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2022 Winter Insights Conference

96  Conferences held

10,000+  Attended

73%  From Industry

70%  C-suite and VP-level attendees

Three Days of In-Person Networking, Continuing Education, and Peer Learning at Winter Insights

January 27-30, 2022 | Naples, Florida

Winter Insights is designed to help you connect in person with the who's who of the sponsored benefits industry, while keeping you apprised of must-know trends and topics. Plus, your conference registration includes access to a networking platform that allows you to connect with other attendees before, during, and after the conference.

Who Attends

Register for Winter Insights



Early Bird Pricing – Ends December 21, 2021


Regular Pricing – Begins December 22, 2021

  • Access to all sessions
  • Access to P2P forums
  • Unlimited 1:1 meetings
  • Breakfasts, a luncheon, and two receptions
  • Access to on-demand recordings
  • 60 days of networking via the conference app




  • Access to all sessions
  • Unlimited 1:1 meetings
  • Breakfasts, a luncheon, and two receptions
  • Access to on-demand recordings
  • 60 days of networking via the conference app


Agenda At A Glance

Thursday, January 27

P2P Advisory Forums

Welcome and Registration


Friday, January 28

Opening Keynote

Company Showcases

The Trends and Challenges to Marketing to Associations

Legislative & Regulatory Update

Insurtech Companies—How They Quickly Became Leaders in Our Industry


Saturday, January 29

PIMA Strategic Update and Board Elections

Affinity Partnerships—How Do You Create and Sustain Them?

Overcoming Privacy Hurdles: Approaches for Challenges in Data Sharing


Closing Keynote

Charity Golf Outing

Closing Celebration

Attendees must be fully vaccinated against COVID-19, or have a negative COVID-19 test within 48 hours of arriving on site. Unvaccinated attendees must wear masks per CDC guidelines.
View our safety measures for more information. 

Golf? I’m Game.

Enjoy a fantastic Florida afternoon with fun, food, and friendly competition in our four-person scramble at Naples Quail Run. Fees include green fees, cart, golf balls, lunch, and transportation to the course. Registered guests are welcome to participate.

Proceeds generated from PIMA’s Winter Insights Charity Golf Outing will be donated to the Bayou Community Foundation and their Bayou Recovery Fund for Hurricane Ida Relief. More than 200,000 residents of the Bayou region will be directly affected by your generosity. As the site of PIMA's summer 2021 and 2023 conferences, we are honored to support the important work they are doing to help rebuild their communities.

$50,000 Hole in One, Closest to the Pin, and Longest Drive Contests Sponsored By:


The sunny and luxurious Naples Grande Beach Resort will provide the ideal backdrop for Winter Insights. Details on booking your stay will be included in your Winter Insights Conference registration.

Promote Your Involvement in Winter Insights!

Whether you are an attendee, sponsor, or speaker, we encourage you to promote your involvement in Winter Insights. To help with this, we’ve created graphics and messages you can post directly on your social channels. Please feel free to post the messages as is or customize them based on your personal style and tone.


View Social Media Toolkit View LinkedIn Event


Marcus Sheridan

Opening Keynote

Marcus Sheridan

The Digital Customer: How Today’s Buyer Has Changed and What Your Business Must Do About It

Sarah Noll Wilson

Leadership Legacy Workshop

Sarah Noll Wilson

Sarah Noll Wilson, Inc.

Wesley Hamilton

PIMA Special Guests

Closing Keynote

Wesley Hamilton

Living Your Best Life

Sponsor & Supporter Opportunities

Make your mark at Winter Insights by becoming a sponsor. Available opportunities include:

  • Winter Insights Golf Outing
  • Insights Awards & The Best of PIMA
  • Welcome Reception
  • Networking Lunch
  • Closing Celebration
  • Company Showcase
  • Conference Supporter
  • Winter Insights Golf Tournament Hole

Level sponsorships are also available.

Learn More

Sponsorship Opportunity PDF