Michael Decastro

WORK HISTORY

EDUCATION

SKILLS

ABOUT MICHAEL DECASTRO

I’m a growth-focused sales leader and strategic operator with over a decade of experience driving revenue, launching markets, and building cross-functional alignment across both high-growth startups and enterprise-level organizations.From helping launch WeWork Canada and scaling new markets across Calgary, Montreal, and Vancouver, to expanding Ritual’s footprint across 20+ U.S. cities, I’ve been at the forefront of go-to-market execution, operational design, and customer retention strategies. At companies like Hootsuite and Insight Global, I consistently ranked as a top performer, earning recognition for exceeding quotas, training new hires, and building scalable sales playbooks.I’ve led high-impact projects alongside CEOs, product teams, and marketing leaders, especially during times of change, most notably when I helped restructure WeWork’s Canadian business during COVID, reshaping customer strategy and retention planning in real time.My superpower? Building genuine relationships that convert into long-term business partnerships. I’m a proactive communicator who thrives in collaborative environments, and I bring a deep understanding of how day-to-day actions align with high-level strategy.Whether I’m helping a Fortune 500 brand refine their operations, launching a coworking space, or partnering with local businesses to grow their digital presence. I’m motivated by creating momentum, delivering results, and leaving teams stronger than I found them.