Seven months pregnant in 2018, Wei Deng rode Uber cars between healthcare facilities, attempting to meet administrative schedulers in person after making hundreds of cold calls a day that ended in immediate hangups. Deng had founded Clipboard Health with an initial mission to help individuals move up the socioeconomic ladder, according to Y Combinator's company profile. Achieving that goal proved far from straightforward: the business underwent six to eight different pivots before landing on its core operational model.
The Search for a Sustainable Model
Initially, Deng focused on alternative financing, introducing income-share agreements to help students cover education costs without traditional bank loans. She pitched the concept first to software engineers, then pivoted to lawyers, and later to medical doctors, finding little commercial traction with each group. The trajectory began to shift when she introduced the agreements to nursing students. In conversations with them, Deng discovered that their primary anxiety was not tuition financing, but securing stable employment post-graduation.
Flipping the Scheduling Paradigm
To address that employment gap, Deng shifted her strategy toward helping nurses build resumes and secure job placements, eventually launching a digital job board dedicated to nursing. However, analyzing the postings revealed an operational flaw in traditional staffing practices. Only staffing agencies posted listings on the board, and after hiring nurses full-time, these agencies assigned them unpredictable monthly schedules—giving a nurse one roster for February and an entirely different schedule for March.
Deng realized that forcing workers into constantly fluctuating monthly commitments created friction for nurses and facilities alike. In 2018, well before the COVID-19 pandemic altered workplace dynamics, Deng began calling healthcare facilities directly. She proposed a different model: rather than requiring a single nurse to commit to an entire monthly block, Clipboard could supply multiple flexible nurses to fill individual open shifts. Facility administrators repeatedly confirmed that severe staffing shortages made single-shift coverage immensely valuable.
The Breakthrough in Walnut Creek
Despite facility demand, existing staffing agencies rejected Deng’s proposed software, preferring pen-and-paper scheduling. Because front-desk receptionists routinely hung up on her phone calls assuming she was seeking a job, Deng took to field visits. Travelling by Uber while seven months pregnant, she knocked on doors directly to reach facility decision-makers.
Her persistence paid off at a facility in Walnut Creek. A site scheduler agreed to test the platform on a trial basis, asking Deng to fill two open weekend shifts. Deng successfully placed nurses in both slots. Impressed by the execution, the Walnut Creek facility signed on as Clipboard Health’s first permanent facility customer, proving that matching independent workers directly to individual shift vacancies was viable.
Iterative Practice and Scaling
Navigating investor pitching presented another hurdle. Deng received sixty rejections from venture capital investors during fundraising efforts. Rather than abandoning the concept, she framed each rejection as iterative practice to refine her presentation and uncover deeper customer requirements. That responsiveness showed up when users began offering intense feedback, expressing strong emotions about feature adjustments and schedule access.
By replacing rigid monthly placements with shift-level marketplace matching, Clipboard Health solved an acute labor constraint for both healthcare workers and providers. The company eventually expanded to work with approximately 5,000 healthcare facilities and reached a valuation exceeding $1.3 billion. Today, Deng applies this shift-matching structure to new healthcare categories like dental and anesthesiology services while developing tools designed to anticipate evolving labor market demands.
AI-generated editorial illustration; not a documentary photograph.
Source: Pivoting to a billion-dollar idea: Lessons from Clipboard Health founder Wei Deng
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