In this episode, host Olivier Lafontaine speaks with David Whitehead, Senior Vice President of Retirement Services Sales and Marketing, and Kyle Ryan, Vice President of Retirement Services Operations from Reliance Standard Life. Together, they reflect on leading multi-year transformations that reshaped how the business manages policies, distribution, and customer service.

David and Kyle discuss efficiency and the process of replacing legacy policy administration systems, consolidating workflows, and distribution management tools. They explain how the company adapted operations to keep projects moving, focusing on small empowered teams and quick wins.

Throughout the discussion, they highlight the importance of balancing between innovation and stability, preparing for long-term scalability, and aligning digital initiatives with brand and financial strength.

Key Takeaways:

1. Data integration was pivotal, turning the new admin system into a hub for DTCC and distribution management that streamlined hierarchies and reduced manual work.

2. Focused decision-making accelerated progress. Empowering small teams and quick wins were essential in sustaining momentum for multi-year modernization projects.

3. Clear MVP focus reduced risk. By concentrating on the functions needed to issue contracts at launch and deferring “nice-to-haves,” RSL kept scope tight, minimized fatigue, and ensured a timely go-live.

Jump Into the Conversation: (00:00) Meet David Whitehead and Kyle Ryan

(02:16) Lessons from consulting to insurance transformation

(06:09) Reliance Standard Life’s history and growth story

(09:52) Early steps in modernization and workflow changes

(12:38) Moving away from legacy systems

(15:46) Shifting to portals and digital-first statements

(18:32) Managing day one versus day two priorities

(23:15) Beating transformation fatigue with quick wins

(25:49) Piloting AI in customer care operations

(29:24) Building data foundations for future innovation

(34:49) Final lessons on modernization and leadership