Courageous Leadership: Making Tough Calls Under Pressure with Gretchen Fitzgibbons
Presales Podcast by Presales Collective
Release Date: 02/02/2026
Courageous Leadership: Making Tough Calls Under Pressure with Gretchen Fitzgibbons
Presales Podcast by Presales Collective
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...
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Storytelling as an Industrial Skill with Jon Billett
Presales Podcast by Presales Collective
In this episode, Jack Cochran is joined by Jon Billett, Founder and CEO of StoryQuadrant, to discuss why storytelling in presales needs to be treated as an industrial skill rather than a soft skill. They explore Jon's framework for the four types of stories every SE should master, the danger of "Mad Libs" style customer stories, and why the most important story is the one told after you leave the room. Jon shares insights from his 15 years in presales and his unique background as a member of the Magic Circle, revealing how structure, rather than content, creates memorable presentations that...
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Shaping Decision Confidence and Overcoming Customer Indecision with Nikhil Sarma
Presales Podcast by Presales Collective
In this episode, Jack Cochran and Matthew James are joined by Nikhil Sarma, Founder of GTM Solutions Consulting, to explore why customer indecision has become one of the biggest challenges in enterprise sales. They discuss the factors driving buyer hesitation, how to diagnose value clarity vs. organizational issues, and practical strategies for helping customers build the confidence to move forward. Nikhil shares frameworks for understanding stakeholder dynamics, the importance of financial fluency for SEs, and why de-risking the implementation is often more important than the technology...
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Stop Paying the Demo Tax: How AI Is Transforming Presales with Justin McDonald
Presales Podcast by Presales Collective
The State of Presales and Demo Technologies, and What's Coming in 2026 In this episode, Jack Cochran and Matthew James are joined by Justin McDonald, Co-founder and CEO of Saleo, to discuss how demo automation technology is transforming the presales landscape. They explore the evolution of presales over the past 20 years, the hidden costs of demo preparation (the "demo tax"), and how AI is revolutionizing how solutions engineers create and personalize demonstrations. Justin shares insights on building relational capital, the importance of in-person meetings, and why the future of presales lies...
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Conquering Imposter Syndrome with Hannah Bloking and Allison Macalik
Presales Podcast by Presales Collective
In this episode, Jack Cochran and Matthew James are joined by Hannah Bloking, and Allison Macalik, co-founders of 4Under3. They discuss the universal challenge of imposter syndrome in the pre-sales profession, exploring how it manifests, why it affects nearly everyone, and practical strategies to address it. Hannah and Allison share insights from their workshops, including powerful techniques like the "lighthouse speaker" mindset and the importance of naming your imposter to take control of those negative thoughts. Thank you to Storylane for sponsoring this episode. Follow the Hosts and Guests...
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Charting Your Presales Career Path with Miriam Graf
Presales Podcast by Presales Collective
Episode 181: Charting Your Presales Career Path with Miriam Graf In this episode, Jack Cochran and Matthew James welcome Miriam Graf, a presales veteran with 20 years as an individual contributor and 10 years in leadership roles. Miriam shares invaluable insights on navigating career growth in presales, from speaking up about your aspirations to recognizing when leadership is and isn’t the right path for you. She discusses the evolution from being "the hero" to becoming a leader who helps others shine, and explores the diverse career opportunities available beyond traditional management...
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From Overloaded to Optimized: Concierge Services and Deal Desks with Rob Bruce
Presales Podcast by Presales Collective
In this episode, Jack Cochran and Matthew James are joined by Rob Bruce, a presales leader at Syndigo with 20 years of experience, to discuss an innovative approach to presales operations: the Pursuit Desk. Rob shares how Syndigo has built a dedicated "concierge team" that handles RFPs, security questionnaires, reference coordination, and other time-consuming tasks, freeing solutions engineers to focus on discovery, solutioning, and building customer relationships. The conversation explores how to operate at the "top of your license," the role of AI in scaling pursuit operations, and practical...
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Presales and Sales Working Together SEAMlessly with Art Fromm
Presales Podcast by Presales Collective
In this episode, Jack Cochran and Matthew James are joined by Art Fromm, author of "Making Seamless Sales" and sales enablement expert, to discuss how presales and sales teams can work together more effectively. Art shares insights from his 25+ years in sales enablement, exploring the common disconnects between SEs and AEs, and provides practical strategies for building stronger partnerships that drive better outcomes. The conversation covers the evolution from tribal knowledge to systematic collaboration, the importance of discovery before demos, and how to create value perception rather than...
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Breaking Barriers: How WISE is Transforming Women's Careers in Presales with Wendy McHenry
Presales Podcast by Presales Collective
In this episode, Jack Cochran and Matthew James are joined by Wendy McHenry, Chair of WISE (Women in Solutions Excellence) at Presales Collective and Former Head of Global Solutions Engineering at CDATA, to discuss the critical need for supporting women in presales careers. They explore the challenges women face in a field where only 18% of solutions professionals are women, discuss unconscious bias in hiring and workplace environments, and highlight how WISE is creating support networks and career development opportunities to advance equity in the solutions field. To join the show live,...
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Tailoring AI for Growth: What Startups and Enterprises Should Do Differently with Akash Ganapathy
Presales Podcast by Presales Collective
In this episode, Jack Cochran and Matthew James are joined by Akash Ganapathi, CEO of Opine, to discuss how AI strategies differ between startups and enterprises in the presales space. They explore the myth of AI replacing SEs, the importance of specialization vs. generalization, and how AI can help presales teams manage more revenue per team member while focusing on strategic, relationship-building activities. Follow Us Connect with Jack Cochran: Connect with Matthew James: Connect with Akash Ganapathi: Links and Resources Mentioned Join Presales Collective Slack: Opine:...
info_outlineIn 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.
Follow Us
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Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/
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Connect with Gretchen Fitzgibbons: https://www.linkedin.com/in/gretchenfitzgibbons/
Links and Resources Mentioned
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Join Presales Collective Slack: https://www.presalescollective.com/slack
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Sol/Con 2026: https://www.presalescollective.com/solcon-2026
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Book mentioned: Think Again by Adam Grant: https://adamgrant.net/book/think-again/
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Book mentioned: Thinking, Fast and Slow by Daniel Kahneman: https://www.goodreads.com/book/show/11468377-thinking-fast-and-slow
Key Topics Covered
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Redefining Courage and Leadership
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Making Tough Calls: Standing Up for Team Members
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Focusing on Your Team rather than on Yourself
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How to Prepare for a Leadership Role
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It’s OK to be Wrong
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Developing Your Leadership Skills
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Grounding Principles for Leadership
Timestamps
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