2026 Annual Report COO and CAO
Strengthening Engagement
![]() Derrick Stewart |
![]() Gordon Bailey |

Derrick Stewart
Executive Vice President and Chief Operating Officer

Gordon Bailey
Chief Administrative Officer
Participant Engagement and Experience
While growth in plan participants and their contributions can be positive indicators (refer to our Financial Data and Participant Statistics on page 12 of the full Annual Report), it is important to realize that every interaction with Y staff is an opportunity to strengthen understanding, trust, and appreciation of the Y Retirement benefit. In FY 2026, participant feedback, digital enhancements, customer service performance, and employee engagement all demonstrated meaningful progress. Together, these results highlight the positive impact of our efforts to strengthen our ongoing partnerships with Y leaders and staff, improve their experience, and support the people who serve their communities every day.
Website Transformation: An Improved Digital Experience for Y Staff
In FY 2026, Y Retirement launched a completely redesigned public-facing website which represented the culmination of the brand transformation work that began in FY 2024. The new website not only looks more like Y Retirement and the people we serve, but the information is written in a way that reflects our brand voice and makes it easier for Y staff, plan participants, YMCA leadership, retirees, and more to find what they’re looking for. The new website will also allow us to scale our digital presence to better meet their needs in the future.
Customer Service and Artificial Intelligence: Achieving Balance
Strong customer service and operational performance were cornerstones of Y Retirement’s success in FY 2026. Most notably, the intersection of human interactions and artificial intelligence (A.I.) delivered results that exceeded expectations by handling a record number of inbound contacts while still outperforming industry benchmarks in key areas. Penny, our website virtual assistant, launched in May 2025 and more participants have started leveraging this resource to answer general questions around login assistance, locating forms, and more because it’s available 24/7. This increased use of Penny allowed our Pension Representatives to deliver an authentic and personal experience to those Y staff whose questions needed additional care either via Live Chats or calls to the Contact Center.
Creating a Great Workplace
At Y Retirement, we believe our people are one of our greatest assets, and by fostering a workplace where employees feel valued, heard, and empowered, we strengthen our ability to serve our mission and the Y Movement. That is why we are so pleased to once again be a Top Workplaces award winner for 2026! This recognition is especially significant because it is based entirely on employee feedback, and it celebrates organizations that prioritize the employee experience and create cultures where people can thrive. This award reflects the collective efforts of our team and the culture we continue to build together — one defined by purpose, collaboration, trust, and growth.