From the back door to the C-suite: how Mary Duncan built an HR legacy

After more than two decades with CAA Club Group, Mary Duncan is in a rare position to reflect on both the evolution of HR and the culture of the organization she’s helped shape.

Since 2016, she has served as chief human resources officer, overseeing human resources, corporate communications, total rewards, corporate facilities and learning and development, following 12 years as vice-president of human resources, communications and corporate services.

When Duncan talks about HR, she goes back to a principle she learned early on: people really are an organization’s most critical asset — but only if you actually make that real.

“[HR] doesn’t have to be administrative, it doesn’t have to worry about being at the table all the time like all those old cliches,” she says. “If you can action, and understand, and you care about the people, which I believe are the most critical assets of any company… to actually make that happen, I think that’s for me what was most outstanding in the HR profession — that it allows you to participate and be that if you want to be that leader... and make a difference.”

Career start in disability claims

Duncan didn’t enter HR through the traditional route. She started in financial services at Canada Life, spending 27 years there and moving through several insurance roles before a merger with Great-West Life and, later, a move to CAA.

“I came in the back door. I came in through disability because I was an adjudicator of disability claims for employees at Canada Life and so moved into HR that way as a specialist,” she says.

From there, Duncan deliberately worked through “all the critical technical areas of HR” — disability benefits, compensation, executive compensation, payroll — before becoming a generalist.

“I felt it was critical to understand those processes in a deep manner, not a superficial, surface-level manner,” she says. “I’m a firm believer that… it’s critical that you learn things in depth as well as breadth.”

Greenfield opportunities at CAA

When Duncan joined CAA in 2004, the organization was smaller and offered what she calls “a lot of greenfield opportunities.” She and her team were able to introduce more sophisticated pay-for-performance approaches and broader benefit plans.

Over time, the focus expanded from solid foundational programs to corporate culture, says Duncan, and the shift coincided with a bold move from the CEO.

“Our CEO, Jay Woo, came in and blew up the basic business school business model of vision, mission, KPIs,” says Duncan. “And just said one statement: ‘Clear line of sight for everybody, obsessed with member safety.’”

CAA Club Group encompasses several entities — travel insurance, home and auto, Echelon as a specialty insurer, plus the Club, which is part of the CAA Federation. That mix is unusual, she notes, combining a non-profit side with profitable insurance businesses.

And while the “obsessed with member safety” statement initially raised questions, over time, people connected the concept to the core of insurance.

“We’re obsessed with member safety because that is insurance,” says Duncan. “It takes care of people when they need it the most.”

She contrasts that with long, sometimes abstract corporate statements that employees struggle to remember.

“We made our values actually living belief statements, so things that were action-oriented as well as very simple. So, everybody can understand how they contribute. For me, that’s critical.”

Building trust with the C-suite

Asked how HR leaders can build the kind of partnership with CEOs that many aspire to, Duncan points to relationship management and trust, referencing Stephen Covey’s concept of a “bank of trust.”

“It’s building that trust through saying what I’m going to do and doing it,” she says. “That ‘walk the talk’ makes sense in that if you say you’re going to do something, deliver it — deliver it well, put everything you have into it.”

She is candid about the effort required. “It takes me 150% to get a 100% result,” she says. “And I think that’s really critical for senior leaders and leaders, everybody, to figure out ‘What is your output?’ And if it takes more effort, then you have to decide if you want to put that effort in to get that 100% result.”

It’s also important to be checking in often, to make sure you’re aligned with leadership, says Duncan, admitting “it’s more difficult… depending on personalities.”

Respect for leaders’ time is also key. “Be mindful of the CEO and that senior leadership team are extremely busy,” she says. “If I think I’m busy, they’re even doubly busy. So be respectful of that — common courtesy goes a long way.”

Duncan also highlights the importance of conflict resolution skills and integrity for HR leaders.

“I've often been told that my ability to deal with conflict is something that people are attracted to because it brings out an honesty in a discussion,” she says.

“If you can become a great facilitator to help holistically get to a win-win, be honest about things.”

