Chief of Staff

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
• Drive cross-functional special projects end to end
• Owes 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
• Lead 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
• Making and communicating Stepful's social impact to investors
• 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
• A highly analytical approach, 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