Chief of Staff

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About the Opportunity

The company is the top-performing AI Shopping Agent, delivering the best products from across the web with unmatched accuracy, quality, and trust.

The Role

The organization is looking for a Chief of Staff to the CEO who can manage the CEO’s priorities 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, nor is it a purely strategic one.

This individual will serve as the CEO’s right hand, her early warning system, and her force multiplier. If the CEO is in a room, this person will either be in it or will have already prepared her for it. If an action item leaves a meeting, this person will 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.

What You’ll Do

• 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 point of view on what deserves her time, what doesn’t, and what can be delegated. Coordinate her involvement in internal and external events.
• Prepare the CEO 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.

What Success Looks like

• The individual knows the CEO’s priorities, communication style, and working preferences thoroughly.
• The weekly executive sync is managed end-to-end. Every direct report knows the individual and knows they will follow up.
• The CEO’s inbox and calendar reflect her actual priorities.

Ideal Background

• 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; experience managing up, across, and down without relying on formal authority.
• Exceptional writer, able to draft clearly and quickly, and adapt their voice to represent someone else at the executive level.
• Experience building polished presentations for executive and board-level audiences.
• High judgment and discretion when handling sensitive information about people, strategy, and the business.
• Ability to build lightweight systems to track what matters and ensure nothing slips through the cracks.

Compensation & Benefits

The expected base salary range for this role is $155,000-$200,000 USD, and will vary based on skills, experience, role level, and geographic location. Final compensation will be determined by considering these factors alongside overall role scope and responsibilities.

In addition to base salary, the company offers:

• Equity in the form of stock options.
• Medical, dental, and vision coverage.
• 401(k) plan.
• Flexible PTO and company holidays.
• Fully remote work within the United States.
• Periodic company offsites and team gatherings.

The company is committed to fair, transparent, and competitive compensation practices.