SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Salary: USD 100,000 - 150,000 / annual
Stepful is a workforce platform training healthcare workers for America's largest health systems. Since 2021, they've trained over 32,000 practice-ready healthcare professionals and partner with half of the top 10 US health systems including NY-Presbyterian, Mt. Sinai, HCA, and Providence. Backed by Y Combinator, Reach Capital, and a recent $55M Series C from Oak HC/FT, Stepful was named the #1 EdTech company in the US by TIME in 2025.
As Executive Assistant to the Founders, you'll be the operational backbone of the executive team, reporting directly to the CEO and supporting the Co-Founder. This high-trust, high-autonomy role requires someone who anticipates needs, protects leadership time, and drives operational excellence.
Key responsibilities include: managing complex, competing calendars for the CEO and executive team across time zones; coordinating domestic and international travel end-to-end (flights, hotels, ground transport, itineraries); preparing expense reports and reconciliations; planning and executing leadership offsites, team events, and board meeting logistics; drafting and managing sensitive executive communications; partnering with the Chief of Staff on meeting agendas and action item tracking; serving as a point of contact for internal and external stakeholders; and driving ad hoc projects that improve executive effectiveness.
You'll need 6+ years of executive assistant or administrative experience with direct C-level support, proven ability to manage complex calendars and logistics in fast-moving environments, exceptional organizational skills with meticulous attention to detail, strong written and verbal communication, discretion with confidential information, and fluency with Google Workspace, Slack, and expense/travel platforms. A proactive, resourceful mindset is essential—you thrive amid ambiguity and shifting priorities.
Bonus experience includes EdTech or healthcare background, or prior support of founders/CEOs at high-growth startups. The role is hybrid, requiring three days per week in the NYC office (Tuesday, Wednesday, Thursday).
