EIF Catalyst Request for Startups Series: Contract Worker Benefits & Upskilling

73 million Americans now work as independent contractors or freelancers—but fewer than 10% have access to portable benefits like health insurance or retirement plans.

The workforce is fragmenting. Contract, gig, and freelance work now represents a growing share of employment in healthcare, education, logistics, and professional services. For many workers, this flexibility is a feature, not a bug—the ability to control schedules, choose projects, and work for multiple clients. But the benefits infrastructure of the American economy remains stubbornly tied to traditional W-2 employment.

The gap is stark. Traditional employees receive benefits packages worth 1.25-1.4x their base salary. Contract workers navigate patchwork solutions—expensive individual market health insurance, no employer retirement match, no paid leave—or go without entirely. The policy environment is finally catching up: Senate portable benefits legislation was introduced in July 2025, and multiple states are advancing bills enabling voluntary portable benefits accounts for gig workers. But policy alone isn't enough—the infrastructure to deliver portable benefits at scale doesn't exist yet.

We're looking for startups building benefits and upskilling infrastructure for the contract workforce. Portable benefits platforms for health, retirement, and leave that move with workers across jobs and employers—benefits that don't disappear when a contract ends. Financial wellness tools reducing reliance on payday loans and providing income smoothing for workers with variable earnings. Skills credentialing that translates project-based work experience into stackable credentials with labor market value. Employer-sponsored upskilling marketplaces offering micro-learning, certifications, and degree pathways funded by platform fees or employer contributions. Career navigation for contract workers showing the wage premiums and opportunities available by investing in specific skills—including pathways from gig work to full-time roles when that's what workers want. Collective platforms enabling contract workers to negotiate for better rates, benefits, and working conditions.

This is an emerging area where we're building our thesis. We understand the policy landscape around portable benefits and the regulatory complexity of benefits administration. We're looking to back founders who can help us learn faster about what's actually working in this space.

Applications for EIF Catalyst's next cohort are open. If you've got early traction and are ready to build a repeatable go-to-market motion, we should talk.

We're looking for U.S.-based founders focused on postsecondary and career outcomes, with in-market traction (often $100K–$1M ARR, with flexibility for sectors with longer sales cycles), and a founder-led sales motion ready to scale.

Working on something outside these RFS themes? Apply anyway—these prompts are meant to spark ideas, not limit them. Know a founder who should apply? Send them the link.