Director, B2B Operations Enablement

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:

Stepful for Business (S4B) is growing fast — new programs, new modalities, new enterprise partners. Every launch is an opportunity to get it right. Every gap in our operational infrastructure is a reason we might not.

As Director, B2B Operations Enablement, you'll own the systems and processes that make enterprise program launches repeatable and scalable. You'll work across apprenticeship and upskill programs, partnering with Customer Success (CS), Product, Learning, and Engineering to design the operational foundation that lets us bring on a new client — or a new program — without reinventing the wheel every time.

You'll manage one direct report and report into our SVP, Operations. This is a hybrid role based out of NYC.

What you’ll do:

• Own the scaling of existing programs and client launch operations. Lead and optimize the end-to-end launch and expansion process for established programs at existing and new clients — including launch planning, QA, cross-functional coordination, and go-live readiness. You will primarily focus on scaling programs like PC-Plus, 12-week Medical Assistant, Phlebotomy, and others as they grow, while also contributing to the rollout of new offerings as we expand.
• Design operational infrastructure for new modalities. When we launch a new delivery model — partner-led enrollment, employer-sponsored sign-up, SSO integration, IT QA processes — you build the operational backbone that makes it work. You think through the implications before go-live, not after.
• Build scalable S4B ops processes. Own ongoing process design for areas like preceptor operations, admissions workflows, sponsorship management, and ops efficiency. The goal is always the same: fewer manual steps, better outcomes, more capacity for the team.
• Work cross-functionally. You'll need to align Product on tooling needs, coordinate with Learning on program readiness, and loop in CS and Solutions Architecture on client-facing implications. You're comfortable in all those rooms and good at getting to a shared plan.

What you’ll bring:

• 8+ years building scalable operations for the delivery of services within a start-up environment, with at least 2 years in the context of B2B partnerships.
• 2+ years of consulting experience (or strategy roles)
• Demonstrated experience designing and documenting operational processes — playbooks, SOPs, workflows — that stick
• Strong project management instincts: you track the details, manage dependencies, and keep launches on schedule
• Experience working cross-functionally on technical or product-adjacent projects (familiarity with SSO, IT QA, or platform integrations is a plus)
• Ability to manage a team while staying close to the work yourself
• Comfort with ambiguity — you can build structure where there isn't any

Bonus points if:

• You worked in healthcare or EdTech
• 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.