Senior Director, Delivery

We are Two Circles. We are a Sports & Entertainment Marketing business. We grow audiences and revenues. We do that by knowing fans best. We work with clients to help them understand & influence what their fans are doing – the way fans spend their money, the events that fans attend, the channels fans respond to, the content fans watch and more. And we use the understanding this gives us to help our clients grow. Grow their audiences and grow their revenues - both direct to consumer and business to business revenues. Our platforms and services are trusted by over 1000 clients globally, including the English Premier League, Red Bull, UEFA, VISA, the NFL, Nike and Amazon. We are over 1000 people, based out of 15 offices, and we deliver work for sports and entertainment businesses of all shapes and sizes all over the world.

Technology and data are core to how we deliver value, and we continue to scale our technology capability globally as a key enabler of our growth.

What You Will Do

As part of our continued growth in North America, we are looking for a Delivery Director to provide senior leadership across our technology delivery portfolio.

This role is responsible for embedding consistent, high-quality delivery practices across North America, aligned with established ways of working across EMEA and APAC. You will play a key role in bringing structure, predictability, and visibility to delivery in a fast-paced, high-growth environment, while retaining the flexibility required to meet client and regional needs.

You will work closely with other Delivery Directors, Engineering Directors, CRM leadership, and senior Technology stakeholders to ensure delivery models support modern engineering practices, data-led initiatives, and strong commercial outcomes.

This is a hands-on leadership role for someone comfortable operating in complex, high-pressure environments and driving maturity at pace.

Your Main Duties & Responsibilities

Delivery Leadership & Ways of Working

• Embed and evolve Two Circles’ delivery frameworks, governance, and operating rhythms within North America.
• Align North America to global delivery standards, adapting models pragmatically where required without reinventing core ways of working.
• Ensure consistent approaches to delivery planning, reporting, escalation, and decision-making across programs.
• Drive continuous improvement in delivery effectiveness using data, insight, and feedback.

Resource Management, Tooling & Commercial Visibility

• Establish clear and consistent approaches to resource planning, capacity management, and utilisation across North America.
• Ensure delivery teams are using agreed tools and processes to accurately track time and effort.
• Create visibility across who is working on what, where, and when, enabling informed prioritisation and planning.
• Work closely with commercial and finance partners to ensure delivery data supports margin management, forecasting, and Statements of Work.
• Use resourcing and delivery insights to proactively identify risks and drive corrective action.

Cross-Regional Collaboration

• Work closely with Delivery Directors across EMEA and APAC to maintain alignment on delivery standards, tooling, and expectations.
• Lift and adapt proven approaches from other regions to accelerate delivery maturity in North America.
• Share learnings and insights from North America to support the continuous evolution of global delivery practices.

Delivery Oversight & Escalation

• Provide senior oversight across multiple concurrent programs in a fast-paced, high-intensity environment.
• Act as a senior escalation point for complex delivery, resourcing, or commercial challenges.
• Lead teams and stakeholders calmly through ambiguity, pressure, and critical delivery moments.
• Balance speed, quality, and sustainability across the delivery portfolio.

People & Leadership

• Lead, coach, and develop delivery leaders across Program and Delivery roles.
• Set clear expectations around accountability, ownership, and delivery quality.
• Foster a collaborative, transparent culture with a strong focus on continuous improvement.
• Build strong relationships across delivery, engineering, product, and client-facing teams.

Requirements

• Significant experience in senior delivery leadership roles within a consultancy, agency, or product-led technology organisation.
• Proven experience delivering complex digital products, SaaS platforms, and/or data-led programs.
• Strong experience embedding delivery frameworks, governance, and operating models at scale.
• Demonstrated experience with resource management, utilisation, delivery tooling, and time tracking.
• Experience working across global or multi-region delivery organisations.
• Strong commercial awareness, with experience using delivery data to inform margins, forecasting, and client outcomes.
• Excellent stakeholder management and communication skills, with the ability to influence senior technical and non-technical audiences.
• Comfortable operating in fast-paced, ambiguous, and high-pressure environments.

Experience with the Following Would Also Be Beneficial

• Exposure to data platforms, DWH, analytics, or cloud-based data stacks.
• Familiarity with modern engineering practices, CI/CD, and DevOps cultures.
• Experience working closely with engineering, CRM, or platform leadership.
• Experience delivering within sports, media, or large-scale consumer digital environments.
• An interest in the business of sport and entertainment.

The range below represents the low and high end of the base salary someone in this role may earn as an employee of Two Circles. Salaries will vary based on various factors including but not limited to professional and academic experience, training, associated responsibilities, and other business and organizational needs. The range listed is just one component of our total compensation package for employees. Salary decisions are dependent on the circumstances of each hire.

• $180,000-$210,000 CAD