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The latest episode of Presales Podcast featured an enlightening conversation with Gretchen Fitzgibbons, Senior Manager of Strategic Solutions Consulting at Airtable. Recorded during the Presales Collective Leadership Next Summit in November 2025, the episode explored what it truly means to be a courageous leader in presales and how to make difficult decisions under pressure. Hosted by Jack Cochran, General Manager of Presales Collective, this conversation drew from Gretchen's two decades of experience advising Fortune 500 customers and leading presales teams.
Listen to the full episode now!
Redefining Courage in Leadership
Gretchen's definition of courage has evolved significantly throughout her career. "Being able to make the same consistent decisions and represent yourself the same way that aligns with your principles, no matter what the dynamics are, no matter how much pressure there is, how much urgency there is," she explained. This isn't about grand heroic acts but rather the everyday commitment to integrity even when it's uncomfortable.
Courage in leadership means accepting that discomfort is part of the job. "You have to be able to really be comfortable that you're going to be uncomfortable in a lot of these situations," Gretchen emphasized. It's about making decisions when you're nervous, when there's fear involved, or when you might lose social currency professionally because you're going against the grain.
Her perspective on leadership itself has also transformed over time. "I used to think of it very much as title and tenure," she shared. "And now I really look at leadership of presence, consistency, and the ability to get people to think bigger than themselves and being willing to be at the forefront when things aren't going well and be able to be in the back clapping when things are going well."
This redefinition is liberating because it means anyone can be a leader, regardless of their position. "You're going to play those roles where you may be put in an influential position, even if you don't have the title to go with it," Gretchen noted. "You have more impact than you think you do."
Standing Up for What's Right: A Case Study in Courage
One of the most powerful examples Gretchen shared involved defending a team member who wasn't even on her direct team. During a performance review cycle, she witnessed a solutions engineer being unfairly categorized as underperforming despite clear evidence to the contrary. After reviewing Gong calls and observing the person's work, Gretchen knew the assessment was wrong.
"I could have very easily said, you know, not my circus, not my challenge, but just from a principal's perspective, I felt that she was being unfairly put in that position," Gretchen recalled. The situation was setting a dangerous precedent where favoritism could trump actual performance.
In a meeting with other managers, she tactfully raised her concerns, bringing specific examples that contradicted the negative assessment. "It wasn't popular with my colleague at the time. And I had to accept that I wasn't going to make everybody happy. But I knew in principle that was something that I felt very strongly about," she explained.
The outcome was positive. Not only was the employee's assessment corrected, but Gretchen worked with other managers to find a better team fit for the individual, addressing underlying dynamics without requiring new headcount. The experience taught her an important lesson about courage: "I wasn't going to make everybody happy. But I knew in principle that was something that I felt very strongly about."
Navigating Organizational Politics with Integrity
One of the recurring challenges in leadership is managing relationships with difficult colleagues or navigating organizational politics. Gretchen's approach centers on maintaining curiosity and assuming positive intent, even when it's challenging.
"Assume someone wants the best, take a best intent standpoint and then learn," she suggested. This doesn't mean being naive, but rather approaching situations with an open mind. "Go in assuming that it's good unless it's proven otherwise."
When conflicts do arise, especially with peers at your level, the key is direct communication. "If you're seeing something that you think is negatively impacting you, your team, or the broader organization, you have to bring it up," Gretchen emphasized. Avoiding difficult conversations only allows problems to fester.
Grounding Principles for Courageous Leadership
Beyond frameworks and decision-making tools, Gretchen emphasized the importance of having simple grounding principles. She mentioned "kind is clear" as one example and a reminder that direct, honest communication delivered with empathy is ultimately the kindest approach, even when it's difficult.
These principles, whether written on post-it notes or kept in journals, serve as touchstones when navigating challenging situations. They help leaders stay aligned with their values when external pressures might push them in other directions.
Looking Ahead
Courageous leadership is about consistency, presence, and the willingness to make tough calls that align with your principles, even when it's uncomfortable. For presales professionals at any level, the message is clear: you have more influence than you think. Leadership isn't about waiting for a promotion or a title change. It's about showing up authentically, standing up for what's right, and helping those around you think bigger than themselves.
The most impactful leaders are the ones who make the right decisions, support their teams with integrity, and maintain their principles under pressure.
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