How Prioritising Health Transformed Dean Swan’s Leadership and Fuelled Monday.com's Explosive Growth
For Episode 207 of The Startup Playbook Podcast, I had the privilege of speaking with Dean Swan, the Vice President and General Manager for Asia-Pacific & Japan (APJ) at Monday.com. Dean’s journey is nothing short of inspiring.
With a career that includes 11 years at Microsoft, a role as the Country Manager for Australia & New Zealand at Dropbox, and now leading Monday.com’s expansion in APJ, Dean has accumulated an incredible wealth of knowledge on leadership, market expansion, and talent acquisition.
But what really stood out in our conversation was how a discussion about leadership evolved into an incredibly powerful story about the transformative impact of taking care of yourself—mentally and physically—and how it ripples out to your team and your business.
In the clip below from the podcast, Dean opens up about a deeply personal experience - the loss of a close colleague to suicide.
This tragedy became a wake-up call for him, reminding him of the critical importance of looking after his mental and physical health. As his role at Monday.com grew more demanding, Dean realised that in order to keep showing up as his best self, he needed to take better care of his well-being.
This wasn’t just about feeling better—it was about transforming his life. Dean lost over 20kg and got into the best shape of his life, but the real shift happened when his commitment to health started influencing his work.
Dean’s personal transformation set the tone for his entire team. He’s a perfect example of how leadership by example—prioritising mental health, physical well-being, and sustainable performance—creates a high-performance culture where everyone feels empowered to do the same. Dean didn’t just grow Monday.com’s business—he built a thriving, resilient team culture.
When Dean joined Monday.com as the first hire in the region, he set an audacious goal: to grow his part of the business to $100 million in 5 years, despite the entire company being valued at just $120 million at the time.
Fast forward to today, Dean’s team has grown from just him to 140 people, and they’re just $2 million shy of hitting that target—months ahead of schedule. In 2021, Monday.com went public and is now valued at $15.97 billion.
Dean’s story is a powerful reminder that self-care is not a luxury—it’s essential for high performance. Prioritising our well-being makes us better leaders, teammates, and individuals. The ripple effect is undeniable: when leaders invest in themselves, they create a culture where everyone thrives.
If you’re looking to elevate your leadership and create lasting success, start by investing in yourself. As Dean’s story shows, the results can be life-changing.
🎧 Tune in to the full episode with Dean Swan here (or watch the full episode below) and get inspired to lead with health, heart, and high performance.
Full show notes are available at startupplaybook.co
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About me
Hi, I’m Rohit and I’m the Founder of The Komo Club, where I help high-performing founders and executives win in business and life through self-leadership and scalable systems. I also host The Startup Playbook Podcast, where I’ve interviewed over 200 of the world’s top founders, investors, and operators, and I’m a General Partner at Playbook Ventures, backing early-stage startups. Before this, I was a founder myself, so I know firsthand how messy the journey can be. Now, my focus is on helping others navigate the ups and downs—through content, community, and conversation.
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