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7 Questions with Kelly Davis

helps you in your leadership.



Jonno White

7 Questions with Kelly Davis

Name: Kelly Davis

Current title: Chief People Officer

Current organisation: Sunwing Travel Group

Kelly Davis is the Chief People Officer for Sunwing Travel Group, North America’s largest vertically-integrated travel company with approximately 24,000 employees across fourteen countries. The group is made up of several businesses including a leisure charter airline with a modern fleet of 40 planes, a luxury charter service with access to private jets to suit all clients, two major North American tour operators, two renowned travel retailers, a hotel division with over 14,500 rooms (Mexico, the Dominican Republic, Eastern Caribbean, Cuba and Costa Rica), a vacation club, a luxury wedding business and an international destination management company. Prior to this role, Kelly was the Senior Vice President of HR, Customer Service and Communications for Town Shoes Limited (Town Shoes, The Shoe Company, Shoe Warehouse and DSW Canada). She led these three functions for the company’s 4 banners and 4000+ associates. Prior to joining Town Shoes Limited, she was the Vice President of People Development at Cara Operations (Milestones, Kelsey’s, Harvey’s, Montana’s and Swiss Chalet) where she worked with the corporate office and franchise partners to deliver HR services to the company’s 700+ restaurants and 30,000 associates. Kelly spent most of her career prior to joining Cara Operations with the Hudson’s Bay Company where she worked for over 12 years in a variety of progressive HR roles including leading the HR function for all Bay and Home Outfitters stores across Canada. Her last role with the Hudson’s Bay Company was in a more specialist function where she led Compensation, Benefits, Associate Relations and Services for the Hudson’s Bay Company in Canada and Lord & Taylor in the U.S. Kelly holds her B.A. from McGill University and her CHRE, CHRL and H.R.C.C.C. (Human Resources & Compensation Committee Certification) designations. Kelly speaks frequently at various HR events and panels including most recently, the annual CHRO Conference held virtually in December 2020. Kelly is a member of the Strategic Capability Network and the HR Advisory Council for the Human Resources Professionals Association. In 2021 Kelly was named on the “Global 100 HR Leaders” list by HRD (Human Resources Director) which recognized HR leaders for their outstanding commitment to their companies and their people over the previous 12 months, throughout the COVID crisis. Kelly is passionate about supporting not for profit organizations. In the past, she has actively contributed to the HR Committee of the Board of Directors for Eva’s Initiatives and to the Leadership Committee of the Board of Directors for Big Brothers, Big Sisters Canada. She recently joined the Black North Initiative as the Co-Chair of their CEO Pledge Committee ( - The Black North Initiative was created by The Canadian Council of Business Leaders Against Anti-Black Systemic Racism to combat anti-Black systemic racism in Corporate Canada. The Initiative challenges senior Canadian business leaders to sign a CEO Pledge committing their companies to specific actions and targets designed to end anti-Black systemic racism and create opportunities for all of those in the underrepresented BIPOC community). She also currently serves as a Board Director and Chair of the HR & Governance Committee for White Ribbon (the world’s largest movement of men and boys working to end violence against women, girls and people of all genders). Kelly is married with two sons and lives in Toronto.

7 Questions with Kelly Davis


1. What have you found most challenging as a CEO or executive of a large enterprise?

I have found it difficult to learn about, respect and lead so many different cultures in so many different countries. It is an amazing challenge to have but there is so much to learn and it is hard to do this work correctly in a way that makes each employee feel unique yet with the end goal of building a shared, global culture across 15 countries.

2. How did you become a CEO or executive of a large enterprise? Can you please briefly tell the story?

I have been a senior HR leader for most of my career. The three previous organizations I worked at were North American in scope. I was really looking for a challenge to have a more global HR portfolio and ideally in a new and challenging industry. When I first interviewed with my CEO he asked me if I spoke Spanish (no), had deep labour experience in the Caribbean (no) and if I had hotel and all inclusive resort experience (also no). I told him he had clearly not used a good executive recruiter! He also said that although those pieces were nice he was looking for someone who wanted to learn about different cultures, would respect the entrepreneurial company he had built and would fit in with his leadership team. It has been an incredible journey so far and I feel like I've only been here for a very short time, although a challenging and interesting time certainly for our industry.

