The New Talent Equation
Freelancers are no longer transactional hires; they are strategic contributors. This session explored how R/GA, Stride, and Hackajob are moving beyond sourcing to create lasting freelance relationships that improve quality, consistency, and speed of delivery. As Jo Libby of R/GA put it, “Freelancers used to be strangers. Now they’re collaborators.”
Freelance Strategy Is Getting Smarter
Organizations are becoming more intentional about how and when they engage independent talent. Stride has implemented a clear leveling framework that designates roles above a certain level as permanent, while roles below are designed to scale with freelancers. This structure enables efficiency, safeguards internal equity, and ensures freelance talent is used where it can have the greatest impact.
“Be fair and equitable. Freelancers notice if they're treated differently,” – Imer Cakiroglu of Stride, highlighting the importance of well-defined role architecture and equitable treatment to avoid talent fragmentation.
Relationships Drive Retention
Attracting quality freelancers is just the beginning. Keeping them engaged and motivated is where top companies differentiate. R/GA invests in community-building before hiring needs arise, hosting design events to connect with talent and establish rapport early. Stride is developing a freelancer loyalty program modeled after luxury retail, rewarding repeated engagements with recognition and perks. Hackajob prioritizes structured offboarding and uses a virtual bench to re-engage top contributors, reinforcing continuity and trust.
“Community events aren’t a luxury. They’re how you build freelance loyalty,” – Jo Libby, Exectuive Director at Talent at R/GA.
Tools and Systems Matter
Supporting freelancers requires more than manual outreach. These companies are investing in systems that mirror the freelancer journey from first interaction to future re-engagement. Worksome is helping teams like R/GA and Hackajob track skills, tag strengths, and automate engagement. Stride uses platforms like Asana and Slack to capture personal preferences, ways of working, and project feedback, making freelancers feel integrated from day one.
“We treat our freelancers like our internal team, and they refer people because of it. Track skills and create feedback loops. Don’t treat freelancers like one-offs.” – Imer Cakiroglu, COO at Stride
Guidance for Talent Leaders
Start by aligning your organization around role clarity. Identify where freelance engagement delivers the most value and design roles that support scalability. Build relationships with top freelancers before you need them. Host events, ask for feedback, and create mechanisms for re-engagement. Invest in tools that support visibility, transparency, and streamlined onboarding.
“Know your audience. Not every freelancer wants the same thing,” – Mark Chaffey, CEO at Hackajob.
Above all, remember that today’s most in-demand freelancers are making choices based on experience, community, and quality of work. The companies that understand this—and act on it—will retain access to top-tier skills without needing to overcommit on headcount.