Chief of Staff

Wizard

15h•$155,000 - $200,000•Remote

About The Position

Wizard is the top-performing AI Shopping Agent, delivering the best products from across the web with unmatched accuracy, quality, and trust. We’re looking for a Chief of Staff to the CEO who can run point on the CEO's world with obsessive follow through and who has the executive presence and judgment to operate as her proxy when needed. This is not a traditional Executive Assistant role — and it's not a purely strategic one either. You are the CEO’s right hand, her early warning system, and her force multiplier. If she's in a room, you're either in it or you've already prepared her for it. If an action item leaves a meeting, you own making sure it gets done. This role is ideal for someone who is equally comfortable building a board deck, drafting a high stakes email on the CEO's behalf, and relentlessly chasing down a direct report for an overdue update. The role reports directly to the CEO and operates with a high degree of visibility and trust across the organization.

Requirements

4–7 years of experience in a Chief of Staff, executive operations, consulting, or similar high-accountability role — startup or high-growth company experience strongly preferred
Comfortable holding senior people accountable; you've managed up, across, and down without relying on formal authority
Exceptional writer, you draft clearly, quickly, and can adapt your voice to represent someone else at the executive level
Experience building polished presentations for exec and board-level audiences
High judgment and discretion when handling sensitive information about people, strategy, and the business
You build lightweight systems to track what matters and nothing slips through the cracks

Responsibilities

Serve as a trusted extension of the CEO — drafting, responding to, and managing email correspondence on her behalf with sound judgment and her voice
Manage and protect the CEO's calendar with a strong POV on what deserves her time, what doesn't, and what can be delegated. Coordinate her involvement in internal and external events.
Prepare Melissa for every meeting, conversation, and commitment with briefings, context, talking points, and pre-reads
Own follow-up with the CEO's direct reports and executive team on goals, priorities, and commitments, relentlessly and diplomatically
Drive weekly syncs, 1:1 rhythms, and cross-functional check-ins: own the agenda, take the notes, and make sure every action item has an owner and a deadline
Track progress against company and CEO-level goals; surface blockers and delays before they become problems
Build and refine presentations for internal and external audiences (exec team, board, all-hands, etc.)
Identify opportunities to improve how the CEO's office operates and implement lightweight systems to support them