Senior Sales Enablement Specialist

About Stepful:

Stepful is reimagining allied healthcare training by offering affordable, online, instructor-led, and AI-supported programs that help learners—especially those from underserved communities—launch high-demand healthcare careers.

In addition to our direct-to-consumer training, Stepful partners with leading healthcare institutions to build talent pipelines and address the growing shortage of allied health workers. Our graduates, including Medical Assistants, Pharmacy Technicians and more, go on to work at major employers like CVS, NY-Presbyterian, and Walgreens.

Stepful is backed by Y Combinator, Reach Capital, and AlleyCorp, with a recent $31.5M Series B led by Oak HC/FT. Additionally, we were named the #1 EdTech company in the U.S. by TIME for 2025 and to GSV's 150 Most Transformational Growth Companies in Digital Learning.

We’re unlocking the full potential of the global workforce—improving access to quality healthcare for everyone, everywhere.

Our values:

We credit much of our success to our exceptional team. We’re looking for mission-driven individuals who thrive in fast-paced, sometimes 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 Sales Enablement Specialist to enthusiastically lead Stepful’s Enterprise GTM enablement work. This role will set our enablement strategy by understanding the unique needs of our Enterprise commercial teams, including Sales, Solution Architecture, and Client Success, and determine the enablement motions to support the teams. This person will design, and deliver enablement programs and resources that accelerate pipeline growth, speed up our sales cycle, and foster collaboration and knowledge sharing across several distinct teams and functions. This role powers the GTM teams to be effective and successful in their roles.

This is a hybrid role based in New York, NY (in-office T/W/Th) and you will report into our Director of Revenue Operations.

What you’ll do:

• Enablement Strategy and Execution:

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

• Onboarding and Certification:

  • Develop onboarding and ongoing certification programs (e.g., pitch certification, program and solution certification) for GTM team members

• Knowledge Management:

  • Build and maintain a structure to house and enable GTM teams to easily find materials and ensure materials are up-to-date

  • 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 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 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

• 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

• Required Excel skills:

  • Create basic data validation (dropdowns)

  • Create pivot tables and bar/line charts

  • Use conditional formatting

  • Use xlookup and/or vlookup, sum, average, if, count, countif, sum, 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 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:

  • Guidance of 15 days PTO annually

  • Stepful closed the last week of December

  • 15 work-from-anywhere days

  • 10 public holidays observed for 2025

The target base salary range for this opportunity is $110,000 - $135,000, 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.