OverviewWe 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 DoAs 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 & ResponsibilitiesDelivery Leadership & Ways of WorkingEmbed and evolve Two Circles ' delivery frameworks, governance, and operating rhythms within North AmericaAlign North America to global delivery standards,



adapting models pragmatically where required without reinventing core ways of workingEnsure consistent approaches to delivery planning, reporting, escalation, and decision-making across programsDrive continuous improvement in delivery effectiveness using data, insight, and feedbackResource Management, Tooling & Commercial VisibilityEstablish clear and consistent approaches to resource planning, capacity management, and utilisation across North AmericaEnsure delivery teams are using agreed tools and processes to accurately track time and effortCreate visibility across who is working on what, where, and when, enabling informed prioritisation and planningWork closely with commercial and finance partners to ensure delivery data supports margin management, forecasting, and Statements of WorkUse resourcing and delivery insights to proactively identify risks and drive corrective actionCross-Regional CollaborationWork closely with Delivery Directors across EMEA and APAC to maintain alignment on delivery standards, tooling, and expectationsLift and adapt proven approaches from other regions to accelerate delivery maturity in North AmericaShare learnings and insights from North America to support the continuous evolution of global delivery practicesDelivery Oversight & EscalationProvide senior oversight across multiple concurrent programs in a fast-paced, high-intensity environmentAct as a senior escalation point for complex delivery, resourcing, or commercial challengesLead teams and stakeholders calmly through ambiguity, pressure, and critical delivery momentsBalance speed, quality, and sustainability across the delivery portfolioPeople & LeadershipLead, coach,



and develop delivery leaders across Program and Delivery rolesSet clear expectations around accountability, ownership, and delivery qualityFoster a collaborative, transparent culture with a strong focus on continuous improvementBuild strong relationships across delivery, engineering, product, and client-facing teamsRequirementsSignificant experience in senior delivery leadership roles within a consultancy, agency, or product-led technology organisationProven experience delivering complex digital products, SaaS platforms, and/or data-led programsStrong experience embedding delivery frameworks, governance, and operating models at scaleDemonstrated experience with resource management, utilisation, delivery tooling, and time trackingExperience working across global or multi-region delivery organisationsStrong commercial awareness, with experience using delivery data to inform margins, forecasting, and client outcomesExcellent stakeholder management and communication skills, with the ability to influence senior technical and non-technical audiencesComfortable operating in fast-paced, ambiguous, and high-pressure environmentsExperience with the Following Would Also Be BeneficialExposure to data platforms, DWH, analytics, or cloud-based data stacksFamiliarity with contemporary engineering practices, CI/CD, and DevOps culturesExperience working closely with engineering, CRM, or platform leadershipExperience delivering within sports, media, or large-scale consumer digital environmentsAn interest in the business of sport and entertainmentCompensationThe 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#J-18808-Ljbffr

📌 Senior Director, Delivery - C$180,000 - C$210,000 A Year (Toronto)
🏢 Two Circles
📍 Toronto