It’s A New Life: The Rise of Multi-Stage Executives (This Isn’t Your Father’s Career Path)
Why top talent are building portfolios instead of climbing corporate ladders, and what CEOs, founders and CHROs can do next.
Once upon a time, a “career” meant working your way up the old corporate ladder. You started in the mailroom or the analyst pool and hoped, with patience and loyalty and luck, you’d earn the corner office and a parking spot with your name on it. Rung by rung you’d climb as high as you could, or wanted to, take your coffee breaks, your stat holidays, and that was that until gold watch retirement. And while upwardly mobile career paths do still exist, it’s seemingly a model fewer executives actually want. In its place is something a generation ago would hardly be recognized as a thing at all: the multi-stage, non-linear, portfolio career.
By all accounts we are now in the age of work where top talent doesn’t want your ladder. Instead they’re building bridges between roles and new ventures. Or rappelling across a cliff face before putting on a wing suit and launching into the wild blue yonder. This is definitely not your father’s career journey.
Executives today are spreading out, not climbing up as we’ve known it, either by dint of necessity or a desire to do something different. They’re moving in and out of employment, traversing sectors, and taking on fractional roles, trading in the traditional and predictable corporate career for a work lifestyle that prioritizes autonomy and variation, flexibility and meaning.
It’s quite a shift in thinking. And it’s creating upheavals both good and bad for companies everywhere.
Lifetime In A Cubicle vs Lifestyle Over Work
It’s not that today’s executive leaders don’t want stability. They do. It’s more that since they entered the workforce it really hasn’t existed, and they’ve been acclimated to uncertainty. Especially true these last five years since Covid. And with the ever accelerating influence of AI, modern executives see that there’s no one there to help them but themselves. Jobs are harder to find than ever and companies are moving to new ways of doing things. This era requires one to roll with the punches. In so doing, more and more executives are at the same time saying, if it’s going to be this way, it’s going to be on my terms.
According to Deloitte’s 2024 Human Capital Trends report, only 23% of workers now view career progression as a vertical climb. Things have changed so radically that a recent LinkedIn study found that career paths are now 50% more non-linear than they were even two decades ago.
The result is a generation of leaders who’ve had three or four distinct careers by their mid-40s. A former corporate CMO might now run a consulting business, sit on two advisory boards, and work part-time as a fractional executive for a startup. A COO might hang up their corporate cleats to build a SaaS product, write a book, and try their hand at vibe coding apps. Once upon a time this might have been interpreted as a failure to commit, a stalled career. Today, it’s just the way it is; for some it’s a strategy to stay sharp, build breadth, and extract more meaning from a working life that spans decades. For others, it’s a reality born from the fragmenting workplace itself.
Teaching Old Companies New Tricks
Companies stuck in old modalities are struggling to keep pace with the change happening all around. They’re still assessing candidates by resume chronology and tenure length, frowning at the gaps, the short stints, the entrepreneurial attempts. But in this new paradigm, the old ways of judging a candidate just don’t apply. Years of learning across contexts has more value than a 20-year stint in the same role at a single firm. An entrepreneurial gap once seen as a red flag is really a green one, a sign of courage, grit, and commitment you can’t train into someone. These resumes are not formulaic and wise companies are understanding that as the times have changed so have the candidates and the rules by which we evaluate talent.
HR leaders inside of companies who are still preferring “career progression” are missing the proverbial bus. Those on the bus have already started identifying and preferring “career architecture.” Namely, a shift in the questions we ask about candidates, like what projects has this leader built? How have they reinvented themselves? Where have they taken calculated risks? Where do you see the courage to face change and attempts to thrive in chaos? These are the new signals of performance potential.
A recent McKinsey survey of high-performing professionals found that 41% had no interest in full-time roles again. That’s huge. Instead, they prefer project-based, fractional, or advisory work that keeps them in control of time and impact. People don’t want to go back to the way things were. In response to the new and growing reality of remote work and consultative preferences, companies like Meta, Nike, Tesla, and Google are all growing their networks of executive freelancers and interim and fractional leaders, bringing in strategic muscle on a rolling basis, rather than hiring permanent heads.
AI Is Accelerating the Shift
It’s worth spending a bit of time discussing the influence AI is having on the new work landscape. The rise of generative AI has added pure rocket fuel to this workplace revolution. AI is replacing not only repetitive tasks but also parts of strategy, analysis, and execution that used to belong to expensive mid- to senior-level roles. Companies don’t need to hire full-time teams to build plans, they can now combine AI tools with fractional experts who direct. It’s even been suggested that a handful of the right fractional leaders and some AI can now compete with companies multiple times larger by head count. AI is a sea change still surging that will change the world of work more than the Industrial Revolution did over 100 years ago.
Here’s an example of changes to come. A BCG analysis noted that 25% of companies now plan to reduce full-time headcount and replace it with AI-augmented freelance or contract professionals. A marketing team might have an AI prompt engineer, a freelance brand strategist, a fractional CMO, and a few content creators. No hierarchical org chart. Just outcomes.
This all means that CHROs must be ready to supply and retain a network of leaders who think like founders and act like free agents. And CEO’s or founders need to lean on this concept as the new pillar strategy that is one of today’s competitive advantages.
Rethinking How to Recruit, Assess, and Retain
Given the new reality of work and working attitudes, strategic hiring needs to be looked at through fresh eyes. Here are four imperatives for talent leaders tasked with making companies more competitive.
- Look Beyond the Resume
Focus on what candidates built, not just where they worked. A portfolio of outcomes across industries or functions can indicate a sharper strategic mind than a neat by the numbers resume. - Segment Your Talent Stack
Not every role needs a full-time head. Build a blend of full-time, fractional, interim, and contract leaders depending on the lifecycle stage and business objective. This can both save money and inject innovation and energy into the mix. - Cultivate a Bench of Talent
Maintain an active bench of trusted specialists and leaders you can call on as needed. Think of it as your internal agency of record for high-level help. And like any free agent business, get these high-functioning people on your team before your competitors do. - Compensate for Value, Not Time
Talent at the top level increasingly wants project-based or equity-tied compensation. Working for hourly wages doesn’t appeal as much. Be ready to negotiate for impact, not hours. You do want your experts to be motivated by their own performance.
For CHROs, CEOs and founders there are challenges and opportunities at hand. The main takeaway from all of this is a company of the present and future cannot recruit like a company from the past. A good majority of the best talent you need aren’t interested in ladders and incremental raises and retirement parties. They live in a reality where they expect to be paid differently, work differently, and achieve personal and professional goals outside of the four walls of any one company.
The great Nina Simone beautifully summed up many yesterdays ago the way it seems today: It’s a new dawn, it’s a new day, it’s a new life.
Let’s see where it takes us.
