of what customers actually experienced, with $630 million riding on it. At a venture firm I took twenty-plus data pipelines from a day’s processing to hours and from hundreds of virtual machines to fewer than ten — the cloud bill followed. At Signal I built the tooling seventy engineers ran a trillion-transaction platform on, at six-sigma uptime. The full dated record runs back to 2001 at my studio.
Four ways to buy it
Technology Health Check
$2,000 · one day
- One day across the whole estate: accounts and identity, email, devices, the file systems, the line-of-business software, every AI tool in use and where its data goes, the cloud bill, backups, and who holds which keys
- A written sheet by the end of it — what you have, what it costs, what’s at risk, and the three things to do first
- The sheet your insurer, your accountant, or your next technology hire will ask for anyway
The Day. Credited in full toward a Read or a Build within 60 days.
Technology & Security Read
$4,500 · one week
- One decision, answered in writing inside a week: build or buy, migrate or stay, this vendor or that one, hire or contract
- Architecture, cloud, vendors, and incident posture reviewed against what the business is actually trying to do
- A 90-day roadmap behind the answer, and a go / no-go on the first Build
The Read. One decision answered in writing, with a 90-day roadmap behind it.
Workspace or Microsoft 365 Migration, Hardened
$6,500–$9,500 · two to four weeks
- Google Workspace or Microsoft 365, for ten to fifty users: every mailbox, calendar, file, and shared drive accounted for before cutover and verified after
- Hardened on the way in — multi-factor authentication, single sign-on where it applies, backup, email authentication — with the evidence packet an insurer or customer can read
- The people who use it told what changed, in writing, before the Monday it changes
A Build, for 10 to 50 users. Zero-loss cutover is the deliverable, not the aspiration.
Backup & Recovery with a Tested Restore
$6,500 · two weeks
- What gets backed up, where, how often, and for how long — decided, documented, and automated
- A restore test, performed and dated, so “we have backups” becomes “we restored this on this date in this many minutes”
- The recovery runbook: who does what, in what order, when the worst morning comes
A Build. Ends with a dated restore test your insurer and your board can read.
Observability & On-Call Stand-Up
$6,500–$12,000 · three to four weeks
- Monitoring that shows what customers experience — page loads, errors, the checkout, the API your partner calls — not just whether a server is up
- Alerts that reach a person who can act, and an on-call rotation that knows who that is
- Dashboards leadership can read without a translator
A Build. Monitoring that shows what your customers actually experience, and a rotation that knows who answers.
Cloud Cost Review & Cleanup
$6,500 · two weeks
- Every line of the bill explained: what it is, who uses it, and whether it should exist
- The cleanup done — idle machines, oversized instances, forgotten storage, the reserved pricing nobody bought — with the savings measured against the bill before
- Tagging and a monthly review so it doesn’t grow back
A Build. If the first year’s savings don’t cover the fee, the Read that follows is free.
Fractional CTO
$6,000 / month floor · about two days a month · embedded $12,000 / month
- Standing technology leadership: architecture, vendors, hiring, security posture, the roadmap, and the room where the decisions get made
- About two days a month at the floor; embedded, about a day a week, at $12,000
- Month to month, billed in advance, two weeks’ notice to end it; at most two retainers at once
The Retainer. Architecture, vendors, hiring, security posture, and the room where the decisions get made — at most two at once.
The five questions you’re actually asking
Why not just ask my MSP?
What do I actually get on the Day?
How fast can you start?
Can I trust you with the keys?
What does it cost to start?
Hand it over
Hand over the system
The migration, the bill, the person who left, the vendor nobody understands. A few sentences is enough — read by me, answered within one business day.
Know it's a fit already? Book a 20-minute fit call › — the highest-intent path skips the form.
Answered within one business day, by me.
No form? Send it as an email instead.
Copy the template, fill in the blanks, and send it to hi@nickcharneykaye.com. One person reads every note and replies within one business day.
The fast way. Twenty minutes, this week, no deck required: book a 20-minute fit call.
The plain way. Email works too — hi@nickcharneykaye.com reaches me directly, answered within one business day. For anything sensitive, my public key is published.
Also taken directly: cyber-insurance renewal & incident readiness · AI workflow readiness · measurement, conversion & AI-search visibility · the four ways to engage.