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Greg
Winsper
Vice President of Field Traing
National Life Group
Greg Winsper is passionate about being part of the National Life Group family, where he leads strategic growth initiatives and field leadership development. He works with a team that brings together decades of financial services experience to design leadership programs focused on attracting talented leaders, strengthening the existing leadership bench, and expanding reach into new markets. His work is centered on creating meaningful impact across the organization’s field force by developing people and programs that help others succeed. Through leadership development and strategic growth efforts, Greg and his team aim to positively influence the professionals they support, who in turn help improve the lives of the clients and communities they serve. Greg welcomes conversations with those interested in learning how National Life Group can make a positive difference in their personal or professional journey.
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21 January 2026 09:15 - 09:45
Fireside chat | Faster ramp, less overwhelm: A practical rubric for new hire onboarding
A launch isn’t the same as adoption and when enablement doesn’t land, the silence afterward can be the hardest part. This fireside chat explores what really happens after rollout, when participation drops, managers disengage, or teams quietly return to old habits. Together, we’ll unpack the hidden friction points that derail enablement and how experienced leaders diagnose whether the issue is messaging, management reinforcement, incentives, or change fatigue. Attendees will contribute real scenarios, vote on likely root causes, and compare how different organizations respond, gaining insight from the collective experience in the room. You’ll walk away with: - A practical framework to diagnose struggling initiatives - Targeted strategies to address specific adoption challenges - Language to re-engage stakeholders and rebuild momentum - Peer connections you can turn to when your next rollout hits resistance