Skip to Main Content

With the Future of Work in Flux, a CHRO Manages the Present

A conversation with Anne Drapeau, CHRO of Toast
November 2021

Anne Drapeau was working in a client-facing role at Digitas when the global marketing agency’s CEO asked if she wanted to run human resources. She thought the idea was crazy; "I don’t know anything about HR,” she remembers telling him.

But the CEO disagreed. Drapeau, as the beneficiary earlier in her career of strong talent programs at J.P. Morgan and PepsiCo, understood the value of a strong human resources function. The CEO recalled that ever since Drapeau had arrived at the company, she had offered up ideas for HR and talent investments at the fast-growing company. “You've been talking about it almost nonstop since you got here,” the CEO said.

Drapeau, who had studied chemical engineering and received her MBA, said she learned a lesson that day: always be willing to abandon your plan.

“Sometimes, other people that you work with will see things in you that you don't see in yourself,” Drapeau said. “I agreed to do that job for a year, but I told him I wanted to go back to my old job when that year was over. That was more than 20 years ago, and I am still in a talent and culture role. He saw in me a passion for the role that talent plays in ultimately delivering on an organization's strategy.”

Now, Drapeau is the CHRO of Boston-based Toast, the all-in-one platform built exclusively for restaurants, which made its initial public offering in September 2021. We recently spoke with Drapeau about changing roles, the shifting importance of leadership during the pandemic, and her advice for future CHROs.

I was energized by it, and it seemed to me to be a natural transition from the strategy roles I had done prior. Strategies are meaningless if you don’t have the right talent and teams to deliver. In particular, I’ve been drawn to businesses that are at a strategic inflection point — they might be scaling like crazy, or they might need to shift their focus in order to continue to be a leader. Either way, it’s all about leadership and building new organizational capabilities.

That said, I had a lot to learn. There are technical aspects of HR that I didn’t understand. And there are some things that you only learn by living through the difficult situations that we as HR leaders inevitably encounter. I am so grateful for the very supportive CHRO community that helped me out in those early days, and continues to teach me new things.

Sometimes, you need really deep subject matter expertise. For instance, when I was in biotech, there were times when we had to find that person who had experience working with rare liver diseases among pediatric patients — there are maybe 20 people in the world who have that. These are people who have devoted their lives to it. In that case, we needed to hire an expert.

But I think you need a blend in any organization, and I love the “athlete” model. People who are deeply curious and are willing to really dig in and learn a business — and, in some cases, gain the technical skill — can be a great addition. Organizations need that versatility on their teams, and ideally people who have had lots of different types of experiences, because those are the people who can connect dots as organizations get more complex.


Every role that we fill is a valuable position, and we are trying to accomplish a lot with that hire, especially in leadership roles. Usually there’s an immediate problem to be solved, but I'm always encouraging our teams to think about those leaders who will be versatile over time. We’re looking for people who will fill out our leadership bench within their functions, or people who can take on roles in different parts of the organization.

A few leadership characteristics have emerged as being especially important. First is a comfort with, and even a desire for, ambiguity and change. Toast is not opportunity-constrained. I know that our business will look different a year or two from now. We look for leaders that embrace the excitement of that uncertainty and ambiguity.

Work is going to look different forever, and so will the way leaders engage their teams. I think that we’ll forever be in a hybrid way of working. The hybrid model will be even more challenging than the fully remote or fully in-office models, in terms of how you drive real inclusion. You have to make sure everyone's voice is heard. It’s about reading the proverbial room when there's no room.

We look for people who can connect the dots, and inherently understand the interdependencies at work. We also look for empathy — for our customers, and for our fellow Toasters.

I also believe that in order for leaders to really scale they need to bring two things to the table. First is an ability to understand tradeoffs across the business; to understand the enterprise view of your organization and not necessarily just be protective of your own turf. The other is being comfortable hiring and leading people who are better than you are. The really successful C-suite leaders lead people whose jobs they can't do.

One thing that’s changed dramatically in the last few years is the level of passion and activism in employees. They’re defining the workplace that they want to be a part of and it's both exciting and challenging. The ways in which we build listening posts across the organization is changing, as is how we're open to innovation and new ways of operating. One really good example is how companies are now supporting mental health in open and innovative ways.

We live in an environment where we want to bring our whole selves to work. My family and my pets showed up in the workplace nearly every day of the pandemic. As that's happening, people are turning to the workplace as a place for support on so many levels.

First, always think of yourself as a businessperson and a strategist first — the talent agenda follows. The CHRO must understand how to create value as a business and what capabilities are needed to get there.

Also, be curious about the business and the people. Not just their skills and development opportunities, but what motivates them, demotivates them, and their hopes and dreams.

Every time I welcome new hires, I open by saying that I have the coolest job in the company. I get to invite amazing people to join us on a rewarding journey, help them realize their potential and find joy at work. It doesn’t get any better than that.