From Global Giants to High-Growth Startups: Caralyn Cooley’s Journey to CPO at FanDuel

With a career spanning global powerhouses like Pepsi and Amazon, as well as high-growth startups, Caralyn Cooley brings a rare blend of operational rigor and entrepreneurial agility to her work. Now, as the Chief People Officer (CPO) at FanDuel – the market leader in the fast-evolving sports entertainment and igaming industry – she is leveraging her diverse experience to help drive innovation, scale and culture at the organization.

I never joined a startup because I wanted to work at a small company. I joined startups because I wanted to build big, generational companies.

Here, Caralyn shares pivotal moments from her career journey, practical insights for embracing change and how saying “yes” can unlock new possibilities for organizations and leaders alike.
 

Building a foundation in HR leadership

Caralyn’s path to the C-suite is defined by a deliberate accumulation of experiences across both global enterprises and startups – each shaping her approach to people leadership in distinct ways.

She began her career at some of the world’s most respected organizations, including Honeywell, Pepsi, and Amazon. In these environments, Caralyn built a strong foundation, learning what “good” looks like at scale. “I saw massive scale, and I saw what good looks like in terms of people, teams, and processes, and how those can work globally and across different functions,” she recalls. These formative years gave her a deep understanding of how large, complex organizations operate and what it takes to build effective, high-performing teams.

A pivotal moment came during her tenure at Amazon, where she had the opportunity to work abroad in the Czech Republic. Immersed in a new culture and tasked with building and launching operations from the ground up, Caralyn discovered her passion for creation and ownership. “Up until then, I had been working within established frameworks. When I started building and launching, I realized I liked having ownership over decisions and seeing the results of those decisions in real-time.”

The experience also “blew up” her US-centric paradigm, forcing her to adapt quickly and learn from missteps, such as designing a payroll system that didn’t fit local legal guidelines. “Luckily, all those things were fixable, and I learned from them. It taught me how important it is to not only understand the problem you're trying to solve, but also the culture and the people you are solving for in a very different way than before I went abroad.”

I had an opportunity to join a startup, and that's where you actually see how good you are. Can you build something great without all the resources, support and guidance of a big, established company?

This global perspective set the stage for her next career chapter: the world of startups. Drawn by the energy and intensity of building something new, Caralyn embraced the challenge of taking on Chief People Officer roles at multiple startups with resource-constrained, fast-paced environments. “It’s very much a roll-up-your-sleeves culture. I got involved in things I never thought I would.” At Jet.com, for example, she found herself managing tasks that entire teams handled for her at larger companies.

Gaining exposure to every part of the people team has prepared me well for the CPO role – I may not be the deepest expert in each specialty, but I know how to partner, challenge and lead across all of them.

This blend of big company discipline and startup agility positioned Caralyn for her current role at FanDuel, which she says sits at the intersection of her prior experiences. She describes FanDuel as a “perfect fit” because, “The important pieces are in place – we’ve got an incredible global team of about 4500 people, a market-leading product our customers love and culture that’s truly special. And the most exciting part? There’s still so much growth ahead.” In this role, Caralyn is eager to “put her fingerprints” on the organization and help scale FanDuel into a “generational company with a strong culture that lasts way longer than my time at the organization.”

Caralyn credits her willingness to embrace change and say “yes” to new opportunities, even when the path forward is uncertain, for leading her to where she is today. “I really believe that if I had not had those experiences, I wouldn't be sitting in the FanDuel CPO seat. I wouldn't have been prepared for it, and I don't think I would have been competitive to get the job.”
 

Prioritizing leader and manager development

As FanDuel continues its rapid growth, Caralyn is focused on building the people and processes that will sustain the company’s momentum. Her top priority is leader and manager development – one that aligns with the number one concern for CHROs in 2025 according to our CHRO Leadership Perspective Survey. “We grew really fast. And usually when that happens, you still need to build some of those foundational pieces… FanDuel has not yet focused heavily on manager upskilling and leadership development, and so this is something we're heavily focused on this year,” Caralyn explains.

