Mar 19 2025 45 mins
What happens when you reach the top of the corporate ladder, only to realize it’s leaning against the wrong wall? Mike Lemire — Drew’s childhood friend who crushed it in the corporate tech world — realized that success at the top wasn’t all it was cracked up to be. Mike walked away from the corporate hustle at the height of his career and now runs his own consulting firm, Harmonic Leadership, hoping to redefine success on his own terms. It’s a deep dive into the messy, scary, and ultimately liberating process of letting go when the big fancy gigs stop serving your soul.
Bio: Mike Lemire is the founder of Harmonic Leadership, with over 15 years of experience in leadership roles within tech and SaaS companies. He specializes in helping leaders improve their executive presence, decision-making, and team dynamics.
Mike started his career in the music industry. After studying music at Berklee College of Music, he began working with the marketing team at Blue Note Records. From there, he worked with an impressive slate of entertainment industry clients, ranging from EMI Classics to Focus Features and the Florida Panthers. He then went on to run Account Management programs for Yahoo!, overseeing the launch of Yahoo India in Bangalore and developing policy around political advertising during the 2008 election.
HubSpot is truly where Mike grew up professionally. While there, he launched the Professional Services team, working with executives from small businesses to Fortune 100 enterprises. After HubSpot's IPO, Mike went on to launch the Customer Success, Support, and Onboarding teams at Notarize.
In 2018, Mike joined the leadership team at Toast, tasked with creating a more scalable customer success team. He focused on data, operational excellence, and culture to help Toast scale from 10,000 customers to over 100,000. After Toast's IPO, he explored the world of AI in the healthcare space by joining Overjet as their VP of Customer Success. While there, he found his passion and skill for coaching and launched Harmonic Leadership in 2024.
Mike’s Social Media: www.HarmonicLeadership.co, @BiggestMike.
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Your Hosts: Alex Kumin (@Alex.Kumin) and Drew King (@DrewKingNYC). Audio mixed by Sarah Webb (@SWAudioPost). Filmed and recorded in the Barrow Lounge at @TheMalin West Village.
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