SkyPoint AI logo
SkyPoint AI logo
july 15-16, 2026 • The ritz-carlton, portland, oregon

Skypoint AI Summit 2026
Healthcare | Senior Living

AI is rewriting the economics of healthcare and senior living. Join 150+ C-level leaders to measure what it delivers in productivity, efficiency, and financial impact.

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What You Will Experience

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Keynotes

Keynotes from AI pioneers and C-level executives on the economic impact of AI.

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12 Sessions

12 focused sessions: 4 Senior Living, 4 Healthcare and 4 Common – all centered on AI automating knowledge work and driving financial impact.

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Live Demos

Live product demos of AI agents, Ai-native applications in action from Skypoint and our strategic partners.

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Workshops

Hands-on workshops & 1:1 partner meetings on how to make AI a reality in your organization.

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Networking

Networking with 150+ C-level executives, partners, and industry leaders.

Featured Speakers

Hear from the visionaries and leaders who are pioneering the future of AI in healthcare and senior living.

Fee Stubblefield

Fee Stubblefield

CEO, The Springs Living
Fee Stubblefield is Founder and CEO of The Springs Living, an Oregon-based operator of 20 senior living communities he founded in 1996. He serves on the NIC Board of Directors and authored the Amazon bestseller “A Culture of Promise,” which chronicles his quest to transform the senior living industry.

Dan Anolik

Chief Technology Officer, Cambia Health

Dan Anolik is Chief Technology Officer at Cambia Health Solutions, bringing 28+ years building and scaling global engineering organizations across digital health and enterprise software, with deep expertise in AI adoption, secure platforms, and post-merger integration.

Dr. Kamal Jethwani

CEO, Decimal Health

Dr. Jethwani is a digital health strategist who builds AI-driven, connected care programs at Harvard-affiliated centers, scaling innovations that improve patient engagement, outcomes, and value-based care across provider networks.

Douglas Thompson

Douglas Thompson

CEO, Element Care

Douglas Thompson is CEO of Element Care. He previously founded Perfect Health, Inc. and served as CFO of the Massachusetts Medicaid program and three Medicaid MCOs, managing operations up to $9 billion. A Harvard graduate, he serves on the Swampscott Select Board.

Amy Silva-Magalhaes

COO, Ultimate Care

COO of Ultimate Care, including The Bristal brand, with 15+ years in senior living, healthcare and hospitality.

Michael Pittore

Michael Pittore

Co-CEO, Agemark Senior Living
Co-CEO of Agemark Senior Living, leading 28 communities with a data-driven, acuity-based staffing approach. Cornell engineer, former Goldman Sachs and Deutsche Bank banker.

Andy Eby

CEO, Bickford Senior Living

CEO of Bickford Senior Living, operator of 60+ communities, Co-Founder of Serviam Care Network, and former NFL offensive lineman.

Venki Krishnababu

CIO, Dutch Bros
Chief Information Officer at Dutch Bros, with nearly 30 years in enterprise technology across healthcare and retail. Formerly CTO at Premera Blue Cross and lululemon, he specializes in data, automation, and AI systems at scale.
Scott Reid.png

Scott Reid

Co-founder, Alignment Healthcare

Scott brings over 20 years of experience revolutionizing senior care models through technology. Join him at the executive dinner for an intimate discussion on value-based care.

Shahzad Shah

Shahzad Shah

SVP, Data, AI and IT, Delta Dental Arizona

SVP at Delta Dental of Arizona. Leading the organization’s digital transformation through AI, data, and applied innovation. Focused on optimizing care delivery, improving quality, and elevating the member experience across every step of the care journey.

Dr. Anthony Zizza

Dr. Anthony Zizza

Chief Medical Officer, Element Care
Dr. Anthony Zizza is Chief Medical Officer of Element Care. A Harvard-trained geriatrician, he joins from Optum at Home and previously led care at Cambridge Health Alliance’s PACE program, Compassus Hospice, and Landmark Health. He completed his Geriatric Medicine fellowship at Harvard Medical School.

Tisson Mathew

CEO, Skypoint

Founder and CEO of Skypoint, replacing legacy healthcare and senior living software with agentic AI deployed at 1,100+ locations across 20+ AI-native applications.