Her own experience at CAA has been shaped by alignment with leadership values. She describes CEO Jay Woo as having a “high moral compass” and being “a brilliant leader” who regularly speaks to frontline employees without prompting. “He does it because he knows in order to run the company, he needs that connection.”

Internal promotion and experiential learning

Duncan is clear that she sees internal promotion as powerful, especially for very senior roles that take time to fully master. Her successor, Carla Spina, VP of HR at CAA Club Group, , started as a payroll clerk roughly 20 years ago and has built her career within the organization, aside from a short break elsewhere.

“I think internal promotion is phenomenal because it speaks volumes internally. It allows people to understand that there’s a potential pipeline,” says Duncan.

Her own transition has been years in the making. “I’ve been telling [my team] for about five years, ‘I’m going to retire. I’m retiring,’” she says.

Duncan used that period to think about how the organization needed to be structured, what the “end game” looked like, and which people she needed to spend more time mentoring in technical disciplines.

“I'm taking knowledge out of the organization. So, I want to make sure that I have others that have that same knowledge and behaviors and skill and that the bench is strong so that they can help each other. That takes a lot of time. That's not something that can be done quickly.”

A major health event — a heart attack — reinforced the importance of not taking time or wellbeing for granted. It has delayed Duncan’s retirement from 65 to 66 and reminded her not to take health for granted.

“I’ve got to make sure I take care of me this time.”

Focusing on executive development

This transition has also prompted changes in how CAA thinks about leadership pipelines. What was once called succession planning is now framed as executive development, she says.

“Succession planning, it’s an old term. It defines something, says, ‘I’m going into that box.’ That box doesn’t always happen… people get disappointed.”

Executive development, by contrast, starts with the question: “What do you need to go to the next level?” she says, adding she wants to see more secondments, more job rotations and more experiential opportunities “to broaden people, to give them opportunity.”

As Duncan looks ahead to her own next chapter, that focus on support remains.

“For me it’s also supporting them as much as I can, as much as they’ll let me support them in their careers,” she says.

Marketable skills and career loyalty

Duncan’s experience of large-scale downsizing at Canada Life–Great-West Life has shaped how she talks to employees about their careers. She recalls colleagues who expected to retire at a big insurance company and were devastated when roles disappeared, often without the transferable skill sets they needed.

“That’s my other learning from looking back is always… look after your career, manage your career. You can have company loyalty for sure, but make sure you have career loyalty first. Take care of yourself.”

At CCG, she actively encourages people to think that way.

“Look at marketable skill sets,” she says. “Put it on your resume. If you get to work on a project, fantastic. Put on the resume, be marketable and then choose to be here.”

The organization, she says, tries to make that choice possible.

“At CAA, we allow that to happen so people can learn those skills, become marketable, choose to be with us and then they can do things and participate in events outside of their day-to-day job,” she says. Based on feedback, she believes that is “quite meaningful” because people feel the corporation “truly cares about them as humans outside — like who we insure, who we provide membership to. It’s all in there.”

Beyond generational labels

In looking at recruitment and retention, Duncan is cautious about labels when it comes to generational differences. While surveys often highlight younger workers’ desire for purpose and alignment with employer values, she prefers a different lens.

“For me… we choose to go on lifestyle cycles — so what’s important as opposed to age and the names of it,” she says. “When people put those labels of ‘All genZs do this,’ ‘All millennials do this,’ it’s so not true because it’s all relevant to your family values, your life cycle, the stage that you’re in.”

And trends today are similar to when she started her career, says Duncan.

“It was important that I do my best… and I wanted to see myself promoted and validated… so I expected a raise, a promotion for working hard. It’s the same thing today.”

And that has implications for how organizations design their models, such as performance reviews and structured feedback, she says: “Absolutely, [it’s about] open communication, feedback — no different than what you would get when you’re in school probably or from your mentors [or] your parents.”

From entering HR “through the back door” to shaping CAA Club Group’s culture at the C-suite, Duncan has proven that clarity of purpose, relentless development and trust-based leadership can transform both an organization and the careers within it.