Executive Assistant to the Founders

About Stepful:

Stepful is a workforce platform redefining how America's largest health systems build, train, and retain their talent. Since our founding in 2021, Stepful’s trained over 32,000 practice-ready healthcare workers.

Layering onto our successful direct-to-consumer training, Stepful partners with leading healthcare institutions to address the growing national shortage of healthcare workers. We’re improving access to quality healthcare for everyone, everywhere, and improving access to healthcare career ladders for those who need them most.

Our students form the talent pipelines for major employers such as NY-Presbyterian, Mt. Sinai, HCA, Providence, CVS, and Walgreens. We have partnerships with half of the top 10 health systems in the US and are in process with many more.

Stepful is backed by Y Combinator, Reach Capital, and AlleyCorp, with a recent $55M Series C led by Oak HC/FT. We were named the #1 EdTech company in the U.S. by TIME for 2025.

Our values:

We credit much of our success to our exceptional team. We’re looking for mission-driven builders who thrive in fast-paced, ambiguous environments, and embody our four core values:

• Care first: We do whatever it takes for our students to succeed.
• Learn quickly: We test, learn with data, and iterate.
• Build together: We win when we rely on each other.
• Own it: We show up, take initiative, and show pride.

The opportunity:

As we prepare for our next phase of growth, we're hiring an experienced Senior Executive Assistant to be the operational backbone of our executive team. This is a high-trust, high-autonomy role for someone who anticipates needs before they're voiced, protects our leaders' time, and keeps the details moving so the business can move faster.

This role reports directly to the CEO and additionally supports our Co-Founder while working closely with the executive team, Chief of Staff, and People and Operations across the organization. You'll be a force multiplier for the people setting Stepful's direction.

This is a hybrid opportunity based out of our NYC office, requiring three days/week (Tuesday, Wednesday, Thursday) in office.

What you'll do:

• Own complex, ever-changing calendars for the CEO and executive team, resolving competing priorities and protecting time for what matters most.
• Manage high-volume scheduling across time zones, including internal meetings, external partner sessions, board interactions, and interviews.
• Coordinate domestic and international travel end to end—flights, hotels, ground transport, and detailed itineraries.
• Prepare and process expense reports, reconciliations, and reimbursements with accuracy and on time.
• Plan and execute leadership offsites, team events, and board meeting logistics from concept through day-of run of show.
• Draft, proofread, and manage sensitive communications and documents on behalf of executives, handling confidential information with discretion.
• Partner with the Chief of Staff to prepare agendas, track action items, and follow up on decisions across leadership meetings.
• Serve as a welcoming, organized point of contact for internal teams and external partners interacting with the executive office.
• Drive ad hoc projects and process improvements that make the executive team more effective.

What you'll bring:

• 6+ years of executive assistant or administrative experience, including direct support of C-level leaders.
• Proven ability to manage complex calendars, travel, and logistics in a fast-moving environment.
• Exceptional organizational skills and meticulous attention to detail—nothing slips through the cracks.
• Strong written and verbal communication skills, with sound judgment about tone and audience.
• Discretion and integrity when handling confidential and sensitive information.
• A proactive, resourceful mindset—you anticipate needs, solve problems independently, and thrive amid ambiguity and shifting priorities.
• Fluency with modern productivity tools (Google Workspace, Slack, and expense/travel platforms).

Bonus points if:

• You've worked in EdTech, healthcare, or another mission-driven industry.
• You've supported a founder or CEO at a high-growth startup.

Interview Process:

• Introductory call with Talent Acquisition team member
• Interview with Hiring Manager
• Take-Home Assignment
• Virtual Panel Interview
• On-Site Panel Interview

Benefits and Compensation:

• Meaningful Equity Stake
• Subsidized Medical, Dental, and Vision insurance plan options
• 401(k)
• FSA, HSA and commuter benefits

• Open vacation policy, including:

  • Guidance of 15 days PTO annually
  • Stepful closed the last week of December
  • 15 work-from-anywhere days
  • 10 public holidays observed for 2026

The target base salary range for this opportunity is $100,000 - $150,000, and is part of a competitive total rewards package including equity and benefits. Individual pay may vary from the target range and is determined by a number of factors including experience, internal pay equity and other relevant business considerations.

Stepful is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision 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 other applicable legally protected characteristic.