The Future of Executive Leadership

Portfolio Careers and the Connected Leader

As I look across the couple hundred global c-level tech executives I work with, I see a pattern emerging amidst the dots. In addition to their roles at the company, more and more senior executives are taking on additional responsibilities. These can sometimes be in the form of fractional consulting in the short-term. More often, they are longer-term commitments that stretch across company boards, startup ventures, research councils, think tanks, advisory boards, digital incubators, policy advisories, mentorship programs, or social advocacy. Welcome to the new "portfolio career".

This isn't incidental. There is a fundamental shift underway in career paths that expands work beyond the traditional, single-job role. Instead of being limited to one organization, leaders are seeking to use their expertise across various domains, blending traditional leadership with entrepreneurial and advisory roles. As an example, on this platform in addition to co-founding LinkedIn, Reid Hoffman is an investing partner at Greylock, serves on multiple boards, is a podcast host, and drives philanthropic initiatives — an executive with a portfolio career.

And this shift is driving the rise of the "connected leader" — a leader with broad experience and a strong network, capable of driving innovation both inside and outside their primary roles.

Executive Perspective: Why the Shift?

Why so? The portfolio career model offers greater autonomy, flexibility, and intellectual stimulation. Leaders at the peak of their careers often look for new ways to learn and to apply their skills and knowledge to high-impact projects, governance roles, and advisory work while still contributing significantly to their primary organizations.

Priorities are changing — many executives today are at a point where they can choose to work differently or choose to work only on the things they love to do. These leaders prioritize continuous learning — seeking opportunities that provide flexibility, variety, and greater influence. As a result, traditional career paths are being reimagined into roles that can contribute across multiple domains while balancing professional success with personal fulfillment and societal impact.

There is more. Many are also rethinking career longevity. Instead of staying tied to a single organization or role, they are embracing opportunities that foster partnerships, expand networks, and develop adaptive leadership skills. Behind this, there is a growing realization that portfolio careers embrace a future-focused approach to leadership that can open up even more opportunities. A recent survey of senior executives found that 70% want to expand their influence beyond their primary organization, viewing board memberships and advisory roles as key opportunities for learning and innovation.

Broadening impact is the defining feature of the connected leaders of tomorrow.

Employer Perspective: A Strategic Advantage

But from an employer's perspective, the rise of portfolio careers presents both challenges and opportunities. Some companies worry external commitments dilute focus or create conflicts of interest. Others are fully embracing this change.

For good reason. In a complex global business environment, driven by changing geopolitics, evolving regulations, and rapid technological change, the pace of change now is only the slowest it will ever be. In that dynamic world of tomorrow, executives with broader skillsets and extensive networks can bring in fresh perspectives, expanded networks, and innovative problem-solving skills learnt-elsewhere, into their primary roles. They are seen as the new leaders in building of durable advantage, transformation, and governance in their companies.

What's more, executives who pursue portfolio careers are no longer being viewed as "job-hoppers". Instead, they are seen as dynamic leaders capable of delivering value because of their multiple roles. Executive search firms know this only too well. Studies have found that organizations with leaders who serve on external boards or advisory roles often see higher levels of innovation and improved governance.

Finally, supporting portfolio careers can also make C-suite positions more attractive to top talent. In today’s competitive market, the flexibility to pursue outside interests makes leadership roles more appealing. Executives with portfolio careers consistently report higher levels of engagement and job satisfaction, fueled by continuous learning and exposure to new challenges. Where talent is tight, employers that lean in — win the long arc of talent.

A Broader View: The Future Workforce

Stepping back, the rise of portfolio careers among executives mirrors a larger trend that is easy to see amongst young professionals now entering the workforce. Many college graduates are routinely taking on "side hustles" and freelance work in addition to their primary roles — which provide flexibility and opportunities to develop a wide range of skills. And unlike their predecessors, these early-career professionals see a future of work where they are not limited to a single job. Data already shows that 34% of the workforce by 2025 is expected to be gig workers — highlighting a fundamental shift in how the careers of tomorrow will be structured. All this has significant implications for the workforce of the future — just as senior executives are evolving to connected leaders, early-career professionals are fundamentally redefining the composition of work.

Breaking the Mold: Executive Leadership for the Future

Portfolio careers are not just a new career option for executives — they’re becoming a hallmark of forward-thinking leadership. I see this clearly across my colleagues at the Executive Technology Board I chair. And corporations that embrace it are not only attracting and retaining top talent, they are also building a leadership culture that thrives on flexibility, external influence, broader networks and diverse expertise — and delivers.

Connected leadership will define the future of C-suites.