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're hiring our first Director, IT & Security to build Stepful's IT and security function currently managed by a third party IT admin. You'll own our path to SOC 2 certification and everything that keeps a fast-growing company running securely — from identity and access management to the laptop that lands on every new hire's desk to meeting with client security and IT teams. This is a hands-on role to start: you'll operate as an individual contributor, set the strategy, and build out a team as the company scales.

This role reports directly to the SVP, Engineering and partners closely with Engineering, Finance, People, and our B2B teams across the organization.

This is a hybrid opportunity based out of our NYC office, requiring three days/week (Tuesday, Wednesday, Thursday) in office.

What you'll do:

• Security & Compliance: Own Stepful's security program end to end

• Ensure we remain SOC 2 compliant

• Define and enforce security policies, identity and access management, and least-privilege controls across the organization (SSO, MFA, access reviews)

• Support our B2B healthcare partnerships by owning security questionnaires, vendor assessments, and customer audit requests

• IT Operations: Own the full equipment lifecycle — procurement, MDM deployment, inventory, and seamless onboarding/offboarding for every employee

• Manage our SaaS application stack, including provisioning, access governance, vendor security reviews, and spend optimization

• Build scalable IT support processes and serve as the escalation point for day-to-day IT needs, rolling up your sleeves while the function is small

• Partner with Engineering on incident response, endpoint security, and infrastructure hardening

• Managing the physical IT presence across multiple sites nationwide - NYC office, St. Louis Campus, Lab sites nationwide

• Team Building: Define the long-term IT roadmap and build, hire, and lead the team as Stepful's needs grow

What you'll bring:

• 8+ years of IT experience, including experience leading IT or security functions at a high-growth startup

• Hands-on experience driving a SOC 2 certification (Type I and II) from readiness through audit

• Deep expertise with the modern IT stack: MDM (e.g., Kandji, Jamf), identity providers (e.g., Okta, Google Workspace), and endpoint security tooling

• Proven ability to operate as a strategic leader and a hands-on individual contributor at the same time

• Strong vendor management skills across hardware, software, and audit partners

• Exceptional communication skills with the ability to make security and compliance accessible to non-technical teams

• A builder's mindset — you're energized by creating processes and systems from scratch, not inheriting them

Bonus points if:

• You have experience with HIPAA or healthcare data compliance

• You've built an IT function from zero at a scaling company

• You've worked in EdTech, healthcare, or another mission-driven industry

Interview Process:

• Introductory call with Talent Acquisition team member

• Interview with Hiring Manager

• Take-Home Assignment and Presentation

• 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:

  • 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 - $250,000, 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:

We're hiring a Data Lead to own Stepful's data function — the infrastructure, analytics, and insights that power decisions across the company, from student outcomes to marketing spend. You'll lead a team of three data analysts and engineers while staying deeply hands-on: writing code, building models, and shipping analyses alongside your team. As we scale past 40,000 students graduates, the leverage of great data work has never been higher.

This role reports directly to the SVP, Engineering and partners closely with Growth, Product, Operations, and Finance across the organization.

This is a hybrid opportunity based out of our NYC office, requiring three days/week (Tuesday, Wednesday, Thursday) in office.

What you'll do:

• Lead, mentor, and grow a team of three data analysts and engineers, setting the standard for rigor and craft

• Own Stepful's data platform end to end — pipelines, warehouse, transformation layer, and BI tooling — and its reliability and scalability

• Define and maintain the company's core metrics across the student journey (enrollment, engagement, completion, certification, placement) and business performance (CAC, LTV, retention)

• Build dashboards and self-serve analytics that put trustworthy data in every team's hands

• Partner with Growth and Product on experimentation — design, instrumentation, and analysis of A/B tests

• Deliver deep-dive analyses that shape strategic decisions, from program design to budget allocation

• Stay hands-on: write production SQL and Python, review your team's work, and take on the hardest technical problems yourself

