In a recent episode of the HRchat Podcast, I had the pleasure of speaking with Dessalen Wood, Chief People Officer at Syntax, a global managed cloud provider for mission-critical enterprise applications.
With a 25+ year career spanning retail, entertainment, and tech—including senior roles at Reitman’s, HBC, Cineplex, and Disney—Dessalen brings a wealth of experience to the ever-evolving conversation around culture, leadership, and workplace flexibility.
Key takeaways from our discussion:
Cross-Industry Insights Shape a Unique People Strategy
Dessalen’s diverse background has given her a well-rounded perspective on organizational culture. She explained that working across different sectors helped her understand how business models and employee expectations influence engagement strategies.
“Retail taught me speed, scalability, and resilience. Entertainment focused me on creativity and emotional connection. And tech? That’s where I really began to challenge traditional systems of communication and collaboration.”
At Syntax, these learnings converge. Dessalen is building a global people strategy that supports both operational excellence and human-centered leadership.
Building Better Leaders, Not Just Better Managers
As Syntax continues to scale globally, Dessalen emphasized that leadership development is at the core of their people strategy.
“We’re not just training leaders to hit KPIs—we’re encouraging them to lead with empathy, adaptability, and humility.”
She pointed out that cultivating a growth mindset and emotional intelligence is critical, especially for those stepping into leadership for the first time in a hybrid or global environment.
Certified as a Great Place to Work
Dessalen also shared the exciting news that Syntax recently earned its Great Place to Work Certification—a major milestone that reflects the company’s commitment to culture and employee wellbeing.
“It’s an acknowledgment of the trust, inclusion, and communication we’ve worked hard to foster—especially through remote and hybrid challenges.”
Rethinking the Office Mandate
With many companies pushing for a return to the office, I asked Dessalen about Syntax’s position on flexibility.
“We do not believe in one-size-fits-all mandates,” she said. “We’ve adopted a flexible approach—some roles require in-person collaboration, others can thrive remotely.”
Syntax’s policy is built on trust and outcomes, not hours at a desk. For roles that can be remote, employees are empowered to work from anywhere that supports their productivity and personal life.
Programs That Keep People Connected
To maintain strong connections across geographies, Syntax offers programs focused on employee development, engagement, and recognition. These include cross-functional learning opportunities, virtual coffee chats, and employee-led interest groups.
“Culture isn’t just created from the top down,” Dessalen noted. “It’s sustained by the daily micro-moments of care, celebration, and collaboration.”
Final Thoughts
In Dessalen’s words, “The future of work is about aligning people strategy with both business goals and human needs.”
As organizations continue navigating hybrid work, global growth, and leadership challenges, leaders like Dessalen remind us that flexibility, intentionality, and empathy are not just nice-to-haves—they’re essential for long-term success.