Director, Operations

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Hiring Remotely in San Diego, CA, USA
In-Office or Remote
145K-165K Annually
Machine Learning
The Role
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.

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The Company
Austin, TX
37 Employees
Year Founded: 2019

What We Do

CourtAvenue is an Operating Network of digital transformation companies that utilizes data, machine learning and emerging technologies to build powerful relationships between brands and consumers.

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