CTO-Led AI Strategy Workshop for Healthcare Executives
This paid, hands-on workshop ($1,095) demonstrates the 14-day assessment methodology I use with fractional CTO clients—without vendor pitches or transformation guarantees. Attendees receive $5,000 credit toward full assessment, making this an entry point to comprehensive fractional CTO services. Learn from a fractional CTO who's implemented enterprise technology transformations for a national integrated health system and 60+ organizations.
Workshop → Assessment Pathway
$1,095 workshop includes $5K credit toward your 14-day fractional CTO assessment ($15,000 value). Attend the workshop, experience the methodology, and receive 33% discount if you engage for full assessment within 90 days.
The AI Vendor Pitch Fatigue Problem
Most healthcare executives are exhausted by AI vendor pitches. Every demo promises transformation. Few explain how to evaluate whether you're actually ready for AI—or which use cases make sense for your clinic's operational baseline.
Common Frustrations
- Vendor ROI claims are best-case scenarios (not conservative models)
- Demos showcase flashy features (not operational fit for your clinic)
- Implementation friction is downplayed (change management, staff adoption, workflow disruption)
- HIPAA compliance requirements are glossed over (BAAs, PHI protection, data security)
- You lack frameworks to compare 30+ vendors objectively
The Gap
Healthcare leaders need assessment tools—not sales pitches. You need conservative ROI modeling that protects your credibility with CFOs. You need vendor evaluation frameworks that work across 30+ vendors. You need pilot program designs that test AI without risking full-scale failure.
Workshops Demonstrate Our Fractional CTO Methodology
This workshop is NOT standalone education—it's an introduction to how I work as your fractional CTO. You'll experience the same systematic assessment frameworks, conservative ROI modeling, and vendor evaluation methodologies I use with fractional CTO clients conducting 14-day comprehensive reviews.
You'll leave with AI readiness insights you can apply immediately, OR you can engage me for a comprehensive 14-day assessment applying the full methodology to your multi-location operations—with $5K credit from your workshop attendance.
What Makes This Workshop Different
1. Conservative 50/20/24 ROI Modeling
Most vendors show best-case projections. I teach the 50/20/24 rule: take their claim, multiply by 50%, assume 20% staff adoption friction, and plan for 24-month payback. This protects your credibility when presenting to your CFO.
2. Objective Vendor Landscape Report
I've evaluated 30+ AI vendors using publicly available data—not cherry-picked demos. No vendor kickbacks, no recommendations disguised as education. You get objective evaluation frameworks, not sales pitches.
3. Operational Readiness Before Technology
75% of AI failures happen because organizations weren't ready—not because the technology failed. The 125-point readiness scorecard identifies foundational gaps before you invest in pilots.
4. HIPAA Compliance Requirements
AI vendors need Business Associate Agreements (BAAs), SOC 2 compliance, and PHI protection protocols. I walk through the exact questions to ask and red flags to watch for.
5. Published Case Studies
10 published case studies with proper citations. Real organizations, real results, real challenges. No fabricated testimonials or unverifiable claims.
- Village Dermatology (Luma Health case study): 0.52% no-show rate (industry average: 5-8%)
- Phyx Primary Care (Suki AI case study): 48 min/day saved on after-hours documentation, 60% decrease in physician burnout
- UChicago Medicine (Abridge AI press release): 40% decrease in physician burnout, 90% of clinicians provided undivided attention to patients
8-Hour Interactive Workshop Agenda
Hands-on exercises, practical frameworks, and real-world case studies
Module 1: AI Fundamentals for Healthcare (Hour 1)
• What is AI, and what is it NOT (dispelling vendor marketing claims)
• Healthcare-specific AI use cases: Patient engagement, clinical documentation, revenue cycle, operational efficiency
• Why 75% of AI implementations fail (operational readiness gaps, not technology failure)
Module 2: AI Ethics & Trust Building (Hour 2)
• Ethical risks: Algorithmic bias, patient harm, data privacy violations
• Building trust with clinicians (transparency, explainability, opt-out options)
• HIPAA compliance requirements (BAAs, PHI encryption, data breach notification)
Module 3: AI Readiness Assessment (Hour 3)
• 125-point readiness scorecard (5 pillars: operational maturity, financial health, compliance readiness, technology infrastructure, organizational culture)
• Interactive exercise: Complete your clinic's readiness assessment
• Gap analysis: Identify foundational work required before piloting AI
Module 4: Common AI Implementation Failure Patterns (Hour 4)
• Failure Pattern #1: Technology before readiness (piloting AI without operational foundations)
• Failure Pattern #2: Vendor promises without validation (trusting demos instead of reference checks)
• Failure Pattern #3: Overpromising to leadership (using vendor claims for board presentations)
• How to avoid these failures: Conservative modeling, reference checks, pilot programs
Module 5: Conservative ROI Modeling (50/20/24 Rule) (Hour 5)
• Why vendor ROI claims are unreliable (best-case scenarios, ideal customer profiles)
• The 50/20/24 methodology: Revenue assumptions (50% of vendor claims), Cost contingency (add 20%), Payback period (24 months maximum)
• Interactive exercise: Build conservative ROI model for your priority use case
• Case study: Village Dermatology (0.52% no-show rate with Luma Health—how to model conservatively)
Module 6: Vendor Evaluation Frameworks (Hour 6)
• 100-point vendor scorecard (7 dimensions weighted by importance)
• How to evaluate 30+ vendors objectively (use case fit, EHR integration, HIPAA compliance, pricing transparency)
• Red flags during vendor demos (vague pricing, no BAA, no published case studies, no reference checks)
• Interactive exercise: Apply vendor scorecard to 3 vendors in your priority use case
Module 7: Leadership & Change Management (Hour 7)
• Building clinician trust (involve clinicians early, address workflow concerns, transparent communication)
• Executive buy-in strategies (conservative ROI models, pilot program designs, Go/Pivot/Stop decision criteria)
• Staff training and adoption (super-user programs, phased rollouts, feedback loops)
Module 8: Implementation Planning & Next Steps (Hour 8)
• 90-day pilot program design (Week 1-4 baseline, Week 5-8 limited rollout, Week 9-12 evaluation)
• Go/Pivot/Stop decision criteria (50% threshold = Go, 20-50% = Pivot, <20% = Stop)
• Your personalized action plan: Next 30, 60, 90 days
• Post-workshop deliverables overview (Vendor Landscape Report, ROI Calculator Templates, Implementation Frameworks)
What You'll Leave With (Tangible Tools)
#1: AI Readiness Assessment Results
- • 125-point scorecard with pillar-by-pillar gap analysis
- • Readiness level: RED (0-62), YELLOW (63-94), GREEN (95-125)
- • Prioritized action plan for closing readiness gaps
#2: Vendor Landscape Report (30+ Vendors)
- • 30+ AI vendors documented objectively
- • Organized by healthcare use case
- • Published case studies with conservative framing
#3: ROI Calculator Templates
- • Excel templates with 50/20/24 methodology built in
- • 4 use case-specific calculators
- • 3-scenario analysis (optimistic/realistic/conservative)
#4: 100-Point Vendor Scorecard
- • Objective evaluation framework for demos
- • 7 dimensions (EHR integration, HIPAA compliance, etc.)
