Reworking The Future Of Work: Scott Siff Of Pivoters On How Employers and Employees Are Reworking Work Together
An Interview with Karen Mangia
The pace of change is accelerating. With AI advancing every year by leaps and bounds, companies will constantly have to adapt and change to keep up. That means employees will likewise have to adapt to constant change and always be ready to learn a new set of skills in their current role and be prepared to learn a new set of skills as that role inevitably evolves.
When it comes to designing the future of work, one size fits none. Discovering success isn’t about a hybrid model or offering remote work options. Individuals and organizations are looking for more freedom. The freedom to choose the work model that makes the most sense. The freedom to choose their own values. And the freedom to pursue what matters most. We reached out to successful leaders and thought leaders across all industries to glean their insights and predictions about how to create a future that works. As a part of our interview series called “How Employers and Employees are Reworking Work Together,” we had the pleasure of interviewing Scott Siff.
Scott is a Founder and Managing Partner at Quadrant Strategies, the premier strategy research firm that helps companies around the world navigate their most pressing challenges and opportunities. Scott also is the Founder and CEO of Pivoters, an innovative AI-native job-matching platform for people 55+. In that role, Scott is reinventing how people think about workers over 55, and how employers looking for a fresh source of high-performing talent can find and hire the most qualified candidates.
Thank you for making time to visit with us about the topic of our time. Our readers would like to get to know you a bit better. Can you please tell us about one or two life experiences that most shaped who you are today.
The two experiences that I think will be most of interest are ones where I switched jobs. Let me start with the most recent one.
I had been working as a senior executive at an operating company that was part of a global holding company that owned hundreds of companies. Perhaps not surprisingly, I did not feel like I had much control over my own destiny. So after grousing for years about all the ways we would do things differently if we were in charge, a colleague at the same operating company and I basically dared each other to put our money where our mouths were and create our own company.
It’s easy to write that now, but at the time, it was a scary prospect. We both had families, who really needed our incomes to do things like eat and live in a house. We would be going up against multi-billion dollar companies with years of credibility and hundreds of client relationships. Plus I was in my 50s at the time. But after goading each other on long enough, we gamed out how long we could survive on our savings, gave ourselves that amount of time — roughly 9–12 months — and we took the plunge.
It was the greatest decision I ever made. The company took off like a rocket. In just a couple years, we had the top global companies as clients, and we worked on their most important challenges and opportunities — often their existential issues. After more than ten years, it’s still amazing every day.
Maybe even a bigger job-switch for me was earlier in my career. I was a lawyer at the time, working as an environmental prosecutor in the US Justice Department. It was such a great job. But after a while, I decided that it would be fun to see what else was out there. I happened to know the head of a strategy and market research firm, who was quite desperate to find someone in DC, which was what I guess made him willing to consider me.
When I started with them, I thought it’d be a short detour from the law, but it turned out to be an amazing job. The two client accounts I worked on at the time were President Clinton, for whom we were the pollsters and top external strategists, and Microsoft, which we were advising as they went through the antitrust cases against them in the early 2000s. In the years since, I’ve worked on many of the highest profile business issues in the past 25 years, including helping one of the biggest banks navigate the 2008 financial crisis, and the antitrust and other issues facing the top global tech companies in more recent years. Needless to say, my new career turned out to be so fun that I never went back to law.
The common lesson from both experiences, obviously, was that risk-taking in business, despite the sometimes high stakes, can sometimes create the moments of highest reward.
Let’s zoom out. What do you predict will be the same about work, the workforce and the workplace 10–15 years from now? What do you predict will be different?
I hate to be trite, but clearly AI will reshape many areas. I think AI will soon replace many of the entry-level and less senior office jobs. The staff that managers will be overseeing will increasingly be AI. That will create lots of dislocation, but it will create lots of new opportunities. It’s still early to say exactly where that reshaping will stop. At a minimum, I think the org structure of companies will move from their current pyramid structure, where there are fewer people at each level as you move up an org, to more of a column, where the numbers of people at each level will be more equalized. That of course will have big implications for HR, training, employee development, promotions, and compensation.
That process will in turn create a need and a desire for hiring people who are much more experienced in the workforce and can more hit the ground running. That need will dovetail with increasing age and experience of the workforce overall — meaning that you will see many more workers over age 55 than you do today. They’ll be the perfect people for a column org structure. And you’ll see that age-group increasing not just at the top of the column, in executive roles, but more importantly, all up and down the column.
