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The Exit Five CMO Podcast (Hosted by Dave Gerhardt)
The Exit Five CMO Podcast (Hosted by Dave Gerhardt)•October 16, 2025

Behind the Scenes of Drive 2025 with Anna Vermillion and Allison Saxon

A behind-the-scenes look at Exit Five's Drive 2025 event in Vermont, discussing the planning process, team dynamics, unexpected challenges, and the importance of creating a memorable, community-focused experience for attendees.
Creator Economy
Corporate Strategy
Remote Work
Anna
Dave Gerhardt
Allison
Harry Dry
Sylvia Lapoitevin

Summary Sections

  • Podcast Summary
  • Speakers
  • Key Takeaways
  • Statistics & Facts
  • Compelling StoriesPremium
  • Thought-Provoking QuotesPremium
  • Strategies & FrameworksPremium
  • Similar StrategiesPlus
  • Additional ContextPremium
  • Key Takeaways TablePlus
  • Critical AnalysisPlus
  • Books & Articles MentionedPlus
  • Products, Tools & Software MentionedPlus
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Podcast Summary

This podcast episode features Dave Gerhardt, founder of Exit Five, along with team members Allison and Anna, diving deep into their event strategy and the behind-the-scenes story of Drive 2025, their annual B2B marketing community event. (01:25) The conversation explores why events have become such a hot marketing channel, driven by post-COVID travel enthusiasm and the human need for authentic connection in an AI-dominated world. (05:09)

  • The episode covers their comprehensive event strategy, from initial planning to execution challenges, including a major last-minute venue change that turned into an unexpected win

Speakers

Dave Gerhardt

Founder and CEO of Exit Five, a B2B marketing community with nearly 5,000 members. Dave is a former CMO and VP of Marketing who has extensive experience in B2B marketing leadership roles and is known for his authentic, no-nonsense approach to marketing strategy.

Allison

Exit Five team member who joined in February 2024 and immediately took on event planning responsibilities. She leads the logistics and operational aspects of Exit Five's events, bringing organizational skills and attention to detail to the team.

Anna

Exit Five team member who joined in June 2024 and became instrumental in planning Drive 2024. She handles vendor relationships and strategic event planning, having learned the ropes through hands-on experience with their flagship annual event.

Key Takeaways

Start with Marketing, Not Logistics

The team learned that beginning with the landing page and marketing offer is crucial before diving into operational details. (12:39) As Allison explained, "building out the landing page makes it more clear what you're looking for when you need to get into the weeds of planning." This approach forces you to define why someone should attend, what they'll learn, and what makes your event unique. It serves as an amazing forcing function that clarifies the entire event vision before getting caught up in catering menus and logistics. The landing page becomes your north star, ensuring every subsequent decision aligns with your core value proposition.

Events Are Products That Require Obsessive Attention to Detail

Dave emphasized that successful events require treating every element as part of the product experience. (29:58) From having iced coffee available to the quality of cocktail napkins, these details compound to create memorable experiences. One attendee specifically praised them for having iced coffee when most conferences don't offer it. The team learned that people will take pictures, tell friends, and return based on these seemingly small touches. This obsession with the product experience becomes the best marketing tool because satisfied attendees become organic advocates who drive future ticket sales.

Create "Third Spaces" for Authentic Human Connection

Anna introduced the concept of "third spaces" - environments that aren't work or home where people can connect authentically. (22:28) Their excursions like pickleball, hiking, yoga, and boat cruises provided these crucial connection opportunities. As Anna explained, "People want a space that's not work or school or home. They want somewhere where they can go and connect with people and just vibe." These activities allow attendees to bond over shared professional language and challenges while engaging as complete humans, not just professional personas.

Plan for Things to Go Wrong

The team experienced a major crisis when their boat venue was double-booked just two hours before the event. (33:34) Allison's key learning: "Document everything in writing." This taught them that contingency planning and clear communication protocols are essential. They learned to expect something will go wrong and prepare accordingly. The crisis actually became a highlight when they pivoted to a brewery, showing that flexibility and team coordination can turn disasters into memorable moments that attendees appreciate even more.

The Event Doesn't End When It Ends

Anna discovered that post-event follow-up requires as much planning as the event itself. (36:02) "The event isn't over whenever it ends," she noted, highlighting the critical importance of post-event content distribution, sponsor recaps, slide sharing, and follow-up communications. Many teams neglect this phase, but it's crucial for sponsor satisfaction, attendee value, and setting up success for future events. Planning the post-event strategy from the beginning ensures smooth execution when everyone is exhausted after the main event.

Statistics & Facts

  1. Drive 2024 achieved an NPS score of 88, indicating exceptionally high attendee satisfaction. (14:02) This score provided quantitative validation of their event quality and became a benchmark for measuring success beyond just ticket sales.
  2. Exit Five's community has grown to nearly 5,000 members, providing the foundation audience that made their event successful. (55:38) This demonstrates the importance of having an engaged community before launching events.
  3. The team sold 200 tickets before Anna even joined the company in June 2024, showing the power of having an established community hungry for in-person connection. (06:25)

Compelling Stories

Available with a Premium subscription

Thought-Provoking Quotes

Available with a Premium subscription

Strategies & Frameworks

Available with a Premium subscription

Similar Strategies

Available with a Plus subscription

Additional Context

Available with a Premium subscription

Key Takeaways Table

Available with a Plus subscription

Critical Analysis

Available with a Plus subscription

Books & Articles Mentioned

Available with a Plus subscription

Products, Tools & Software Mentioned

Available with a Plus subscription

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