Dr. Andy Mendenhall

CEO, Central City Concern

President and CEO of CCC, addiction and family medicine physician, OHSU-trained, co-founder of HealthWorks NW, acquired by Hazelden Betty Ford.

Torben Nielsen

CEO, Uptiv Health

CEO of Uptiv Health, co-founder of HealthSparq (acquired by Kyruus), former ZoomCare CEO, and digital health innovator featured in works by Scott Galloway.

Marina Simonian

Co-founder and Head of Product, Uptiv Health

Marina is Co-founder and Head of Product at Uptiv Health, a hybrid infusion care platform transforming specialty care delivery through patient-centered innovation. Over her 20+ year career, she has developed healthcare technology solutions across physician practices, ambulatory surgery centers, hospitals, and virtual care settings. Today, she focuses on harnessing AI and modern healthcare technologies to improve operational efficiency, elevate patient experiences, and expand access to specialty care. 

Amber Bardon

CEO, Parasol Alliance
Amber Bardon is Founder and CEO of Parasol Alliance, a managed technology provider serving the senior living industry since 2015. A certified PMP, she previously led IT at CJE SeniorLife and sits on the NIC AgeTech Committee.

Monica Chopra

VP of Health and Wellness, Cascadia Senior Living
Monica Chopra, RN CLNC, is VP of Health & Wellness at Cascadia Senior Living & Fieldstone Communities. A WHCA board member and AHCA/NCAL committee leader, she drives clinical excellence and resident-centered care across long-term care.

Bill Frerichs

President, Frontier Dermatology

President and COO of Frontier Dermatology, the leading dermatology provider with over 40 locations. 25 years building and transforming healthcare organizations. Former interim CEO of Zoom+Care, overseeing its transition to PeaceHealth. Proven track record turning around healthcare operations and driving growth.

Sujay Subramaniam

Principal, Deloitte

Sujay Subramaniam is a Principal in Deloitte Consulting’s Healthcare practice with over 20 years of experience leading enterprise transformation across healthcare and life sciences. He has extensive experience advising national and regional organizations on post-merger integration, enterprise design for growth, core business and technology modernization, and emerging technology adoption. As a transformation architect, he is passionate about helping organizations align strategy, operating models, and technology investments to accelerate growth, enhance performance, and deliver measurable business outcomes.

 

John Element Care

John Coolong

CIO, Element Care
John Coolong is Chief Information Officer of Element Care, where he has led IT and business transformation since 2013, including a decade heading its Managed Care Division. He brings 20+ years of healthcare technology leadership

Skip Newberry

CEO, Technology Association of Oregon
Skip Newberry is President & CEO of the Technology Association of Oregon, where he has spent over 14 years building an inclusive innovation economy across Oregon and SW Washington. He also serves as Honorary Consul for Estonia.
Matt Reiners

Matt Reiners

Chief Growth Officer, Parasol Alliance
Matt Reiners is Chief Growth Officer at Parasol Alliance and host of the Connecting the Dots: Senior Living Success podcast. He co-founded Eversound, a senior living audio company acquired by Uniguest, and was named to Forbes 30 Under 30 for Consumer Tech. 

Kishore Bhattacharjee

CTO, Skypoint

Senior executive leading technology strategy, cloud SaaS platforms (AWS, GCP, Azure), AI/ML and LLM solutions, SaMD development, regulatory compliance (HIPAA, GDPR, ISO), and DevSecOps transformation across healthcare and consumer experience.

Tony Holland

Managing Partner, Integrity

Managing Partner at Integrity, the largest insurtech platform in the US serving seniors, backed by Silver Lake and serving millions of clients through more than 750 healthcare payers. Part of the Baltimore Orioles ownership team, passionate Medicare Advantage and senior healthcare advocate, and partner of Livmor AI, the first AI-driven Medicare intelligence platform helping seniors worry less and live more.

Rob MacNaughton

COO, Skypoint

Top 50 Healthcare Technology CEO (2020), active investor in senior living, and board member across healthcare and technology companies.