I’ll just interject here that as more people 55+ hit the workplace, we’re going to need a new word to describe them. Today we call them older workers or the silver workforce, words that immediately conjure negative associations. We need a word that better encapsulates their energy and momentum, their savvy and smarts. At my company, we call them Pivoters, a word that we think better captures that spirit.
Now back to what I was talking about. I think that despite all the changes I mentioned, the workplace may well be more similar than different from how it is today. At least for the foreseeable future, the interaction of people with people is still not replaceable by AI. So even though AI will replace a lot of the development of workproduct, it will be slower to replace the delivery and brainstorming on the implications of that work product. That process may well look and feel fairly similar, even in ten years, to what it is today.
What advice would you offer to employers who want to future-proof their organizations?
The biggest point about future-proofing, I think, is that future-proofing is no longer possible. The world is moving too fast, and the pace of that change is increasing too quickly, for companies to get to a point where they can sit back and say, ok, we implemented that big set of changes, so we should be good for a few years and we can just focus now on operations and marketing. Constant change will be the mandate throughout every aspect of a company, from HR to sales to operations to strategy — not just technology. So my biggest advice on this is to give up the whole notion of future-proofing, and instead to wake up every morning asking what changes — and I mean major changes — should we be making — and in tandem with that, how are we going to reshape and restructure the organization’s workforce to implement those changes. Don’t assume the org structure and staff you have today will last you very long, and don’t let the momentum of the current org structure be a barrier to making the changes you need to make.
What do you predict will be the biggest gaps between what employers are willing to offer and what employees expect as we move forward? And what strategies would you offer about how to reconcile those gaps?
As organizations and employers increasingly adopt constant change as their fundamental operating principle, employees will have to do the same. That will mean a constant readiness and willingness for employees to learn not just new skills, but whole new systems and ways of doing things. That will come with a need for employees to be more understanding of the needs the organization is facing, and patient in the face of constant change. Employers in turn will have to offer really robust training opportunities for existing employees as the organization changes, because it’s almost always the case that it’s easier to train an existing employee for a new role than to hire a new one, but at the same time, employers will no longer have the freedom to coax people along or, to be blunt, to deal with employees who are more prickly. The employers will just have to change them out. You will thus see a greater emphasis on finding and retaining workers who are willing to dig in for the organization, be flexible, and stay longer.
As it turns out, people 55+, our Pivoters, meet those needs particularly well. They tend to stay in jobs longer; they’re more loyal to the organizations where they work, in large part because they understand that the goal of doing a job is advancing the organization where they work and not personal fulfillment; and they’re actually more collegial workers. All of that will be increasingly important.
A few years ago, we simultaneously joined a global experiment together during COVID called “Working From Home.” How will this experience influence the future of work?
I think we are still stabilizing the balance between in-office vs. remote work following covid. The covid era identified certain areas where remote work can be effective and even advantageous. But in many circumstances, we are still working remotely when in-office is clearly better. I have found in my own businesses that in-office has many advantages. Younger employees learn the mores of a work environment much more quickly when they are in-office. They also benefit immensely from being around people more senior. New employees get up to speed, in our experience, as much as 3 times more quickly when they are in-office and working alongside colleagues, mentors, and supervisors, vs. remote.
Culture is also much stronger in an in-office environment. When people are remote, even part of the time, interactions with colleagues and clients tend to be much more transactional. That hits company culture, the sense of shared mission, the enjoyable aspects of being in person with colleagues, and the effectiveness of teamwork. Video conferencing simply does not come close to replicating the connections, the joint team creativity, and problem-solving and mentoring that are present when people are together in person. I think we still have a ways to go to find the right balance.
What societal changes do you foresee as necessary to support a future of work that works for everyone?
I believe that the biggest change coming will be the increasing reliance, to the benefit of companies and of society more broadly, on workers over 55. The American economy has been powered for years by population growth, which sets us apart from countries with more stagnant economies, like Japan and much of Europe. But the two main forces that have driven our population growth, namely immigration and birth rates, are both screeching to a halt. Immigration is ending by bipartisan consensus, even if there is disagreement about the specific methods. And our birthrates now look more like Europe’s than they do like the United States of even a generation ago. In a country like ours, which tends to operate at pretty close to full employment, that means we need to worry about our continued economic growth.
