Chief of Staff

Stepful

Chief of Staff acting as a trusted advisor to Stepful’s co-founders. Overseeing key initiatives, managing special projects, and ensuring organizational alignment as the company scales.

Posted 7/15/2026full-timeNew York City • New York • 🇺🇸 United StatesLead💰 $140,000 - $160,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates strong analytical skills and the ability to translate leadership decisions into actionable communication. Proven experience in managing cross-functional initiatives and maintaining organizational health through effective tracking of KPIs and strategic planning.

Highest-signal resume keywords

5+ Years Experience In ConsultingBusiness OperationsHighly AnalyticalExcellent Written And Verbal CommunicationCross-Functional Collaboration

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Data AnalysisKPI TrackingProject ManagementStrategic PlanningBusiness Review Facilitation

Soft Skills

Sound JudgmentCollaborationInitiativeAdaptabilityInfluence

Tools & Technologies

Rhythm Of BusinessBoard Materials PreparationInvestor Communication

Industry Keywords

High-Growth StartupHealthcare CareersOrganizational HealthStakeholder CoordinationEmployee Experience

About the role

Key responsibilities & impact

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

What you’ll need

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

Comp & perks

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