VP of Delivery

VP of Delivery

Two Circles · Vancouver, Canada (Hybrid) · Full-time · Posted 2026-10-09

Workplace: hybrid

Department: Delivery Management

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.

Requirements

•      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.

Benefits

What can we offer you?

We offer a benefits package to suit you and your lifestyle! Out of a core monthly budget, you can choose your own comprehensive benefit package

• 19 standard days of PTO (+1 Birthday, 1 Admin Day, 1 Big Life Event Day, + 1 Wellbeing Day, + Time Back)
• Dental, Extended Health Care, Vision, Long Term Disability, Life Insurance, etc.
• Discretionary Bonus based on company performance
• Performance Reviews every 6 months with discretionary salary increases
• Registered Retirement Savings Plan
• Parental Leave
• Mobile Phone Contribution
• Sport Challenge Contribution
• Office Perks

Though these are the basics written down, we will principally be recruiting for energy, values and commitment – both to Two Circles and to your career. Even if you feel you don’t tick 100% of the boxes but feel you could bring value to the role, we’d still love to hear from you! Our recruitment process will be honest & thorough, and so will our roles. In return, we can offer honesty, integrity, and the chance to progress in the organisation as quickly as you develop within it.

Two Circles is committed to creating a diverse environment and is proud to be an equal opportunities employer. All qualified applicants will receive consideration for employment without regard to race, colour, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status.

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