Stepful is on a mission to revolutionize vocational education. We train people with a high school education in 4 months or less and places them into healthcare jobs. Healthcare is the fastest growing industry in the US accounting for 40% of all jobs added including medical assistants, nursing assistants, and phlebotomists.

About Stepful: Stepful partners with healthcare institutions to build talent pipelines and career pathways. We are reimagining allied healthcare training with a digital-first environment for student cohorts that prepare job-ready graduates five times faster, at a fraction of the cost. Stepful graduates, primarily from underrepresented communities, go on to work at leading healthcare institutions. Stepful is backed by Y Combinator, Reach Capital and AlleyCorp and recently closed a round led by Oak HC/FT.

About the Role

We’re looking for a highly organized, resourceful, and reliable Executive Assistant to support Stepful’s two Founders across both their professional and personal responsibilities. This is a high-impact, strategic role that goes beyond calendar management—you’ll be a key partner in helping the Founders stay focused on the most important priorities.

You’ll work closely with the Chief of Staff and act as an extension of the Founders—understanding what matters most to them, ensuring their time is aligned with company goals, preparing them for key meetings, and proactively removing friction from their day-to-day. You’ll work alongside the Founders from our Tribeca office in NYC on a hybrid schedule, with in-office presence expected Tuesday–Thursday each week.

This role is ideal for someone who thrives in a fast-paced environment, enjoys working behind the scenes, and takes pride in being a trusted thought partner and operator.

What You’ll Do

• Strategic Time Management:
  • Own the day-to-day calendars for both founders with an emphasis on prioritization and alignment to top business and personal priorities.
  • Act as a strategic gatekeeper—ensuring time is protected, distractions are minimized, and schedules reflect what’s most important.
  • Understand the broader business context to anticipate where founders should be spending their time and flag gaps or misalignments.
• Founder Enablement:
  • Prepare the founders ahead of key internal and external meetings, including background research, agenda setting, and briefing materials.
  • Track follow-ups, decisions, and action items to ensure continuity across meetings.
  • Act as a liaison across internal teams and external stakeholders on behalf of the founders, ensuring clear communication and timely responses.
• Project Coordination:
  • Partner with the Chief of Staff on special projects, cross-functional initiatives, and leadership communications.
  • Jump in on one-off operational needs or process improvements where your support adds leverage.
• Personal Support 
  • Assist with personal tasks and logistics that allow the founders to stay focused on their professional responsibilities. This may include scheduling personal appointments, coordinating personal and professional travel, handling reservations, gift-giving, errands, and household coordination.
  • Maintain professionalism and confidentiality across both personal and professional domains.

This Role is for You If

• You have 8+ years of experience supporting senior leaders in a fast-paced startup  environment, ideally at a growth-stage company.
• You are detail-oriented and highly organized, with a strong ability to manage shifting priorities and anticipate needs.
• You’re a confident communicator—concise, clear, and professional across written and verbal interactions.
• You operate with sound judgment and discretion when handling sensitive information.
  You thrive in environments where you’re given autonomy and trust to make decisions.
• You’re energized by working closely with leaders, understanding how they think, and helping them operate at their best.

You’re not just task-oriented—you’re a strategic partner who enjoys helping leaders focus on what matters most.

Compensation:

Base salary: $100K - $120K and equity

At Stepful, we're an equal opportunity employer and value diversity at our company. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

Our current stack is based on Postgres, Rails and React.

We are building the best student experience ever!