Reinventing Event Revenue: Michelle Troop on Customization, AI Tools, and Selling Beyond the Booth

In this episode of The Revenue Room, host Heather Holst-Knudsen speaks with Michelle Troop, Chief Revenue Officer of Ai4, the world’s largest artificial intelligence event. Michelle shares how she helped scale Ai4 from boutique gatherings into an 8,000+ attendee juggernaut—and how her entrepreneurial mindset has led to multiple successful event acquisitions.

She breaks down the playbook behind Ai4’s revenue transformation, including:

• How to enable your sales team to go beyond square footage
• Why modern sponsors expect customization and real-time ROI
• How to use AI tools like ChatGPT to boost outbound performance
• Rethinking hosted buyer models and 1:1 meetings
• What signals you're ready to scale or sell

Whether you lead events, sales, or strategy, Michelle’s insights will inspire you to rethink how you monetize audience, data, and content in today’s fast-moving B2B environment.

About Michelle Troop

Michelle Troop is currently the Chief Revenue Officer of Ai4, the largest and most significant international artificial intelligence event, which was recently acquired by CloserStill Media—a global events organization with over 200 award-winning brands spanning Business Technology, Learning, HR & Education, Healthcare, and Future Transport & Infrastructure.

With over 35 years of trade show experience across consumer events, trade shows, and conferences, Michelle has consistently transformed and scaled events into industry-leading platforms. Her career highlights include rebuilding key trade shows into Trade Show Top 35 events, traveling the globe for the launch of the original PlayStation, and—over the past 13 years—co-founding and building several premier events such as InsureTech Connect (ITC), Mobile Apps Unlocked (MAU), and LeadsCon. All of these grew from launch to critical mass and were ultimately acquired by Clarion and Access Intelligence.

Most recently, she helped reshape the strategy and scale of Ai4, growing it from a series of 300-person events in New York into the leading global AI event, drawing over 8,000 attendees to Las Vegas.

Michelle is passionate not only about building great events, but also building exceptional teams. Together, they’ve delivered exponential growth in attendance, revenue, and audience experience.

When she's not driving innovation in the events world, Michelle enjoys rescuing an

About RevvedUP 2026
RevvedUP 2026 is where CEOs and revenue-critical C-Suite leaders reset their growth playbook for the AI-first economy. Taking place March 23–24, 2026 at The Vinoy Resort in St. Petersburg, FL, this two-day strategy lab helps leaders pressure-test how AI moves from cost center to growth driver and turn data and disruption into competitive advantage.

About Heather Holst-Knudsen
Heather Holst-Knudsen is the founder and CEO of H2K Labs and Revenue Room™ Connect. A seasoned executive and operator across media, marketplaces, events, and technology, she specializes in digital transformation, data-driven growth, and customer-centric value creation. Heather shares her insights on multisided business models through The Revenue Room™.

About Revenue Room™ CXO
Revenue Room™ CXO is a private executive community for CEOs and revenue-critical C-Suite leaders navigating growth in the data and AI economy. Through curated peer discussions and strategy sprints, members tackle real-world challenges in revenue transformation, customer intelligence, and business model innovation.

Learn more or apply for membership at info.h2klabs.com/apply-cxo.

Transcript

[00:00–02:00] Introduction

• Michelle Troop introduced as CRO of AI4, the world’s largest AI event.
• Career highlights: co-founder of InsureTech Connect, Mobile Apps Unlocked, and LeadsCon, all acquired.
• Early career at Sony supporting the original PlayStation launch.

[02:00–05:00] Corporate vs. Entrepreneurial Journey

• Transition from corporate to entrepreneurial roles highlighted.
• Emphasis on nimbleness, quick decision-making, and community-focused event building.
• Key success driver: ability to build valuable, scalable, acquisition-ready event assets.

[05:00–08:00] Scaling Events Through Revenue Philosophy

• Events have evolved: success no longer defined by business cards collected, but ROI delivered.
• Key principles:
  • Listen to the customer.
  • Customize offerings (without over-customizing).
  • Avoid static, “boxed” packages that lose relevance over time.

