Chief of Staff

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.

Responsibilities

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; Run the company’s operating system (Rhythm of Business); Translate leadership decisions and priorities into clear, actionable communication for the broader team; Facilitate quarterly and annual planning; Track company-wide KPIs and maintain the systems behind them; Lead executive, board, and investor communications; Draft Board materials and monthly investor updates; Drive cross-functional special projects end to end; Own high-impact, cross-functional initiatives from problem definition through execution; Support leadership on select external and partner relationships; Set direction for company-wide events that celebrate wins and strengthen culture

Requirements

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.