Executive development, particularly for VP-level and above, is an area where Caralyn is investing significant resources. She notes that many leaders at FanDuel are in the biggest roles of their careers, and as the company grows, these roles will only become more complex. To address this, her team is providing both individualized and cohort-based development opportunities, with the goal of accelerating the readiness of senior leaders and ensuring FanDuel can nurture and promote talent from within as the organization scales.

At all levels of management, Caralyn is not only focusing on the traditional elements of great leadership, but also on identifying the unique characteristics that make a manager successful at FanDuel. “Our goal isn’t to create generic management training – it’s to equip leaders to be successful at FanDuel, within our systems, culture and ways of working,” she says. By translating role model leaders into clear competencies and tailoring development to FanDuel’s unique culture, Caralyn is ensuring the company’s leadership pipeline is ready to support its ambitious growth.

What excites me is that we’re approaching leadership development from multiple angles — making sure new managers are set up for success and experienced leaders keep growing, too.

Caralyn is also prioritizing strengthening FanDuel’s talent management and performance processes. As the organization has scaled rapidly, there’s an opportunity to bring clarity and consistency to how talent is identified, developed, and elevated. She is now leading efforts to create consistent, scalable frameworks that align talent with business priorities: “What it comes down to is making sure that we can find, grow and keep the talent that we need to achieve the goals that we have today and into the future.”
 

Advice for CHROs

Reflecting on her career, Caralyn shares several key lessons and advice for HR leaders new to their roles:

1. Ensure value alignment with leadership: Caralyn believes it is critical to have personal value alignment with the founder or CEO, especially in founder-led organizations, and she cautions against being swayed solely by a charismatic leader or an interesting product when considering a role. She notes that while differences in approach are inevitable, shared values around culture and how people are treated are essential for trust and effective partnership. “Finding that values fit is really important… When I talk to CPOs who’ve had tough experiences or struggled in their first or second CPO job, it so often comes back to a misalignment on values,” she shares.
2. Build a team of utility players: Caralyn advises HR leaders – particularly those in small or mid-sized companies or those with limited budgets – to prioritize building a team with “utility players.” In rapidly changing environments, generalists who can flex across roles and adapt to new challenges provide critical leverage. While specialists are critical in a few key areas, versatile team members who can tackle a wide range of issues can be invaluable. She stresses, “In fast-moving environments, having utility players on your team isn’t just helpful – it’s a competitive advantage.”
3. Core values should be “guardrails for the culture”: Caralyn emphasizes that an organization’s core values or principles should truly define how people are treated, the pace at which the organization moves, and how priorities are set. “Make sure that your organization’s core values or principles are right and reflective of the culture that you have – and  the one you’re trying to build… That’s one of  the biggest lessons for me,” she remarked.
   
   At FanDuel, she regularly leverages their ten core principles in decision-making. One has a particular focus on simplification, which is especially important as the business scales. “I am challenging myself and my team to constantly be simplifying – simplifying communication, simplifying programs, and simplifying through technology,” she says. “It’s one of the most powerful ways we can reduce friction and help people move faster.”
4. Cultivate a Strong Peer Network: Caralyn underscores the importance of cultivating a strong peer network, noting how the CHRO/CPO role can feel isolating. She credits her own network – including the Gartner CHRO Community – as a vital source of support, advice, and perspective. Caralyn encourages new HR leaders to invest in building these connections and to give back by supporting others navigating similar challenges.
    

Caralyn Cooley is the Chief People Officer at FanDuel and a valued Governing Body Member of the New York CHRO Community. To connect with CHRO peers in your local community, join Gartner CHRO Communities. If you are already a member, sign in to the Gartner C-level Communities app to register for upcoming community gatherings.
 

Special thanks to Caralyn Cooley and Fanduel.

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