A CHRO, a CFO and a CIO walk into Workday Rising…
And immediately have a problem: there’s too much good content.
Between hundreds of sessions, product announcements, customer stories, Braindates, partner meetings, coffees and cocktails, building a Rising agenda can quickly become a strategy exercise of its own.
But the real question isn’t simply which sessions look interesting?
It’s which conversations will matter when you’re back in the office making decisions about 2027?
That’s where TopBloc’s Office of Customer Experience (OCX) comes in.
Our OCX brings together experienced CHRO, CFO and CIO perspectives from leaders who have operated Workday and understand the questions executive teams are asking around AI, workforce strategy, financial transformation, governance and productivity.
So we asked them: If you were advising a CHRO, CFO or CIO heading to Rising, which sessions would you make sure were on their calendar?
For the CFO: Move AI From Interesting to Impactful
For Finance leaders, the AI conversation is quickly moving from experimentation to execution. The priority now is understanding where AI can create measurable value—reducing manual work, accelerating close processes, identifying exceptions earlier and giving lean Finance teams more time for strategic decision-making. Angela’s recommendations focus on where AI, automation and Finance transformation intersect.
Here are all the sessions I’m prioritizing:
★ TOPBLOC CUSTOMER SESSION | Lemonade + Arch Capital Group
Turn AI Pilots into Payoffs: How Insurers Scale on Workday [26-INLP1954]
Lemonade and Arch Capital Group are moving AI into production in one of the most highly regulated industries, making this especially relevant for Finance leaders balancing innovation, governance and ROI. As TopBloc customers, their stories also offer a practical look at how organizations are moving beyond AI experimentation and into real operating models.
👓 Angela’s lens: Listen for what allowed these organizations to move from pilot to production, how they are measuring value, and how Finance, HR and IT are governing AI together.
Top 5 Financial Management Agents [26-FNTS1988]
This session gets practical about what AI agents can actually do in Finance today—from automating routine work to identifying exceptions and creating more capacity for strategic analysis.
👓 Angela’s lens: Angela’s lens: Pay attention to what is available now versus what is still on the roadmap, and where agents could create meaningful efficiency inside existing Finance processes.
Demo: The Intelligent Close – Unifying Planning, Consolidation, and Reporting [26-PLD1981]
A faster close remains a major Finance priority, but speed only matters if accuracy, visibility and auditability improve with it.
👓 Angela’s lens: Watch for how Adaptive Planning and AI agents can reduce handoffs, manual reconciliation and investigation time while creating a more connected close process.
★ TOPBLOC CUSTOMER SESSION | Midtown Athletic Club
Unifying People, Money, and Systems: Agentic HR, Finance, and T&E from Workday for Midsize Companies [26-P2028]
Midsize organizations are often being asked to do more without adding resources at the same pace. MidTown Athletic Clubs brings that challenge to life, showing how a midsize organization can think more holistically about people, Finance, systems and automation.
👓 Angela’s lens: Look at AI as a capacity strategy. Where can automation absorb administrative work, connect fragmented processes and improve efficiency without creating additional risk? For midsize organizations, this is a strong example of how technology strategy can directly support a leaner operating model.
For the CIO: Build the Foundation Before You Scale the Agents
For CIOs, Workday’s AI story is about more than the agents themselves.
The bigger questions are about architecture, governance, data controls, consumption and how AI fits into the broader enterprise technology strategy. Kristin recommends using Rising to understand that foundation before jumping straight to individual use cases.
Here are all the sessions I’m prioritizing:
Accelerating Innovation: Scaling AI and Agents with Workday [26-ITTS2825]
If terms like UMSA, Flex Credits and Agent System of Record are entering your Workday conversations, this session is an important starting point.
👓 Kristin’s lens: CIOs should leave with a clearer understanding of how Workday expects customers to license, govern and scale AI over time—not just which features are available today.
Governing the Agents: Architecting a Modern Responsible AI Framework [26-ITTS2812]
Agentic AI changes the governance conversation. Autonomous agents can access information, initiate actions and participate in enterprise workflows in ways traditional policies weren’t designed to address.
👓 Kristin’s lens: CIOs should leave with a clearer understanding of how Workday expects customers to license, govern and scale AI over time—not just which features are available today.
The Agent-Ready Enterprise Platform: Empowering CIOs to Transform Work [26-KEY6]
This is the deeper technology conversation, with Workday showing how governed agents, trusted enterprise data, developer capabilities and measurable ROI can come together.
👓 Kristin’s lens: Pay particular attention to the architecture connecting data, agents, governance and extensibility. The long-term question is whether Workday can become part of the enterprise control plane for AI.
For the CHROs: Focus on the Frontline
Lynn’s perspective on creating better experiences for frontline employees, managers, and the teams supporting them.
Here are all the sessions I’m prioritizing:
Connect Workday HR Agents to the New Ways of Work [26-HRP2640]
AI is changing how HR teams support employees and managers across the talent lifecycle. For frontline organizations, that means faster recruiting and onboarding, easier access to HR support, and more consistent experiences across distributed teams.
👓 Lynn’s lens: I’ll be listening for where Workday HR Agents can make the biggest impact for frontline workers and managers, especially across recruiting, onboarding, payroll, benefits and day-to-day HR support.
Empower Your Frontline: How Nordstrom Optimizes Every Shift [26-INLP1963]
For retail and hospitality leaders, workforce management directly affects labor costs, employee experience and customer service. Nordstrom’s approach brings scheduling, time and pay together across a 50,000-person frontline workforce.