• Establish data governance and quality practices that scale with the company

What you'll bring:

• 7+ years of data experience across analytics and data engineering, with at least 2+ years managing a team

• Proven success as a player-coach — you set direction and manage people while still shipping your own work

• Expert-level SQL and strong Python, with hands-on experience across the modern data stack (e.g., dbt, Snowflake/BigQuery, Airflow, Looker/Metabase)

• Strong product and business sense — you connect data work to outcomes, not just deliverables

• Experience designing and analyzing experiments in a high-growth environment

• Exceptional communication skills with the ability to make complex findings clear to non-technical stakeholders

Bonus points if:

• You've built or scaled a data function at an early or growth-stage startup

• You've worked with marketing attribution or funnel analytics at scale

• You've worked in EdTech, healthcare, or another mission-driven industry

Interview Process:

• Introductory call with Talent Acquisition team member

• Interview with Hiring Manager

• Take-Home Assignment and Presentation

• 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:

  • 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.

What you’ll do as a Brand Designer at Stepful:

We're a company on a mission to transform how people launch careers in healthcare, and we're building a transformative brand to match. We want work that breaks the mold of typical B2B and consumer marketing: distinctive, premium, and unmistakably Stepful across every place we show up.

We're looking for a Brand / Marketing Designer to help shape how Stepful expresses itself across digital, print, campaigns, and key brand moments. This role is for a designer with strong fundamentals and an eye for detail; someone who cares about typography, composition, and the small decisions that elevate the whole. You understand what makes work feel premium and lasting, while bringing fresh ideas to the table. You stay attuned to cultural shifts, new tools including AI, and the visual language of the channels we live on.

You'll report to the Head of Design and partner closely with our Product Marketing Manager, alongside cross-functional partners across marketing and product, to translate strategy into visual expression. You'll own the systems that keep us coherent as we scale and the craft that makes each touchpoint feel considered. The ideal candidate is curious, meticulous, and invested in how a brand evolves across every surface, from a marketing website to a sales deck to the swag at an event.

This is a hybrid opportunity based out of our NYC office, requiring three days/week (Tuesday, Wednesday, Thursday) in office.

What you'll own

• The marketing design system. Build and maintain a unified print + digital system with templates, components, and guidelines that keeps every surface on-brand and empowers the team to produce without bespoke design each time

• Digital surfaces. Marketing website(s), landing pages, digital assets, and campaign creative that are designed to convert and to feel unmistakably Stepful

• Print & physical. One-pagers, flyers, brochures, event collateral, and swag, with a consistent identity across everything physical

• Decks & sales collateral. A deck system and polished, on-voice materials for both B2B and consumer audiences

• B2B client-facing materials. Immaculate, accessible-by-default (WCAG 2.1 AA) materials, produced in close partnership with Product Marketing

• Brand consistency. Bring our core and employer-facing surfaces onto one coherent visual language, and keep them there as we grow

What we're looking for

• 4+ years of experience in brand or marketing design with a portfolio spanning both print and digital work

• A strong creative and visual bar. Show off your portfolio of distinctive, original brand and marketing work across both print and digital

• Systems thinking. We build for scale and want to see how you build and work within design systems as well– how do you design for scale and reuse rather than one-offs.

• Range. Comfort moving between a marketing website, a print brochure, a sales deck, and a social-ready asset, for both B2B and consumer audiences.

• Strong collaboration. You work with partners and can present your work and rationale to stakeholders.

• Accessibility awareness. You factor WCAG 2.1 AA into design decisions by default.

• Comfort with ambiguity. You are comfortable operating with ambiguity and ownership as our first dedicated brand hire.

