Senior Executive Assistant to the Founders

About Stepful:

Stepful is reimagining allied healthcare training by offering affordable, online, instructor-led, and AI-supported programs that help learners—especially those from underserved communities—launch high-demand healthcare careers.

In addition to our direct-to-consumer training, Stepful partners with leading healthcare institutions to build talent pipelines and address the growing shortage of allied health workers. Our graduates, including Medical Assistants, Pharmacy Technicians and more, go on to work at major employers like CVS, NY-Presbyterian, and Walgreens.

Stepful is backed by Y Combinator, Reach Capital, and AlleyCorp, with a recent $31.5M Series B led by Oak HC/FT. We were named the #1 EdTech company in the U.S. by TIME for 2025.

We’re unlocking the full potential of the global workforce—improving access to quality healthcare for everyone, everywhere.

Our Values:

We credit much of our success to our exceptional team. We’re looking for mission-driven individuals who thrive in fast-paced, sometimes 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:

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:

• Founder Enablement:

• Project Coordination:

• Personal Support

• 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.
• 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.
• 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.
• 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.

What You'Ll Bring:

• 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’re energized by working closely with leaders, understanding how they think, and helping them operate at their best.
• 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.

Interview Process:

• Introductory call with Talent Acquisition team member

• Take-Home Assignment

• Team Interview

• Interview With Co-Founders

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 2025

The target base salary range for this opportunity is $90,000 - $120,000, 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.

Please note we do not have a bonus structure at this time so all cash compensation will come in the form of base salary. The total compensation package will also include our benefits package and an equity (ISOs) package.

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.