AI Strategy Built on a
Foundation of Risk
Helping professionals and businesses navigate career transitions, AI adoption, and insurance planning — with clarity, honesty, and a risk-first mindset.
AI is Changing Everything — Most Strategies Don't Account for the Risk
Organizations are rushing to adopt AI tools without a structured framework for managing the risks. Individuals are navigating career pivots without knowing how AI will reshape their field.
At Kimrey Consulting, we believe the best AI strategy starts with understanding what can go wrong — and building a plan that's resilient because of that clarity.
Learn Our Approach*Industry estimates for illustrative context. Kimrey Consulting does not independently verify these figures.
Jack Kimrey
Founder, Kimrey Consulting LLC
Honest Advice at the Intersection of Risk, AI, and Career Strategy
I founded Kimrey Consulting LLC to fill a gap I kept seeing: professionals and organizations trying to navigate major transitions — in careers, technology adoption, and insurance coverage — without access to thoughtful, unbiased guidance.
My background spans healthcare operations, insurance, and business education at the University of Michigan. That combination gives me an unusual vantage point: I understand how organizations operate under regulatory pressure, how AI is reshaping roles, and how individuals can position themselves to thrive.
I'm a licensed insurance producer, which means I can advise on — and in some cases place — insurance coverage for individuals and small businesses. I don't oversell. I don't guarantee outcomes. I give you my honest read of the situation.
Credentials & Background
Licensed Insurance Producer
Licensed to advise on and place insurance products for individuals and small businesses.
University of Michigan
Business student focused on strategy, operations, and emerging technology.
Healthcare Operations
Experience navigating complex operational environments with regulatory dimensions.
AI Strategy Advisory
Advising on responsible AI adoption, risk management, and workforce positioning.
Why “Built on a Foundation of Risk”?
Most AI strategy conversations start with the upside. The organizations that navigate AI successfully tend to start by understanding what they're taking on: operational risk, talent risk, reputational risk, compliance risk.
At Kimrey Consulting, that risk-first lens isn't pessimism. It's what makes the strategy actually work.
Advisory Services Built for the AI Economy
Every engagement starts with a clear-eyed assessment of risk, opportunity, and fit — not a generic playbook.
AI Strategy & Organizational Readiness
Framework-driven advisory to identify AI opportunities, assess adoption risks, and build a responsible roadmap.
- AI opportunity assessment for your specific workflows
- Risk framework development and leadership alignment
- Phased adoption roadmap matched to your capacity and budget
- Vendor evaluation support (advisory, not technical audits)
Career Positioning & Strategy
Identify your competitive edge in the AI economy and build a personal brand that positions you for emerging roles.
- Career direction clarity and target role identification
- Personal brand development across your full professional presence
- AI-era positioning for skills that remain valuable
- Job search strategy and pipeline management
Resume & LinkedIn Optimization
ATS-optimized resumes and LinkedIn profiles that communicate your value to algorithms and hiring managers alike.
- Full resume rewrite or detailed review and edit
- LinkedIn profile optimization for recruiter search
- Cover letter strategy and targeted drafting
- Keyword alignment to your target role and industry
Interview Preparation
Structured coaching and mock interviews that build confidence and prepare you for high-stakes conversations.
- Behavioral interview coaching using STAR method
- Mock interviews with direct, honest feedback
- Company and role research strategy
- Offer negotiation preparation
Insurance Advisory
As a licensed insurance producer, Jack helps individuals and small business owners identify and close coverage gaps.
- Personal coverage gap assessment
- Options exploration in plain language, no pressure
- Small business insurance guidance
- Advisory support for major life transitions that affect coverage
Organizational AI Readiness
Help your team understand where AI adds value, what risks it introduces, and how to align leadership around a clear posture.
- Leadership AI alignment sessions
- Organizational readiness assessment
- AI policy and governance framework guidance
- Team education and change readiness support
Context-Driven Advisory Across Key Sectors
AI disruption doesn't look the same in every industry. Our advisory is grounded in the specific risks, regulations, and opportunities of your sector.
Healthcare
Navigating AI adoption against a backdrop of HIPAA, clinical risk, and operational complexity.
Financial Services
AI strategy and career positioning for professionals in banking, insurance, and wealth management.
Education
Helping educators and administrators adapt to AI's impact on learning and academic careers.
