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 . .

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 are seeking a highly motivated Program Director to lead our nursing programs in Ohio. This is a dynamic, high-impact role for someone who is passionate about healthcare education and committed to expanding access to nursing careers for working adults.

The Program Director will be responsible for the day-to-day operations of the programs, ensuring they meet rigorous educational standards and that every student receives the highest quality experience. This person will also play an important role in Stepful's enterprise partnerships — working alongside our team to support relationships with healthcare employer partners who hire our graduates and sponsor our programs.

This role requires frequent in-person presence in Columbus, Ohio, and reports to the Senior Director, Nursing Programs.

If you are driven by the opportunity to shape the future of nursing education and make a meaningful difference in students' lives, we'd love to hear from you!

What you'll do:

• Teach and facilitate learning — carry a teaching load that may include didactic instruction (online), skills lab facilitation (in-person), and clinical education (in-person), with flexibility across modalities as program needs evolve.

• Oversee nursing curriculum — collaborate with internal teams to review, refine, and continuously improve content across nursing program curriculum.

• Manage program enrollment — support program enrollment, including recruitment, admissions, orientation, and registration processes.

• Support student success — oversee student progress and performance, including grading, academic advising, and program completion.

• Build and lead the team — support the hiring process, train, and supervise a team of adjunct instructors, fostering a collaborative and supportive environment.

• Partner with enterprise clients — serve as a key point of contact for Stepful’s enterprise healthcare partners in Ohio, supporting program alignment and ongoing relationship management.

• Manage resources responsibly — develop and oversee program budgets and operational resources.

• Ensure regulatory compliance — serve as a primary point of contact with the Ohio Board of Nursing, managing ongoing compliance and regulatory requirements for Stepful's nursing programs in the state of Ohio.

• Drive program quality — conduct ongoing program evaluation and assessment, using data to make recommendations for improvement and ensure compliance with accreditation and regulatory requirements.

• Maintain scheduling flexibility — some evening and weekend obligations are required.

What you'll bring:

• Current, unencumbered licensure as a Registered Nurse in Ohio (or eligibility to obtain, if you’re licensed in another state)

• A master's degree in nursing

• 5+ years of RN nursing practice experience

• 2+ years experience as a faculty member with a registered nursing education program, with BoN site visit experience and accreditation involvement

• Demonstrated ability to teach across modalities — didactic, skills lab, and clinical settings

• Experience with Laerdal manikins, or similar simulation technology

• Familiarity with accreditation and regulatory compliance for nursing education programs, including Ohio Board of Nursing requirements

• Experience engaging with external partners, clinical sites, or employer stakeholders — a collaborative, relationship-oriented approach is a must

• Strong ability to work cross-functionally with faculty, staff, students, and institutional partners

Interview Process:

• Introductory call with Talent Acquisition

• Interview with Hiring Manager

• Take-Home Assignment

• Final Panel Interviews

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 2026

The target base salary range for this opportunity is $100,000 - $125,000, 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 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 . .

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:

Stepful is scaling! To address our ambitious hiring needs, we’re adding a Business Recruiter to our Talent Acquisition team to support hiring across our G&A, GTM, Growth, Learning and Operations teams. You’ll play a critical role in helping to scale Stepful’s non-technical teams via full-cycle recruiting, management of structured and equitable hiring processes, and delivery of both a memorable and positive candidate experience.

This role will report into and partner with the Business Recruiting Lead. You will leverage existing recruiting infrastructure to independently manage your own portfolio of searches while continuously keeping an eye on ways to automate and improve the efficiency of our processes.

This opportunity is best suited for someone with a foundation of both agency and in-house recruiting experience who is seeking to develop their career within a fast-paced, mission-driven startup setting.

What you’ll do:

• Full-Cycle Recruiting

  • Lead end-to-end recruiting for a portfolio of non-technical searches (across departments and levels), inclusive of sourcing, screening, managing interview processes, extending offers and ensuring both a memorable and positive candidate experience

  • Build and manage candidate pipelines through proactive outreach, leveraging automation, AI tools and creative sourcing techniques to surface high-quality candidates

• Hiring Manager Partnership

  • Partner closely with stakeholders across the business to understand their talent needs, define role requirements, build structured interview processes and develop recruitment strategies that drive exceptional hiring decisions

• Strategic Support

  • Tap into existing systems and best practices while continuously identifying ways to improve tools, workflows, and the candidate experience

What you’ll bring:

• At least 3 years of full-cycle recruiting experience, ideally with a blend of agency and startup experience

• Experience partnering with stakeholders to close a variety of roles across departments and levels

• Exceptional sourcing skills with a track record of identifying and engaging talent through both creative methods and automated, AI-powered tooling

• Strong communication skills and the ability to thrive in a fast-moving, cross-functional environment

• Attention to both detail and process optimization with a commitment to a great candidate experience and high-quality hiring

Bonus points if you have:

• Operated in a high-growth startup experience

• Experience with Ashby

• Experience with automation/AI-based recruiting tools

Interview Process:

• Interview with Hiring Manager

• Take-Home Assignment

• Team Panel Interview

The hourly rate range for this opportunity is $75/hour. 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 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 . .

