Freelance CEOs Talk AI And The Future Of Talent Matching

The very core of the freelance revolution is a match between a skilled independent professional (freelancer) and a client organization. Clients seek freelancers who bring what they believe is the best mix of expertise, experience, availability and cost. Freelancers also have priorities. They are eager for interesting, well-paid, work that is, for which they have the right skillset, the timing is right, and for clients who understand and appreciate the role and contribution of freelancers and how to work effectively with them.

These days freelancers have become a significant global workforce. AI has exploded on the scene providing new capabilities. Clients are increasingly interested in sourcing complete teams – as platforms like A.team, Innovify, and Catalant have noted – in addition to highly skilled individual professionals. As such, the way that marketplaces match or “curate” is undergoing a significant upgrade. It made sense to ask freelance leaders of major platforms around the world how they see the matching process improving.

Here’s what freelance leaders from the US, UK, Brazil, Germany, France, Denmark, Spain, Argentina, and India had to say when asked about the next 3-5 years:

Runar Reistrup, CEO YunoJuno.com “At YunoJuno we are disrupting ourselves with AI as I am certain that AI will again revolutionize how freelance talent connects with clients. We are enhancing the platform to base matchmaking on advanced, unbiased, algorithms that not only match skills but also consider diversity, work preferences, personality, and past project success. This ensures more accurate pairings, reduces mismatches, and leads to better project outcomes for talent and client. Looking ahead, I expect we’ll have built predictive matching that anticipates the needs of clients based on deep integrations with internal systems.”

Michael Solomon, co-CEO 10X Management.com “Looking five years down the road right now is unthinkable. The development and adoption of new technologies is accelerating. Two years ago, we couldn’t have anticipated the impact AI had in a short time. Within two years 75% of knowledge workers have begun using AI and 86% of students report using AI. That’s bonkers. We think AI can take over the matching process when it is better than humans. We get the match right 95% of the time with our first pick for clients. When AI is able to effectively take all the subtle variables into consideration as well as humans do and beat our success rate, it can and will have our jobs.”

Sean Middleton, CEO Sentinelguild.net “We see a shift toward evaluating skills based on real-world outcomes and continuous learning. Rapid technological change, especially in security, necessitates this. We’re already leveraging AI and data analytics to match independent cybersecurity professionals with projects that align with their expertise and their interests and career goals. This approach leads to better outcomes for clients and more fulfilling work for talent. The future of talent curation will be more personalized, precise, and responsive to evolving industry needs.”

Pat Petitti, CEO Catalant.com “While this depends much on the type of work the freelancer does, in the world of independent business consulting curation is essential. We partner closely with top consultants in our network, expert who were partners at McKinsey or C-level functional leaders or business general managers at Fortune 500. Their expertise and deep experience allows us to connect them with clients not just for an identified project, but also to share insights or best practices that help leaders identify new ways to achieve their top priorities. This is the future for high-end freelancers – partnering closely with a platform like Catalant to jointly work closely with clients in all facets of the relationship.”

Cem Ciftgul, Proteams.com “Talent profiling and curation will likely become more data-driven and personalized in the next 3-5 years. AI will enable smarter matching, combining freelancer skills, experiences, and client references, and considering soft skills and cultural fit by looking into profile background information. Predictive analytics will provide estimations about candidate availability and rates. New technologies enable a more dynamic and tailored approach to aligning freelance talent with client needs, resulting in higher project success rates and satisfaction.”

Omer Güven, CEO Fintalent.com “I think we’re seeing a big shift towards smarter, AI-driven matching – especially for niche fields like M&A. Our platform is already moving in this direction, not just focusing on skills but also personality fit and past project experiences. This means freelancers and clients will find each other more easily, leading to better, longer-lasting collaborations. Also, more freelancers are teaming up for bigger projects, which is an exciting way to bring more expertise to the table.”

Alvaro Oliveira, Chief Talent Officer Andela.com “AI will drive significant advancements in profiling and curating freelance talent. It helps us gather and integrate the data on freelancers’ work styles and preferences and achieve higher-quality matches. For example, if you are a freelancer that easily integrates into existing teams, that’s valuable information when projects require high speed outcomes. This deeper, context-rich understanding will revolutionize the matching process by considering the nuanced needs of both parties.”

Jaime Castillo, Chief Growth Officer and co-Founder, Shakersworks.com “The future of curating freelance talent will be driven by artificial intelligence and real-time data. Algorithms will become increasingly accurate in identifying emerging skills and predicting compatibility based on values and work styles, not just technical competencies. Additionally, we’ll see more specialized and collaborative platforms where personalization is key to matching freelancers with the right projects. Talent selection will be more agile, adaptive, and predictive, focusing on long-term and successful relationships for both parties.”

Chandrika Pasricha, CEO FlexingIt.com “With the widespread adoption of AI tools, the role of platforms becomes even more important ensuring we match the right skills and qualifications to projects. Some innovations we expect include more fine-grained micro-talent curation around very specific areas of expertise and custom talent pooling around key capabilities. All platforms that use AI tools to make the process more efficient will benefit. But platforms that also integrate proprietary insights like prior feedback and client demand patterns will outperform.”

Ramiro Gonzalez Forcada, CEO TheFlock.com “Like others, we see a significant transformation in profiling and curating freelance talent. AI will enable us to create dynamic profiles that combine technical skills but also other qualities. However, the rapid evolution and adoption of new technologies isn’t free. Change causes disruption. For example, the half-life of certain tech skills has dropped to just 2.5 years. AI will accelerate that trend, with obvious impacts on organizations and freelancers.”

Karina Rehavia, CEO Ollo.is “I foresee a blend of AI-driven advancements and human expertise reshaping how we profile and curate freelance talent. While AI and machine learning will enhance the precision of matching based on skills and experiences, human intuition, understanding nuances, and assessing cultural fit will remain vital. The future will need platforms that combine these elements.”

Marc Clemens, CEO 9am.works “Historically, matching clients with perfect freelance talent required a significant manual effort. The combination of incomplete profile data, poorly written job ads, and misaligned keywords forced human intervention. By automating profiles, suggesting better keywords, guiding job ads, AI frees us to spend more time focusing on soft-skill factors using interviews, case studies, and tests to supplement decision making.”

Vincent Huguet, CEO Malt.com “We see three elements that will drive the future of matching: The first is AI powered staffing. These are AI tools that help hiring managers better define skill and budget requirements while also automating the search process – essentially a digital recruitment consultant. Next is the role AI plays in talent matching. Third, lets remember that the human element is essential. Freelance platforms that nurture their communities and provide human support will retain a talent edge, regardless of the technology available.”