Chief of Staff

Role Overview

• 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)

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.

Benefits

• Offers Equity