Chief of Staff, New Verticals

In this role, you will act as a strategic operator and execution partner for the development and scaling of new business verticals, ensuring alignment between strategy, experimentation, and operational delivery. Your responsibilities will include:

• Driving the end-to-end strategy and execution of new vertical initiatives, including early-stage testing, scaling frameworks, and performance evaluation.
• Designing and running experiment pipelines to identify effective client acquisition and growth channels, including partnerships, outreach models, and paid acquisition tests.
• Building and iterating user-facing intake and onboarding workflows to improve conversion, qualification, and user experience.
• Developing structured frameworks to evaluate and prioritize new business opportunities, including market analysis and strategic sequencing of vertical expansion.
• Partnering with cross-functional leaders to translate ambiguous problems into structured plans, data-driven insights, and actionable solutions.
• Leading high-priority initiatives with direct visibility to senior leadership, ensuring alignment, accountability, and execution quality.
• Contributing to organizational design and operational systems that support scaling new lines of business effectively.

Requirements

The ideal candidate is a strategic thinker and hands-on operator who thrives in fast-moving, ambiguous environments and is comfortable building from the ground up. You should bring strong leadership experience, analytical rigor, and a passion for solving complex, real-world problems. Key qualifications include:

• Proven experience making high-stakes strategic decisions and prioritizing across competing business initiatives.
• Experience leading teams of high-performing individual contributors, ideally in cross-functional settings.
• Strong ability to analyze complex systems, structure ambiguous problems, and translate insights into actionable strategies.
• Hands-on experience designing and executing projects involving data analysis, experimentation, and operational implementation.
• Excellent communication skills with the ability to influence stakeholders and build alignment across teams.
• Demonstrated leadership presence with a collaborative, empathetic approach to team building and culture.
• Strong motivation to contribute to meaningful, mission-driven work that supports people in critical life situations.
• Bonus: Experience in marketplace businesses or complex consumer services (e.g., insurance, fintech, healthcare, real estate), or exposure to customer research and user empathy work.

Benefits

• Competitive base salary range of $160,000–$180,000, plus equity
• Fully remote work with flexibility and autonomy
• Comprehensive medical and dental insurance, with 100% of employee and dependent premiums covered
• Generous paid time off, including ~15 vacation days and ~20 holidays annually
• End-of-year company shutdown period for rest and recharge
• Free OneMedical membership
• Annual stipends for internet, education, and training
• Student loan repayment assistance up to $1,200/year
• 401(k) plan with optional HSA/FSA
• Regular in-person offsites and quarterly travel for collaboration and team building
• Mission-driven environment focused on meaningful social impact