At the same time, we have 110 million people over the age of 55. 74% of them want to work, but only around 40% of them do work. In part that’s because the average age of job-seekers on the main jobs boards is around 28 years old. That means we have a pool of almost 40 million people ready and eager to work. And they want to work — for economic reasons, health reasons, happiness reasons, and longevity reasons.
On top of that, as mentioned, workers over 55 are better employees in nearly every dimension. So I think the workforce will look dramatically different over the next few years as these workers over 55, the Pivoters, make up an increasing share of the workforce.
What is your greatest source of optimism about the future of work?
I think change is exciting and invigorating, and I think work is changing faster now than it ever has. Probably each decade of the 20th century, you could have made the argument that that was the fastest rate of change in history, and yet that rate of change seems only to be increasing through today. If you’re not crazy about your job, get ready to get a new one. And if you love your job, it’s likely to get even better. You just have to be ready to change as quickly as the world of work changes.
What innovative strategies do you see employers offering to help improve and optimize their employee’s mental health and wellbeing?
I think the main thing that employers will have to offer employees is help adapting to new roles and new workstyles. As the pace of change accelerates, workers will have to be constantly changing. At the same time, because so many jobs will be quite different from what they were just a few years before, or even completely new jobs, workplaces will bear more of the burden of getting people ready for these new jobs, and also helping them work through those changes. Employers have to realize that as much as change is increasingly an imperative, it still will take additional support to help employees make those changes, both to learn the new skills, but also simply to adapt on a more human level. At the same time, I think having constant opportunities for professional development will help people feel more challenged at work, and that should bring a new level of mental engagement of the kind that I think and hope people will really thrive on.
For a while it seemed like there was a new headline every day. ‘The Great Resignation’. ‘The Great Reconfiguration’. And now the ‘Great Reevaluation’. What are the most important messages leaders need to hear from these headlines? How do company cultures need to evolve?
To me, what’s interesting about the list of social phenomena you mention is not any one of them individually, but that we’ve had so many of them in just the last few years. Just as the pace of technology change is happening more quickly, the pace of social change is also happening more quickly. Think how much and how many times the workplace culture has changed since 2020. To me, that pace of social change further highlights why Pivoters will be even more prized than ever. Pivoters have been through numerous changes in their lives, and they know how to navigate them, by rolling with the changes as they adapt and learn — in contrast to many younger people, who often are much more thrown off balance by changes or swing sharply as a result of those changes.. Pivoters are much more understanding of workplaces that have to make changes. It’s why their job satisfaction numbers are much higher than younger groups. They know that employers don’t change for the sake of change; they change because they need to in order to stay current and stay competitive. Pivoters are more likely to be in it with their employer in times of change.
Let’s get more specific. What are your “Top 5 Trends To Track In the Future of Work?”
A couple of these I’ve already touched on, but this will provide a nice summary.
- The pace of change is accelerating. With AI advancing every year by leaps and bounds, companies will constantly have to adapt and change to keep up. That means employees will likewise have to adapt to constant change and always be ready to learn a new set of skills in their current role and be prepared to learn a new set of skills as that role inevitably evolves.
- The labor supply is tightening quickly. With the dramatic declines in immigration and birthrates, the existing pool of labor will no longer keep up with economic growth. That means it will be harder to find people to do many jobs. To keep up, companies will have to find new pools of talent.
- Loyalty and adaptability will be increasingly valued as employee traits. As businesses are forced to change more quickly to keep up, employees will have to change more to keep up, and they will have to be more loyal to their employers in order to remain on board through those changes. Evolving employees in that way is resource intensive, so employers will want to know that they are putting that change effort into employees who are likely to make it through the change and remain on-board long enough afterward to pay back the organization’s investment. As a result, the related employee traits of savvy, calm, and collegiality will likewise be increasingly important.
- The Pivoters are coming. Because the labor supply is dwindling and because employers are actively seeking loyal and adaptable workers, the number of Pivoters in the workforce will continue growing quickly. 55+ workers are a very large and underutilized pool of employees who more strongly embody the traits that employers will need in the near future. So their numbers will increase in the workplace not just because employers need a new pool of workers, but because Pivoters overindex on the qualities that employers will increasingly value.
- Remote work will continue to fade. Though some jobs can be done as well remotely as in-person, most cannot. As the pace of change at many workplaces accelerates, even an incremental advantage in onboarding and training that comes from in-person work will be increasingly important, and employers will be less able and less willing to accept remote work in those circumstances.
