Our team went to Workday Rising 2026 in Las Vegas with one goal: connect and listen to Workday customers. Our CEO, Larry Angeli, our VP of Product Engineering, Ryan Bickham, and our Director of Client Success, Tim Kamen, spent most of the conference in Braindates, the one-on-one meetings Rising sets up between attendees who want to talk through a specific problem.
Over the three days, they sat down with 10 people who run HR systems and payroll at their organizations. Those organizations ranged from about 280 employees to nearly 30,000 workers, including contingent staff. They spanned county government, a regulated utility, healthcare, financial services, non-profits, energy, media, and e-commerce.
As a Workday partner, we care a lot about what Workday customers are trying to do with their org data. Here's what we heard, and what it means if you lead HR, Finance, or IT.
Workday is building a governed home for AI agents
The biggest message from the main stage was that Workday wants AI agents to do real work inside HR and finance, with your existing permissions and approvals applied every step of the way. The word you heard everywhere was "lawful." Workday CTO Gabe Monroy summed it up this way: "Headless can't mean lawless."
A few announcements stood out to our team:
- Autopilot agents. Workday introduced agents that run in the background across hiring, payroll, accounting, and compliance, and bring people in when a decision needs human judgment.
- Specialized agents over one assistant. Instead of a single assistant that tries to do everything, Workday is building agents that each own a defined job.
- An open door for outside agents. Workday Data Cloud and Agent-Ready Tools are now generally available, so agents built elsewhere can work with live Workday data while Workday's security rules stay in place. Agent Passport and the Agent System of Record extend that governance to agents Workday didn't build, and Workday also agreed to acquire C1.ai, an identity platform for people and agents.
- Usage-based pricing. Workday sells AI usage through Flex Credits, which tie cost to how much the agents actually do.
These build on partnerships Workday announced earlier this year, including zero-copy data access with AWS and Workday agents inside Google's Gemini Enterprise.
Larry came away with a clear read on what this means for Workday customers: "Workday wants to be the governed system of record that third-party AI plugs into. That makes clean, permissioned integration with Workday's agent layer more important to HR buyers."
In other words, the org structure inside Workday is about to do more work than ever. When an agent routes an approval or answers "who owns this?", it leans on who reports to whom.
What Workday customers told us in Braindates
Almost every conversation came back to the same gap. The structure that keeps Workday running smoothly isn't always the org chart people need to see when they're trying to get work done.
The org people work in doesn't always match the org on paper
Supervisory organizations do important work in Workday. They organize workers under managers so approvals and security route correctly. But the way people actually collaborate is often messier than that.
A Workday lead at a financial services firm explained the disconnect. Their offshore teams report to a local manager for HR tasks like leave and performance reviews, but the business leaders who direct their daily work sit in the US, and that relationship doesn't show up in the reporting line. When someone tries to trace who a worker supports, "they land up with the [local] manager, and that's where the hierarchy ends."
A payroll and benefits specialist at a healthcare organization put it more simply. Leaders who run several sup orgs can appear several times on the chart. "Sally Sue shows up four different times because Sally runs four different [sup orgs]," they said. What they wanted was to see each leader "listed one time… not necessarily the orgs, but the people."
We heard versions of this from an energy company with growing agile and project teams, a media company whose sales teams organize around client accounts, and an e-commerce company whose leaders run teams across separate business lines. That last company runs about 200 reorgs a month, so keeping one clear view of every team a leader owns is a daily challenge.
Keeping org charts current still takes manual work
The data lives in Workday. But the picture people want to share often gets rebuilt by hand.
An HRIS and people analytics manager at a non-profit described her process: "It's the org chart, so it's very manual. I was handed a Visio diagram… I just run reports out of Workday for hires, terms, job changes." Then comes the formatting. "Sometimes I can't get the lines to match up, and that drives me crazy."
An HCM lead at a county government handles shift changes for public safety teams. "Every other month… I'm moving probably 100-plus people," she told us, one person at a time. Another HR systems lead had built his own AI routine to draft org chart PDFs ahead of upcoming changes, because leadership still wanted a polished document every time something moved.
