Chief of Staff Director, People

Role Overview

Chief of Staff Director, People for a leader in the Finance & Insurance space. This role advances people and talent initiatives to strengthen organizational effectiveness, leadership capability, and employee experience in a regulated financial services environment.

Remote role for US-based candidates only.

Responsibilities

• Serve as a thought partner to the Chief People Officer (CPO), evaluating priorities and trade-offs
• Articulate the People organization’s strategy and impact to a range of stakeholders
• Drive execution of People team initiatives while maintaining leader alignment
• Manage organizational rhythms (meetings, planning sessions) to support effective decision-making
• Create high-quality presentations and executive updates for the CPO
• Facilitate communication and collaboration across the People leadership team
• Lead special projects from inception through completion, ensuring stakeholder alignment
• Represent CPO priorities in cross-functional discussions and decisions

Requirements

• 10+ years of experience in business management or HR/People strategy (preferably high-growth tech or fintech)
• Deep understanding of People organization functions and how they interconnect operationally
• Experience serving as a strategic partner/advisor to executive leadership (especially CPO/senior leaders)
• Strong storytelling skills to turn complex information into clear narratives
• Self-directed, high judgment and discretion suited to a senior executive context
• Strong analytical and problem-solving abilities in ambiguous situations
• Excellent communication skills; ability to influence without authority and articulate succinctly
• Ability to use AI tools to produce executive-ready content

Nice to Haves

• Experience specifically in scaled people operations and culture/talent strategy (implied by scope)

Benefits

• 100% subsidized medical, dental, and vision coverage for you and dependents
• Generous stipends for technology, food, lifestyle needs, and family planning expenses
• Competitive vacation and holiday schedule
• Employee Stock Purchase Plan (discounted)

Location & Work Eligibility

• Remote; candidates must be US-based only
• No visa sponsorship available