In this episode, Ben Rosenberg, Senior Director of Customer Support, Enablement, and Community at ChurnZero, shares his journey from hospitality to becoming a leader in the SaaS industry. Ben discusses his passion for mentorship and leadership development, his adaptable approach to managing teams, and his insights into how customer experience is evolving with AI and automation.

We explore the challenges of balancing automation with human connection, strategies for enabling remote teams, and why curiosity and empathy are critical traits for professionals in customer-facing roles. Ben also reflects on his personal hobby of woodworking and how it parallels his approach to leadership—embracing mistakes as learning opportunities.

Whether you’re a CX professional, a SaaS leader, or simply curious about the future of customer success, this episode offers valuable lessons and practical takeaways.

Key Topics Covered:

0:00 – Welcome & Introduction
Scott introduces Ben Rosenberg and his journey from hospitality to SaaS leadership.

3:15 – Leadership in Action
Ben discusses his adaptable leadership style and the importance of transparency and trust.

7:00 – Mentorship and Growth
Why mentorship has been a cornerstone of Ben’s career and how he pays it forward.

10:30 – Energizing Work
Ben shares what motivates him—solving problems, developing leaders, and learning from hobbies like woodworking.

15:00 – Challenges in CX
The push-and-pull of automation and human-led support in the customer experience landscape.

20:00 – Building Remote Team Culture
How ChurnZero fosters collaboration and engagement with remote teams.

25:30 – The Future of Customer Success
Why specialization and AI tools are reshaping customer success and how Ben envisions human-led support evolving as a competitive advantage.

30:00 – Personal Philosophy
Ben’s advice to aspiring professionals: stay curious, embrace learning, and focus on customer-centric solutions.

Key Takeaways:

• Leadership is situational: Adapt your approach based on the moment and the needs of your team.
• Mentorship matters: Sharing knowledge and helping others grow is both rewarding and impactful.
• The balance of automation and connection: While AI can optimize processes, human-led support remains crucial in complex B2B scenarios.
• Curiosity is key: A curious mindset opens doors, builds connections, and drives professional growth.

Notable Quote:

“I like to think of support as the central nervous system of an organization—picking up on the pain and joy of the customer experience and relaying it back to the business.” – Ben Rosenberg