Fractional Sales Enablement Lead

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:

We're looking for a Fractional Sales Enablement Lead to help build the foundation of Stepful's sales enablement function during a critical growth phase. In this remote, contract engagement, you'll serve as a key connector across Sales, Client Success, Solutions Architecture, Product, Marketing, and RevOps — ensuring our commercial teams have the knowledge, tools, and training they need to operate effectively in a fast-moving environment.

This is a hands-on, high-impact engagement for someone who thrives in a greenfield environment and can hit the ground running. You'll bring structure and strategy to an enablement function that's just getting started, with real ownership over the work from day one.

This role will report to the Director of Revenue Operations.

What you’ll do:

• Enablement Strategy and Execution:

  • Take initiative to identify key areas of GTM enablement, and prioritize those areas based on connection to our key business priorities, urgency, and resourcing required

  • Lead Stepful’s GTM enablement work, including cross-functional planning and collaboration structures, and enablement forums and rhythms of business

  • Be a key connector between our commercial teams and our B2B product, learning and ops, and marketing functions

• Knowledge Management:

  • Leveraging AI, build and maintain a structure to house and enable GTM teams to easily find materials and ensure materials are up-to-date

  • Leveraging AI, develop and execute communications approaches (e.g., async comms, live touch points) to ensure GTM teams receive critical information in a timely and easily digestible manner

• Training and Behavior Change:

  • In collaboration with cross-functional SMEs (Marketing, Ops, Learning, Product, GTM leadership), identify what GTM teams need to know and be able to do

  • Prioritize and organize a wide range of information across functions to ensure that the GTM team is successful and that information is shared in a timely, yet manageable, manner

  • Design and facilitate training experiences and manage tools to support this

  • Support and monitor adoption 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

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

• Case Study Exercise

• Virtual Team Interviews

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.