Director, Operations

Gigantic Playground, a CourtAvenue company,  is a fast growing creative technology agency that creates immersive and interactive experiences that connect people, places, and products in extraordinary ways. Our unique experience + technology approach blends creativity, immersive storytelling, and product innovation to create dynamic experiences that captivate, engage and delight. 

As we continue to grow, we are seeking a Director of Operations to help lead the business with rigor, clarity, and momentum—ensuring the agency, our teams, and our clients are set up for long-term success.

The Director of Operations plays a critical leadership role at Gigantic Playground, responsible for agency-wide operational excellence, financial performance, team resourcing, and delivery execution. This role blends strategic oversight with hands-on leadership, serving as a key partner to executive leadership, account teams, and clients alike.

• Own and manage agency-level P&L, including forecasting, margin management, utilization, and financial reporting
• Lead resourcing strategy across disciplines, ensuring the right people are in place at the right time to support client and agency needs
• Hands-on project management lead for complex, high-value engagements (not just overseeing but active PM)
• Partner with department leads to ensure projects are scoped, staffed, and executed effectively
• Manage Statements of Work (SOWs), contracts, change orders, and renewals in close collaboration with finance and legal partners
• Establish and maintain operational processes (with focus on AI) that support scalable growth, delivery quality, and team health
• Serve as a senior escalation point for client delivery, resourcing, and operational challenges
• Align internal teams around priorities, timelines, and expectations across multiple concurrent initiatives
• Drive continuous improvement across operations, delivery workflows, and financial performance

• Strong business and financial acumen with demonstrated experience managing agency or consultancy P&L
• Proven ability to balance strategic planning with hands-on execution
• Deep understanding of modern AI tools, resourcing models, utilization management, and capacity planning
• Excellent project and program management instincts, particularly for complex, multi-disciplinary engagements
• Clear, confident communicator who can work effectively with executives, clients, and cross-functional teams
• Comfortable operating in a fast-moving, creative, and technology-driven environment
• Highly organized, detail-oriented, and proactive in identifying and solving problems
• Strong leadership presence with the ability to motivate, align, and support teams

• 6–8+ years of experience in operations, delivery, or leadership roles within a digital agency, creative studio, or technology services provider. 
• Direct experience managing multiple client engagements and internal teams simultaneously
• Demonstrated experience with AI Tools, contract negotiation, SOW development, and change management
• Familiarity with creative technology, digital products, or interactive experiences is strongly preferred
• Bachelor’s degree in Business, Operations, Management, or a related field (or equivalent professional experience)
• Experience working with senior clients and stakeholders in a client-services environment 

• Gigantic Playground is a remote-first agency environment with team members located across the US.  
• Candidates in San Diego, California will have the advantage of being close in proximity to several of our core team members.
• Candidates located in Orlando, FL, Chicago, IL, New York, NY or Seattle, WA will also be considered.