Stepful’s $31.5M Investment Focuses on People Over Tech to Transform Healthcare Training

Carl Madi knows the power of transformation. Having spent much of his career with platforms like Uber and Handy, Madi was instrumental in bringing thousands of workers into the gig economy, helping them find jobs as drivers, handymen, and cleaners. But the pandemic reshaped his outlook entirely. Seeing so many people lose their livelihoods overnight, he realized that gig work wasn’t always a stable path to economic security. When he saw the tremendous strain on healthcare, he saw an opportunity to create something more stable and transformative: an accessible, fast-track healthcare training program that could open doors for underserved communities. From this vision, Stepful was born.

Launched in 2021 with co-founders Tressia Hobeika, a former executive at Udacity, and ex-Apple engineer Edoardo Serra, Stepful was designed to address two critical gaps: a booming demand for healthcare workers and a need for viable, affordable pathways for people transitioning into healthcare roles. The program offers an AI-powered curriculum to help train individuals from low-income backgrounds as medical assistants, pharmacy technicians, and other entry-level roles in just four months for a fraction of the cost of trade schools. This approach has already helped Stepful graduate over 1,000 students, 93% of whom are women, 90% are Black or Latinx, and 88% come from low-income backgrounds. For many, Stepful has provided the first step into a stable career with attractive pay and benefits—a stark contrast to the gig economy jobs Madi once championed.

Stepful’s unique training model addresses a well-documented healthcare workforce crisis. The U.S. healthcare system is projected to face a shortage of over 3.2 million workers, including allied health professionals such as medical technicians, assistants, nurses, and mental health practitioners. According to Vig Chandramouli, a partner with Oak HC/FT who led Stepful’s recent $31.5 million Series B funding round, the healthcare system needs a sustainable solution that doesn’t just shuffle professionals around but creates new ones. "Stepful stood out because it’s increasing the supply of healthcare workers by upskilling hourly workers into stable, salaried positions with proper benefits,” he said.

Stepful’s model is both innovative and surprisingly simple. Rather than relying on traditional trade schools or community colleges that can cost up to $20,000 and take years to complete, Stepful’s program costs an average of $2,500 and is completed within four months. The company offers a structured yet flexible curriculum that’s mobile-friendly and designed for adult learners. Students complete bite-sized lessons on their phones at their convenience but also attend a weekly instructor-led class and work in cohorts, creating a supportive, community-based learning environment.