Trainee
Controller
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 adding a Controller to our Finance team to establish world-class accounting operations and lead our transition to Big 4 audits. You'll play a critical role in building scalable processes, ensuring audit readiness, and supporting our leadership team with strategic financial insights as we prepare for our next phase of growth.
This role reports directly to the Head of Finance and partners closely with cross-functional teams across the organization. You will establish robust accounting operations while maintaining the rigor required for financial accuracy and audit compliance.
This is a hybrid opportunity requiring three days/week (Tuesday, Wednesday, Thursday) working out of our office located in TriBeCa.
What you’ll do:
Own all aspects of accounting operations, including GL, AP, AR, payroll, revenue recognition, and tax compliance
Prepare and review monthly, quarterly, and annual financial statements in accordance with US GAAP
Lead preparation for and management of annual external audits with Big 4 accounting firm
Oversee revenue recognition policies in accordance with ASC 606, ensuring accuracy for B2C and B2B subscription usage models
Manage GL reconciliations and maintaining internal controls to ensure financial integrity
Maintain compliance with federal, state, and local reporting requirements, including timely and accurate preparation of tax filings
Implement and monitor internal controls to ensure compliance with audit requirements
Optimize accounting workflows and documentation for scalability
Partner with FP&A on budgeting, forecasting, and financial analysis
Manage relationships with auditors, tax advisors, and other external partners
Oversee an in-house and outsourced team of accounting professionals, including overseeing accounting operations for a recent acquisition
Lead ongoing accounting ERP implementation with Rillet
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Drive process improvements to enhance accuracy, efficiency, and transparency
What you’ll bring:
CPA with 8–12+ years of progressive accounting experience, including at least 5 years in a leadership role
Track record of hiring, training, and developing high performing teams
Public accounting background (Big 4 preferred) with direct audit experience.
Experience in high-growth venture-backed companies (ideally Series B–D stage)
In-depth knowledge of US GAAP, ASC 606, and internal control frameworks
Proven track record of successfully preparing a company for Big 4 audits
Hands-on operational accounting skills with ability to dive into details while managing strategic initiatives
Strong ERP experience (Rillet is a plus) and ability to lead system implementations
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Exceptional organizational skills with ability to manage multiple priorities under tight deadlines
Bonus points if:
Experience in SaaS, technology-enabled services, or subscription-based revenue model
Exposure to IPO readiness
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Advanced Excel and experience with business intelligence tools
Interview Process:
Intro call with Talent Acquisition team
Interview with Hiring Manager
Take-Home Assignment
-
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 - $240,000 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.
Senior Manager, Healthcare Strategy & Operations
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 Senior Manager, Health Strategy & Operations you will own key special projects as we scale our Allied Health portfolio. You will become a subject-matter expert and experiment with solutions that can support profitable, 10x growth in active students. In this role, you will work cross-functionally with Learning, Product, Sales, Customer Success, and other Operations teams. You will be responsible for building a key pillar of Stepful’s growth story.
This role reports to our SVP, Growth.
What you’ll do:
-
Program Performance & Execution Support
Support program performance by driving execution against agreed-upon goals related to profitability, margin, and unit economics
Partner with functional leaders to build and maintain program-level scorecards, including financial and qualitative metrics
Execute against a program roadmap defined with the SVP of Growth, while surfacing insights, risks, and opportunities to inform prioritization and decision-making
Identify gaps in performance and works with cross-functional partners to drive improvements
Contribute to the development of business cases for program initiatives, investments, or optimizations
-
Cross-Functional Coordination & Alignment
Facilitate coordination across Sales, CS, Learning, and Ops to ensure teams are aligned on program priorities
Support integrated planning processes across functions to drive cohesive execution
Identify and escalates risks, misalignment, or tradeoffs impacting program outcomes
Help drive accountability across teams for delivering against shared goals
-
Stakeholder Management & Communication
Support coordination with instructors, SMEs, and other stakeholders for key initiatives and B2B opportunities
Prepare program performance updates, risks, and insights for senior leadership reviews
Partner with leadership on external stakeholder interactions (e.g., accreditors, regulators, trade associations)
Contribute program insights to resource allocation and prioritization discussions
What you’ll bring:
You have 7+ years of experience, including in an operational role at a high-growth startup
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
Bonus points if:
You’ve worked in EdTech or HealthTech
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 $170,000 - $185,000, 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.
Teacher (Primer Leader) | Alabama
Teacher (Primer Leader) | Florida
Market Manager - Houston, Texas
Senior GTM Strategy Manager, Allied Health
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 Senior GTM Strategy Manager, you will own key special projects as we scale our Allied Health portfolio. You will become a subject-matter expert and experiment with solutions that can support profitable, 10x growth in active students. In this role, you will work cross-functionally with Learning, Product, Sales, Customer Success, and other Operations teams. You will be responsible for building a key pillar of Stepful’s growth story.
This role reports to our SVP, Growth.
