Riley Consultation · IT Advisory & Technology Strategy
Riley Consultation provides senior technology advisory to healthcare, financial services, and growth-stage organizations navigating cybersecurity, compliance, AI adoption, and digital transformation.
What we solve
Each engagement starts by identifying the specific version of the problem your organization is facing — not a template built for someone else.
01 · Cybersecurity & HIPAA Compliance
In 2026, the threat landscape has outpaced most internal IT teams. Unresolved HIPAA findings, pending audits, and cybersecurity gaps create regulatory, financial, and reputational exposure that compounds the longer it sits unaddressed.
Active engagement: Currently leading HIPAA remediation for a Sumitomo-owned national DME company — 20 open findings, penetration test execution, and full IT governance framework.
02 · AI Strategy & Implementation
The AI honeymoon is over. Boards want measurable ROI. The question is no longer whether to adopt AI — it’s which workflows to automate, which vendors to trust, and how to implement without creating new risk in regulated environments.
Current role: VP of Customer Success & investor at Psympl — an enterprise Psychographic AI platform purpose-built for financial services and wealth management.
03 · Objective Third-Party Assessment
Internal teams suffer from proximity bias and political exposure. The large consulting firms give you a framework built for someone else. What’s missing is a senior advisor with no stake in the outcome — who will surface the variables your team can’t see and tell you what’s actually true.
Board experience: Elected Trustee and technology advisor to the Risk & Audit Committees at Country Bank since 2016 — providing exactly this function at the governance level.
04 · Digital Modernization & Legacy Exit
Legacy systems, manual processes, and siloed data create friction that compounds as organizations scale. Modernization isn’t about chasing the newest technology — it’s about building infrastructure aligned to where you’re actually going.
Prior experience: Led HIE, CRM, virtual care, and mobile health platform modernization for Baystate Health — one of New England’s largest health systems, serving 750,000+ patients across Western Massachusetts.
The approach
After 20 years as a technology executive, I’ve learned that most IT problems are not technical failures. They are visibility failures — the real issue is obscured by proximity, politics, or assumptions that have never been questioned.
My approach is structured around one discipline: surfacing the variable that changes everything. Not delivering a pre-built framework. Not telling you what worked at another organization. Sitting down with your specific situation, asking the questions nobody has asked, and helping you see it clearly enough to act.
The conversation is the methodology. The clarity is the deliverable.
Step one
The issue your team describes is rarely the issue that’s actually blocking progress. The first engagement is always diagnostic — mapping the full variable set before recommending anything.
Step two
As an outside advisor with no political stake, I can ask the question your team can’t ask. That question is usually the one that unlocks everything else.
Step three
Not a 200-page report. A prioritized, sequenced action plan — scoped to your resources, your team, and the outcomes your board actually needs to see.
Always
Every engagement ends the same way — with clarity you didn’t have when we started, and a next step you’re confident taking.
Industries served
HIPAA compliance, clinical technology portfolios, HIE, patient engagement platforms, and population health infrastructure. Former CIO and Director at UMass Memorial and Baystate Health — 20 years navigating the regulatory and operational complexity of healthcare IT.
Technology risk governance, digital banking strategy, vendor management, and AI adoption in regulated environments. Current board member advising on cybersecurity posture and technology risk at a regional community bank.
Organizations that built technology for the company they were — and now need infrastructure for the company they’re becoming. Scalability planning, vendor rationalization, and technology governance built for the next phase of growth.
Why Ken Riley
Most technology advisors have run projects. Ken Riley has run organizations — as CIO of a community hospital, as Director of IT for one of New England’s largest health systems, and as an elected board member advising on technology risk at a regional bank.
That combination — operational CIO experience, board governance fluency, and active advisory engagements — means he can work at any altitude your situation requires. From hands-on remediation to board-level strategy communication.
He also brings something most advisors can’t: genuine intellectual honesty. No methodology to sell. No firm to protect. No junior team executing a senior partner’s framework. One person, fully engaged, whose only measure of success is yours.
There’s more to the story. Read about Ken →
Engagement types
Start here
Independent evaluation of your technology environment, security posture, compliance standing, and vendor relationships. You leave with a prioritized roadmap and an honest accounting of risk.
Learn more →Ongoing
Monthly access to a trusted thinking partner. Technology decisions, vendor relationships, compliance posture, organizational dynamics — everything is on the table. Nothing is templated.
Learn more →Project
A defined engagement with a clear beginning, middle, and end. Surface the variables that haven’t been named, challenge the assumptions, and build a path forward you can actually execute.
Learn more →Start here
No pitch. No intake form. A direct conversation about your specific situation — and whether I’m the right person to help.
Start the conversationI respond personally within 24 hours.
(413) 345-5050 · ken@rileyconsultation.com