Chief of Staff

About Stepful

Stepful is a workforce platform transforming how major American health systems recruit, train, and keep their talent. Founded in 2021, we have trained over 32,000 ready-to-work healthcare professionals. We partner with leading health institutions to combat the national shortage of healthcare workers and enhance access to quality healthcare and educational career paths nationwide. Our talent pipelines serve leading employers such as NY-Presbyterian, Mt. Sinai, HCA, Providence, CVS, and Walgreens, and we collaborate with half of the top 10 US health systems.

Backed by Y Combinator, Reach Capital, AlleyCorp, and a recent $55M Series C led by Oak HC/FT, we were recognized as the top EdTech company in the US by TIME for 2025.

Our Values

• Put care first to ensure our students succeed.
• Learn quickly through testing, data, and iteration.
• Build collaboratively, relying on each other for success.
• Own initiatives by taking pride and showing initiative.

Role Overview

As Chief of Staff, you will be a trusted advisor and operational right hand to the co-founders, managing cross-functional challenges, and helping align and accelerate the leadership team’s initiatives. You will oversee organizational systems such as operating rhythms, planning cycles, and communication channels to maintain focus during rapid growth. This dynamic role requires self-motivation and adaptability to complex, evolving priorities.

Key Responsibilities

• Serve as a strategic partner to co-founders and leadership by monitoring major initiatives and organizational health; proactively identify risks and opportunities for leadership decisions.
• Accurately represent leadership perspectives and handle confidential information with discretion.
• Manage leadership time by setting agendas and ensuring follow-up on action items to focus on priorities.
• Oversee the company’s operating system by translating leadership decisions into clear communication for the entire team.
• Coordinate quarterly and annual business planning, improving core operating cadences such as Monthly and Quarterly Business Reviews.
• Maintain and track company-wide KPIs, collaborating with finance to ensure data accuracy.
• Lead communications for executives, board, and investors by preparing board materials and monthly updates based on data analysis.
• Manage end-to-end cross-functional special projects spanning Learning & Operations, Growth, Product, Sales, and other teams.
• Conduct data-driven analyses to uncover insights and guide actionable results.
• Support leadership with select external and partnership relationships.
• Plan and direct company-wide events that celebrate achievements and enhance culture, working closely with the Employee Experience Manager (e.g., the annual Stepfest offsite).

Examples of Past Projects

• Developing strategic partnerships to broaden student career pathways.
• Launching new revenue channels that support growth.
• Measuring and reporting Stepful's social impact for investors.
• Implementing internal AI tools to boost productivity.

Candidate Profile

• Minimum 5 years of experience in consulting, business operations, or a similar role within a high-growth startup environment.
• Strong analytical skills with the ability to decompose ambiguous problems and work directly with data.
• Exceptional written and verbal communication, able to clearly and credibly convey information to senior and external stakeholders.
• Collaborative leader skilled at influencing and orchestrating diverse stakeholders across organizational levels.
• Exemplary judgment and integrity when handling sensitive and confidential information.
• Proactive ownership mentality, driving initiatives to completion with a high standard of quality.
• Comfort thriving in fast-paced, uncertain environments and eager to learn through experimentation.
• Deeply committed to Stepful's mission of empowering communities by providing accessible healthcare career pathways regardless of background.

Interview Process

• Initial recruiter screening call
• Introductory conversation with the current Chief of Staff
• Take-home assignment followed by presentation
• Onsite interview at the SoHo office in New York City

Compensation and Equal Opportunity

The base salary for this role ranges between $140,000 and $160,000 annually. Stepful values diversity and is an equal opportunity employer, prohibiting discrimination based on a wide range of legally protected characteristics including race, gender, age, disability, and more.