👓 Lynn’s lens: I want to hear how Nordstrom is using mobile-first tools and AI to make scheduling easier for employees while giving leaders more control over labor planning, staffing and workforce costs.
Demo: Cut Labor Costs and Empower Your Frontline With Smarter Scheduling [26-HRD2634]
Smarter scheduling is becoming a major opportunity for organizations balancing labor demand, compliance, employee preferences and overtime. Workday AI is bringing more automation and forecasting into that process.
👓 Lynn’s lens: Watch for how AI-powered forecasting and automated scheduling can help retail and hospitality teams better match staffing to demand while still creating a stronger experience for frontline employees.
For the CHRO: The Strategic CHRO Agenda
The HR organizations that get the most value from AI won’t simply automate existing processes. They’ll rethink how workforce planning, skills, talent mobility and employee support connect to the broader business.
Here are all the sessions I’m prioritizing:
Workforce Analytics & Planning: Strategy and Vision [26-PSVHR2623]
The challenge: Agile headcount and scenario planning. Workforce planning can no longer be an annual headcount exercise. Finance increasingly expects HR to connect workforce decisions directly to cost, capacity and business outcomes.
👓 Rizal’s lens: Look for ways to turn real-time workforce data into predictive models that create a common language between HR and Finance.
AI: Strategy & Vision [26-PSVIT2745]
The challenge: Agentic AI integration. Most HR leaders don’t need another explanation of why AI matters. They need a roadmap for where to start.
👓 Rizal’s lens: Focus on how to prioritize use cases, improve employee self-service and reduce administrative handling time while building the right adoption and governance model before deployment scales.
Workday Talent Development: Strategy and Vision [26-PSVHR2644]
The challenge: Dynamic skills gaps and internal mobility. Organizations increasingly need to understand not only the roles employees hold today, but the skills they possess and the capabilities the business will need tomorrow.
👓 Rizal’s lens: Listen for how Workday plans to connect skills intelligence, development and internal mobility to help organizations fill more talent needs internally and reduce reliance on external hiring.
The Practical CHRO Agenda: Find the Use Cases That Move the Needle
Steve’s view is straightforward: AI can no longer sit on the edge of HR strategy. The opportunity now is to identify specific, high-impact use cases where AI can add meaningful capability, reduce expensive manual work or improve how HR supports the business.
Here are all the sessions I’m prioritizing:
Empower Careers: Turn Skills Into Action at GE Vernova, Presented by Censia AI [26-SPTS2062]
The challenge: Making skills data actionable. Organizations need to understand the skills they have today and connect them to career development, mobility and future workforce needs.
👓 Steve’s lens: Listen for how GE Vernova is putting skills strategy into practice and how Censia AI is helping turn skills intelligence into more meaningful talent decisions.
How to Model and Plan for Your Total Workforce With Adaptive Workforce Planning [26-HRP2602]
Workforce planning works best when HR and Finance are looking at the same picture. Adaptive Planning gives both teams a stronger way to model headcount, skills and future workforce needs together.
👓 Steve’s lens: Listen for how HR and Finance leaders are using Adaptive Planning together, and where workforce planning becomes more powerful as Workday’s broader AI, engagement and skills capabilities come together.
It hits my customer presentation check box and what better way to learn about Workforce Planning than hearing from an HR and a Finance exec talk about it together.
🌟 Bonus: Scaling Union Compliance at Wright Service Corp: A Time Tracking–Driven Payroll Precision Framework [26-INTS1971]
If your organization manages a complex union workforce, this one deserves a spot on the calendar. Wright Service Corp manages payroll across 65 active union jurisdictions, where rates, fringes and differentials vary by contract, geography and job. Working with TopBloc, Wright built a solution that uses actual time worked to automate payroll calculations and corrections across its union environment. The result: payroll review time was reduced by 50%.
Why it stands out: For Payroll, HRIS and HR leaders managing union complexity, this is a chance to hear directly from a customer that has solved a notoriously difficult Workday challenge at significant scale. And yes—65 unions.
One Rising. Three Executive Lenses. One Bigger Conversation.
If there’s one theme running through our OCX recommendations, it’s this:
AI has moved from a product conversation to an operating model conversation.
For CFOs, that means proving ROI and redesigning Finance processes. For CIOs, it means building the architecture and governance that allow AI to scale responsibly. For CHROs, it means determining how AI changes workforce planning, skills, talent mobility and the work performed by HR.
And increasingly, those conversations are interconnected.
That’s also what makes the customer stories at Rising so valuable. Sessions from organizations like Lemonade, Arch Capital Group, MidTown Athletic Clubs and Wright Service Corp offer the opportunity to see what these strategies look like once they leave the roadmap and enter the real world.
The most interesting opportunities at Rising may be the ones that sit between functions—where people, money, data and AI come together.
So as you build your Rising agenda, don’t simply ask: What do I want to learn?
Ask: What decisions do we need to be ready to make when we get home?
Start there.
See you in Las Vegas.
And while you’re building out your Rising schedule, don’t forget everything happening with Everforth TopBloc throughout the week. From executive dinners and industry events to Braindates, advisory sessions, and customer-led conversations, we’ve pulled it all together in one place so you can see what fits your agenda.
Explore everything Everforth TopBloc has happening at Workday Rising →