The people who need the org chart most often aren't in it
Several organizations told us that a large share of their workforce works in the field, on shifts, or on site. At a human services non-profit, about 70% of staff work out in the field. At the energy company, just under half the workforce is blue collar, and many of those employees open Workday mainly to look up who they're talking to.
Then there are the people outside the core employee record. The county HCM lead told us their volunteers aren't "part of any org structure whatsoever." A regulated utility company tracks about 11,000 contingent workers alongside 18,000 employees. When those groups don't appear anywhere, nobody has the full picture of who is doing the work.
AI raises the stakes on clean org data
This is where the Braindates and the main stage met. That HRIS lead at a regulated utility company told us his leadership hoped AI could replace dedicated org charting. "They can just take a report [out of] Workday, [feed it] into AI, make charts. I've tried that… it's really bad." For a utility company that includes org charts in regulatory filings, "really bad" isn't an option.
An HR systems leader at the e-commerce company raised a related point. Their org structure doubles as their permissions layer, so any AI agent they bring in needs to know exactly who reports to whom before it can safely work with team data.
Why one manager can show up twice on an org chart
Ryan heard the same question in several Braindates and offered a simple way to explain it. Workday builds its org chart from supervisory orgs, because sup orgs are what drive business processes and security. People tend to read an org chart as people: who is my manager, and who are my peers? Both views are valid. They just answer different questions.
Here's an example; say a company has a Technology sup org led by Jane Doe, the CTO. Under it sit two sup orgs, Web Development and Infrastructure, and John Smith leads both. Because the chart is drawn sup org by sup org, John appears in two boxes under Jane. One box holds his Web Development team and the other holds his Infrastructure team. The person we spoke with simply wanted all of John's reports to roll up to him in a single box.
The same structure shows up when someone changes managers. In Workday, a manager change means moving the worker into a different sup org. At many companies, one or two people handle every move, so they need to know which sup org belongs to which manager. The county HCM lead we met looks up sup org numbers across more than 800 sup orgs and tracks each move in a spreadsheet.
Leaders also told us they want to see several levels of the organization at once, not just one manager and their direct reports at a time.
Ryan left Rising convinced that Workday customers want a live org chart that reflects how their people actually work together, and that many of the people who need it most aren't daily Workday users.
Getting ahead of change starts with org data you trust
Tim spends most of his time with customers after they roll out an org chart, so he listened at Rising with a practical question in mind: once AI agents arrive, what will HR teams actually ask them to do?
His answer is that the most valuable questions all depend on accurate org data. Leaders will want to model a reorg before they announce it, and to map internal mobility paths for people whose roles are changing as AI takes on more of the work. He also expects teams to start sketching hybrid structures, where people and agents share the work of a single team. None of that works if the reporting lines underneath are out of date or hard to read.
Tim's takeaway for his own process follows the same logic. He wants customer success to be proactive instead of reactive, using AI to spot gaps in processes and to flag early signs that a customer needs help before a small issue becomes a bottleneck. It's the same shift he expects HR leaders to make, and it starts with trusting the data you're looking at.
What this means for HR, Finance, and IT leaders
If your organization runs on Workday, here's what we'd take away from these conversations.
Treat your org structure as AI infrastructure. As agents start acting on Workday data, a confusing or outdated org structure stops being a visibility problem and starts affecting what those agents can safely do. Now is a good time to look at how clearly your reporting lines and sup orgs reflect reality.
Keep Workday as your system of record, and give people a clear view of it. Nearly everyone we spoke with wanted Workday to stay the single source of truth. What they wanted on top of it was a live view that shows people instead of administrative containers, including matrix relationships and project teams.
Count everyone who does the work. Frontline staff often sit outside the org chart people use day to day, and contractors and volunteers often sit outside Workday entirely. If they're part of how work gets done, your planning and your AI tools need to know they exist.
Start thinking about where agents fit in your org design. If agents are going to do real work alongside your teams, it's worth asking who owns that work and how it changes the shape of a team. We don't think anyone has fully answered that question yet, and we expect to hear a lot more about it at next year's Rising.
Where Sift fits
Sift connects to Workday through a certified integration, so your org chart updates automatically as changes happen in Workday. People see reporting lines by person, with dotted lines and project teams in one place, right where they already work in tools like Microsoft Teams and Slack. Workday stays your system of record. Sift helps everyone else see it clearly.