David Kohel

David Kohel

CEO, Livmor AI

CEO of Livmor AI and ex-CTO of Zoomcare, the first AI-driven Medicare intelligence platform. 25 years building category-defining healthcare platforms. Early AI/ML adopter for predicting health outcomes. Passionate senior healthcare advocate.

Gavin McLaughlin

Gavin McLaughlin

VP, Customer Success, Skypoint
VP of Customer Success driving customer retention, expansion, and value realization across Skypoint’s AI platform for healthcare and senior living organizations.

Caitlin Jones

M.S., CCC-SLP, Skypoint

Caitlin Jones, M.S., CCC-SLP is a healthcare technology and revenue executive with a background in speech-language pathology and healthcare operations. As Vice President of Revenue and Growth at Skypoint AI, she leads go-to-market strategy, executive partnerships, and AI adoption initiatives across senior living and healthcare organizations.

JR Southerland

Growth Executive, Inspiren

JR Southerland is a growth and enterprise sales executive with more than 20 years of experience driving business development, strategic partnerships, and customer engagement. He currently serves as Growth Executive at Inspiren

Joelle Poe

Vice President of Strategy, SafelyYou

Joelle Poe is a healthcare strategy and product executive with extensive experience leading innovation across digital health, senior care, and healthcare technology organizations. She currently serves as Vice President of Strategy at SafelyYou and Strategic Advisor at Centered Care, focusing on growth, transformation, and operational excellence.

Josh Studzinski

Chief Growth Office, CarePredict

Josh Studzinski is a growth and marketing executive with extensive experience leading revenue, sales, and go-to-market strategy for healthcare and technology companies. As Chief Growth Officer at CarePredict, he oversees sales, marketing, and business growth initiatives focused on advancing senior care technology.

Brooke Cowan

Applied AI Executive, Cambia Health Solutions

Brooke Cowan is an experienced AI executive and MIT-trained machine learning researcher who has spent over 15 years building AI products, leading engineering and data science teams, and driving enterprise AI strategy across healthcare, fintech, and technology.

Revolutionizing Care Economics

Our 2026 summit focuses on how artificial intelligence optimizes operational workflows and enhances the economic viability of patient and resident care.

Operational Excellence

Streamlining administrative tasks and staffing through AI to reduce burnout and overhead.

Clinical Efficiency

Enhancing clinical efficiency with AI for better outcomes and payemnts.

Economics

Analyzing the long-term financial benefits and cost-reduction of AI across senior living and healthcare.

Agenda Highlights

Two main tracks focusing on care breakthroughs and operational sustainability. Discover how AI is being deployed today.

11:00 AM 
The Ritz-Carlton Lobby

Registration & Welcome

Arrive at The Ritz-Carlton, check in, pick up your badge, and settle in before the evening begins.
1:00 PM 
Limo departs from hotel

LucidWild Estate Wine Tour

Travel by limo from the Ritz-Carlton to LucidWild Estate in the Dundee Hills. Join fellow executives for a guided tour of Oregon’s premier wine country, with vineyard walks, tastings, and food pairings, capped by dinner among peers. The best networking happens over a glass of Pinot Noir. More info: https://lucidwildestate.com/

6:00 PM
Wine Country

LucidWild Estate - Opening Dinner

Seated dinner in the heart of wine country, surrounded by stunning vineyard vistas. A welcome address from leadership sets the stage for tomorrow’s Summit. Great food, great company, and the perfect start to two days among peers.

8:30 PM
The Ritz-Carlton

Return to The Ritz-Carlton & After Party

Limo ride back to the Ritz-Carlton after dinner, where our sponsors host the after-party. Keep the conversations going before the Summit kicks off tomorrow.

8:00 AM

Ballroom Foyer

Breakfast & Networking

8:30 AM 

S1

Common

Opening Keynote: AI Doing Real Work

The state of AI across healthcare and senior living: AI agents are already automating knowledge work, cutting labor costs, and driving new revenue. A grounded look at the technology, culture, and organizational change needed to make it real.

