Annmarie Neal is the Chief People Officer at Zendesk. Previously, she was a Partner & Chief Talent Officer at Hellman & Friedman. Her primary responsibility is to help Zendesk drive value by improving the organizational and leadership effectiveness. Annmarie has over twenty years of experience working with global organizations on executive leadership, talent management, and organizational development. Prior to H&F, she ran her own consulting firm and held the Chief Talent Officer roles at both Cisco Systems and First Data Corporation. Additionally, she was a senior consultant with RHR International. Her education includes Boston College; Santa Clara University, Master’s Degree in Counseling; Harvard University, Graduate Certificate of Special Studies; California School of Professional Psychology Alameda/Berkeley, Doctorate in Clinical Psychology with an Emphasis in Management Psychology.

Our New York-based Partner, Matt Healey, sat down with Annmarie to explore how leaders can stay ahead in an AI-first world. Matt specializes in functional HR executive search and has spent 15 years partnering with clients across North America, EMEA, and APAC to recruit chief human resources officers and their direct reports across diverse industries.

Their conversation explores how leadership is evolving, why AI demands a new organisational architecture, and what skills define competitive advantage in the years ahead.

How do you define great leadership, and how has that evolved throughout your career?

Great leadership is the ability to create clarity, unlock potential, and drive meaningful progress – especially in the face of constant change. It means building environments where people are empowered to experiment, take smart risks, and challenge the status quo. Leadership today requires the courage to innovate without a roadmap, the discipline to align teams quickly, and the vision to stay focused on long-term impact while navigating short-term complexity.

That definition has evolved with experience. Leadership is no longer about having the answers, it’s about playing on multiple chessboards at once: managing today’s execution while shaping tomorrow’s possibilities. The most effective leaders operate at the edge of what’s known, moving with agility across strategy, talent, and culture. They connect people to purpose, create space for bold thinking, and mobilize teams to act, fast and fearlessly.

Is there anything you wish you’d known when you started your career? And anything you would tell yourself at an earlier stage in your career?

What I wish I’d known sooner is that real breakthroughs come from embracing complexity, learning deeply from failure, and committing to the long game. Careers, and high-performing organizations, are built on resilience, patience, and an openness to evolving realities over time.

My advice? Pursue excellence, not perfection. Excellence is an internal standard that drives continuous growth and pushes you to become a master of your craft. Treat every challenge as an opportunity to build lasting capabilities. Surround yourself with people and environments that stretch your thinking and expand your sense of what’s possible. Progress isn’t a sprint – it’s steady momentum powered by learning, strong relationships, and the ability to adapt at the pace of change.

What changes to your industry do you anticipate over the next two years, and are you excited by this?

We’re at a critical juncture in the customer and employee experience industries. AI and automation are fundamentally reshaping operating models, enterprise value creation, and sustainable competitive differentiation. In the next two years, we’ll see a decisive shift from transactional service to intelligent, end-to-end experiences – designed for speed, driven by data, and delivered with precision. Technology will power it, but trust and human connection will still define it.

What’s equally transformative is the impact on how work gets done. The future of work is now about architecting organizations to deliver against strategy in real time. That means moving beyond traditional (and static) structures toward dynamic, cross-functional teams. It requires accelerating mission-critical skills development at the pace of the market and embedding adaptability into the core of how decisions are made and executed. Leadership will evolve from acquiring and managing resources to mobilizing capability – at scale, fluidly across the enterprise.

The opportunity ahead is clear: build organizations that can flex with volatility, scale with confidence, and execute with clarity. AI will be a powerful enabler, but sustained performance will come from how effectively companies align talent, technology, business processes and strategy. This will be the edge in tomorrow’s AI-first market.

AI and digital landscapes are ever-evolving. What skills or areas are you currently focusing on to ensure your organisation remains at the forefront?

We are doubling down on digital fluency, cross-disciplinary collaboration, and adaptive problem-solving – core skills that underpin both operational excellence and innovation, must-haves for an AI first world. At Zendesk, our focus is on architecting cross-functional teams that iterate rapidly, scaling what works and moving on from what doesn’t, so every advance in digital and AI capability is translated into business value.

Equally, we remain close to our customers and markets, ensuring our talent and systems stay in lockstep with evolving expectations and opportunities for differentiated service.

How do you foster a culture of continuous learning within your teams?

Continuous learning is a business imperative and it requires structured investment. We drive this by giving teams not only the permission but the expectation to experiment, challenge, and adapt. We invest heavily in manager and leader capability, strategic workshops, formal mentorship, and digital learning platforms while ensuring accountability for development outcomes.

We create intentional forums where teams engage with the latest technology, diverse perspectives, and real-world business challenges, ensuring learning is both practical and measurable.

What strategic role do you see AI playing in your business over the next 3–5 years, and how are you preparing your teams for it?

Three industries are undergoing rapid and profound transformation: industries that create (such as the movie industry), code, and support. We sit squarely in the third—and unlike many, we are not reacting to disruption, we are preparing to lead it. AI and automation are fundamentally reshaping how support organizations operate, moving from large, people-heavy teams to leaner models where small numbers of humans oversee large AI-powered workloads. This is not speculative, it’s already underway. The AI for customer service market is expected to grow from roughly $13 billion in 2024 to over $80 billion by 2033, with companies already reporting significant gains in resolution speed, cost reduction, and customer satisfaction.

This shift is changing everything, from how support organizations are structured to how they go to market. CX leaders will no longer manage headcount, they’ll manage performance across hybrid teams of humans and AI. Pricing models will increasingly be outcome-based, focused on resolution speed, CSAT, or deflection, not hourly rates. Technical operations will evolve to support new capabilities like AI QA, continuous tuning, and intelligent escalation paths. And the skills required across CX organizations will change, from repetitive task execution to strategic oversight, content governance, empathy-driven exception handling, and cross-functional orchestration.

At Zendesk, we are in the thick of this transformation. Our teams are undergoing the same evolution that our customers face. That shared experience is a strategic differentiator. It positions us to be more than a software provider, we can be true thought partners. We understand the operational, technical, and organizational shifts required, and we’re already applying those lessons internally. That makes our guidance not only informed, but credible. As our customers adapt, we’re uniquely equipped to help them not just implement AI, but redesign the very shape of their customer experience organization.

Are you seeing AI redefine the roles or skills you need at the leadership level?

Absolutely. AI is fundamentally reshaping what effective leadership looks like. It demands leaders who can bridge the gap between emerging technologies and tangible business outcomes, those who can navigate ambiguity, accelerate change, and align cross-functional teams around a clear vision.

Digital literacy is no longer optional; leaders must understand enough to challenge assumptions, ask the right questions, and make informed, strategic decisions. But just as critical is the ability to inspire and mobilize people through change. The traditional model of deep but narrow functional expertise is giving way to a new leadership archetype: one that blends operational rigor with adaptive thinking and complex problem solving, data-driven execution with human-centered insight.

The leaders creating the most enterprise value today are those who can move seamlessly between strategy and detail, unify diverse teams, and keep both customer impact and workforce transformation in focus.

What barriers have you faced in adopting AI internally, and how did you overcome them?

The barriers are as much cultural as they are technical: skepticism, fear of disruption, or the myth that AI is a replacement rather than a partner. We overcome these by fostering open conversations, sharing small wins, and providing clear opportunities for skill-building.

We don’t implement technology for its own sake; we focus on solving real problems and listening to the lived experience of our teams and customers. Trust is built through transparency – demystifying what AI can and cannot do, and inviting people along every step of the journey.

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