Retail & E-Commerce
Competitive AI strategy for operators navigating automation and customer experience shifts.
Small Business
Practical AI adoption and risk management guidance for SMBs without dedicated technology leadership.
Career Transitions
For professionals pivoting industries in a landscape being reshaped by automation and AI.
A Transparent, Four-Phase Process
Clarity up front leads to better outcomes. Every engagement follows the same core structure.
Discovery
Listen and understand your goals, constraints, risk tolerance, and the context that makes your situation specific.
- Structured intake questions before the call
- 60-minute discovery conversation
- Written summary of our understanding
Assessment
Diagnose what's actually going on beneath the surface — so we're solving the right problem.
- Situation analysis specific to your goals
- Risk and opportunity mapping
- Prioritized perspective on what matters most
Strategy
Build a concrete plan — specific actions, prioritized steps, and a framework for decisions as things evolve.
- Written strategy document or advisory memo
- Deliverables based on engagement type
- Prioritized action plan with timeline
Execution Support
Stay engaged through implementation — reviewing materials, refining your approach, adapting as you learn.
- Feedback on drafts and applications
- Check-in conversations as needed
- Adjustments based on results and new information
A Note on Scope and Pricing
We work on a project or retainer basis. Pricing is discussed during discovery based on the actual scope of your situation. We do not take engagements where we do not think we can genuinely help — and we'll tell you if that's the case.
Practical Guides & Frameworks
Honest, actionable resources on AI strategy, career positioning, and insurance planning — coming soon.
AI Adoption Risk Checklist
A structured framework for evaluating risks before your organization commits to a new AI tool or platform.
Coming SoonCareer Positioning Worksheet
A guided worksheet for identifying your competitive edge and narrative in the AI economy.
Coming SoonATS Resume Optimization Guide
What applicant tracking systems actually look for — and how to write a resume that clears the screening round.
Coming SoonInsurance Coverage Gap Finder
A self-assessment to identify potential gaps in personal or small business insurance coverage.
Coming SoonInterview Story Builder
A STAR-method framework and practice guide for behavioral interview answers.
Coming SoonLinkedIn Profile Audit Guide
A step-by-step review process for your LinkedIn presence, optimized for recruiter search.
Coming SoonGet notified when resources launch
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Insights on AI, Career, and Risk
Practical writing on AI strategy, career navigation, and the decisions that matter most. Articles in development — sign up to be notified.
The Risk-First AI Framework: Why Most Adoption Plans Get It Backwards
Most organizations start AI strategy with the upside. Here is why starting with the risks leads to better outcomes.
How to Position Yourself for the AI Economy (Without Pretending You're a Data Scientist)
AI is reshaping every professional field. Here is how to build a career narrative that is honest and strategic.
The Coverage Gaps Most People Don't Know They Have
A plain-language breakdown of the most common insurance blind spots for individuals and small businesses.
Evaluating AI Vendors Without a Technical Team: A Framework
You don't need a CTO to evaluate AI tools critically. Here is a structured approach any leadership team can use.
What Employers Actually Look for in a Resume in 2025
ATS systems, recruiter screen time, and what the research says about resume effectiveness.
AI Risk Is Not IT Risk: Why the Distinction Matters
Organizations that treat AI governance like a cybersecurity checklist miss the most important risks.
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Frequently Asked Questions
Working With Us
AI Strategy
Career Services
Insurance
Let's talk about what you're working on
Fill out the form and we'll follow up to schedule a call. The initial conversation is free and there is no obligation.
Location
Michigan — serving clients nationwide
Tell us about your situation
Message received!
Thanks for reaching out. We'll follow up within one business day to schedule your call.
Honest Advisory. No Inflated Claims.
Risk-First Thinking
Every engagement starts with a clear-eyed assessment of what can go wrong. AI strategy that ignores risk isn't strategy — it's optimism.
No Hype, No Guarantees
We don't promise specific salary increases, AI ROI percentages, or outcomes we can't substantiate. You get honest analysis and clear guidance.
Cross-Domain Perspective
With a background spanning healthcare operations, insurance, and business education, Jack brings a uniquely grounded perspective to AI and career consulting.
Let's Build a Strategy That Actually Holds Up
A free 30-minute call is the best way to see if we're the right fit.
Stay in the loop
Occasional insights on AI strategy, career navigation, and insurance planning — no filler.