New York, New York, United States · Hybrid
$90k–$120k/yr
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 wo…
Skills: Calendar Management, Executive Support, Travel Coordination, Expense Reporting, Event Planning
New York, New York, United States · Hybrid
$100k–$130k/yr
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 wo…
Skills: Program Management, Curriculum Development, Instructional Design, Data Analysis, Online Pedagogy
New York, New York, United States · Hybrid
$140k–$160k/yr
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 he…
Skills: Paid Media Strategy, Meta Ads, Google Ads, YouTube Ads, CAC Optimization
New York, New York, United States · Hybrid
$100k–$120k/yr
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 he…
Skills: Revenue Operations, HubSpot Administration, Data Analysis, Financial Forecasting, CRM Management
Columbus, Ohio, United States · Remote Solely
$50/hr–$50/hr
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 he…
Skills: Online Instruction, Curriculum Delivery, Practical Nursing Education, Student Mentorship, Virtual Classroom Management
New York, New York, United States · Hybrid
$145k–$165k/yr
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 he…
Skills: Client Relationship Management, Project Management, Commercial Acumen, Data Analysis, Strategic Planning
Columbus, Ohio, United States · On-site
$100k–$125k/yr
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 he…
Skills: Nursing Education, Curriculum Development, Clinical Instruction, Regulatory Compliance, Student Success Management
Columbus, Ohio, United States · On-site
$50/hr–$50/hr
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 he…
Skills: Clinical Supervision, Nursing Education, Skills Lab Instruction, Student Mentoring, Curriculum Delivery
New York, New York, United States · Hybrid
$75/hr–$75/hr
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 he…
Skills: Full-cycle Recruiting, Sourcing, Candidate Experience, Stakeholder Management, Pipeline Management
New York, New York, United States · Hybrid
$180k–$210k/yr
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 he…
Skills: Curriculum Development, Instructional Design, Academic Program Management, Education Operations, Learning Strategy
New York, New York, United States · Hybrid
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 he…
Skills: Lifecycle Marketing, Growth Automation, Customer Engagement, Workflow Design, CRM Management
New York, New York, United States · Hybrid
$191k–$254k/yr
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 he…
Skills: B2B Product Management, Product Strategy, Roadmap Ownership, Stakeholder Management, SQL
St. Louis, Missouri, United States · Hybrid
$110k–$120k/yr
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 he…
Skills: HRIS Administration, Payroll Operations, Workforce Lifecycle Management, Rippling, Employee Relations
New York, New York, United States · Hybrid
$138k–$174k/yr
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 he…
Skills: Operations Management, Data Analysis, Team Leadership, Career Coaching, Job Placement
New York, New York, United States · Hybrid
$180k–$210k/yr
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 he…
Skills: Learning Strategy, Curriculum Development, Instructional Design, Academic Program Management, Education Operations
New York, New York, United States · Hybrid
$80k–$100k/yr
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 he…
Skills: Legal Operations, Project Management, Regulatory Compliance, AI Implementation, Information Management
New York, New York, United States · Hybrid
$180k–$210k/yr
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 he…
Skills: Operational Leadership, Strategic Planning, Cross-functional Collaboration, Analytical Problem Solving, Program Delivery
New York, New York, United States · Remote OK
$190k–$220k/yr
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 he…
Skills: Clinical Strategy, Nursing Leadership, Stakeholder Management, Go-To-Market Strategy, Clinical Validation
Columbus, Ohio, United States · On-site
$50/hr–$50/hr
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 he…
Skills: Clinical Supervision, Nursing Education, Curriculum Delivery, Student Mentorship, Practical Nursing
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The role serves as the operational backbone for the CEO and Co-Founder, managing complex calendars, travel, and high-volume scheduling. Additionally, the assistant handles sensitive communications, coordinates leadership offsites, and partners with the Chief of Staff to track action items.
Candidates must have over 6 years of experience supporting C-level leaders with a proven track record in logistics and calendar management. Proficiency in modern productivity tools like Google Workspace and Slack, along with a proactive mindset, is required.
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 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.
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.
As we prepare for our next phase of growth, we're hiring an experienced Senior Executive Assistant to be the operational backbone of our executive team. This is a high-trust, high-autonomy role for someone who anticipates needs before they're voiced, protects our leaders' time, and keeps the details moving so the business can move faster.
This role reports directly to the CEO and additionally supports our Co-Founder while working closely with the executive team, Chief of Staff, and People and Operations across the organization. You'll be a force multiplier for the people setting Stepful's direction.
This is a hybrid opportunity based out of our NYC office, requiring three days/week (Tuesday, Wednesday, Thursday) in office.
Own complex, ever-changing calendars for the CEO and executive team, resolving competing priorities and protecting time for what matters most.
Manage high-volume scheduling across time zones, including internal meetings, external partner sessions, board interactions, and interviews.
Coordinate domestic and international travel end to end—flights, hotels, ground transport, and detailed itineraries.
Prepare and process expense reports, reconciliations, and reimbursements with accuracy and on time.
Plan and execute leadership offsites, team events, and board meeting logistics from concept through day-of run of show.
Draft, proofread, and manage sensitive communications and documents on behalf of executives, handling confidential information with discretion.
Partner with the Chief of Staff to prepare agendas, track action items, and follow up on decisions across leadership meetings.
Serve as a welcoming, organized point of contact for internal teams and external partners interacting with the executive office.
Drive ad hoc projects and process improvements that make the executive team more effective.
6+ years of executive assistant or administrative experience, including direct support of C-level leaders.
Proven ability to manage complex calendars, travel, and logistics in a fast-moving environment.
Exceptional organizational skills and meticulous attention to detail—nothing slips through the cracks.
Strong written and verbal communication skills, with sound judgment about tone and audience.
Discretion and integrity when handling confidential and sensitive information.
A proactive, resourceful mindset—you anticipate needs, solve problems independently, and thrive amid ambiguity and shifting priorities.
Fluency with modern productivity tools (Google Workspace, Slack, and expense/travel platforms).
You've worked in EdTech, healthcare, or another mission-driven industry.
You've supported a founder or CEO at a high-growth startup.
Introductory call with Talent Acquisition team member
Interview with Hiring Manager
Take-Home Assignment
Virtual Panel Interview
On-Site Panel Interview
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 $100,000 - $150,000, 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.
Stepful Healthcare Staffing & Training Solutions
Our mission is to empower communities with accessible pathways to healthcare careers, regardless of background or circumstance. Our healthcare staffing programs are designed to fill vacancies quickly and reduce hiring costs. We also provide medical career advancement training. Stepful specializes in training and placing healthcare professionals in various healthcare roles, including Medical Assistants, Coders & Billers, Pharma Techs, EKGs, and Phlebotomists.
Offices: 550 West 45th Street, New York, New York 10036, US
Stepful Healthcare Staffing & Training Solutions
Our mission is to empower communities with accessible pathways to healthcare careers, regardless of background or circumstance. Our healthcare staffing programs are designed to fill vacancies quickly and reduce hiring costs. We also provide medical career advancement training. Stepful specializes in training and placing healthcare professionals in various healthcare roles, including Medical Assistants, Coders & Billers, Pharma Techs, EKGs, and Phlebotomists.
Offices: 550 West 45th Street, New York, New York 10036, US