Director, Chief of Staff

Wrapbook

1d•Remote

About The Position

Wrapbook is looking for a Director, Chief of Staff to serve as a strategic partner to our CEO and Senior Leadership Team. This is a high-impact role for someone who wants to operate at the center of company strategy and execution. You’ll help drive company priorities, lead critical cross-functional initiatives, and ensure our leadership team is aligned and moving quickly. We’re looking for an operator — someone with strong business acumen who understands complex industries, builds strong points of view, turns ambiguity into clarity, and drives work forward.

Requirements

7+ years of experience in a high-performance environment (consulting, banking, operating role, etc.).
A systems-level thinker who leverages AI as a force multiplier in planning, analysis, and executive workflows.
Demonstrated experience owning complex, cross-functional initiatives.
Strong analytical skills and business judgment.
Ability to form independent points of view and make clear recommendations.
Excellent, executive-level written and verbal communication skills.
High agency, curiosity, and a bias toward action.
Comfort working directly with senior leaders and navigating ambiguity.

Responsibilities

Be AI Native
Use AI as a core operating tool — not a supplement.
Own and evolve the CEO's AI-powered operating system.
Build and maintain agentic workflows that extend the CEO's and SLT's leverage.
Be a force multiplier for the company's AI adoption: model best practices, share what works, and help the broader organization develop fluency with AI tools and workflows.
Stay on the frontier. Continuously evaluate new AI tools, techniques, and capabilities — and translate what's relevant into practical leverage for the CEO and leadership team.
Strategic Partner to the CEO
Develop a deep understanding of Wrapbook’s business, priorities, and operating model.
Synthesize information from across the company, escalating the most urgent items to the CEO and creating clear recommendations.
Help shape and clarify company-level strategy and priorities.
Proactively identify risks, gaps, and opportunities.
Leverage AI and emerging tools to increase executive and company-wide leverage - improving synthesis, decision-making speed, and operating efficiency.
Drive Cross-Functional Outcomes
Own and lead high-priority, cross-functional initiatives from scoping through execution.
Align stakeholders, clarify decision-making, remove blockers and ensure follow-through.
Step into ambiguous areas and create structure where needed.
Improve How We Operate
Own company-level planning and communication processes (annual planning, OKRs, MBRs, All Hands).
Design and facilitate leadership meetings that drive clear decisions and accountability.
Continuously improve operating rhythms and cross-team coordination.