Operations Architect for Founder-Led Growth

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

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.