Head of Operations- Miami, Florida

thecalendargroup; Miami (FL); On-site; USD 150,000 - 175,000; Full time

Job summary

thecalendargroup 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 growth stage. This hands-on leadership role sits in a lean, founder-led organization, owning day-to-day operations and building the team.

You will establish scalable systems, create accountability, define KPIs, and partner with finance, legal, and vendors.

Qualifications

• 8+ years of experience in operations, business management, or organizational leadership.
• Proven ability to build teams, systems, and processes in founder-led or high-growth environments.
• Strong experience in team leadership, recruiting, project management, and organizational development.
• Experience managing budgets and collaborating with finance, accounting, legal, and external partners.
• Ability to turn loosely defined ideas into structured plans and measurable results.
• Experience in media/entertainment, digital content, creator economy, production, or startup is preferred.
• Based in Miami and willing to travel occasionally.

Responsibilities

• Serve as the founder's operational right hand and primary execution partner.
• Translate priorities into structured plans, timelines, and deliverables.
• Build scalable systems, SOPs, reporting structures, and communication rhythms.
• Define roles, ownership, KPIs, and reporting relationships.
• Lead recruiting, onboarding, and employee development.
• Manage and develop staff while fostering ownership and accountability.
• Maintain operational visibility across content production and post-production.
• Plan, staff, budget, schedule, and execute projects.
• Collaborate with production teams and outside vendors to prevent delays.
• Identify new business opportunities and translate ideas into actionable plans.
• Expand revenue through partnerships, products, IP, live experiences, and other ventures.
• Work with accounting, finance, legal, and external advisers.
• Establish and monitor budgets; support forecasting and financial planning.
• Review spending and negotiate with vendors and partners.

Skills

Operations leadership

Team building

Budget management

Recruiting & onboarding

Cross-functional coordination

Strategic planning

Vendor negotiation

Forecasting & reporting

Startup experience

Job description

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.