Director, Strategy & Operations

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 the Director of Strategy & Operations, you will be responsible for building, maintaining and scaling our surgical services programs. You will become a subject-matter expert and experiment with solutions that can support 10x growth in active students. You will work cross-functionally with Product, Sales, Customer Success, and Operations to advance a key pillar of Stepful's growth story, and will oversee a team of Program Directors, instructors, and coordinators.

This role is ideal for a strong operator who is passionate about expanding access to healthcare careers and delivering measurable student outcomes.

This role reports to the SVP, Operations and is hybrid in NYC.

What you’ll do:

• Own the end to end program delivery of our surgical services programs, with the opportunity to expand to other programs

• Develop and execute innovative initiatives and experiments to accelerate enrollment, student retention, and program scale

• Collaborate regularly with our Curriculum, Product, Policy, Sales, and Customer Success teams to meet the high bar of regulators and accreditors, provide an exceptional student experience, and deliver impactful results for our healthcare provider clients.

What you’ll bring:

• You are passionate about helping students change their lives through access to education

• You thrive in a fast-paced, ambiguous environment

• You are highly analytical, taking a structured approach to breaking down complex problems

• You have excellent communication skills that reflect in clear and concise writing and presenting

• You are an expert collaborator who is able to lead through influence and coordinate diverse stakeholders at various levels

• You are willing to do whatever it takes to get the job done successfully and maintain a high bar for execution

• You learn quickly through experimentation

• You have 7+ years of experience, including in an operational role at a high growth startup

Bonus points if:

• You worked in healthcare or EdTech

• You’ve led a team of clinicians, program directors or instructors

• You have experience in remote educational delivery (online teaching, virtual simulations, virtual reality etc.)

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

• Learning stipend

• 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 $200,000 - $230,000, 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.