VP, Product & Engineering

Adelphi Group•Toronto, ON

1d•CA$180,000 - CA$200,000•Hybrid

About The Position

Flywheel’s suite of digital commerce solutions accelerate growth across all major digital marketplaces for the world’s leading brands. We give clients access to near real-time performance measurement and improve sales, share, and profit. With teams across the Americas, Europe and APAC we offer a career with real impact, endless growth opportunities and the support you need to be the best you can be. Perpetua is the Challenger brand retail media platform within the Flywheel Commerce Network, and we are looking for a VP of Product and Engineering to own it end to end. Reporting to the General Manager of Perpetua, you will be the definitive product and engineering leader for the business accountable for the roadmap, the architecture, the team, and the outcomes. This is not a role that inherits a strategy and executes it. You will set the technical and product direction for a focused, high-leverage team and have the autonomy to move quickly, the backing of a global commerce network behind you, and a direct line to the GM to clear the path. Retail media is the fastest-growing corner of digital advertising, and the ground is shifting fast. Amazon and the other large retailers are now shipping their own AI agents that plan, build, and optimize campaigns natively inside their consoles. That raises the bar for what an independent platform has to do to stay essential, and it is exactly where Perpetua wins. Perpetua is built for the challenger brand and the agencies who serve them: the operators who cannot out-spend the category leader and have to out-execute instead. Perpetua works across Amazon, Walmart, Instacart, and more within the retail media landscape.

Requirements

A track record of leading both product and engineering, including 5+ years in senior leadership (VP, Director, or equivalent) owning a product line or business unit, not just a function.
Deep technical credibility in full-stack development; comfortable making architecture calls and earning the trust of senior engineers. Direct experience with our stack (Python/Django, React/TypeScript) is an asset; the ability to go deep in any modern stack matters more.
Demonstrated ability to define and execute product strategy that drives revenue growth, market expansion, and competitive differentiation.
Expert-level knowledge of distributed systems design, cloud architecture (GCP/AWS), microservices, and data infrastructure at scale.
Genuine fluency in building with AI; LLM-based product features, agentic workflows, and protocols like MCP. You should be opinionated about where AI creates real leverage and where it does not.
Background in retail media, digital advertising, ecommerce, or a comparable data-and-API-intensive B2B SaaS domain.
Proven ability to recruit, develop, and retain top engineering and product talent in competitive markets.
Experience with cross-functional leadership spanning sales, customer success, marketing, finance and operations.
Track record of successful product launches, go-to-market strategies, and market expansion in competitive segments.
Exceptional communication skills (both strategic and tactical) with ability to influence stakeholders at all levels.
Strong emphasis on customer obsession and user-centric design with demonstrated ability to translate customer insights into product strategy.
Solid understanding of security, compliance, and data privacy requirements in regulated environments.
Experience with agile methodologies, continuous delivery, and rapid iteration cycles.

Nice To Haves

Direct experience with our stack (Python/Django, React/TypeScript) is an asset

Responsibilities

Own the complete product and engineering strategy for Perpetua, including roadmap prioritization, resource allocation, and business outcomes aligned to company KPIs.
Build and scale high-performing product and engineering teams, including hiring, mentoring, and developing leaders who drive innovation and operational excellence.
Partner with executive leadership to define business strategy, manage P&L, and drive GTM initiatives.
Own the product end to end, from discovery through delivery, across Amazon, Walmart, Instacart, and emerging retail media networks.
Own system design and architecture for the platform; the GCP-hosted services and data pipelines that ingest and act on retail media data at scale, and the newer layer of AI inference, evaluation, and agent orchestration that increasingly sits on top of it.
Own Perpetua's AI strategy across its different forms from the machine-learning systems that already optimize and execute campaign decisions autonomously to the generative and agentic layer that plans, reasons, and explains in natural language, with a clear point of view on which approach is right for which problem.
Shape Perpetua’s platform strategy around the Model Context Protocol (MCP): both consuming external MCP servers (including retailers’ own) and exposing Perpetua’s capabilities as an MCP server, so that AI agents, ours and our customers’, can plan and transact against the platform directly.
Champion an AI-native engineering culture, equipping the team with modern AI development tooling, Claude Code among them, and establishing the practices that let a focused team ship at a pace well above its headcount.
Set the bar for engineering quality on code review, security, testing, and deployment and keep it high as the team adopts AI-assisted development, so that velocity and rigor rise together.
Identify and execute key technology initiatives, architectural improvements, and infrastructure investments that reduce technical debt and improve platform scalability.
Drive product-market fit expansion and feature development through deep customer insights, competitive analysis, and market research.
Foster a culture of innovation, ownership, and collaboration across product, engineering, design, and go-to-market teams.
Manage vendor relationships, third-party integrations, and platform partnerships critical to Perpetua's growth.
Drive metrics-driven decision making by establishing KPIs, monitoring performance, and iterating on product and operational strategies.