Perspectives: A hundred-year-old assumption keeps millions out of the workforce
One founder has a goal of changing this.
This weeks’s Perspectives is an interview with Scott Siff, the founder and CEO of Pivoters, an AI-native job-matching platform built for workers 55 and over. He is also the Managing Partner of Quadrant Strategies, a Washington, D.C.-based strategy research and communications firm. His professioanl and personal experiences led him to see the structural forces operating against older workers and inspired Pivoters.
This interview has been edited for length and clarity.
Anna Burgess Yang: Tell me a little bit about your career.
Scott Siff: I founded a company called Quadrant in 2015. We work with some of the biggest companies in the world on their toughest problems, and we do it using data. So, through my job, I’m constantly exposed to the most interesting trends and issues in the corporate world. Earlier in my career, I worked in political strategy, which helped me see what the levers are for making things better.
I will admit I’m a bit of a workaholic. I just kind of like getting stuff done. I like feeling in the morning when I wake up that I have some cool things I get to do. Things that could make a difference. And I like feeling at the end of the day that it was a good day. I’m conscious of how many days we have left, and I want to make sure I’m doing something fun and worthwhile with each one of them.
ABY: What made you decide to do something different with your career?
SS: The initial spark came from my father. He is my hero. He’s been an inspiration my whole life, and he continues to be. He’s showing me how to age gracefully.
When he was in his 70s, he was looking for a new job. He wasn’t one to retire; he’s a workaholic like me. And so he came to me and said, “Could you help me find a new job?”
I thought to myself, I solve problems. I know data. I know how to find solutions — this should be no problem at all. My dad’s one of the smartest, hardest-working, dedicated, amazing people. Who wouldn’t want to hire him?
So I started diving into it, and it turned out the opposite was true. It was impossible. The existing resources that help people get jobs are biased against people 55 and over. And it’s partly institutional. They might not be set out to be biased, but if you look at the stats, the people that use the big job matching sites tend to be in their late 20s, early 30s.
When you show up as somebody 55+, 60+, 70+, you’re going to stand out as a little odd on those sites. And if you combine that with the natural ageism that exists in society, it makes it really tough.
ABY: What did you learn throughout that experience of working with your dad?
SS: I initially started as a son trying to help his father get a job. And then I switched to my Quadrant hat: this is an issue that needs to be solved.
It’s actually a really interesting set of problems. The idea of retirement itself is a new concept. It didn’t exist through human history. The first spark of it came in the late 1800s from Germany, from Otto von Bismarck. He thought this would be a nice giveaway to people in society.
In the beginning of the 20th century, a bunch of big institutional actors in the US picked this up. Companies liked it because it gave them a chance to get rid of older workers and instead hire cheaper, younger workers. Financial companies liked it because the idea of retirement was going to give them billions of dollars to manage. Eventually there was a whole retirement industrial complex: retirement homes, travel, financial management.
The last actor to come on board was the U.S. government. In 1935, it passed the Social Security Act as part of the New Deal. At the time, the average life expectancy was 61. Now, fast forward almost a full century to today. The retirement age is still basically 65. It hasn’t moved. But if you’re 55, your life expectancy has gone from 61 to your mid-80s. People now live decades past retirement. And it set up this huge problem.
Everyone thinks that once you hit 65, you ought to be done. We think 65-year-olds probably don’t have the physical or mental capacity to continue working. All of our conceptions of what people can contribute in those years — all wrong. Part of it is because we have this legacy legal structure. There’s ageism built into the framework with Social Security.
ABY: From your work at Quadrant, how do companies approach the workforce in that age group?
SS: Let me talk about the macroeconomics and why this is such an important problem. The US economy has outperformed most other economies because of population growth. Population growth means more people creating more GDP.
The two drivers of population growth have both ended. Birth rates now in the US are about 1.6 births per woman. The replacement rate (the number of births needed to sustain the population) is 2.1 births per woman. Around the world, economies with low birth rates are really stagnant because of population decline.
The second driver is immigration. Previously, it’s been masking our decline in birth rates. 2025 was one of the few years in US history when we had net negative immigration. That means we don’t have enough people to fill all the jobs. To keep the economy growing, we need more people in the workforce.
