Leading Through Uncertainty: Purpose-Driven Leadership with Annette Gregg

In this episode of The Association Insights Podcast, we close out our March Leadership Series with Annette Gregg, CMM, MBA, CIS, CEO of the Society for Incentive Travel Excellence (SITE). Annette leads SITE’s 3,100 global members across 90 countries and brings deep expertise in business events, leadership, and community building.

Annette shares how she’s guided SITE through rapid growth post-pandemic, what it takes to lead a global and multigenerational membership, and how associations can stay grounded in their values during turbulent times.

Key Highlights:

Growing with Purpose – How SITE achieved 40% growth by focusing on core strengths and evolving with intention.

Leading a Global Membership – Annette’s approach to expanding brand awareness while respecting cultural and generational differences across 90 countries.

Navigating Disruption – Insights from Annette’s LinkedIn article on moving forward in uncertain times, and how association leaders can balance optimism with realism.

Staying Grounded in Your Values – Why SITE is doubling down on inclusion, community, and leadership development—and how associations can stay true to their missions even amid political or economic headwinds.

Protecting Your Mindset – How leaders can care for themselves and their communities to maintain focus, clarity, and connection.

The Stockdale Principle – Annette’s leadership north star and advice for staying hopeful while facing hard truths head-on.

🎧 Listen now for a candid, energizing conversation on resilience, values-based leadership, and finding calm in the chaos.

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Coming Soon: Tune in weekly as we share practical insights, smart strategies, and powerful conversations with association leaders on the challenges—and opportunities—shaping our sector.

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