Executive Assistant to the Founders

About Stepful

Stepful is a dynamic workforce platform revolutionizing how major health systems in the U.S. attract, train, and retain their workforce. Since its inception in 2021, Stepful has successfully trained over 32,000 healthcare professionals ready to practice. By collaborating with prominent healthcare institutions, Stepful addresses the nationwide shortage of healthcare workers while expanding quality healthcare career pathways for underserved populations. Our students serve as the key talent pipeline for leading employers such as NY-Presbyterian, Mt. Sinai, HCA, Providence, CVS, and Walgreens. Currently, we partner with half of the top 10 health systems in the country, with many more in progress.

Backed by notable investors including Y Combinator and Oak HC/FT, Stepful was honored as the #1 EdTech company in the U.S. by TIME for 2025.

Our Core Values

• Care First: Committed to doing whatever it takes to support our students.
• Learn Quickly: Embrace data-driven testing and iterative learning.
• Build Together: Success through collaboration and mutual reliance.
• Own It: Demonstrate initiative, accountability, and pride in our work.

Role Overview

We are seeking a seasoned Senior Executive Assistant to provide crucial support to our executive leaders during this exciting growth phase. This high-responsibility position requires proactive management of multiple priorities, shielding leadership’s time, and ensuring smooth operations. Reporting directly to the CEO and assisting the Co-Founder, you will work closely with the broader leadership team, including Chief of Staff and People & Operations. This hybrid role is based in New York City, requiring onsite presence three days per week (Tuesday through Thursday).

Key Responsibilities

• Manage intricate and evolving calendars for the CEO and executive team, balancing competing demands to prioritize effectively.
• Coordinate a high volume of meetings across multiple time zones with internal stakeholders, external partners, board members, and candidates.
• Oversee end-to-end travel arrangements domestically and internationally, arranging flights, accommodations, ground transport, and detailed itineraries.
• Accurately prepare and promptly submit expense reports and reimbursements.
• Organize and execute leadership retreats, team events, and board meetings, managing logistics from initial planning to day-of facilitation.
• Draft, edit, and handle confidential communications and documents on behalf of executives with utmost discretion.
• Collaborate with the Chief of Staff to set meeting agendas, monitor action items, and ensure timely follow-up on leadership decisions.
• Serve as a professional, welcoming liaison for internal teams and external partners interfacing with executive offices.
• Lead special projects and recommend process improvements to enhance executive team effectiveness.

Qualifications

• Minimum of 6 years' experience as an executive assistant or in a comparable administrative role supporting C-level leaders.
• Demonstrated expertise in handling complex scheduling, travel, and logistical arrangements in a fast-paced setting.
• Exceptional organizational abilities with a sharp attention to detail, ensuring nothing is overlooked.
• Excellent written and verbal communication, with strong judgment regarding tone and audience sensitivity.
• Proven discretion and integrity managing confidential or sensitive matters.
• Proactive, resourceful problem-solving approach, comfortable working independently amid ambiguity and shifting priorities.
• Proficient with contemporary productivity platforms such as Google Workspace, Slack, and expense/travel management software.

Preferred Experience

• Background in educational technology, healthcare, or mission-driven sectors is advantageous.
• Previous support experience for founders or CEOs in high-growth startups is a plus.

Hiring Process

• Initial screening call with Talent Acquisition team.
• Interview with hiring manager.
• Completion of a take-home assignment.
• Virtual panel interview.
• On-site panel interview.

Compensation and Benefits

• Competitive base salary range: $100,000 to $150,000 annually, subject to individual factors such as experience and internal equity.
• Meaningful equity participation opportunities.
• Subsidized medical, dental, and vision insurance plans.
• 401(k) retirement plan.
• Flexible spending accounts (FSA), health savings accounts (HSA), and commuter benefits.
• Open vacation policy, with recommended 15 days paid time off per year.
• Company closure during the last week of December.
• 15 days remote work flexibility per year.
• Ten public holidays observed in 2026.

Equal Opportunity Statement

Stepful is an equal opportunity employer. We commit to fair hiring practices without discrimination based on race, color, religion, national origin, age, sex, marital status, ancestry, disability, genetic information, veteran status, gender identity or expression, sexual orientation, pregnancy, or any legally protected characteristic.

Compensation Range

The salary range for this role is between $90,000 and $120,000.