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 our Head of Learning, you will define and execute Stepful’s learning strategy across a growing portfolio of healthcare programs. You will own the quality and effectiveness of our learning experience, from curriculum development, instructional delivery, on-the-ground clinical rotation design, to student outcomes and continuous improvement.

You will lead a team of curriculum developers, instructional designers, and subject matter experts and work closely with Product, Operations, Compliance, and healthcare partners. This role is ideal for a hands-on learning leader who can set a clear vision, build scalable systems, and use data to improve outcomes for students.

This role reports into our SVP, Learning and Operations.

What you’ll do:

• Learning vision and strategy: Define the vision and strategy for Stepful’s learning offering based on student needs, business priorities, and healthcare workforce demand.

• Program and content roadmap: Develop and own the roadmap for new programs, curriculum improvements, assessments, and learning modalities.

• Program development: Lead the end-to-end development and launch of high-quality online and blended healthcare programs.

• Learning operations: Build repeatable processes to develop, maintain, and improve curriculum efficiently across a growing portfolio of programs.

• Learning innovation: Develop new learning modalities and apply AI and emerging technologies to personalize learning, improve engagement, and strengthen skill development.

• Industry alignment: Build strong relationships with healthcare employers, academic experts, and industry organizations to understand emerging learning and workforce needs.

• Cross-functional collaboration: Partner closely with Operations, Compliance, and Workforce Solutions to incorporate student and instructor feedback and shape the broader learning experience.

What you’ll bring:

• 10+ years of experience in online or blended learning, curriculum development, academic program management, instructional design, or education operations.

• Experience in healthcare education, EdTech, or workforce development.

• Experience managing curriculum developers, instructional designers, subject matter experts, or other learning teams.

• Highly analytical mindset, using data to improve learning experiences and student outcomes.

• Ability to translate complex healthcare or technical subject matter into clear and effective learning experiences.

• Strong communication and cross-functional collaborative skills

• Ability to thrive in a fast-paced, ambiguous environment.

• Passion for helping students change their lives through access to education.

Bonus points if:

• You have clinical experience or have designed learning experiences and curriculum in a healthcare setting

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 2026

The target base salary range 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 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 . .

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.

About the role

This is not a traditional lifecycle marketing role and it is not a campaign-management role.

You will own the end-to-end student engagement surface as a product. Students stall in predictable places (e.g. between signup and enrollment, before their first class, when momentum dips mid-program). Right now, the comms that should catch them are scattered across teams and tools, with overlap in some places and gaps in others. Your job is to turn that into one coherent engagement engine: a system that understands where a student is, decides the right next action, and runs it reliably without someone manually pushing every step.

You'll do this hands-on, building directly in tools like Customer.io rather than handing specs to someone else. But the tools are the implementation detail. What we actually need is someone who owns the outcome—students moving forward with clarity and confidence—and has the judgment to design the logic, the measurement, and the guardrails behind it.

This is a builder-and-owner role with real decision authority over the student comms stack. It reports into Product. If you want a mature lifecycle function with established playbooks, this isn't it. If you want to build that function, it's yours.

What you'll own

• The end-to-end student comms surface. Every touchpoint from course enrollment through payment, onboarding, pre-class readiness, activation, and success milestones; owned as one coherent system rather than a set of disconnected sends.

• The decisioning logic behind next-best-action. The triggers, segmentation, branching, routing, and escalation that decide what happens for a given student based on their behavior and context, including when to send, when to route a question, and when to hand off to a human.

• The measurement system. How we know engagement is working: the metrics, experiments, holdouts, and goals that prove a flow moves students forward, and the discipline to kill what doesn't.

• The guardrails. The standards that keep automated and AI-assisted communication clear, supportive, and human. Scaled comms feel like a great admissions advisor or coach, not a chatbot.

What success looks like

In your first 90 days, you might:

• Map the existing student lifecycle end-to-end and untangle where comms currently overlap, conflict, or leave gaps. You turn the current fragmented picture into a single source of truth.