- • Scoring rubric for each dimension
#5: Implementation Planning Frameworks
- • 90-day pilot program design template
- • HIPAA compliance checklist for AI vendors
- • BAA template review guide
- • Go/Pivot/Stop decision criteria worksheet
Published Case Studies Featured in Workshop
Village Dermatology (Luma Health)
Result: 0.52% no-show rate (industry average: 5-8%)
Use Case: Patient engagement AI (automated appointment reminders, waitlist optimization)
Phyx Primary Care (Suki AI)
Result: 48 min/day saved, 60% decrease in burnout
Use Case: AI-powered clinical documentation assistant
UChicago Medicine (Abridge AI)
Result: 40% decrease in burnout, 90% undivided attention
Use Case: Ambient AI clinical documentation
BAYADA Home Health (Waystar)
Result: $3.7M in recovered revenue
Use Case: Revenue cycle AI (claims management, denial reduction)
Ryan Health (Luma Health)
Result: $300K revenue increase within 6 months
Use Case: Intelligent scheduling and patient engagement
WebPT (PT/OT Clinics)
Result: 34% reduction in no-shows
Use Case: Patient engagement, scheduling, outcome tracking
Workshop Investment & Registration
$1,095 per attendee
Includes $5K credit toward full assessment
What's Included
- 8-hour interactive workshop (single day, in-person)
- All 5 workshop deliverables (assessment, vendor report, ROI calculators, scorecard, frameworks)
- Post-workshop support: Vendor report (Day 3), Implementation resources (Day 7), 30-min consultation (Day 14)
- Limited to 12 participants for personalized attention
About Your Facilitator
Craig Trulove, Fractional CTO/CIO
Craig Trulove brings 18+ years of enterprise technology leadership experience, rose to Director of Cloud & AI Platforms at Perficient, and implemented transformation initiatives for a national integrated health system (5-year engagement) and 60+ organizations. After investing 100+ hours researching AI implementation approaches and evaluating 30+ vendors, he created this practical framework to help healthcare leaders navigate AI adoption safely and effectively.
Healthcare Domain (40%)
Multi-location specialty clinics (pediatric therapy, behavioral health, outpatient rehab)
Technology Leadership (30%)
EHR optimization, clinical workflow automation, multi-location IT infrastructure
AI Implementation (30%)
Conservative ROI modeling, vendor evaluation frameworks, pilot program design
"Assessment before investment. Conservative modeling protects credibility. Pilot programs validate vendor claims before full deployment."
Frequently Asked Questions
Is this workshop vendor-neutral?
Yes. I evaluate 30+ AI vendors using publicly available data only. I receive no vendor kickbacks, referral fees, or paid placements. The vendor landscape report provides objective documentation—not recommendations.
What if our clinic isn't ready for AI yet?
That's exactly what the 125-point readiness assessment identifies. Many clinics discover they need 6-12 months of foundational work (data quality, workflow standardization, HIPAA compliance remediation) before piloting AI. Knowing you're not ready is valuable—it prevents costly failed pilots.
Can I bring vendor proposals for evaluation?
Absolutely. If you've received AI vendor pitches, bring them to the workshop. We'll apply the 100-point vendor scorecard during Module 6 and identify red flags or missing information.
What if I can't attend in person?
This workshop is in-person only for interactive exercises and hands-on tools. If you'd like a virtual option, contact [email protected] to discuss custom virtual workshops for your leadership team (minimum 5 participants).
What happens after the workshop?
You receive 3 post-workshop follow-ups:
- • Day 3: Vendor Landscape Report delivery (30+ vendors organized by use case)
- • Day 7: Implementation planning resources (HIPAA checklist, BAA review guide, pilot design framework)
- • Day 14: Complimentary 30-minute consultation to discuss your assessment results
Is this workshop FTC-compliant regarding AI claims?
Yes. All workshop content follows FTC guidelines for truthful advertising. I make no guaranteed outcome claims, no fabricated testimonials, and no unverifiable ROI promises. All case studies cite published sources and include conservative framing ("your results will vary").