About this episode

Scott Siff discusses the need for new pathways in careers and retirement for experienced talent.

Retirement. You could wing it. Why not design it? Our next group proram starts in September and is limited to 10 people. The Very Early Registration discount (45%) ends on June 21st. Learn more here . _______________________ In our last conversation, Dan Pontefract gave us a demographic wake-up call. The future of work is aging, and longer lives will require new thinking about careers, retirement, and contribution. Today, Scott Siff brings that to the practical level: how do we create better pathways for people who want to keep contributing, but not necessarily in the same way? And what are employers missing when they overlook experienced talent? His story begins with his father’s frustrating search for a new job in his 70s, and builds into a larger conversation about age bias, unretirement, labor shortages, and the need to redesign work for longer lives. __________________________ Bio Scott Siff is the founder and CEO of Pivoters , a job-matching platform focused on helping people 55+ connect with employers seeking experienced talent. His story begins with his father’s frustrating search for a new job in his 70s, and builds into a larger conversation about age bias…

People in this episode

Host: Retirement Wisdom

Guest: Scott Siff

Topics covered

• retirement
• career pivot
• age bias
• unretirement
• labor shortages
• work redesign

Keywords

• retirement
• career pivot
• age bias
• unretirement
• labor shortages
• experienced talent

Mentioned in this episode

Organizations: Pivoters, Quadrant Strategies

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• Grand Expectations & and the Unspoken “But” – Celia Dodd · June 29, 2026 · 29 min
• Design for Optionality: Rethink Retirement – Pam Krueger · June 22, 2026 · 43 min
• The Future of Work is Grey – Dan Pontefract · June 15, 2026 · 32 min

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