With AI and automation reshaping industries, what role do reskilling and upskilling play in preparing employees for the future? What can companies do to help their workers transition into new roles created by AI?
I think I jumped the gun on this one and answered much of it in prior answers. As mentioned, reskilling will become increasingly important, driven both by the promise of efficiency improvements, but also by the necessity of keeping up with the competition. It will certainly be in employers’ interest to implement ever more robust transition programs to keep their employees changing along with the organization and its technology, because reskilling is generally cheaper than new hiring, especially when many of the new jobs will be so new that there won’t be many already-trained prospective employees anyway. At the same time, employers will likely have less flexibility to be patient with employees who are either not very agile in adapting to new skills, or not loyal enough to push through the process of reskilling. So the imperative for reskilling will definitely be a two-way street, and at its best, the basis for a deeper partnership between employers and employees.
As AI takes on more administrative or operational tasks, what will the role of managers look like in the future? How can leadership evolve to focus more on innovation, emotional intelligence, and strategic vision?
In office settings, frontline employees will soon have new reports, in the form of AI. That means even frontline jobs will increasingly need to be able to juggle different tasks calmly. Leadership and HR will thus have to put an ever higher premium on those traits in the hiring process, and will look for groups of people that exhibit them. Not to be a broken record, but this is further reason that Pivoters will be ever more valued. Those are some of the traits that they will most prominently exhibit in comparison to their younger peers, because of having lived through more change and having learned to be calmer in a changing environment.
The Pivoters platform is itself a good example of this, especially if we look at it from the perspective of the employer or an HR professional. Some studies say that recruiters at companies review on average 250 resumes per hire. That’s partly because they have too little or not the right information on people; partly because the major job boards surface a firehose of mismatched candidates; and partly because a large number of candidates are not really interested in a job, not real people, or somehow fraudulent. Pivoters, as an AI native platform, addresses all those issues. We use AI to get the right kinds of information on each person, as well as on the job itself that an employer is listing. We match the right person to the right job using AI, so that employers should be reviewing just a handful of highly targeted candidates instead of hundreds. And because we require that employees pay a small fee to talk to the employer, it means the candidates are real people, verified by their payment, who have a real interest in the job. It’s a great example of AI at its best, taking much of the administrative drudgery out of hiring, and leaving humans to do work that makes the best use of their judgment and skills.
With AI streamlining many processes, do you think employees will have more freedom and flexibility to achieve a better work-life balance? How can companies leverage AI to support employee well-being in new ways?
To be honest, I’m not sure. On the one hand, AI will make people much more productive, and in theory that might provide the possibility of more free time, more flexibility, and better work-life balance. But on the other hand, nearly all organizations will have AI and so everyone will be more productive — which means that to remain competitive, employers will continue to have to get all they can out of employees. The last generation of technology already significantly broke down the divide between work life and personal life. I think it could well be the case that that trend continues.
I keep quotes on my desk and on scraps of paper to stay inspired. What’s your favorite “Life Lesson Quote”? And how has this quote shaped your perspective?
My parents used to have a refrigerator magnet that said, Luck is where preparation meets opportunity. I feel like that’s still a pretty good formula for success in almost every work situation.
We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He, she, or they might just see this if we tag them.
Yes, I would say I’d love to talk to anyone who is filling jobs that they feel like their company is spending too much time on, only to settle for people who could be better. One person I’d love to talk to in particular is Deirdre O’Brien, Apple’s leader of retail and online teams. I know Apple is always at the forefront of age diversity, and I think we’d have a great conversation. I’d love to hear her thoughts, and I think I might have some ideas that could be of some help to Apple as well. As our platform is dual-sided, I’ll take this opportunity to also list someone on more of the employee side. I would love to chat with Mel Robbins. She’s all about changing behavior, shifting your mindset and improving your life — things that we at Pivoters strive to do for the over 55 job seeker.
Our readers often like to continue the conversation with our featured interviewees. How can they best connect with you and stay current on what you’re discovering?
For sure. Whether you’re looking to hire people, or you’re a Pivoter looking to be hired (or the friends or family of a Pivoter), visit www.pivoters.com and you can sign up to receive updates or to reach out. We’ll be live this Fall, 2025.
Thank you for sharing your insights and predictions. We appreciate the gift of your time and wish you continued success and good health.
Reworking The Future Of Work: Scott Siff Of Pivoters On How Employers and Employees Are Reworking… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.