Navigating the Shift from Individual Contributor to Leader with Ben Pippenger

Executive Evolution

“Great leaders know when they’re wrong.”

In this episode, Craig Anderson talks with Ben Pippenger, Co-Founder and Staff Product Manager of Zylo, about the evolution of leadership and the lessons learned from building and scaling a company. Ben shares his journey from an individual contributor to a leader, emphasizing the importance of understanding what truly motivates a team. He discusses how recognition—not just money—keeps employees engaged, why leaders must carve out time for their people, and how making mistakes can be a powerful learning tool. Ben also reflects on lessons from his time at Salesforce, the challenges of maintaining company culture at scale, and why leadership isn’t just about getting things done—it’s about bringing people along with you.

After You Listen:

• Connect with Ben Pippenger on LinkedIn

• Check out Zylo

• Connect with Craig on LinkedIn

• Subscribe to Craig’s "The Evolving Leader" newsletter

Key Takeaways:

• Understand what motivates your team to drive engagement and performance

• Prioritize recognition over money to build lasting team appreciation

• Embrace mistakes as learning opportunities to grow as a leader

Things to listen for:(00:00) Intro (01:30) Ben’s transition from contributor to leader (04:12) The role of motivation in building a high-performance team (07:28) How Salesforce’s leadership principles influenced Ben’s approach (10:18) Why leadership isn’t just about more productivity (14:23) The importance of career paths for non-managers (18:30) Creating a culture of recognition and peer feedback (22:45) The one leadership lesson Ben would tell his younger self