About the Cascade Summit
AI has moved beyond experimentation. Today’s enterprise leaders are focused on scaling AI responsibly, reducing operational complexity, aligning HR and IT, and delivering measurable business outcomes.
Cascade Summit is bringing together leaders from organizations like Microsoft, Xerox, Mercer, Boeing, Stripe, and Intuit — for a focused day of real conversations.
Content Covered
- Executive strategies for deploying AI across HR and IT operations
- Lessons from live enterprise deployments at organizations represented in the room
- Practical frameworks for governance, security, and measuring AI ROI
Featured Speakers
Steve Bandrowczak
Former CEO, XeroxFormer COO and CIO, Alight Solutions
Former CIO, Avaya, HP, Avnet
Led enterprise transformation as both CEO and CIO across three public companies — including Alight, one of the largest HR and benefits technology platforms in the world.
Prasad Setty
Former VP, People Operations & Analytics, GoogleOpenAI Advisor
Stanford GSB Lecturer
Built the people analytics function at Google and is now an industry luminary and advisor to multiple companies at the intersection of talent, technology, and the future of work.
Tom Davis
GM & Partner, Microsoft for StartupsHelps founders go from idea to scale at Microsoft for Startups — shaped by founding and exiting two companies, and driven by a commitment to outcomes, diversity, and decisive teams.
Roger Beggs
Vice President, TPG CapitalFocused on the HR function, Roger partners with CHROs to drive value through HR operations, employee benefits spend management, technology deployment, and AI-driven efficiencies.
Eylul Kayin
Ex-Partner, GradientEx-Partner at Gradient Ventures — previously backed category-defining companies at NEA and SoftBank, including Brex, Chime, Flexport, and Ethos.
Stacy Kruger
Vice President, Smurfit WestrockBuilt and scaled enterprise HR and total rewards programs across four major organizations — currently supporting 40,000+ employees.
Dylan Landers-Nelson
Director, Business Group on HealthWorks with hundreds of large employer members to drive value in healthcare cost containment, strategy, and innovation in health and well-being outcomes.
Britt Provost
Senior Vice President, Human Resources, SunbitBuilds the people infrastructure high-growth companies need to scale — with 11+ years as Chief People Officer guiding organizations through IPOs, M&A, and global expansion.
Agnes Quiggle
Partner, Health & Benefits Transformation Consulting, MercerAdvises the world’s largest employers on healthcare strategy and benefits technology. Leading Mercer’s work on how AI reshapes the employer-employee health equation.
Ian Flatt
Senior Vice President, LocktonDelivers people, risk, and employee benefits solutions at Lockton — the world’s largest independently held insurance broker, answering to no one but its clients.
Justice West
Enterprise Platform Solutions,OneOncology
Oversees the enterprise systems that touch nearly every part of the organization — from ITSM and CRM to marketing technology, legal, HR, and practice-facing digital platforms.
Topics We Explored:
Every session was designed around the questions enterprise leaders are asking right now:
Building the AI-native enterprise
What it takes to move from AI pilots to enterprise-wide deployment — the organizational, technical, and governance shifts required.
HR & IT: One employee experience
Why the organizations getting real ROI from AI are the ones redesigning processes and getting IT and HR to lead together.
Governance, security, and trust
How to move forward on AI adoption while managing the real risks around data privacy, compliance, and security.
Lessons from live enterprise deployments
What organizations like those in this room have learned from deploying AI across HR, benefits, and IT operations.
Measuring AI ROI beyond the hype
How to keep the focus on outcomes — not process — and build the business case that earns continued investment.
Attendees:
Senior leaders who are making AI and technology decisions for their organizations, specifically:
- Chief Human Resources Officers or Chief People Officers (CHROs / CPOs)
- Chief Information Officers (CIOs)
- VP / SVP of HR Operations & Shared Services
- VP / SVP of IT & Digital Transformation
- Heads of Employee Experience
- Benefits & Total Rewards Leaders
- Enterprise Architecture & AI Strategy Leaders
Attending Organizations
Agenda
| Time | Session | Speaker(s) |
|---|---|---|
| 8:30 AM | Doors Open Coffee and breakfast. | |
| 9:05 AM | Opening Remarks Welcome, objectives, and framing for the day. | Ana-Maria Constantin CEO & Co-Founder, Cascade AI |
| 9:15 AM | How Agents are Rewiring the Enterprise Stack How new best-in-class AI agents and a trusted startup ecosystem are replacing the traditional enterprise stack. | Tom Davis GM & Partner, Microsoft for Startups |
| 9:30 AM | AI Transformation as a CEO Mandate Why AI transformation must be driven from the top and how leaders should organize for success. | Steve Bandrowczak Former CEO, Xerox |
| 11:00 AM | A Practical Guide to AI in HR & IT Where AI is driving measurable outcomes, where adoption is stalling, and lessons from enterprise deployments. | Eylul Kayin Former Partner, Gradient Roger Beggs VP and Operating Partner, TPG Justice West Enterprise Platform Solutions, OneOncology |
| 12:00 PM | Lunch & Introductions Networking and discussion with attendees and speakers. | |
| 12:30 PM | AI and the Future of Work AI’s impact on employees, managers, organizations, and the future of work. | Prasad Setty Stanford GSB / Former VP & People Ops, Google |
| 1:30 PM | AI and Healthcare Transformation Healthcare costs, AI-enabled benefits experiences, care navigation, and what employers should expect next. | Ana-Maria Constantin Co-Founder & CEO, Cascade AI Agnes Quiggle Partner, Health & Benefits Transformation, Mercer Dylan Landers-Nelson Director, Business Group on Health Stacy Kruger VP Total Rewards, Smurfit Westrock |
| 2:25 PM | AI Implementations: Lessons from the Field How leaders moved AI from concept to production — stakeholder alignment, change management, governance, and lessons learned. | Ian Flatt VP, Lockton Britt Provost SVP HR, Sunbit Justice West Enterprise Platform Solutions, OneOncology Jimmy Ye Customer Success, Cascade AI |
| 3:10 PM | Company Updates & Product Roadmap Key takeaways related to company growth and product innovations | Ana-Maria Constantin CEO & Co-Founder, Cascade AI |
| 4:00 PM | Happy Hour Networking reception at The Lakehouse restaurant, co-sponsored by Lockton |
