Chief of Staff

Company

DropCap (Startup)  

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Experience: 5+ Years  

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Compensation: 90k-110k + Stock Options  

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As Chief of Staff, you will be the CEO’s right hand for execution. You will run weekly meetings, own processes from start to finish, and lead our first major automation project: using AI to streamline how book metadata flows through our systems. The work changes from week to week, and the pace is fast. In a single week you might run a KPI review, plan logistics for an international book fair, and build an AI workflow that takes manual work off the team’s plate.

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What we are looking for

• An entrepreneurial operator who takes ownership of processes and has been trusted with more responsibility, sooner than their peers. Your mindset and track record matter more to us than your industry background, and this role can be a big step up for someone ready to lead.

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Responsibilities

• Plan and lead weekly leadership meetings and other recurring meetings, keep a record of decisions and action items, and follow up until each item is closed.
• Turn company priorities into plans with clear owners, timelines, and checkpoints, and keep them on track.
• Keep the business moving when the CEO is traveling for book fairs and partner meetings.
• Manage cross-functional projects, including recruiting, international expansion, book fair planning, vendor selection, and internal reporting.
• Coordinate with outside partners, including legal counsel and key vendors.
• Define and track company KPIs, and report progress to the CEO and leadership team.
• Prepare presentation materials and pull metrics for the CEO on request.
• Oversee people operations, including hiring logistics, onboarding, benefits administration, and coordination with international employment partners.
• Supervise and develop direct reports.
• Lead our automation work, starting with AI workflows for metadata management, then customer onboarding and other core processes.
• Own the internal tools and systems the team uses to plan and track work.

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Qualifications

• Bachelor’s degree
• 5+ years of experience in operations, project management, or a related role, ideally at a startup or small company
• Hands-on experience implementing AI workflows or agents from end to end, beyond using AI tools to work faster
• Experience supervising staff
• An entrepreneurial mindset: you have owned processes across teams, seen them through, and been given more responsibility faster than your peers
• Operational experience beyond customer-facing work, with results you can measure and share
• Hold yourself to a high standard and are comfortable holding colleagues to their commitments