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 the Director of Healthcare 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:

The target base salary range for this opportunity is $180,000 - $210,000 , 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.

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 $31.5M Series B 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 :

We’re hiring a Senior Manager, GTM Enablement to build and scale Stepful’s GTM enablement function from the ground up. This role will serve as a key connector across Sales, Client Success, Solutions Architecture, Product, Marketing, and RevOps—ensuring our commercial teams have the knowledge, tools, training, and communication needed to operate effectively in a fast-moving environment.

The ideal candidate is both strategic and hands-on, with experience creating scalable enablement programs, organizing knowledge and resources, driving adoption and behavior change, and building processes that improve team performance and accelerate revenue growth. This person will play a critical role in bringing structure, alignment, and operational efficiency to Stepful’s growing Enterprise organization.

This hybrid role is based out of our lower Manhattan office (in-office T/W/Th) and reports into our Director of Revenue Operations.

What you’ll do :

• Enablement Strategy and Execution:

• Knowledge Management:

• Training and Behavior Change:

What you’ll bring :

• B2B-specific GTM enablement experience with a track record of taking initiative, owning the function, and fostering behavioral changes

• Skill in building and delivering enablement programs that improve performance and revenue outcomes

• Experience thriving in a startup environment and comfort navigating evolving processes and complex offerings

• Exceptional organization and strategic prioritization skills

• Strong communication and stakeholder management skills

• Data-driven mentality and decision-making with proficiency in Google Suite and Excel

• Ability to manage and analyze CRM data

• Knowledge of AI tools (inclusive of, but not limited to, LLMs) with a clear perspective on where they're headed and how to apply them in a GTM enablement context

Required Excel skills:

• Create basic data validation (drop downs)

• Create PivotTables and bar/line charts

• Use conditional formatting

• Use XLOOKUP and/or VLOOKUP, SUM, AVERAGE, IF, COUNT, COUNTIF, and SUMIF formulas

• Bonus points for INDEX + MATCH usage

Bonus points if :

• You have EdTech and/or healthcare experience

• You have worked in a B2B2C setting

• You have experience with and knowledge of learning best practices

• You worked within enablement across several GTM functions (i.e., both sales enablement and client success enablement)

• You have experience using Gong and HubSpot

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:

The target base salary range for this opportunity is $140,000 - $160,000 , 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.