- Lead the Market. Redefine What’s Possible.
You know you need AI. But you don't have a plan.
300+ SaaS vendors screaming for your budget. Legacy tech holding you back. The fear of missing out vs. the fear of a million-dollar mistake.
The organizations that win aren’t the ones with the biggest budgets – they’re the ones that move first, scale what works, and turn AI into advantage.
Brett Kiley has spent 20+ years inside the system – leading billion-dollar CX transformations at CVS, Caremark, and digital-health ventures.
He’s seen what separates hype from results.. and what it actually takes to lead.
impact
supported
served
improvement
I Don't Sell Software. I Sell Outcomes.
The market is flooded with “AI Experts” who just installed ChatGPT yesterday. I’ve spent years executing CX strategies at the enterprise level, from CVS Health to high-growth challengers.
My role stands between you and chaos. I help you decide whether to build your own competitive advantage or buy speed and convenience.
“I’ve sat in your seat. I’ve led the same transformations. I’ve made the mistakes you’re trying to avoid.
My mission now is to help you lead faster, smarter, and avoid making those mistakes”
From Inside the System to
Industry Stage
Brett talks about what actually happens in healthcare transformation. What he has lived through and the lessons he learned.
His keynotes are built for leaders who want to lead first in the market and deliver measurable progress in environments built to resist it.
- How to make AI actually work in care environments
- Predictive Outreach: From firefighting to proactive care
- Agentic AI: Guardrails, safety, and measurable ROI
Results
Healthcare doesn’t move because of big ideas – it moves because of systems that work.
Predictive Outreach for Specialty Pharmacy
→ Cut inbound calls by 48%, increased retention, and unlocked measurable ROI.
Agentic AI for Care Coordination
→ Automated triage, shortened cycle time 40%, elevated CSAT across 1.4M+ interactions.
Omnichannel CX at CVS
→ Unified experience for 1,900 clients, +44% NPS, $100M+ EBIT growth.
$100M+ EBIT added
1.4M+ patients served
2.4× client ROI
67% reduction in cloud costs
Book Brett for your next leadership event or transformation session.
Services
Break Into First™ - Advisory
Leadership advisory for healthcare teams that want to move the market, not react
to it.Healthcare organizations are under pressure to innovate faster, modernize patient
experience, and deliver measurable value from AI and digital investments.Through tailored executive partnerships, Break Into First™ helps leaders aligntechnology, people, and performance to drive market-shaping transformation.
Our advisory work helps you:
- Reimagine your CX, technology, and AI strategies through a healthcare-specific lens.
- Evaluate and select vendors with clarity and confidence.
- Build operating models that connect innovation with execution — and change that lasts.
Services include:
- Fractional CXO partnerships
- Executive Advisory (CX, Technology, and AI in Healthcare)
- Digital Transformation & Vendor Selection
Strategic Consulting:
Skip the reading. Let’s look at your current CX roadmap and identify exactly where AI drives ROI in the next 90 days.
Book a meeting:
Fractional Chief CX Officer & Advisory:
Organizations are under pressure to innovate faster, modernize patient experience, and deliver measurable value from AI and digital investments. Deciding whether to build vs. buy, reimagine CX, or build and AI strategy is what I built my career on and I help you do.
Our advisory work helps you:
- Reimagine your CX, technology, and AI strategies
- Evaluate and select vendors with clarity and confidence
- Build operating models that connect innovation with execution
- Protect your ops - build a human + AI strategy that lowers ops costs and won't break your CX
Speaking & Leadership Events:
Speaking engagements and roundtable events bring together healthcare leaders to share what’s working, what’s changing, and what’s next in digital health and patient experience.
Through stories, strategy, and evidence-based frameworks, Brett helps leadership teams evaluate and take action on CX and AI.
Programs include:
- Leadership Exchange - invite-only roundtables for executives
- Keynotes & Workshops - focused on measurable transformation, AI ROI, and change management
- Speaking Engagements - exploring AI in healthcare, CX, vendor selection
Select Your Gender
Select Your Country and City
What’s your typical annual innovation or technology budget?
How clearly is your AI strategy defined?
How quickly can your organization scale proven initiatives?
What’s your measurable outcome focus?
How aligned is leadership around transformation?
Your Leadership Readiness Score
Calculating...
Not sure where to start?
Take the quiz to find your best path to Breaking Into First™.
In less than a minute, you’ll get a tailored recommendation on whether you’d benefit most from Advisory Partnerships, Fractional Leadership, or Speaking & Leadership Experiences - including estimated time commitment and next steps.
What kind of support are you looking for right now?
How involved do you want Brett to be?
What kind of event or engagement are you interested in?
Which topic best describes your focus area?
Featured In
