Associate Director, Strategy & Operations

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. Additionally, we were named the #1 EdTech company in the U.S. by TIME for 2025 and to GSV's 150 Most Transformational Growth Companies in Digital Learning.

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:

As our Associate Director of Strategy & Operations, you will own the growth of our national network of hiring partners. Stepful is now serving tens of thousands of students across multiple programs. A key part of our programs is securing externships for students to get hands-on experience and act as a gateway to a successful career in healthcare. You will oversee a team that is growing our supply of partners, ranging from individual provider offices to the largest hospital systems, pharmacy chains, and outpatient clinics. You will optimize the processes by which we recruit, onboard, activate, retain, and expand new partnerships.

You’ll be the voice of our hiring partners internally, advocating for improvements to our learning experiences and employer-facing products. In this role, you will work cross-functionally with learning, product, sales, customer success, and other operations teams. You will be responsible for building a key pillar of Stepful’s growth story.

This is a hybrid role reporting to our VP, Operations.

What you’ll do:

• Oversee operations for a growing network of 6,000+ clinical partners nationwide, ensuring they deliver the right experiential learning experiences for our students.

• Develop and execute creative initiatives and experiments to fast-track the growth of our hiring supply.

• Monitor and improve key metrics, including new site activation, seat retention and growth, and capacity utilization.

• Work collaboratively with our enterprise sales team to unlock externship capacity at key enterprise partners and participate in team pitches.

• Collaborate regularly with our Learning, Product, Policy, Sales, Customer Success, and Operations teams to design and implement solutions to provide an exceptional student experience and deliver impactful results for our healthcare provider clients.

What you’ll bring:

• You have 10+ years of experience, including consulting and operational experience at a high-growth startup

• You have experience scaling the supply side of a marketplace

• You have managed teams of 5+ direct reports and are familiar with managing contractors at scale

• You’re an effective manager who can set ambitious goals, motivate teams to over-achieve, and oversee large initiatives end-to-end

• You are highly analytical and use structured thinking to break down complex problems

• You have strong commercial acumen – a knack for identifying opportunities to better serve clients and the ability to influence toward deepening a partnership.

• You thrive in a fast-paced, ambiguous environment.

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

Bonus points if:

• You have worked in management consulting or a B2B go-to-market role (e.g., solutions consulting, account management, client success, sales, business development, strategic partnerships)

• Experience working in education, talent/workforce development, healthcare, or B2B tech-enabled services companies

• You are excited to help build a new function – partnering to evolve our ways of working, systems, and tools

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 $165,000 - $190,000, 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.