How Freelancing Is Becoming The New Leadership Path

A rise in the frequency of freelancers has been a constant trend in the last five years. A recent study from 2020 to 2023 showed a 90% growth in the number of freelancers across the US—around 72.1 million Americans.

Besides an increase in the volume of freelancers, freelancing is proving to be a viable, high-earning, and sustainable career path. 4.6 million individuals are making over $100,000 as independent freelancers, up 53% since 2020.

The result is that freelance is becoming normalized in society, with Harvard Business Review noting that “companies are embracing the freelance model more than ever before. Increasingly, the new workforce will consist of an inner circle of employees and outer circles composed of a range of independent workers.”

An important aspect of this normalization is leadership and executive-level individuals choosing freelance career paths over traditional career paths. Historically, freelancers have been highly skilled specialists taking on individual outcomes. The full-time equivalent would be individual contributor work, with clear deliverables – but what about the freelancing equivalent for leadership and management-based work? Take a Director or VP or C-suite Executive: The external equivalent would be consultancies, professional service firms, or agencies, but what about freelancers?

As you’ll learn in this article, executive-level freelancing is quickly gaining steam.

In this article, I’ll introduce you to Riley Kaminer, a full-time freelancer who has chosen his own freelance agency over the normalized promotional path that would lead him to be VP or above in the traditional career path.

Side note: executive freelancing is not new. There is an existing interim management industry. Right now, a fractional movement is quickly growing with 14 fractional-focused talent platforms in Human Cloud’s Freelance Industry Landscape.

As you’ll see with Riley, the defining difference is that executive-level responsibilities are able to be provided for clients while maintaining a freelancer status. Meanwhile, for his own career ladder, he’s able to grow client relationships and progress in a similar way to how individuals start as associates, grow into management, and then earn executive leadership.

Freelancing is fluid, covering the full employee life cycle

The entry to freelancing can be as early as college. For instance, Parker Dewey is a freelance platform for students in the US, along with UniTaskr in the UK.

For Riley, after graduate school at the University of Cambridge, one of his professors offered him project-based work. “That really helped give me a flavor of what it is like to work on a fractional basis,” Riley shared. He didn’t immediately start freelancing full-time. Instead, his freelance project led to a full-time position, but in his words, “I had definitely got bit by the freelance bug at that point!”

This is a crucial point about where work is heading. Rather than singular and binary career paths, individuals are opting for fluidity. They might freelance today, work full-time tomorrow, or combine the two and bounce between freelance full-time and ‘freelance lite’. In Jon Younger’s article “Meet The ‘Freelance Lite’ Employee: They’re The Future”, Younger states, “Freelance lite employees are tuned into the freelance life through their side gig. They keep in touch with other freelancers through the platforms they’ve joined and know from well-publicized survey research that a majority of full-time freelancers are more satisfied, earn as much or more income as they did as employees, and enjoy greater flexibility and work-life balance.”

The implication of workers becoming more fluid is that companies need to rethink employee experience and talent management. Rather than thinking about talent in terms of internal or external, and using success metrics like average tenure, companies need to prioritize the individual and plan for the individual to seek fluidity. The way companies can do this is by understanding that it shouldn’t matter whether an individual is an internal employee or an external freelancer. They’re still building relationships, delivering work, and learning the company culture no differently than full-time employees. In fact, they might be gaining broader perspectives, building more relationships, and learning more about the company as a freelancer. This is rewarding long-term since they can work across the company without typical HR, budget, and headcount restrictions. Thus instead of putting up barriers, companies can benefit from prioritizing freelancers just as much as internal employees.

If done right, companies can increase productivity, loyalty, and overall growth by keeping top talent and working teams by accessing skills as needed. Freelancers want to stay working with clients they like. If companies can embrace a reusable freelance talent pool rather than always hiring net new, it creates immediate productivity and a positive impact for both sides.

In Riley’s case, his work as a freelance journalist started as a student. It ended up creating an on-ramp for when he was ready to start freelancing full-time. Instead of starting from scratch, Riley knew how to freelance (especially with his background in tech and startups). This eventually enabled him to start working directly for tech companies and investors as a full-time freelancer.

Same career ladder, different path: From individual to executive responsibilities

Traditionally, individuals like Riley would have two promotional paths: an individual contributor or a management path.

But freelancing enables Riley a third option, by scaling his impact through his freelance content firm ClearCritical.

ClearCritical explicitly uses freelancers to scale, leveraging a network of over a dozen individual contributors who have deep insights into clients’ specific areas of focus.

As Wethos co-founder Rachel Renock aptly states, “most agencies are three freelancers under a trench coat” – and that’s the case with ClearCritical. This model allows Riley to offer ClearCritical’s clients the flexibility of freelance work combined with the scale and responsibility of executives and agencies. Riley can make a significant impact on his clients and his career, comparable to having a team and budget. As Riley says, “Through this unique, freelancer-focused model, I’m able to make an equal, if not greater impact, than the executive career path while keeping all the advantages of remaining an independent worker.” And the results speak for themselves: ClearCritical has contributed to its clients collectively fundraising upwards of $1 billion over the last five years.

The implication for companies is that individuals like Riley should be on a leadership track, yet most companies get stuck trying to fit freelancers into an internal employee or vendor bucket. As mentioned above, Riley and ClearCritical have the same characteristics as top leaders. They want long-term relationships with their clients. They progress like employees do, increasingly earning more responsibility, and potentially leading teams. But a key difference between freelancers and full-time employees is that they measure success differently. Riley might exceed his promotion equivalent goals in six months, whereas normalized promotional measures prioritize years of experience.

If companies can’t adjust to this rising talent pool, they risk missing out on top future leadership talent.

Building your leadership pipeline from the outside is no longer a bad thing

Individuals like Riley are where the freelance economy is headed for two main reasons.

First, companies need it. They need to reduce their number of freelance options, which means freelance models need to service larger scopes of work, yet the larger scopes get, the more management layers are needed. As Mina Bastawros, VP of Creative and Digital Marketing at Airbus said, “for a corporation like ours, we want an Amazon model where it’s on the same place, same payment methods, same types of conditions, same ways of getting things to my front door”.

Second, individuals like Riley want to execute at the strategic level of responsibility that comes with the promotional paths of Directors, VPs, GMs, and the C-Suite. This breaks many norms of the traditional work system, while also revolutionizing the way companies function.

A small number of companies are doing this right. Microsoft’s freelance leader Nuri Demirci Lopez recently published the book Leading The Unknown: Strategies for Leading Remote or GIG Teams. Unilever launched an Open2U Talent Community. Salesforce uses a Culture in a Box Process that onboards both employees and freelancers together. J&J has a freelancer portal in their Careers Page, along with “Sponsors” who have a supervisory relationship with freelancers. According to Peter Fasolo, chief human resources officer (CHRO) at Johnson & Johnson, having roles that build a bond between freelancers and J&J prioritizes broader professional development.

If done right, embracing the next wave of freelance talent can do more than help your company access the right skills at the right time, it can grow your leadership pipeline as well as your company performance.

Is your company ready to tap into the next wave of leaders like Riley?