A fractional Head of AI for your team.Built to pass security review.
I help leaders at small and medium-sized firms get real leverage from AI, with teams that use it every day and automations that give them their time back and hold up in production. I'm a CISO, so it all clears security review.
A 30-minute call with Ryan to talk through where AI could give your team time back.
Who it’s for
- CEOs, owners, and partners
- COOs, CFOs, and operations leaders
- CTOs and IT leaders without an in-house AI team
Ryan Cummings
Founder · CISSP · ITILv3
The record.
Real work, described without client or employer names. The full history is on LinkedIn.
Outcomes delivered
- From a handful of people to nearly 80% of staff using AI, after a firm-wide enablement program and usage policy at a tax and risk advisory firm. Case study
- An AI operating layer including a loan operating system built alone with AI tools, secured from the start, and running in production.
- Over 50% reduction in annual technology costs, from an AI and automation operating-model shift run with a lean 20-person team.
- A new business line's day-to-day operations, designed around AI agents.
- StopByApp, his own AI-integrated app for real-estate open-house tours.
Why it clears review
- Zero findings from build to sustainment, across every SOC 2 Type 2 program built.
- CISO at highly regulated organizations, including HITRUST and HIPAA compliance through a post-acquisition transformation.
- A new security program stood up across 112 senior living communities, plus an inherited core program taken from prior findings to a clean SOC 2 report.
Speaker and panelist on AI and security at the Iowa State Bar Association and the Secure Iowa Conference, 2024–2025. Talks
The Three Peaks.
Enable, automate, secure: a cycle that repeats every month of the engagement.
01
Enable
Get your people using AI in their daily work with team workshops, practical prompting frameworks, a usage policy they follow, and a monthly forum to keep it going.
02
Automate
Take the repetitive work you've ranked together and build it, with automations and AI agents that work inside your CRM, email, and documents, put to work in your business.
03
Secure
Put every build through the security review a CISO would run, with access controls, logging, and human review where it matters, so it holds up in everyday use.
Who needs to change first?
What each one includesOne role, run as a monthly cycle. We start with discovery: working with you to find where AI will return the most value, then ranking those opportunities by ROI. Scope and price are worked out together on the intro call.
The whole firm
CEOs, owners, COOs, CFOs, and operations leaders
Your whole team using AI every day, and the repetitive work steadily coming off their plates.
Best for: Firms where AI use is scattered or hasn't started, and leaders want the whole team working the same way, with a usage policy that holds up.
Your developers
CTOs, engineering leads, and IT leaders
Your engineers using AI tools well and safely, with guardrails your security reviewers and auditors will accept.
Best for: Engineering teams in regulated firms that want AI in their workflow and need security to sign off on it.
Both
Leaders who need both, and someone to own AI
One owner for AI across the firm: both groups moving together, a roadmap you own with your leadership, and reporting your board can act on.
Best for: Firms with no one to own AI, that want a senior leader in the room every month to set direction, keep security in the loop, and keep the work moving.
Not sure which fits? Start with the intro call and we’ll size it together. Book an intro call (opens in a new tab)
You don’t need a full-time Head of AI to get the leadership.
A 30-minute intro call with Ryan, the person who would do the work.