Chief of Staff

About Stepful

Stepful is transforming allied healthcare education by providing affordable, online, instructor-led, and AI-assisted programs that enable learners from diverse backgrounds to start careers in healthcare fields with high demand. Beyond direct consumer training, Stepful collaborates with leading healthcare organizations to help mitigate the nationwide shortage of healthcare professionals. Our alumni, who become Medical Assistants, Pharmacy Technicians, Nurses, and more, support employment pipelines at top organizations such as CVS, NY-Presbyterian, HCA, Providence, and Walgreens. Backed by investors including Y Combinator, Reach Capital, AlleyCorp, and Oak HC/FT, and recognized as the #1 EdTech firm in the U.S. by TIME for 2025, Stepful is dedicated to expanding access to quality healthcare services and career opportunities for underserved communities.

Our Core Values

• Care first: Dedicated to doing everything possible to support our students' success.
• Learn quickly: Employing data-driven experimentation and iterative approaches.
• Build together: Success is achieved through teamwork and collaboration.
• Own it: Demonstrating initiative, accountability, and pride in all endeavors.

Role Overview

The Chief of Staff will be a trusted advisor to Stepful’s founders, acting as their operational right hand. This position focuses on managing cross-functional challenges, streamlining leadership focus, and accelerating company growth. Responsibilities include maintaining alignment through operating rhythms, overseeing planning cadences, managing leadership communications, and leading high-impact special projects. Flexibility and self-direction are essential due to the role's dynamic nature. The position reports directly to the CEO and is based onsite in New York City’s SoHo district.

Key Responsibilities

• Collaborate closely with co-founders and leadership to maintain an overview of major initiatives and organizational wellbeing, proactively identifying risks, trade-offs, and opportunities to facilitate informed decisions.
• Represent leadership perspectives accurately and manage confidential information with integrity.
• Organize agendas and ensure follow-through on critical leadership tasks to optimize executive time usage.
• Manage Stepful’s operating framework, including translating strategic decisions into clear communications for the entire staff, running business reviews, and overseeing KPI tracking in partnership with Finance.
• Prepare materials for executive leadership, board members, and investors by compiling data analysis for regular updates and presentations.
• Lead comprehensive, cross-departmental projects—from scoping to execution—across teams like Learning & Operations, Growth, Product, and Sales/Workforce Solutions.
• Analyze data and workflows to derive actionable insights; personally develop analytical frameworks as necessary.
• Support external and partner relations on behalf of leadership.
• Coordinate company-wide events that promote culture and celebrate successes, working with HR partners to organize initiatives such as the annual Stepfest offsite.

Examples of Past Projects

• Developing strategic partnerships to broaden career pathways for students.
• Launching new growth channels that generate revenue.
• Measuring and conveying Stepful’s social impact for investors.
• Implementing AI tools internally to enhance productivity.

Qualifications

• At least 5 years of professional experience in consulting, business operations, or comparable roles within fast-growing startups.
• Strong analytical skills with a structured approach to resolving ambiguous challenges and comfort working directly with data.
• Exceptional written and oral communication skills, capable of engaging senior and external stakeholders clearly and persuasively.
• Effective collaborator who influences and coordinates across diverse teams and organizational levels.
• Demonstrated sound judgment and discretion when handling sensitive information.
• Entrepreneurial mindset with a proactive attitude, accountability for results, and commitment to high-quality execution.
• Ability to adapt and thrive in rapidly evolving and uncertain environments, learning swiftly through experimentation.
• Deep passion for Stepful’s mission of expanding healthcare career access for those from all backgrounds and circumstances.

Recruitment Process

• Initial screening interview with recruiter.
• Introductory discussion with current Chief of Staff.
• Completion and presentation of a take-home assignment.
• Onsite interview at Stepful’s SoHo office in New York City.

Compensation and Equal Opportunity

The salary for this position ranges from $140,000 to $160,000 annually. Stepful is committed to diversity, equity, and inclusion, and is proud to be an equal opportunity employer. Discrimination based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability, or any legally protected characteristic is strictly prohibited.