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 Chief of Staff, you will act as a trusted advisor and the operating right hand to Stepful’s co-founders, owning cross-functional problems and helping the leadership team run the company with focus, speed, and clarity as we scale. You will own the systems that keep the organization aligned (our rhythm of business, planning cadences, and leadership communications) while driving high-priority special projects. Rather than a fixed set of tasks, you will handle complex, evolving challenges, so success requires self-direction and the ability to create value without constant oversight.

This role reports directly to the CEO.

What you'll do

Act as a trusted partner to the co-founders and leadership team

• Maintain a bird’s-eye view of key initiatives and organizational health across Stepful; proactively surface risks, tradeoffs, and opportunities to leadership and drive teams to clear decisions

• Represent leadership’s thinking accurately and handle confidential information with sound judgment

• Set agendas and follow up on action items so leadership time is spent on the highest-priority items

Run the company’s operating system (“Rhythm of Business”)

• Translate leadership decisions and priorities into clear, actionable communication for the broader team (e.g., All Hands for both full-time and contractor teams)

• Facilitate quarterly and annual planning: Own and continuously improve Stepful’s core operating cadences (Monthly and Quarterly Business Reviews)

• Track company-wide KPIs and maintain the systems behind them, partnering with Finance to keep leadership’s source of truth accurate and up to date

Lead executive, board, and investor communications

• Draft Board materials and monthly investor updates, assembling the underlying data analysis

• Capture and communicate the state of the business clearly and concisely for both internal and external audiences

Drive cross-functional special projects end to end

• Own high-impact, cross-functional initiatives from problem definition through execution, working across teams like Learning & Operations, Growth, Product, Sales/Workforce Solutions, and more

• Dive into data and processes to find the insight that matters and turn it into action; build the analysis yourself where needed

• Support leadership on select external and partner relationships

• Set direction for company-wide events that celebrate wins and strengthen culture, partnering with the Employee Experience Manager to bring them to life (e.g., now-annual company-wide Stepfest offsite)

Examples of past special projects: Building strategic partnerships to expand student career opportunities; opening a new revenue-driving growth channel; measuring and communicating Stepful's social impact to investors; and rolling out internal AI tooling to improve productivity.

What you’ll bring

• 5+ years of experience, including in consulting, business operations, or a similar role at a high-growth startup.

• Highly analytical, with a structured approach to breaking down ambiguous problems; comfortable working directly with data

• Excellent written and verbal communication: clear, concise, and credible with senior and external audiences

• A strong collaborator who leads through influence and coordinates diverse stakeholders across levels and functions

• Sound judgment and discretion with confidential and sensitive information

• An owner’s mindset: you take initiative, drive work to outcomes, and hold a high bar for execution

• You thrive in a fast-paced, ambiguous environment and learn quickly through experimentation

• Passionate about Stepful’s mission: Empowering communities with accessible pathways to healthcare careers, regardless of background or circumstance.

ABOUT THE INTERVIEW

• Step 1: Screening Call with Recruiter

• Step 2: Intro Call with Current Chief of Staff

• Step 3: Take-home assignment & presentation

• Step 4: Onsite interview at office in SoHo, NYC

COMPENSATION
Base Salary: $140K - $160K

At Stepful, we're an equal opportunity employer and value diversity at our company. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

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.