Nice to have

• Prior experience in EdTech, healthcare, or another mission-driven industry

• Illustration experience

• Experience across both B2B and B2C brands

Interview process

• Introductory call with Talent Acquisition team member

• Interview and portfolio review with Hiring Manager

• Live Design Workshop

• 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:

  • 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 - $130,000, 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 $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 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:

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 $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 Role

Stepful is launching the next frontier of our mission: helping healthcare providers upskill their own employees through Stepful for Business (S4B), our enterprise offering. We already have early enterprise customers who love the product, despite the fact that nearly everything still runs on spreadsheets and manual workflows. Now we’re ready to build real software, at scale, from the ground up. This role is your chance to own that journey.

As the founding Product Manager for S4B, you’ll work directly with healthcare systems, AEs, client success managers, operators, and executives to build scaled offerings that solve a massive workforce problem in healthcare. You’ll be operating in true 0→1 and 1→100 territory: high-autonomy, high-visibility, and high-impact. You’ll define what we build, how we scale it, and how it becomes fundamental to Stepful’s growth and long-term success as a business.

What You’ll Do:

As the Product Lead for Stepful for Business, you will be responsible for creating and scaling the end-to-end product experience for thousands of healthcare employees. In this role, you can expect to:

• Build the complete product strategy and roadmap for Stepful for Business, turning manual workflows into scalable software that delights enterprise customers.

• Partner closely with AEs, client success managers, and S4B operators to deeply understand customer pain points and prioritize what gets productized (and what doesn’t).

• Own the full product lifecycle: from discovery, prototyping, and stakeholder alignment through execution, launch, and iteration.

• Collaborate with product designers and engineers to ship product quickly, balancing speed with thoughtful architecture in a deeply operational environment.

• Translate enterprise customer needs into strategic roadmaps that meet expectations while staying aligned with Stepful’s long-term vision.

• Build relationships with high-stakes enterprise customers, gather feedback directly, and ensure Stepful becomes an indispensable partner in their workforce development strategy.

• Measure product success using clear metrics tied to customer adoption, engagement, and retention. We are not a feature factory and have no intention of becoming one!

This job is for you if:

• You have 10+ years of B2B product management experience building exception products to support complex workflows.

• You’ve built and scaled 0→1 B2B or enterprise products and can point to launches where you drove strategy, execution, and adoption.

• You have strong product fundamentals:focused backlog prioritization, roadmap ownership, hypothesis-driven experimentation, structured discovery, clear documentation, etc.

• You’re exceptional at stakeholder management and influencing others; you can work with AEs, operators, execs, and technical teams and earn their trust quickly.

• You are comfortable traversing across complex data sets and enjoy writing SQL to generate your own insights.

• You can clearly articulate tradeoffs and make decisions with imperfect information.

• You move quickly, know how to find the 80/20, and can demonstrate a track record of delivering measurable impact fast.

• You’ve operated in complex or operationally-heavy environments where tech empowers humans, not replaces them.

• You have excellent written and verbal communication skills and know how to craft narratives that drive alignment and action.

_ Bonus points if: _

• You’ve built products for healthcare, education, workforce development, or similar regulated industries.

• You have experience navigating enterprise procurement or working with large healthcare systems.

• You’ve worked closely with sales, customer success, or go-to-market teams to shape product strategy.

• You’ve built internal tooling or workflow automation products.

• You’ve personally worked with (or built solutions for) operational teams who manage cohorts, certifications, or employee development programs.

Interview Process:

Step 1: Intro Call with Talent Acquisition Lead

Step 2: Call with hiring manager (past project deep dive and mini case)

Step 3: Onsite interview at office in SoHo, NYC

Compensation:

New Hire Base Salary Bands:
Staff I - $191,000-$241,000
Staff II - $201,000-$254,000

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.

Compensation for this role will fall within the pay range listed and will be determined based on job-related factors including, but not limited to, skills, experience, qualifications as well as interview evaluation. Ranges are market-dependent and may be modified in the future.

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 $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 :

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.

This is a hybrid opportunity entailing three days/week working out of our office located in SoHo.

What you’ll do :

• Full-Cycle Recruiting

• Hiring Manager Partnership

• Strategic Support

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 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.

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 not 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.

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:

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 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 :

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:

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.