3. How do you structure your work days from waking up to going to sleep?

I am very focused on working out, mainly to manage stress and overall health. I work out almost every morning first thing in the morning. With the recent COVID challenges, I then deal with my two kids and get them ready for school which of course has often been at our dining room table this last year! I usually have a day full of a lot of my meetings but I try to structure my weeks so that I don't have any standing meetings on Fridays. With the pandemic, I've tried to rebalance my life a little bit. I have a father who is not well and now that I've been working from home, I try to always spend one hour with him on Thursday or Friday afternoons which was very hard to do before (I had a total of a 2 hour commute per day). I am also active in the not for profit space and usually do that work in the evenings after my children go to bed. I try to decompress a bit most evenings by watching films with my husband who is a filmmaker.

4. What's the most recent significant leadership lesson you've learned?

Never underestimate the challenges that people will rise to. Like in a marriage, sometimes we all sign up for the good times and this last year has truly tested us professionally. It has been interesting that some leaders who we thought of as A+ talent before COVID have not shown up that way and there have been some others who weren't as on the radar before who have become stars and have risen to the top during these challenging times - a real leadership test in my opinion.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

Dare to Lead by Brene Brown. I had the pleasure of hearing Brene speak at the Work Human Conference in Austin, Texas in 2018. I find her message around vulnerability as an asset is particularly powerful. In today's world where all of us HR leaders and most leaders in general are trying to learn more and push more of a robust and transparent D,E&I agenda, vulnerability is key. We will not move forward unless we let ourselves be vulnerable and scared as leaders - it is only from this place that we can learn and do better. I also think sticking to your core values, even during the worst of times shows your employees and your customers that you mean it, they are not just words on a piece of paper. Finally, I love her point that failure teaches bravery. We cannot innovate and lead without willing to gloriously fail first. Very powerful and these are all lessons I try to share with my team and across the organization when we connect with our leaders.

6. How do you build leadership capacity in a large enterprise?

This is something we work on every day. I would say that it primarily stems from innovating and never staying the same. This last year has pushed our leaders' capacity levels in ways we never imagined. All of a sudden, our industry has been turned upside down and quite frankly devastated. Our leaders have had to become inspirational speakers, customer service jugglers, public health messengers, vaccination promoters and the list goes on in terms of things that were not necessarily on everyone's radar 12 months ago. Even during normal times though, we are fans of hiring for overall fit and letting people learn and grow their capacity through interesting and challenging work assignments across our 7 lines of business. We also have the benefit of a very diverse leadership and employee base and we are able to offer job assignments in multiple divisions and countries which really helps on this front.

7. What is one meaningful story that comes to mind from your time as a CEO or executive of a large enterprise so far?

About 2 and a half years ago, we wanted to build a set of corporate values that would span our 7 lines of business, 15 countries we operate in, 3 official languages and be meaningful to 24,000 employees. We got a group of employees together from all areas, countries and from different levels. We knew that it would be easier to remember if the values happened to form an acronym. It was such a cool and organic process as without using any outside support or over leveraging our senior team, we had an employee from our Atlanta, Georgia office suggest EPIC (we knew we had to have Entrepreneurial as one of the values as well as Customer-Centric). We were sure there'd be no way this word would happen to work in all three of our official languages (English, French and Spanish) but we had some employees from Quebec, Canada in the room as well as from Cancun, Mexico and they all jumped up and said that yes, the word worked in all three languages! From here our values were born (Entrepreneurial, Passionate, Inspirational and Customer-Centric). Our industry has been hit very hard, at one point we had 95% of our employees on lay-off status. It is hard to think or feel very EPIC during these times. However, the power and resiliency of our people would bring tears to your eyes. I am still sent almost monthly videos of our employees across this company preparing and planning for customers to return to having amazing vacations under our wing. Truly EPIC in my mind!

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