• Cut the redundant and competing sends that create noise across the student journey, and establish a clear logic for what fires when.

• Ship one measurably better flow. For example, a redesigned activation or pre-class readiness sequence with a real success metric and a holdout to prove the lift.

Over time, you'll move Stepful from fragmented, team-by-team outreach to a coordinated engagement engine that scales with the business and helps every student take the next step with clarity and confidence.

You may be a fit if

• You've built a lifecycle, growth, or engagement system that ran at scale without you manually operating every step and you can point to the outcome it drove, not just the workflows you shipped.

• You're energized by replacing manual processes with systems, and you build directly in automation, CRM, or workflow tools rather than only writing briefs.

• You can reason through a full workflow end-to-end: what triggers it, what context it needs, what logic powers it, what channel it uses, when it escalates, and how success is measured.

• You understand student (or user) motivation well enough to design communication that helps people act without feeling robotic, spammy, or confusing and you care about owning the outcome, not just the build.

• You're practical and curious about AI as a way to improve workflow design, routing, personalization, QA, and scale (not just to generate content).

Helpful background (not required): hands-on experience with a lifecycle/automation platform (Customer.io, Braze, Iterable, HubSpot, Klaviyo, or similar); AI agent or support-automation tools (e.g., Decagon); SQL, APIs, webhooks, or low-code tools (Retool, Zapier, Make, n8n); and a complex-user-journey domain like edtech, healthcare, marketplace, or consumer subscription.

This role is probably for you if

• You prefer managing campaign calendars over building systems.

• Your experience is primarily top-of-funnel, brand, content, or creative marketing with limited automation or workflow-building.

• You prefer writing strategy or briefs but don't want to build directly in tools.

• You need a mature lifecycle function and fully defined processes already in place.

• You're excited by AI mainly for content generation, rather than for solving practical workflow problems.

• You're a pure technical builder who doesn't want to own messaging quality, student experience, or business outcomes.

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Benefits and Compensation

Base compensation range: $111,000 - $160,000

• 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

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Interview Process

Step 1: Intro Call with a Talent Acquisition Partner (30 mins)

Step 2: Interview with the Hiring Manager (45 mins)

Step 3: Case Study (45 mins)

Step 4: Onsite interview at Stepful HQ in SoHo, NYC (2 hours)

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 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 . .

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:

Stepful is hiring a People Operations Specialist to join the People Operations team as a hands-on, execution-focused resource across a broad range of People programs and processes. This role sits at the intersection of HRIS administration, payroll operations, workforce lifecycle management, and People program support.

This role will serve as the primary People Ops point of contact for our frontline workforce - coaches, instructors, and contractors - owning their lifecycle end-to-end and escalating to the Associate Director of People Operations as needed. Alongside that primary ownership, this role will support the execution of broader People programs and initiatives that impact the full employee population.

This hybrid role (3 days/week at our Fenton, MO campus) reports to the Associate Director, People Operations.

What you’ll do:

HRIS & People Systems

• Own administration and ongoing optimization of Rippling across contractor and instructional staff populations, with support for HQ employees.

• Maintain high data integrity across all employee and contractor records - ensuring records are accurate, complete, and audit-ready at all times.

• Build and improve automations, workflows, and system processes as the workforce scales.

• Serve as the internal go-to for system questions, troubleshooting, and process guidance.

• Support key annual processes including open enrollment and any HRIS migrations or implementations.

• Partner with the compliance and legal teams to build and maintain Rippling workflows that capture the specific reporting requirements, classification rules, and documentation needs of our instructional workforce.

Payroll Support

• Support payroll processing for hourly and program-based instructional staff in Rippling, ensuring accurate and timely pay runs.

• Manage compensation and rate changes, ensuring updates are reflected correctly in Rippling and processed on cycle.

• Coordinate contractor invoice and payment workflows, including final pay processing for offboarding contractors.

• Identify and resolve payroll discrepancies in partnership with Finance and the Associate Director of People Operations.

Frontline Workforce Lifecycle

• Manage onboarding workflows for contractors and instructional staff - ensuring agreements are executed, documentation is complete, and system access is in place before day one.

• Own ongoing lifecycle administration: compensation changes, role or scope changes, status changes (including contractor-to-employee transitions), and record updates.

• Serve as the primary point of contact for employee relations matters for frontline team members - including performance management documentation (e.g., PIPs), manager guidance, benefits questions, and day-to-day HR support - escalating to the Associate Director as needed.

• Support leave management for frontline staff - tracking leave requests, coordinating documentation, and ensuring accurate reflection in payroll and records.

