Weighing Risks Before Speaking Up

In this episode recorded at the Presales Collective Leadership Next Summit in November of 2025, Jack Cochran sits down with Gretchen Fitzgibbons, Senior Manager of Strategic Solutions Consulting at Airtable, to discuss what it means to be a courageous leader in presales. They explore how to make difficult decisions under pressure, navigate organizational politics with integrity, and build the support systems that enable consistent leadership. Gretchen shares powerful stories from her two decades of experience advising Fortune 500 customers and leading presales teams, including standing up for a team member being unfairly assessed and creating win-win solutions in challenging situations.

• Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/

• Connect with Gretchen Fitzgibbons: https://www.linkedin.com/in/gretchenfitzgibbons/

• Join Presales Collective Slack: https://www.presalescollective.com/slack

• Sol/Con 2026: https://www.presalescollective.com/solcon-2026

• Book mentioned: Think Again by Adam Grant: https://adamgrant.net/book/think-again/

• Book mentioned: Thinking, Fast and Slow by Daniel Kahneman: https://www.goodreads.com/book/show/11468377-thinking-fast-and-slow

1. Redefining Courage and Leadership

2. Making Tough Calls: Standing Up for Team Members

3. Focusing on Your Team rather than on Yourself

4. How to Prepare for a Leadership Role

5. It's OK to be Wrong

6. Developing Your Leadership Skills

7. Grounding Principles for Leadership

00:00 Welcome and Introduction

02:14 Defining Courage and Leadership in Presales

05:15 Making Tough Calls: A Story of Standing Up for What's Right

11:20 Focusing on Your Team rather than on Yourself

22:07 How to Prepare for a Leadership Role

27:40 It's OK to be Wrong

30:30 Developing Leadership Skills

37:42 Final Takeaways and Grounding Principles