AI and Benefits: How Intelligence Tools are Reshaping Employer Benefits and Employee Care

July 14, 2026

About the Webinar

Open enrollment is changing fast, and HR teams can’t rely on yesterday’s playbook. In this session, experts from VensureHR and Healthee break down what today’s employees expect, why traditional enrollment methods fall short, and how AI is transforming benefits decision‑making. You’ll learn how to reduce administrative burden, improve employee confidence, communicate more effectively, and prepare your organization for an AI‑supported enrollment experience. We’ll also explore how AI enhances, not replaces, human guidance in healthcare navigation. Walk away with practical steps you can implement before your next open enrollment.

What You Will Learn:

Key Takeaways:

Learn how AI helps employees make more informed benefits decisions with greater confidence.
Reduce HR administrative workload through personalized benefits guidance and automation.
Improve employee engagement and benefits utilization during open enrollment.
Create a more streamlined, modern, and employee-centric enrollment experience.
Prepare your organization for the future of benefits administration and open enrollment.

Ideal For: HR leaders, benefits administrators, business owners, and people managers looking to improve benefits communication, increase employee satisfaction, and modernize their open enrollment strategy through AI-driven innovation.

Meet VensureHR

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About your Hosts

Dan Thomspons

Chief Benefits Officer

As Chief Benefits Officer, Vensure Employer Services, Division President Thomspon Risk, Dan Thompson brings leadership to over 200+ benefits division employees spread out both in the US and near shore. Vensure offers both a traditional open market benefits consulting services to it's clients along with the traditional offerings of Master Plans. Vensure's $165B in payroll, serving more than 3.4 Million Americans and over 19,000 employer clients brings massive scale and resources. Dan is responsible for Vensure's benefits team, acquisition of benefits agencies strategy and many more initiatives to serve/support the largest Private PEO/ Payroll Co. in the US.

Guy Benjamin

Co-Founder and CEO of Healthee

Guy Benjamin is the Co-Founder and CEO of Healthee, bringing a unique blend of leadership, technical expertise, and real-world problem-solving to the healthcare space. Born and raised in Israel, he spent 12 years as an F-16 fighter pilot in the Israeli Air Force before earning a BA in Information Technologies and Physics and later attending the Yale School of Management. He went on to serve as an Associate Partner at McKinsey & Company, where he focused on digital and analytics transformations for technology companies. Driven by a mission to simplify and improve the healthcare experience in the United States, Guy co-founded Healthee to empower employees and organizations with smarter, more accessible health benefits navigation.

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