Dessalen Wood isn’t just a Global Chief People Officer; she’s a culture curator, a talent transformer, and a passionate advocate for human potential. At Syntax, she’s the driving force behind the people strategies that empower over 2,800 employees, fostering a vibrant and inclusive workplace. With a career spanning more than 25 years, Dessalen has left an indelible mark on renowned Canadian and US enterprises, from Reitmans Canada and Hudson’s Bay Company to The Disney Stores, and most recently, Syntax.
Her journey is a testament to the power of empathy and the relentless pursuit of one’s vision. Before Syntax, Dessalen served as Chief People Officer at ThoughtExchange and Vice President of Talent Development at Cineplex Entertainment, honing her expertise in building and nurturing high-performing teams. But her story begins in a most unexpected place: a downtown mall, selling bathing suits.
The Unexpected Launchpad
“During my psychology degree, I found myself selling bathing suits,” Dessalen recalls. “It might seem unrelated, but it taught me invaluable lessons about empathy and understanding people’s emotions.” Her ability to connect with customers and address their insecurities led her to become the top salesperson in a 40-store chain. But Dessalen’s ambition didn’t stop there.
Recognizing the potential to share her skills, she proposed a sales training role to management, only to be turned down. Undeterred, she crafted a proposal and presented it to Reitmans Canada Limited, securing her first official HR role as a “Training and Recruitment Coordinator” at just 23. In this pivotal position, she designed the “Smart Mind” training program and traveled across Canada, recruiting top talent. This seven-year chapter laid the foundation for her remarkable career, proving that a file folder full of ideas and a heart full of passion can indeed change the world of work.
Dessalen’s story is a powerful reminder that every experience, no matter how unconventional, can shape a leader’s path. She continues to inspire and innovate, building bridges between people and potential, one culture at a time.
In our latest Faces, meet Dessalen Wood.
Who is/was your biggest influence in the industry?
My biggest influence, bar none, was Ken Blanchard, the creator of the world-renowned leadership program, Situational Leadership II. In the mid 90’s, I attended a major US conference, ATD (American Society for Training and Development). This conference had close to 40,000 professionals attending, and I was in awe of the size and scope of the event, which attracted the biggest names in the industry. I could see Steven Covey, Tom Peters, and Ken Blanchard, the father of Situational Leadership II, all live.
I can still remember sitting in the front row, being taught the concepts of Situational Leadership II by Ken Blanchard himself. The man is a gifted speaker, and the notion of Servant Leadership resonated deeply with me. I felt compelled to become certified and bring it back to my company. I became, for lack of a better term, a true groupie. I must have seen Ken Blanchard speak at 4 or 5 subsequent events, each time getting a picture with him. When the Blanchard team was looking to beta test a new program called “Optimal Motivation,” I was invited to attend the first session at their campus in San Diego, asked to provide notes on the program, and was able to spend time with Ken, his wife Margy, his son Scott and the team there. It was a dream come true, and I am still using SLII as my foundational leadership framework at Syntax, almost 30 years later.
What’s your best mistake and what did you learn from it?
My biggest mistake was taking a job I knew I would not be successful at. It was just after the stock market crash in 2008, and our family was relocating to Toronto. The media was full of stories of layoffs and the rising unemployment rate. I was so concerned I would not find a role I was applying everywhere and following up with emails and phone calls. I was so relieved when I was able to land a role as a Director of HR in the insurance industry. However, even in the interview process, I had a feeling this industry was a poor fit for me, but I let my desperation get the best of me and did not listen to myself.
After three weeks on the job, I knew I would never be successful there. I was the wrong profile, and I was miserable. It took all my courage to pack up and leave after just seven weeks, knowing that the longer I remained, the more confidence I would lose. I had seen that happen to others and understood the toll it can take on a person.
Just as I was leaving, I got a call back from Cineplex for the role of Director of Talent Development. This was perfect, again leading the training and recruitment function at a blue-chip Canadian brand. I remained with Cineplex for 10 years, growing the VP level and leading a large team of HRBPs, recruiters and trainers. I learned from that experience to trust my instincts about where I will be happy and valued and where I will be neither. Or better put, I learned the important lesson that sometimes, you just need to fire yourself.
