An author is seeking an experienced Chief of Staff to oversee the day-to-day operations of a growing publishing and entertainment business. This role serves as the central hub across publishers, literary agency partners, marketing, publicity, advertising, digital, entertainment, and other collaborators. The Chief of Staff will ensure projects move forward seamlessly, teams are aligned, and the author receives clear, well-vetted recommendations and decision points.

The ideal candidate is operationally strong, highly organized, discreet, and comfortable working behind the scenes to support a creative business.

Key Responsibilities

- Manage the author’s calendar, scheduling, Zoom links, travel coordination, and shifting priorities.
- Serve as the primary point of contact and coordination across publishers, agents, publicists, social media managers, advertising partners, retailers, producers, and other external collaborators.
- Prepare meeting agendas, briefing materials, action items, and concise executive updates.
- Maintain a master calendar for current and future book projects, including traditional publishing and self-published ebook and audiobook releases.
- Track editorial, production, cover reveal, marketing, publicity, advertising, metadata, retailer, and distribution milestones.
- Coordinate launch activity, including website updates, digital listings, pricing changes, cover updates, and release-day troubleshooting.
- Review materials, approvals, deliverables, invoices, and payment requests before escalating to the author; flag anomalies and provide clear context.
- Lead cross-functional check-ins to ensure teams are aligned on priorities, timelines, dependencies, and ownership.
- Keep projects moving by tracking deliverables, assigning action items,



following up with stakeholders, and resolving routine issues independently.
- Supervise two existing assistants, providing direction, prioritization, and oversight while delegating work appropriately.
- Build and improve workflows, trackers, reporting, and systems that create greater clarity, communication, and operational efficiency.
- Support long-range planning for future releases, business initiatives, and entertainment opportunities.
- Protect confidential information and exercise excellent judgment in all communications.

Qualifications

- Significant experience in a Chief of Staff, senior executive assistant, operations, project management, or comparable role.
- Strong background in publishing, digital publishing, book marketing, publicity, or author/creative-brand management.
- Familiarity with both traditional publishing and self-publishing workflows, including digital retailers, metadata, ebook/audiobook launches, and marketing coordination.
- Experience supporting a high-profile principal, founder, executive, or creative professional is strongly preferred.
- Exceptional project-management skills, with the ability to manage many moving parts, priorities, stakeholders, and deadlines.
- Strong financial judgment and comfort reviewing invoices, budgets, and payment requests.
- Excellent written and verbal communication skills,



with the ability to synthesize complex information into concise recommendations.
- High degree of discretion, professionalism, emotional intelligence, and sound judgment.
- Comfortable giving direction, holding teams accountable, and managing up without creating unnecessary friction.
- Adaptable, resourceful, and able to handle shifting priorities and occasional time-sensitive needs.
- Strong sense of humor and a calm, solutions-oriented approach.
- Proficient with Google Workspace and comfortable using project-management and financial tools such as Asana and QuickBooks.

Schedule, Location & Compensation

- Location: Fully remote with travel. Candidates based in the Eastern Time Zone are strongly preferred
- Schedule: Full-time availability during standard business hours, with flexibility for occasional time-sensitive publishing launches, travel, or urgent matters.
- Travel: Occasional travel may be required.
- Compensation: $160,000–$180,000 USD DOE
- Benefits: A healthcare stipend

Pocketbook Agency is acting solely as a recruiting and placement firm for this position and is not the employer of record for this role unless otherwise explicitly stated. All hiring decisions, compensation, benefits, and employment terms are determined by the client employer. By applying, you acknowledge that submission of an application does not guarantee placement or employment. Pocketbook Agency is an equal chance recruiting firm and does not discriminate in its recruiting, screening, or placement practices based on race, color, religion, sex, gender identity, sexual orientation, national origin, age, disability, veteran status, or any other protected characteristic under applicable law.

📌 Chief of Staff (Greater Toronto Area)
🏢 Pocketbook Agency
📍 Greater Toronto Area