Work with Ken
You leave with clarity you didn’t have when you arrived — and a next step you’re confident taking.
How it works
Not a discovery call. Not a needs assessment. Not a proposal process. A real conversation — about what you’re facing, what you’ve already tried, and what’s actually at stake.
From that conversation, the right engagement structure becomes obvious. Sometimes it’s ongoing. Sometimes it’s a defined assessment. Sometimes it’s a longer advisory relationship. The structure follows the problem — never the other way around.
First
No agenda. No pitch. You tell me what’s keeping you up at night and I listen — for the variable you haven’t named yet. This conversation is free. It’s also usually the most useful one you’ll have had in a while.
Then
Based on what you’re facing, we decide together what kind of engagement makes sense — an assessment to understand the full picture, a defined project, or ongoing advisory. Or sometimes I’ll tell you I’m not the right person and point you to who is.
Always
Every engagement ends the same way. Clarity, a defined next step, and the confidence to take it. Not a report. Not a list of recommendations. A decision you own.
Start here
“Before you can fix it, you need to see it clearly.”
Most organizations don’t have an accurate picture of where they actually are. They have a picture of where they think they are — built from the inside, filtered by proximity, shaped by what people are comfortable saying out loud. An independent assessment changes that.
In a defined engagement, I examine your technology environment, security posture, vendor relationships, compliance standing, and operational practices — and I tell you what’s true. Not what’s comfortable. What’s true. You leave with a prioritized roadmap and an honest accounting of risk.
This is the right fit if
Pricing is scoped to the engagement. Start with a conversation →
In practice
“A national enterprise acquired by a foreign holding company had 20 open HIPAA findings and no remediation plan — nine months after their security risk assessment was completed. Within 90 days we had a governance framework, a vendor in place, a penetration test underway, and a board-ready roadmap. The holding company stopped asking questions.”
Ongoing
“The trusted voice in the room — with no competing agenda.”
Monthly access to a thinking partner who knows your situation, your goals, and your constraints as well as you do. Technology decisions, vendor relationships, compliance posture, organizational dynamics — everything is on the table. Nothing is templated. Every conversation starts from where you are right now.
This is for leaders who are making consequential technology decisions regularly and need a senior advisor who will tell them the truth — not validate what they’ve already decided.
This is the right fit if
Pricing is scoped to the engagement. Start with a conversation →
In practice
“A 750,000-patient health system needed a technology leader who could sit at the intersection of clinical operations, data governance, and enterprise IT — someone who could translate between the medical staff, the board, and the vendor ecosystem simultaneously. Over a decade, that relationship produced a patent, a population health platform, and a care coordination model that paid every participating institution more than they invested.”
Project
“See your organization — or your situation — completely clearly for the first time.”
A defined engagement with a clear beginning, middle, and end. We go deep on your specific situation — surfacing the variables that haven’t been named, the assumptions that haven’t been challenged, and the path forward that’s been obscured by proximity. You end with a prioritized roadmap you can actually act on — not a document you have to interpret.
Not a framework built for someone else. A clear-eyed accounting of your specific reality and a sequenced plan for moving through it.
This is the right fit if
Pricing is scoped to the engagement. Start with a conversation →
In practice
“A regional health system managing 1.2 million patient records across 20+ connected practices discovered thousands of records had been incorrectly merged due to a single interface update. In 48 hours we identified the source, designed a rollback algorithm, remediated the breach, and implemented monitoring that would catch the same problem before it could happen again. The organization sent required patient notifications and closed the incident with no regulatory penalty.”
Who this is for
I work best with leaders who are intelligent, accomplished, and self-aware enough to know that the problem isn’t information — it’s clarity. They’ve usually already tried the big firms, the frameworks, and the internal conversations. None of it moved the needle the way they needed.
You’re probably the right fit if
Not every problem is the right one for me. If the first conversation makes clear that someone else would serve you better, I’ll say so directly — and point you toward who that is. That’s not a loss. That’s the job.
What to expect
Day 1
A short message is enough. Tell me what’s on your mind. No formal brief required. I read everything personally.
Within 24 hrs
Not an automated response. Not an assistant. Me — with a direct reply and a suggestion for how to have the first real conversation.
First call
This conversation is free. Its only purpose is to understand what you’re facing well enough to know whether and how I can help. If there’s a fit, the right engagement structure will be obvious by the end of it.
From there
Some engagements start immediately. Some need a week of scoping. The structure follows the problem. What stays constant is that every step is transparent, direct, and tailored to where you are.
Ready to start
Tell me what’s keeping you up at night. That’s usually where we start.
Start the conversationI read every message personally. You’ll hear from me within 24 hours.
(413) 345-5050 · ken@rileyconsultation.com