Base pay range: $110,000 - $135,000 per year.
Stepful reimagines 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. Stepful partners with leading healthcare institutions to build talent pipelines and address growing shortages. Graduates include Medical Assistants, Pharmacy Technicians and more, working at major employers like CVS, NY‑Presbyterian, and Walgreens. Stepful is backed by Y Combinator, Reach Capital, AlleyCorp and recently raised $31.5M Series B led by Oak HC/FT. It was named the #1 EdTech company in the U.S. by TIME for 2025.
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.
Opportunity We’re hiring a Senior Sales Enablement Specialist to enthusiastically lead Stepful’s Enterprise GTM enablement work. This hybrid role is 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
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; open vacation policy, including 15 days PTO annually, 15 work‑from‑anywhere days, and 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. 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.
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Stepful reimagines 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. Stepful partners with leading healthcare institutions to build talent pipelines and address growing shortages. Graduates include Medical Assistants, Pharmacy Technicians and more, working at major employers like CVS, NY‑Presbyterian, and Walgreens. Stepful is backed by Y Combinator, Reach Capital, AlleyCorp and recently raised $31.5M Series B led by Oak HC/FT. It was named the #1 EdTech company in the U.S. by TIME for 2025.
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.
Opportunity We’re hiring a Senior Sales Enablement Specialist to enthusiastically lead Stepful’s Enterprise GTM enablement work. This hybrid role is 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
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; open vacation policy, including 15 days PTO annually, 15 work‑from‑anywhere days, and 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. 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.
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