What’s your favorite part about working in the industry? What’s your least favorite part, and how would you change it?
My favorite part of this role is working with leaders and developing their skills. The greatest value we can offer is to transfer knowledge and develop others. As a People team leader, you get to really understand the experience of the teams by being in a classroom with them, helping them apply concepts to their roles. It also keeps you humble, as we tend to oversimplify the roles of others. In the classroom, I can understand the reality versus the image senior leaders may have about what it’s like to get work done in our organization. I started my career in training, and for me, it’s still the most important skill I have, and it is by far my happiest place!
My least favorite aspect of being a People team leader is that over the past 5 years, I have seen an increase in the individuals who expect their organizations to take the lead in managing their career movement and future roles. I firmly believe that we have a responsibility to provide learning and interesting experiences that help people grow and that we should also be actively ensuring people feel included, heard and supported. I also believe that you own your own work/life satisfaction and career movement by performing at a high level, networking with people outside your inner circle, and presenting ideas and projects that you want to work on or, even better, lead.
The People team must remain close to individuals who display these traits and actively seek to grow their careers, keeping these high performers in mind with other leaders when roles become available or during talent mapping conversations. The best thing our team can do is help those who want to grow to understand what they need to do to stand out; then, the ball is in their court. In certain situations, the accountability for growing your career has moved to the wrong place.
How can HR most effectively demonstrate its value to the leadership team?
This question about how the HR function can demonstrate value always makes me smile because I have never felt sidelined or didn’t have “a seat at the table.” I prefer to see my role as BYOC (Bring Your Own Chair).
The key to differentiating yourself from the administrative stereotype is understanding the business model, how decisions are made, and the key relationships that drive meaningful outcomes. If you prioritize your focus and attention on these areas, you will be viewed as a strategic partner who must be involved in shaping the organization’s future.
- Align with business goals: Make sure HR initiatives support the company’s main objectives. This shows how HR contributes directly to success.
- Use data wisely: Share insights from HR data, such as turnover rates and training impacts, to demonstrate real contributions to the company.
- Enhance employee experience: Create a positive workplace culture that boosts productivity and keeps people around.
- Support change: Help guide teams through changes smoothly, showing HR’s role in managing transitions.
- Develop leaders: Focus on identifying and nurturing future leaders to ensure strong leadership for the future.
- Share success stories: Regularly highlight HR wins to show the impact on the organization.
Where do you see the industry heading in five years? Or are you seeing any current trends?
As AI becomes integral to our roles, HR leaders will play a crucial role in helping redefine team expectations for the “augmented employee.” This shift requires leaders to develop new skills and adapt to changing responsibilities. HR will need to clearly articulate these evolving expectations to the executive team and the broader organization. By guiding this transition, HR ensures leaders and employees are equipped to thrive in an AI-enhanced work environment.
What are you most proud of?
I am most proud of the individuals who I have been able to work with who have grown into the CHRO roles themselves. This is the most satisfying experience a leader can have. I have regular check-ins with my former employees who are now my colleagues, and I can’t help beaming with pride at the powerful leaders they are and how much I learn from them.
Do you have any advice for people entering the profession?
Entering the “People” profession offers a unique opportunity to make a significant impact on the work satisfaction of the people in your company. To effectively drive change and influence others, HR professionals should focus on honing several key skills:
- Develop business acumen: Understanding the core aspects of how a business operates is crucial for aligning your initiatives with organizational goals.
- Enhance presentation skills: Being able to clearly and confidently communicate ideas is vital, whether it’s proposing a new HR initiative or presenting data to leadership.
- Cultivate assertiveness: Having the courage to voice insights and perspectives is important for influencing decision-making and driving change. Assertiveness allows HR professionals to advocate for initiatives that benefit the organization and its employees. Remember, BYOC!
- Build influential relationships: Establishing trust and strong connections across the organization is fundamental to influencing others and moving from the sidelines into the boardroom. By understanding the needs and challenges of different teams, HR can tailor approaches to be more impactful.