We continue our "5 Questions With" series, featuring the impressive list of industry leaders on Sage's 2026 Client Advisory Board.
Next up is Joseph Hessley, Chief Executive Officer at Pines Senior Living.
1. What first got you into the senior care space?
I first became involved in senior care during my junior year of college. I had the opportunity to take the lead on some programs for a large health system. I fell in love with the work that summer and have remained passionate about the industry ever since.
2. What do you see as the biggest challenges in the industry today?
For me, the biggest challenges are labor management, retention of hourly workforce, and remaining innovative to new generations of seniors.
3. What’s the biggest leadership lesson you’ve learned and would want to share?
Whoa. That’s a good one! Over the past thirty years, I’d say there have been several. The biggest senior care leadership lesson I’ve learned is to always be transparent, even when it requires having difficult conversations. Establishing trust—and maintaining it—is invaluable.
4. What do you think the industry needs to do better over the next decade?
I think we can be better about consistently creating exciting and worthwhile programs and activities for our residents.
5. What gives you the most optimism about the future of senior care?
It’s been incredible to see more active seniors choosing to move in earlier. That gives them more opportunities to fully enjoy everything we can offer and live their best lives.
