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. Key Responsibilities

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

Essential Skills & Capabilities

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

Requirements

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 

Work Location

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.