AI in Action

HR Leadership Summit

What does it mean to lead — and to be led — when AI is rewriting the rules of work? Our 2026 HR Leadership Summit brought together some of the most forward-thinking practitioners, researchers, and executives in the field to find out.

Key takeaways from our HR Leadership Summit

Don’t manage AI — design for it

The organizations seeing real AI adoption aren’t the ones with the best tools. They’re the ones that treat AI as a teammate, not a technology. That shift requires leaders to understand their culture first — and build their AI strategy around it.

The identity question is the hardest one

When cognitive work changes faster than careers do, people face something more disorienting than a job change. HR leaders are uniquely positioned to help employees navigate the human side of AI adoption — not just the skills side.

HR needs a seat at the governance table

Boards are no longer asking about AI tools. They’re asking about AI strategy, workforce transformation, and risk. HR leaders who aren’t in those conversations are missing an opportunity to shape outcomes for their organizations — and their people.

The engagement gap is personal

Generic benefits content and static portals aren’t closing the utilization gap. Employees need guidance that connects their specific financial situation to their specific benefits — in plain language, at the moment they need it.

Session summaries

What we learned

Relationship Design: From AI Tools to AI Teammates

Andrew Hogan | Head of Insights, Figma

Tamara Moellenberg | Associate Partner, ReD Associates

Jacob Taylor | Fellow at Brookings Institution, Founder at Two Hands Human Performance

AI adoption is a culture problem, not a technology problem. Most organizations have the tools. What they’re missing is an understanding of the cultural drivers shaping how — and whether — people actually use them. Organizations that have cracked adoption aren’t those with the best platforms; they’re those that stopped treating AI like software and started designing around human behavior.
The shift from “AI for me” to “AI for us” requires a different kind of rollout. Individual productivity gains are real but limited. The bigger unlock comes when teams define what good work looks like together — and build shared AI context from that conversation. Measuring individual usage dashboards keeps organizations stuck in tool mode. Team-level KPIs are what drive the mindset shift.
Context is what humans bring that AI can’t manufacture. Generative AI models are stateless — they don’t know your organization, your culture, or your strategic priorities unless you tell them. Teams that are winning with AI have developed a discipline around specification: surfacing the tacit knowledge, the priorities, and the judgment calls that make their work distinctly theirs — and making that context machine-readable.
The next frontier is exploration, not just execution. When AI absorbs the grunt work, it creates capacity. The organizations that will pull ahead are those that reinvest that capacity into new value creation — not those that just knock off for a coffee when the tasks run out.

Connecting the Dots: HR's Role in AI Strategy, Governance, and Adoption

Lori Castillo Martinez | SVP, Workforce Experience Innovation & Analytics, McKesson

Shannon Nash | Chief Operating and Financial Officer, Vibrant Planet

Boards have moved from AI curiosity to AI accountability. The question is no longer “what tool did you buy?” It’s “how are you winning with AI, and what does that mean for your workforce?” HR leaders who aren’t actively shaping those board-level conversations are ceding ground they won’t easily recover.
AI adoption requires three things: autonomy, the right people leaders, and fit-for-purpose tools. Employees need to see how AI fits into their actual work — not as a generic capability deployed from IT, but as something that makes their job better in ways they can feel. People managers are the single most powerful lever: if your direct supervisors are skeptical, adoption stalls regardless of what the CEO says. And the tool has to be the one people actually want to use.
The “random acts of AI” problem is real — and it’s costing organizations. When AI lives in isolated pockets with no coordinated strategy, the result is duplication, risk, and missed opportunity. The organizations that are moving fastest have built some form of coordination — an AI council, cross-functional ownership, a designated champion — to connect the dots before the dots multiply.
Stop holding AI to a standard you don’t apply to humans. One of the most underused AI applications in HR is compliance monitoring — the kind of systematic, 24/7 pattern-detection that human teams simply can’t sustain. Some of the bias hiding in your current processes is only visible when you put AI next to it. That’s not a reason to fear AI in HR. It’s a reason to use it more thoughtfully.

Who Are You Now?

BingYune Chen | CEO and Managing Partner, Active Digital

Jonathan Raymond | Founder and CEO, Ren

The identity disruption is real — and it’s happening at every level. When AI can do what you spent your career getting good at, the professional question and the personal question start to blur. The leaders navigating this best aren’t the ones with the most technical fluency. They’re the ones who’ve learned to tie their value to judgment, accountability, and trust — the things AI can’t replicate.
Younger workers are facing something their experience hasn’t prepared them for. Digital natives may be comfortable with the tools, but they’ve never navigated a genuine career disruption. For a 25-year-old software engineer who just realized there’s no such thing as a junior engineer anymore, this isn’t a role change — it’s an identity shift. HR leaders are uniquely positioned to help them through it.
The “what do humans do now” question is the wrong frame. A more useful one: what value can a human add that AI can’t? The answer points to things like handling ambiguity, building trust, taking accountability when something goes wrong. Those aren’t soft skills. They’re the core of the job now.
We should not be prisoners of the moment. What’s true about managers and agents and the future of roles right now will look different in six months. The leaders who will adapt fastest are those building organizational cultures where people can keep learning — not just reskilling for the current wave, but developing the capacity to navigate whatever wave comes next.

The Generic AI Chatbot Era Is Over

Ben Levine | Chief Product Officer, Candidly

Laurel Taylor | Founder and CEO, Candidly

Benefits engagement has a last-mile problem — and it’s a computation problem. Employees aren’t disengaged because they don’t care. They’re disengaged because no tool has ever connected their specific situation — their income, their debt, their enrollment status — to the specific benefits their employer offers. Static content and one-size-fits-all portals are one-size-for-no-one.
A specific number changes everything. The difference between a generic explanation and a personalized plan isn’t just format — it’s action. When Cait™, our Conversational AI Tool, surfaces a suggestion tied to a real number and a real next step for that employee, users take action 71% of the time. That’s not a nudge. That’s a transformation in how benefits drive outcomes.
Financial wellbeing means the full picture, not a single product. Employees aren’t making decisions in financial silos. A 32-year-old Marine veteran managing student debt from a school that lost accreditation, a 16-year-old planning for college while supporting his family — these are the actual financial lives your benefits touch. Guidance that treats them as such is fundamentally different from guidance that treats them as a persona.
The workplace is where financial guidance can reach the people who need it most. Expert-level, personalized financial guidance has traditionally been the province of the wealthy. It doesn’t have to be. The workplace is where 35 million households intersect with the financial system — and where Candidly is building the connective tissue to make those benefits actually land.

Introducing Candidly Circle

We kicked off the Summit with a lunch just for the Candidly customer community, where we reconnected, shared exclusive updates on what we’re building, and launched Candidly Circle — a new customer advocacy program recognizing HR leaders who drive real impact for their workforces.