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Two Circles

Delivery Director

Remote, Canada

Workplace: Remote
Posting language: English
Posted: Sep 25, 2026

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Original job description

We are Two Circles. We are a Sports & Entertainment Marketing business. We grow audiences and revenues by knowing fans best.

We work with clients to help them understand and influence fan behavior - how fans spend their money, the events they attend, the channels they respond to, and the content they engage with. We use this understanding to help our clients grow both direct-to-consumer and business-to-business revenues.

Our platforms and services are trusted by over 1,000 clients globally, including the English Premier League, Red Bull, UEFA, VISA, the NFL, Nike and Amazon. We are over 1,000 people, based across 15 offices worldwide, delivering work for sports and entertainment organizations of all shapes and sizes.

Technology and data are foundational to how we deliver value, and North America is one of our fastest-growing and highest-priority markets globally.

North America is one of our fastest-growing markets, and we are investing in senior delivery leadership to match that growth. As the portfolio has scaled, we want dedicated, senior ownership of delivery so that specialist talent across the region is deployed where it adds the most value, and so delivery has a clear, accountable leader who can bring order and pace to a growing and increasingly complex portfolio.

You will be a key delivery partner to our EVP, Technology - North America. This is a hands-on leadership role, not a governance or process role sitting apart from the work. You will take direct ownership of the delivery portfolio, freeing up senior leadership time to focus on regional strategy, team growth and client relationships, while you own how delivery runs day to day.

This role also means operating as a business partner to Product and Go-To-Market leadership - working through delivery, resourcing and prioritization decisions together with those teams from the outset, rather than receiving requirements after the fact.

This is a senior, hands-on leadership role for someone who thrives on bringing order to complexity at pace, wants real accountability rather than an advisory mandate, and is energized by operating in a fast-moving, high-growth environment.

Key Responsibilities:

Delivery Leadership & Ownership

Take direct, senior ownership of the North America technology delivery portfolio - not oversight from a distance, but hands-on accountability for how delivery actually runs.

Embed and evolve Two Circles' delivery frameworks, governance and operating rhythms within North America, aligned to global standards and adapted pragmatically to regional realities.

Ensure consistent, disciplined approaches to delivery planning, reporting, escalation and decision-making across programmes.

Act as the senior escalation point for complex delivery, resourcing or commercial challenges - resolving issues at the right level rather than allowing them to land on the EVP by default.

Partnering with the EVP and Senior Leadership

Operate as the EVP's key delivery partner, absorbing the operational complexity of the portfolio so senior leadership time is spent on strategy, people and client relationships.

Build genuine business-partner relationships with Product and Go-To-Market leadership, working through resourcing, prioritization and delivery trade-offs collaboratively and end-to-end rather than as a downstream function.

Represent North America delivery with credibility in front of senior technical and non-technical stakeholders, including client executives where required.

Resource Management, Tooling & Commercial Visibility

Establish clear, consistent approaches to resource planning, capacity management and utilization across North America.

Ensure delivery teams use agreed tools and processes to track time and effort accurately, creating real visibility into who is working on what, where and when.

Partner with commercial and finance colleagues to ensure delivery data supports margin management, forecasting and Statements of Work.

Use delivery and resourcing insight proactively to identify risk early and drive corrective action before it escalates.

Cross-Regional Partnership

Work as a genuine peer with the Delivery Directors in EMEA and APAC to maintain alignment on standards, tooling and expectations globally.

Bring proven approaches from other regions into North America to accelerate delivery maturity, and feed North America's own learning back into the global model.

People & Leadership

Lead, coach and develop delivery leaders across Programme and Delivery roles, setting a high bar for accountability and ownership.

Build a collaborative, transparent culture with a strong bias towards continuous improvement.

Build trusted relationships across delivery, engineering, product and client-facing teams that make the operating model function in practice, not just on paper.

Significant experience in senior delivery leadership roles, ideally including experience operating as a direct partner to an executive-level leader (CTO, EVP or equivalent).

Proven track record delivering complex digital products, SaaS platforms and/or data-led programmes within a consultancy, agency or product-led technology organisation.

Strong experience embedding delivery frameworks, governance and operating models at scale, including in fast-growing environments.

Demonstrated experience with resource management, utilisation, delivery tooling and time tracking.

Experience working across global or multi-region delivery organisations, with the credibility to operate as a peer to senior delivery leaders elsewhere in the business.

Strong commercial awareness, with experience using delivery data to inform margin, forecasting and client outcomes.

Excellent stakeholder management and communication skills, with genuine ability to influence senior technical and non-technical audiences, including client executives.

A track record of thriving, not just coping, in fast-paced, ambiguous, high-pressure environments - this role sits inside a period of significant growth and change in North America.

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More about this job

Responsibilities

The Delivery Director will take direct, hands-on ownership of the North America technology delivery portfolio to ensure operational excellence and pace. They will act as a key business partner to the EVP of Technology and other leadership teams to align delivery, resourcing, and strategy.

Requirements

Candidates must have significant experience in senior delivery leadership roles, ideally partnering with executive-level leaders. A proven track record in delivering complex digital products or data-led programs within a consultancy or product-led organization is required.

Skills

Delivery Leadership
Stakeholder Management
Resource Management
Strategic Planning
Governance
Commercial Awareness
Team Leadership
Project Management
Data Analysis
SaaS Platforms
Digital Product Delivery
Change Management
Capacity Planning
Business Partnering
Risk Management

Visa sponsorship

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Keywords

Delivery Director
Technology
Sports Marketing
Entertainment
SaaS
Digital Products
Data-led Programs
Governance
Resource Management
Capacity Management
Commercial Visibility
Margin Management
Forecasting
Statements of Work
Stakeholder Management
Strategic Leadership
Business Partnering
Consultancy
Agency
Product-led Technology

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