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.

Stepful’s platform integrates AI to offer personalized learning experiences, ensuring that students remain engaged. The AI system tracks student progress and sends customized reminders to those who may be falling behind, with human coaches stepping in when necessary. “Our approach combines the flexibility of asynchronous learning with the structure of in-person engagement,” Madi said. “It’s a much more engaging way of learning.” This model has resonated strongly, with a 75% graduation rate and a rapidly expanding student base; Stepful expects to enroll around 30,000 students in 2024.

Stepful’s primary value lies in its ability to train students quickly and affordably, making it a competitive alternative to traditional community colleges and trade schools. The use of AI technology for personalized education, combined with real-world clinical partnerships, sets Stepful apart from competitors. By shortening the training period to four months and keeping costs low, the platform appeals to a wide audience, especially those looking for rapid upskilling without incurring massive debt.

Upon completing their online coursework, students are placed in hands-on externships through Stepful’s network of over 8,000 partner clinics and hospitals across the U.S. During one to two months of practical training, students gain essential on-the-job experience, and healthcare providers can observe potential hires in action. “Employers are eager to host and train our students,” Madi explained. “They see this as an opportunity to find skilled workers they can hire directly.” This hands-on component has contributed to Stepful’s impressive job placement rate—over 80% of graduates land positions within two months of completing the program.

Beyond individual students, Stepful’s reach is amplified by partnerships with healthcare systems eager to address staffing shortages through sustainable workforce development. Stepful’s offerings include upskilling programs for existing employees, apprenticeships for new candidates without healthcare experience, and externships to build talent pipelines. This multi-faceted approach makes Stepful a versatile partner, capable of filling immediate staffing needs and creating long-term career pathways for underserved communities.

The recent $31.5 million Series B round, led by Oak HC/FT with participation from Y Combinator, Reach Capital, and AlleyCorp, among others, will enable Stepful to expand its offerings and invest further in its AI-driven support system. This investment follows a $12 million Series A round just nine months earlier, a testament to the confidence investors have in Stepful’s scalable solution to the healthcare workforce crisis. Oak HC/FT’s Chandramouli believes Stepful’s use of generative AI is a crucial differentiator, allowing the company to function more like a tech company, keeping operational costs lower and supporting large student volumes without relying on high human involvement.

Stepful’s impact is not just financial but deeply personal, as it creates pathways to prosperity for individuals who have been historically underserved. “At Stepful, we’re not just investing in technology; we’re investing in people,” Madi said. “Our mission goes beyond training; it’s about creating opportunities for individuals and communities.” With each graduating class, Stepful not only addresses an urgent healthcare staffing need but uplifts individuals who gain stable careers and increase their income by an average of 25%.

This mission-driven approach has attracted impressive additions to Stepful’s Board of Directors. Wanda Cole-Frieman, Senior VP of Talent Acquisition at CommonSpirit Health, and Tanya Beja, Managing Partner at AlleyCorp Impact, have joined the board, bringing decades of experience in healthcare and workforce development. Allison Baum Gates from Sempervirens Ventures has also joined as a board observer, adding further expertise in workforce and healthcare innovation. Together, these leaders will guide Stepful as it expands its reach and continues its work to diversify the healthcare workforce.