What you’ll do:
-
Program Performance & Execution Support
Support program performance by driving execution against agreed-upon goals related to profitability, margin, and unit economics
Partner with functional leaders to build and maintain program-level scorecards, including financial and qualitative metrics
Execute against a program roadmap defined with the SVP of Growth, while surfacing insights, risks, and opportunities to inform prioritization and decision-making
Identify gaps in performance and works with cross-functional partners to drive improvements
Contribute to the development of business cases for program initiatives, investments, or optimizations
-
Cross-Functional Coordination & Alignment
Facilitate coordination across Sales, CS, Learning, and Ops to ensure teams are aligned on program priorities
Support integrated planning processes across functions to drive cohesive execution
Identify and escalates risks, misalignment, or tradeoffs impacting program outcomes
Help drive accountability across teams for delivering against shared goals
-
Stakeholder Management & Communication
Support coordination with instructors, SMEs, and other stakeholders for key initiatives and B2B opportunities
Prepare program performance updates, risks, and insights for senior leadership reviews
Partner with leadership on external stakeholder interactions (e.g., accreditors, regulators, trade associations)
Contribute program insights to resource allocation and prioritization discussions
What you’ll bring:
You have 7+ years of experience, including in an operational role at a high-growth startup
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
Bonus points if:
You’ve worked in EdTech or HealthTech
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 $170,000 - $185,000, 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.
Admissions Representative
Senior Engagement Manager, Client Success
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 a Senior Engagement Manager you will be responsible for overseeing a portfolio of Stepful for Business clients, ensuring successful delivery of our healthcare training programs and driving key commercial outcomes, including program adoption and renewals. You will manage the client relationships, deeply understanding their needs and acting as a thought partner in helping them achieve their talent goals.
In this role, you’ll serve as the primary point of contact for your clients, addressing their needs, tracking key performance metrics, and ensuring program success. You’ll collaborate with internal teams to deliver on learning outcomes, while proactively identifying opportunities to expand Stepful’s impact within each client organization.
What you’ll do:
In this role, you can expect to:
Serve as the primary client point of contact, building strong client relationships and addressing concerns effectively
Develop and manage delivery of Stepful's programs, collaborating with internal teams to ensure strong outcomes and high client satisfaction
Monitor key program metrics, including commercial outcomes (e.g., seat activations) and learning outcomes, and identify and take action to address any issues that may impact them
Own contract renewals and identify and pursue expansion opportunities (in partnership with sales)
Translate client needs into actionable account strategies, outlining clear success roadmaps that meet both Stepful’s commercial objectives and the client's strategic and talent goals
Become a trusted advisor to clients by deeply understanding their needs, providing thought partnership and insights, and delivering key initiatives that position Stepful as their most valuable partner
Act as a client advocate, providing feedback to internal teams on how we can evolve our solution and operations to better serve our employer partners
What you’ll bring:
You have proven experience independently managing senior client relationships at large, complex organization – building trust, understanding needs, managing difficult conversations, and influencing clients
You have very strong project management skills, with the ability to manage complex programs and multiple stakeholders
You have strong commercial acumen – a knack for understanding opportunities to better serve a client, and the ability to influence toward deepening a partnership
You love operating both at both the “big picture” and “detailed” altitudes – you can think strategically, and execute to bring that vision to life
You are very comfortable analyzing data and tracking to track progress and drive decision making
You have excellent verbal and written (e.g., client-ready slides, emails) communication skills
Bonus points if:
You have worked in management consulting or a B2B go-to-market role (e.g., solutions consulting, account management, client success, sales, business development, strategic partnerships)
Experience working in education, talent/workforce development, healthcare, or B2B tech-enabled services companies
You are excited to help build a new function – partnering to evolve our ways of working, systems, and tools
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 $145,000 - $165,000, and is part of a competitive total rewards package including a performance-based cash bonus, 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.
Practical Nursing Adjunct Instructor - Virtual Didactic (Evenings)
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 experienced and passionate Adjunct Instructors to join Stepful’s bench of virtual educators supporting the synchronous didactic portion of our Board of Nursing–approved Practical Nursing program in the state of Ohio. In this role, you will support student success by delivering engaging online instruction that helps prepare future nurses for clinical practice and licensure.
This role is ideal for educators who are interested in supporting existing cohorts as substitute adjunct instructors when coverage is needed, while also being considered for future cohort teaching opportunities as new classes launch.
This opportunity is well suited for a Registered Nurse with faculty experience in RN or LPN education who enjoys teaching in a virtual classroom environment. Didactic courses take place Monday–Thursday from 4:30-7:00pm or 6:30–9:00pm EST.
This is a 1099 contract role, with hours varying based on the number of courses taught.
What you’ll do:
Teach live, virtual didactic lessons via Stepful’s LMS
Deliver curriculum content, answer student questions, and provide timely feedback
Act as a subject matter expert in practical nursing education
Foster a positive and supportive learning environment for students
What you’ll bring:
2+ years of experience as faculty in an RN or LPN education program
2+ years of professional experience as a Registered Nurse, with 5+ years of varied nursing experience across clinical practice, nursing education, and/or administration
Bachelor’s degree in Nursing (BSN)
Active, unencumbered Ohio RN license
Ability to collaborate effectively with faculty, staff, students, and external partners
Interview Process:
Intro Call with Talent Team
Case Study Assignment
Final Interview
The hourly pay rate for this opportunity is $50.00/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.
The full posting opens here — pay, setting and the full description, without leaving the list.