In this episode of The Seat, host Ray Erickson sits down with Michael Rosen, Chief Revenue Officer at Origin Media, for an honest conversation about leadership, mentorship, and what it really takes to build and scale high-performing teams.

Michael shares his journey across media, marketing, and sales leadership roles, from early career lessons to executive leadership, highlighting the mentors who shaped his path, the importance of empathy, and the balance between accountability and care. He unpacks how trust, vulnerability, and perspective-driven leadership create stronger organizations and better outcomes.

Whether you’re an aspiring sales leader or a seasoned executive, this conversation offers practical insights on leading through change, empowering teams, and growing as a leader while staying grounded.

Key Themes & Topics Discussed

• The role of mentorship in long-term career growth
• Leading with empathy without sacrificing accountability
• Building trust and psychological safety within teams
• Navigating organizational change and uncertainty
• Developing leaders by encouraging initiative and perspective
• Why vulnerability and honesty strengthen leadership credibility
• Lessons learned from scaling teams across media and tech

Key Takeaways

• Mentorship plays a critical role at every stage of a career
• Empathy is a leadership strength, not a weakness
• Trust and open communication drive better team performance
• Continuous learning is essential for long-term growth
• Great leaders empower others rather than control outcomes

Notable Quotes

• “I think mentorship comes in three flavors.”
• “I want you to come with a perspective.”
• “Leadership is about caring deeply and being honest.”

Episode Chapters

00:00 - Early education and career aspirations

03:27 - Mentorship and early career lessons

06:35 - Transitioning into leadership roles

12:31 - Navigating change management

17:22 - Rebranding and revenue challenges

19:47 - Building and leading strong teams

25:40 - The evolving role of mentorship

32:06 - Empathy, vulnerability, and leadership

39:29 - Michael’s current role at Origin Media

40:02 - Closing thoughts

About the Guest:

Michael Rosen is the Chief Revenue Officer at Origin Media, a connected TV creative ad platform. He brings over 25 years of experience building and scaling media businesses across companies including Intersection, Foursquare, First Look Media, AT&T, WeatherBug, and Bloomberg. Michael also serves on the boards of The New York Pops and Sandy Hook Promise and is co-chair of the UJA-Federation of New York Marketing Council.

Keywords / Tags

leadership, mentorship, sales leadership, media executives, career development, empathy, team building, change management, professional growth, ad tech, marketing leadership, CRO

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