Director, Clinical Strategy

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 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.

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

As Stepful’s Director of Clinical Strategy, you will serve as the clinical voice for our go-to-market organization, walking into rooms with top CNOs and being recognized immediately as a peer, not a vendor. You will challenge CNO thinking, validate our program designs, and bridge the gap between what sales communicates and what clinical executives actually believe.

Success in this role will be measured by your direct impact on clinical stakeholder relationships, the credibility of Stepful’s brand in nursing leadership circles, and partnership-building velocity. You will spend the majority of your time speaking with clients or presenting at conferences, with the remainder devoted to internal coaching, program quality, and strategic external presence.

This is a remote role with a significant travel component (30% expected travel). This role reports to our SVP of Growth.

What You’ll Do

In the Field (60–70%)

• Join sales as the clinical voice—not to present, but to converse peer-to-peer with clinical executives, leveraging lived experience and authority rather than talking points

• Challenge and reframe clinical objections in ways an Account Executive simply cannot

• Build trusted, lasting relationships with clinical champions inside target accounts that persist beyond any single transaction

• Co-own clinical validation during the sales process, helping buyers construct their internal business case

Internal (20–30%)

• Serve as the voice of the clinical operator on our program and product roadmap, stress-testing decisions, messaging, and use cases against real-world nursing workflows

• Coach the sales team on clinical fluency: terminology, care delivery models, and what CNOs actually worry about

• Review and stress-test clinical claims in marketing materials, case studies, and ROI models

• Help develop clinical content—white papers, webinar presence, conference speaking—that builds Stepful’s credibility with nursing leadership

Strategic (10–20%)

• Advise GTM strategy through a clinical lens, identifying which programs, buyers, and problems resonate most

• Represent Stepful externally at nursing and health system conferences

• Build and cultivate a network of clinical advisors and reference customers

What You’ll Bring

• 10+ years of clinical nursing experience, with at least 5 years in a senior nursing leadership role (Director of Nursing, VP Patient Care, CNO, or equivalent) at a recognized health system; you’ve sat in the seat our buyers sit in

• Demonstrated ability to operate in a commercial environment. You’ve worked with vendors, led evaluations, or made significant technology or operational purchasing decisions

• Comfort with ambiguity and a commercial mindset. You love being in deals, not just advising from a distance

• The willingness and confidence to challenge the status quo of healthcare education, push back on buyers, and push back on our own team when the clinical logic doesn’t hold

• Excellent communicator in both small group settings and in front of large audiences

• At least a Master of Science in Nursing (MSN)

Bonus Points If…

• You hold your DNP or another relevant certification (CENP, NEA-BC)

• You have experience at a top-tier, complex health system—academic medical center, large IDN, or magnet-designated system—whose brand names our buyers recognize and respect

• You’ve held a clinical advisor, CMO/CNO-in-residence, or commercial clinical role at a health tech or medical device company

• You’ve published, spoken at national nursing or health system conferences, or come with an established professional network in nursing leadership

• You have exposure to, or ownership of, Clinical Education or Clinical Professional Development

Interview Process

• Introductory call with a Talent Acquisition team member

• Interview with Hiring Manager

• Take-Home Assignment

• Virtual Panel Interview

• On-Site Panel Interview

Benefits & 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 $190,000 – $220,000, 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.