So how do we solve this problem? We can’t easily get people to have more babies. Countries have tried to do that, and it’s really hard. And the political winds have changed on immigration. The solution is right in front of us, and it’s workers 55 and older.
I have a goal to change attitudes about people in that age group. Businesses around the country are struggling to fill jobs, despite all the talk about AI, and we’ve got the workers. It’s a giant gap in the labor market.
ABY: What does career pivoting look like for someone in that age group?
SS: It is very hard to pivot. There’s so much working against you. With employers, there’s a strong bias in favor of looking for somebody young, even though they’re working on hundred-year-old assumptions about age. And the second problem is the job boards. Most people in the country rely on job boards to get jobs, but the big job matching platforms cater to people in their late 20s and early 30s.
At the moment, the shorter-term approach is the old-fashioned way: networking. Ask your friends’ friends. Try to get a chance to make your case live. Let them see how healthy and smart and capable and experienced you are. Because if they only see you on paper, they’re going to write you off.
Longer term, I hope that Pivoters and other similarly focused platforms will solve the problem. Once we get them into the workforce, the tide will turn. People don’t want to retire at 65, or most people can’t retire at 65. They don’t have enough money for retirement.
The truth is, people in that age group — 55 and over — actually have longer tenure in jobs than other people. They are also the happiest cohort of anybody else in the workforce. If you want a happier workforce, a more loyal workforce, you want to have more people in that age group. When you have happy employees in the workforce, there’s a ripple effect.
ABY: How do you think about finding the right job and accepting a job in that age bracket?
SS: I would say rush to accept the first thing you’re offered and don’t worry about the fit. This idea of fit is a little bit of a young person’s game, in the sense that young people tend to be looking for careers. They want a job that’s meaningful, that they can grow with, that offers professional development.
People 55 and over — they’re looking for a job, not a career. Most of the benefits that you get from a job come from having a job, not from having a specific job. Most of them will find that most jobs are better than no job.
Don’t pass unless it’s a completely horrible option. Most of the time, it’ll be better than not doing anything.
ABY: You’ve built Pivoters as an AI-driven platform. How do you think about the role of AI and its impact on work?
SS: AI is actually really good in the workplace for people 55 and over. Up until just a few years ago, one of the most important things employers looked for was being tech-savvy. To be tech-savvy five years ago meant you needed to know how to code or use different tools. People 55 and over didn’t know how to do that. With AI today, all you have to do is talk. The technology has become so simple and accessible that the theoretical barrier against people 55 and over disappeared.
For the job-finding process itself, AI is a disaster at the moment. You can get a bot that will scan the Internet and apply to every job out there with a customized resume and letter for you. So where people used to apply to three to ten jobs, now they can apply to thousands. On the other side, employers are getting flooded with applicants. And they’re using AI to sort through them, because there’s just no other way to do it. The system is really creaking and starting to break down. I’m sure it will sort itself out in the next few years, but at the moment it’s making the problems worse.
ABY: Tell me about what makes Pivoters different from traditional job boards.
SS: We reverse the process. You won’t apply to a job — cutting-edge AI technology will go and search different job listings for you and match you. It’s also going to look at things beyond just your resume or work history, such as your strengths, your skills, your work style.
So it’ll make the employee experience better. They don’t have to sort through thousands of job listings. On the employer side, we’ll tee up the very best person in the whole database as your first candidate. Instead of sorting through thousands of applications, you’re going to sort through two to five, because it’s going to be the best ones on the first try.
ABY: If someone reading this is in their 50s or 60s and feeling stuck in their career, what advice would you give?
SS: Jobs provide lots of the important things you need in life to feel happy and useful. You have purpose — a reason to get up in the morning. You have structure — it just gets you out of the house. And the last, which may be the most important, is social interaction. For most of us, your job provides a core part of the people you interact with on a day-to-day basis. If you lose that built-in social interaction, a lot of people get lonely.
The rates of depression for people in that age group who have retired have increased significantly. People who feel a sense of purpose live longer and feel better.
Keep an open mind and don’t rule things out too quickly. The concept of pivoting is really important — don’t assume that your only job option is what you’ve been doing for the last 20 years.
Thinking about a career change? Download my guide: 5 Types of Career Pivots.
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