• Manage offboarding for contractors and instructional staff - documentation, system access removal, final pay coordination, and agreement closure.

• Track and manage program contract renewals for instructional staff - maintaining a system of record for active agreements, renewal dates, and rate structures, and partnering with Legal to ensure renewals are executed on time.

People Programs & Cross-functional Support

• Support execution of company-wide People programs and initiatives led by the Associate Director of People Operations, including performance review cycles, policy rollouts, and employee communications.

• Manage logistics for the performance review cycle - tracking timelines, coordinating with managers, and ensuring process runs on schedule.

• Support the preparation and distribution of People team communications and program materials across the full employee population.

• Take on ad hoc People Ops projects as the team and company scale, stepping in where execution support is needed most.

What Success Will Look Like

• Contractor and instructional staff records in Rippling are accurate, complete, and audit-ready at all times.

• Payroll runs for hourly and program-based instructional staff are processed accurately and on time, with discrepancies identified and resolved quickly.

• Program contract renewals are tracked proactively - no agreements expire without a deliberate decision.

• Rippling workflows and automations reflect the actual complexity of our instructional workforce, including classification rules and reporting requirements.

• Onboarding and offboarding for contractors and instructional staff is consistent, compliant, and well-documented.

• Internal stakeholders have a reliable, knowledgeable partner for People Ops questions, system issues, and process guidance.

• People program logistics - including performance review cycles and broader initiative execution - run on schedule and with consistent follow-through.

What you’ll bring:

• 3+ years of experience in People Operations, HR, or a related operational role.

• Experience supporting or managing hourly workforces, contingent workers, or high-volume contractor populations.

• Strong HRIS skills - Rippling experience strongly preferred; must be comfortable building workflows and maintaining data integrity, not just using the system.

• Solid understanding of payroll operations, including hourly and program-based pay structures.

• Exceptional attention to detail - you catch errors before they become problems.

• Strong process orientation; you build structure, document clearly, and improve systems over time.

• Ability to manage multiple workflows and competing priorities without dropping the ball.

• Strong communication skills and comfort working across People Ops, Legal, Finance, and business leaders.

Interview Process:

• Introductory call with a Talent Acquisition team member

• Interview with Hiring Manager

• Take-Home Assignment

• Virtual Assignment 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 2026

The target base salary range for this opportunity is $110,000 - $120,000, 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.

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 . .

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 our Director of Learning Programs, you will define and execute Stepful’s learning strategy across a growing portfolio of healthcare programs. You will own the quality and effectiveness of our learning experience, from curriculum development, instructional delivery, on-the-ground clinical rotation design, to student outcomes and continuous improvement.

You will lead a team of curriculum developers, instructional designers, and subject matter experts and work closely with Product, Operations, Compliance, and healthcare partners. This role is ideal for a hands-on learning leader who can set a clear vision, build scalable systems, and use data to improve outcomes for students.

This role reports into our SVP, Learning and Operations.

What you’ll do:

• Learning vision and strategy: Define the vision and strategy for Stepful’s learning offering based on student needs, business priorities, and healthcare workforce demand.

• Program and content roadmap: Develop and own the roadmap for new programs, curriculum improvements, assessments, and learning modalities.

• Program development: Lead the end-to-end development and launch of high-quality online and blended healthcare programs.

• Learning operations: Build repeatable processes to develop, maintain, and improve curriculum efficiently across a growing portfolio of programs.

• Learning innovation: Develop new learning modalities and apply AI and emerging technologies to personalize learning, improve engagement, and strengthen skill development.

• Industry alignment: Build strong relationships with healthcare employers, academic experts, and industry organizations to understand emerging learning and workforce needs.

• Cross-functional collaboration: Partner closely with Operations, Compliance, and Workforce Solutions to incorporate student and instructor feedback and shape the broader learning experience.

What you’ll bring:

• 10+ years of experience in online or blended learning, curriculum development, academic program management, instructional design, or education operations.

• Experience in healthcare education, EdTech, or workforce development.

• Experience managing curriculum developers, instructional designers, subject matter experts, or other learning teams.

• Highly analytical mindset, using data to improve learning experiences and student outcomes.

• Ability to translate complex healthcare or technical subject matter into clear and effective learning experiences.

• Strong communication and cross-functional collaborative skills

• Ability to thrive in a fast-paced, ambiguous environment.

• Passion for helping students change their lives through access to education.

Bonus points if:

• You have clinical experience or have designed learning experiences and curriculum in a healthcare setting

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 2026

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 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 . .

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 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:

  • 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 $200,000 - $230,000, 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 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 . .

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 Chief Nursing Officer, 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 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.