Keynote Panel – 40 Minutes (3 total, including moderator)

9:10 AM 

Break • 5 Mins

9:15 AM 

S2

Common

Driving Successful Digital & AI Transformation: Process, People & Technology

Digital and AI transformation efforts fail more often than they succeed—and it’s rarely the technology’s fault. This panel brings together leaders who’ve actually driven change to break down what works across the three things that make or break it: process, people, and technology. Honest lessons on sequencing, change management, and avoiding the pilots-that-go-nowhere trap.

Panel • 40 Minutes

9:55 AM 

Break • 5 Mins

10:00 AM 

S3

Common

AI-Driven Organization & Sector Driven Change

A transformation isn’t a deployment — it’s an organizational shift, and increasingly a sector-wide one. This session brings together the leadership team driving AI transformation inside a PACE organization alongside the consulting partner guiding the change. The conversation will cover the strategic vision behind the decision to transform, the operational reality of moving an entire organization into the AI era, an honest accounting of what it may cost, and a look ahead at where sector-level collaboration is heading. Less about any single tool, more about how leaders rewire an organization and a model around AI.

Panel • 40 Minutes

10:40 AM 

Break • 5 Mins

10:45 AM 

S4

Senior Living

AI-Powered Senior Living Operations: Occupancy Growth and Labor Cost Optimizations

How senior living operators are filling communities faster and running leaner at the same time. This panel goes inside the move-in funnel and the staffing model: AI agents qualifying and following up on leads so inquiries don’t go cold, census-driven scheduling that matches labor to actual need, and overtime and agency spend that shrink without cutting care. Operators share real occupancy gains and labor savings delivered with zero additional headcount — plus what didn’t work along the way.

Panel • 40 Minutes

10:45 AM 

S5

Provider / Payer

Provider Productivity: AI Agents Automating Front Office & Clinical Administration

AI agents are clearing the administrative drag on provider front offices — the phone tag, manual scheduling, and fax machines that slow everything down. This panel digs into what’s actually running in production: documentation automation, prior auth assistance, and inbox triage that hand providers back their time. The result is more patients seen and clinicians who go home on time. Expect real time-savings data from health systems, an honest look at where these tools still fall short, and what operators would do differently.

Panel • 40 Minutes

11:25 AM 

Break • 5 Mins

11:30 AM 

S6

Senior Living

AI NOI: Agentic Analytics

Real-time visibility across every community — occupancy, revenue, labor spend, and AR aging — in one dashboard tracking 350+ KPIs. This panel shows how operators run their portfolio like a command center: AI watchlists that surface at-risk communities, performance scorecards that hold teams accountable, and exception reporting that catches problems before they hit the P&L. Operators walk through what they actually monitor day to day, where the dashboards earned their keep, and what they’d build differently.

Panel • 40 Minutes

11:30 AM

S7

Value-based Care

Growth: AI-Enabled Member Acquisition and Retention for Value-Based Care

Value-based care is reshaping how Medicare Advantage organizations, agents, providers, and senior living operators work together to grow membership, improve outcomes, and operate more efficiently. This session explores how AI is being used across the full member lifecycle, from identifying and educating prospective members to improving agent productivity, automating Scope of Appointment compliance, and supporting more personalized enrollment experiences.


The discussion also goes beyond acquisition to focus on retention: using remote patient monitoring, predictive insights, and AI-driven outreach to keep members healthier, more engaged, and enrolled year over year. Panelists will share how senior living operators can participate in the value-based care ecosystem, support stronger partnerships with physicians, home health providers, and Medicare Advantage plans, and turn resident data into proactive care interventions.


Attendees will leave with practical examples, lessons learned, and clear first steps for building an AI-enabled value-based care strategy.

Panel • 40 Minutes

12:15 PM 

Lunch and Sponsor Live Demos • 45 Mins • Grand Ballroom

01:00 PM 

S8

COMMON

The ROI of AI: AI Agents Making Financial Impact

Real numbers from real operators and health systems. How AI agrents are automating administrative work, remote patient monitoring —work that used to take FTEs now runs before your team clocks in. The hype around AI in healthcare is loud, but operators don’t have the luxury of theory — they need margin. This panel skips the abstractions and goes straight to the people signing the checks and reading the variance reports. We’ll hear from CEOs and CFOs who have put AI employees to work on the workflows that used to chew up nights and weekends: census reporting, labor cost variance, AR follow-ups, board packets, and claims processing. Expect real numbers, real surprises, and an honest take on what’s working, what isn’t, and what they’d do differently.

