The Calendar Group
The Calendar Group is a full-service staffing firm which provides professional and personalized staffing to high net worth families,
- Open roles
- 104
- New role every
- ~1.1 days
- Posting trend
- 3.2× vs prior 90d
Company signals
Score: 77Job facts
- Location
- Miami, Florida, United States of America
- Type
- Full-time
- Posted
- Aug 25, 2026
Last verified live 1 month, 1 week ago · checked directly on the company's JazzHR / ApplyToJob
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Head of Operations- Miami, Florida
at The Calendar Group
A media and entertainment brand is seeking a highly driven Head of Operations to serve as the Founder's operational right hand and help lead the company through its next stage of growth. This is a hands-on leadership role within a lean, founder-led organization. The successful candidate will take ownership of day-to-day operations, build and develop the team, establish scalable systems, create accountability, and ensure priorities move forward. The ideal candidate combines strong operational discipline with a startup mentality and is energized by building an organization.
Responsibilities
- Serve as the Founder's operational right hand and primary execution partner.
- Translate ideas and priorities into structured plans, timelines, and deliverables.
- Build scalable systems, workflows, SOPs, reporting structures, and communication rhythms.
- Establish clear priorities, ownership, timelines, and accountability across the organization.
- Define roles, responsibilities, KPIs, and reporting relationships.
- Identify hiring needs and lead recruiting, interviewing, onboarding, and employee development.
- Manage and develop employees while creating a culture of ownership, communication, and follow-through.
- Maintain operational visibility across content production and post-production.
- Ensure projects are properly planned, staffed, budgeted, scheduled, and executed.
- Collaborate with internal production teams and outside vendors to prevent delays and operational breakdowns.
- Evaluate new business opportunities and turn Founder-led ideas into actionable plans.
- Help expand and diversify revenue through partnerships, products, intellectual property, live experiences, and other ventures.
- Partner with accounting, finance, legal, and other external advisers.
- Establish and monitor company, departmental, and project budgets.
- Support forecasting, financial reporting, and operating plans.
- Review spending, identify opportunities to improve efficiency, and negotiate with vendors and partners when appropriate.
- Reduce the Founder's involvement in day-to-day management so they can focus on content, creative direction, brand growth, and major opportunities.
Qualifications
- 8+ years of experience in operations, business management, or organizational leadership.
- Demonstrated success building teams, systems, and processes within a founder-led, entrepreneurial, or high-growth organization.
- Strong experience in team leadership, recruiting, project management, and organizational development.
- Experience managing budgets and working with finance, accounting, legal, and external partners.
- Proven ability to turn loosely defined ideas into structured plans and measurable results.
- Media, entertainment, digital content, creator economy, production, consumer brand, or startup experience strongly preferred.
- Based in Miami and willing to travel occasionally.
Compensation: 150,000-175,000, depending on experience.