What we actually do.
Three doorways into the same work.
Hudson Sky helps businesses adopt modern technology — especially AI — without the risks. The work shows up under different headings depending on what's pressuring you: a regulator, a customer audit, an AI tool that arrived without a policy, an operator's hour stuck on broken tech. Pick the doorway that fits where you actually are. Or talk to a strategist and we'll figure it out together.
Pick the doorway that matches the pressure.
The work is mostly the same regardless of door — security, AI governance, technology that works. The framing changes depending on whether your audience is a regulator, a customer, or your own team trying to get through the day.
Industries.
When a regulator, an auditor, or a contracting officer is the audience.
Defense contractors under CMMC. Healthcare under HIPAA. Professional services under SOC 2 and the questionnaire your biggest client just sent. Financial services under SEC, FINRA, GLBA, and 23 NYCRR 500. Manufacturers under customer audits and OT/IT pressure. Different vocabularies, the same underlying work — done so it holds up in front of someone whose job is to find the gaps.
Operators.
When the issue is the technology in front of you, not the regulator behind it.
For SMBs and operators where no acronym fits but the work still matters — chambers of commerce, family businesses, lakefront restaurants, dealerships, distributors, real estate firms, schools, nonprofits. We do the work that protects the business and makes the technology serve the team. Not the other way around.
AI Adoption.
When AI is showing up faster than your team can govern it.
Three steps that work for anyone — regulated or not. Start with the AI Readiness Scorecard (90 seconds, free, no email gate). Walk through the AI Governance Quick Start checklist (16 minutes, free, ungated). When the self-serve work isn't enough, the AI Exposure Report is the 5-day fixed-fee diagnostic that produces the artifact your leadership team can actually use.
Six service categories that span all three tracks.
Whether you came in through Industries, Operators, or AI Adoption, the underlying capabilities draw from the same set. The framing is the part that changes by audience — the work, mostly, doesn't.
Information security & compliance.
SOC 2, HIPAA, CMMC, GLBA, FTC Safeguards, 23 NYCRR 500. WISPs, SSPs, Risk Analyses, POA&Ms. The artifacts a regulator or customer audit expects to see — written for your environment, defensible under scrutiny, and operating as a real program rather than a folder you opened twice last year.
AI governance & adoption.
From the visibility inventory ("what AI is actually being used here") through written policy, vendor contract review, customer-facing AI scrutiny, and the operating cadence that keeps it all current. Pairs cleanly with the AI Readiness Scorecard, the Quick Start checklist, and the Exposure Report.
Cybersecurity & threat defense.
MFA across every credential surface. EDR/XDR on every endpoint. Email security and phishing defense. Vulnerability management with results that drive action. SIEM where it earns its cost. Network segmentation including OT where it applies. The defenses that actually move the dial — not the ones that look good in a security vendor's pitch deck.
Cloud architecture & operations.
Microsoft 365, Google Workspace, Azure, AWS — set up the way they should have been the first time. Identity federation. Conditional access. Backup that's been tested restoring. Cost optimization that doesn't sacrifice posture. Tenant hygiene for organizations that grew faster than their cloud footprint did.
Incident response & recovery.
Pre-built runbooks. Immutable backups your team has actually tested restoring. Tabletop exercises. The 3 AM call that gets answered. Notification clocks for SEC (4 days), NYDFS (72 hours), state AGs, and the customers and partners who need to hear it from you before they hear it elsewhere. We've made these calls.
Vendor & supply chain risk.
Real inventories of who's connected to your data and your network. AI vendors included. Contract review that catches what most form contracts hide. Annual diligence that's actually performed, not pencilwhipped. Customer audit response built on top so the next questionnaire is an hour, not a week.
Three things you won't get from a generic vendor.
Senior practitioners doing the work, not handing it to juniors.
The person who scopes the engagement is the person doing the work. Most firms structure differently — partner sells, associate delivers, junior writes the artifacts. We don't, because the artifacts are where the value lives. If a junior could write your SSP or your risk analysis, the assessment that follows would already be smoother than ours.
Fixed-fee diagnostic upfront so you can see how we work before signing a longer engagement.
The AI Exposure Report is the most concrete example — a 5-day fixed-fee engagement that produces a real artifact, with a refund guarantee if the deliverables aren't useful. We use the same shape for compliance gap assessments, customer audit prep, and incident-readiness diagnostics. Letting you read our work before committing is how trust builds — not how we scare it off.
We treat your regulators, customers, and auditors as the audience — not just the budget.
An assessment isn't won by writing it well; it's won by writing it for someone whose job is to find the gaps. The same goes for a customer questionnaire, an OCR inquiry, an SEC exam letter, or a procurement audit. We build the artifacts and the program with that audience in mind from the start — which is why ours hold up when those audiences eventually show up.
The questions we get most often.
Bring sharper questions to the strategy call and we'll go further. These are the starters.
What's the difference between Industries and Operators?+
Are you an MSP?+
How do you price?+
Do you work outside Chicago?+
How quickly can you start?+
What if we already have an MSP or an IT team?+
Three ways in. Pick what fits.
No qualifying call before the qualifying call. Each path is real, each one's free or fixed-fee, each ends with you having a better answer than you walked in with.
Strategy call.
Bring whatever's pressuring you — the regulator, the customer audit, the AI tool that arrived without a policy, the operator's hour stuck on broken tech. We'll tell you which doorway fits, what the real gaps are, and roughly what closing them costs. No qualifying call before the qualifying call.
Schedule the call →Take the AI Readiness Scorecard.
If you came in through the AI Adoption track — or you just want a quick read on where you stand — the Scorecard is the fastest way. Twelve questions, a real grade, no email gate. Useful as a first step before any deeper conversation.
Start the Scorecard →Browse the resource library.
Four ungated checklists — CMMC readiness, HIPAA risk analysis, AI governance quick start, customer audit response. The same work we'd do with a paying client, sized down to a self-serve format. Read on a phone, print, share. No email gate.
See all resources →