Panel • 40 Minutes

1:40 PM 

Break • 5 Mins

01:45 PM 

S9

COMMON

From Days to Minutes: AI-Powered Prior Auth & Member Experience

How health plans are using AI to take the friction out of prior authorizations, benefits verification, and member communications — at scale. This panel shows how payers are compressing turnaround from days to minutes, cutting administrative costs by 40%+, and lifting member satisfaction scores along the way. It also covers AI-powered fraud detection and payment integrity that protect the bottom line without slowing members down. Expect real numbers from health plans in production, an honest look at where these tools still fall short, and what teams would do differently.

Panel • 40 Minutes

02:25 PM 

Break • 5 Mins

02:30 PM 

S10

COMMON

From Firefighting to Forecasting: AI-Driven Workforce Planning

How healthcare and senior living organizations are using AI to control labor costs without compromising care. This panel covers AI-optimized scheduling built around census, acuity, and compliance requirements, with real-time labor spend tracked against budget down to the location, department, and individual level. Leaders share how they’re cutting agency spend and overtime while holding staffing ratios — moving from “fighting fires” to predictive workforce planning. The conversation also covers AI for compliance and admin automation, how connected devices and monitoring ease staff workload, and an honest look at the privacy and compliance concerns that come with it — plus what teams would do differently.

Panel • 40 Minutes

03:10 PM 

Break • 5 Mins

3:15 PM 

S11

Common

Under the Hood: How Agentic AI Actually Works

A plain-English look at what’s really happening inside agentic AI. This session breaks down the building blocks — models and harnesses, tool calling, skills, and MCPs (Model Context Protocols) — and how they come together so AI can reason, take action, and even write its own software. The conversation covers how tools like Claude Code are changing what’s possible and, most importantly, what it all means for AI systems in senior living and healthcare. No hype, just a clear mental model of how these systems work and where they’re headed.

Panel • 40 Minutes

03:55 PM 

Break • 5 Mins

4:00 PM 

S12

Common

AI Legal Risk & Compliance: Guardrails for the Real World

What operators need to know to deploy AI responsibly in senior living and healthcare. This session covers the legal and regulatory landscape — from HITRUST r2 certification to the AI guardrails that keep sensitive data protected and decisions defensible. The conversation tackles where legal risk actually lives, how to put the right controls in place without grinding innovation to a halt, and an honest look at the questions every organization should be asking before they scale AI.

Technical Deep Dive + Closing Keynote • 40 Minutes

04:40 PM 

Break • 5 Mins

4:45 PM 

Closing Remarks

Tisson Mathew, CEO  •  15 Mins

5:00 PM 

Summit Concludes

Thank you for joining us. Safe travels!

Accommodations

The Ritz-Carlton, Portland, OR

900 SW Washington St, Portland, OR 97205

  • Room block available for Summit attendees
  • Special group rate — book via registration link
  • Block closes June 20, 2026
  • Check-in July 14, check-out July 17
Hotel & accommodations.webp
Transportation

By Air

Portland International Airport (PDX) – approx. 20 min drive. Uber, lyft and taxi available.

Parking

Valet parking available at the hotel. Self-parking nearby at Smart Park on SW 10th Ave.

FAQ

Healthcare C-level  executives, senior living operators, payers, providers, and technology leaders looking to understand how AI automation can transform their organizations.

The Ritz-Carlton, Portland — 900 SW Washington St, Portland, OR 97205. The conference takes place July 15–16, 2026.

The wine tasting event (1:00–5:30 pm on July 15) is a separate ticketed experience at The Lucid Wild Estate (https://lucidwildestate.com/) and is not included in the standard conference registration.

A link to the Ritz-Carlton group rate will be provided upon completing your conference registration. The block closes June 20, 2026.

Select sessions will be recorded. Registered attendees will receive access to recordings after the event.

See What AI Delivers in Healthcare and Senior Living

Early bird registration ends June 15, 2026. Join us at The Ritz-Carlton, Portland, Oregon for the most impactful AI event of the year.

Request an Invite