[08:00–10:00] Customization Case Study

• Example: Sponsor idea turned into a productized lead-matching tool at InsureTech Connect.
• Resulted in a scalable and profitable product offering, showing responsiveness to customer innovation.

[10:00–12:00] Signs of Acquisition Readiness

• Key moment: inbound sales surpass outbound efforts.
• Large sponsors begin coming to you.
• Signals market validation and creates internal momentum toward acquisition strategy.

[12:00–16:00] Scaling AI4 from 300 to 8,000 Attendees

• AI4 began as premium, small events focused on quality.
• COVID forced pivot to digital, which broadened global reach.
• Post-COVID: consolidated into a large-scale Las Vegas event.
• Created flexible sponsor offerings (not square-footage-dependent).

[16:00–21:00] Sales Philosophy: Thinking Outside the Booth

• Sales team trained to sell full-spectrum solutions, not just booths.
• Extensive role-playing, product immersion, and customer feedback loops.
• Culture of openness, coaching, and empowerment built around curiosity.

[21:00–26:00] Hosted Buyer / 1:1 Meetings Approach

• Avoids “hosted buyer” term — simply called 1:1 meetings.
• Buyers are eager to learn; sponsors value time-efficient engagements.
• Meetings are opt-in and finite (e.g., 15 mins).
• Not all industries suit this model — fit matters.

[27:00–30:00] Post-Acquisition Structure with CloserStill Media

• CloserStill allows autonomy while offering infrastructure and support.
• 3-year window for continued growth under their ownership.
• Partnership built on trust and shared entrepreneurial values.

[30:00–33:00] Building & Retaining Top Teams

• Culture built on trust, flexibility, and shared purpose.
• Remote-friendly, outcome-driven.
• Full-cycle sales: each rep owns outreach, closing, and renewals.
• Fosters ownership and pride in business development.

[33:00–36:00] Revenue Insights & Data Transparency

• Transparent dashboards shared across team:
  • New vs. repeat business
  • Pipeline pacing
  • Individual performance
• Encourages team participation in strategy and innovation.

[36:00–38:00] Use of AI in Sales & Marketing

• AI tools like ChatGPT used to improve messaging and campaign personalization.
• Emphasis on creative reinvention of outreach strategies.

[38:00–40:00] AI Tools and Content Strategy

• No uniform conversational intelligence tool used across the team.
• Content team built around curiosity and constant market analysis.
• Content excellence drives both attendee quality and sponsor engagement.

[40:00–42:00] Managing Sponsor Content

• Sponsors are coached to avoid sales pitches.
• Talks must focus on problem-solving and use cases.
• Presentations are reviewed and optimized by the team pre-event.

[43:00–45:00] Key Advice on Scaling Revenue

• Evolve your offerings and embrace experimentation.
• Shift with changing customer expectations — today’s buyer wants personalized options and value clarity.
• Avoid the trap of “this is how we’ve always done it.”

[45:00–47:00] Rapid Fire #1 – Best Meal

• Chef-prepared anniversary dinner at home with her husband — magical, personalized experience.

[47:00–48:00] Rapid Fire #2 – Favorite Book

• Douglas Adams’ Hitchhiker’s Guide to the Galaxy — inspires exploration, curiosity, and breaking boundaries.

[48:00–50:00] Advice for Rising Female Revenue Leaders

• Listen to your voice and don’t be afraid to fail.
• Embrace risk, learn from mistakes, and be persistent in trying new things.

💡 Final Takeaways

Michelle Troop embodies a modern revenue leader who:

• Blends deep operational experience with creative risk-taking.
• Champions team empowerment through trust and training.
• Builds agile organizations that scale through customer listening and continuous reinvention.

Her work with AI4 is a masterclass in:

• Building acquisition-ready assets.
• Leveraging crises (like COVID) to catalyze expansion.
• Positioning events at the intersection of thought leadership and business value.