Senior Operations Manager, Career Coaching

About Stepful:

Stepful is reimagining allied healthcare training by offering affordable, online, instructor-led, and AI-supported programs that help learners—regardless of background or circumstance—launch high-demand healthcare careers.

In addition to our direct-to-consumer training, Stepful partners with leading healthcare institutions to address the growing national shortage of healthcare workers. Our graduates, including Medical Assistants, Pharmacy Technicians, Nurses, and more, form the talent pipelines at major employers like CVS, NY-Presbyterian, HCA, Providence, and Walgreens.

Stepful is backed by Y Combinator, Reach Capital, and AlleyCorp, with . .

We’re improving access to quality healthcare for everyone, everywhere, and improving access to healthcare careers for those who need them most

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

Stepful is scaling fast — from 30,000 active monthly students today to 100,000+ — and how we get students from enrollment to employment is central to that growth.

As Senior Operations Manager, Career Coaching, you'll own the end-to-end career and externship experience for D2C students at scale. You'll lead a team of coach managers and the coaches under them, building the systems, processes, and culture needed to deliver consistently excellent outcomes as our student base grows 3x and beyond.

This role reports into our Group Operations Manager.

What You'll Do

• Build for scale, not just for today. Focus on designing and implementing operating infrastructure with an emphasis on leveraging AI tools like Claude to drive efficiency and scalability. Develop playbooks, workflows, automation, and quality frameworks that empower larger teams to deliver high-quality placement outcomes, allowing growth without a proportional increase in headcount.

• Lead a growing team of coach managers responsible for frontline career coaching and job placement support — developing their skills, setting performance standards, and creating the conditions for them to do their best work.

• Drive placement outcomes. Own the metrics that matter: placement rates, time-to-placement, employer satisfaction, and student career outcomes. Identify where we're falling short and build action plans to close the gap.

• Experiment and iterate. Test new approaches to career coaching, externship matching, and employer engagement. Use data to evaluate what's working and move fast on the findings.

• Work cross-functionally. Collaborate with Product, Learning, and Engineering teams to share insights from the coaching team and contribute to the development of tools and features that support student career success.

What You'll Bring

• 3+ years of operations or consulting experience

• 2+ years in a D2C startup environment

• Experience managing managers, not just individual contributors

• Strong analytical skills and a track record of using data to improve outcomes at scale

• Ability to hold strategy and execution at the same time — you can set the direction and roll up your sleeves

• Comfort operating in a high-growth, fast-changing environment

Bonus points if:

• You have an MBA

• You've previously built or scaled a coaching or placement operation

• You have experience in healthcare or workforce development

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.