Sr. Director, Analytics and Insights

Roots•Toronto, ON

About The Position

As a member of the senior leadership team, the Sr. Director, Analytics & Insights is accountable for building and leading a best-in-class analytics function that drives commercial strategy, unlocks growth, and enables data-driven decision-making across all areas of the Roots business. Reporting to the Chief Commercial Officer, this leader plays a pivotal role in shaping how Roots identifies and pursues its biggest opportunities — across channels, categories, customers, and markets. This role is responsible for establishing the organization's analytics operating model — including a centralized data and engineering capability and embedded analyst partnerships within Ecommerce, Retail, and Merchandising — and for ensuring that the right insights reach the right people at the right time. As a trusted strategic partner to the CCO and the broader commercial leadership team, the Sr. Director translates data into a competitive advantage: surfacing growth opportunities, informing investment decisions, and bringing an evidence-based perspective to every major commercial initiative. This leader brings both technical credibility and deep commercial acumen, and is as comfortable shaping channel strategy as they are working through a data model with their team.

Requirements

15+ years of progressive analytics or data leadership experience, with a minimum of 5 years leading analytics teams in a retail, ecommerce, or consumer brand environment.
Demonstrated track record of building and scaling analytics functions that have driven measurable commercial outcomes — revenue growth, margin improvement, customer retention, or channel expansion.
Deep expertise across the retail commercial analytics landscape — including ecommerce performance, customer and loyalty analytics, merchandising and inventory analytics, marketing effectiveness, and competitive intelligence.
Proven ability to act as a strategic growth partner to commercial leaders — not just reporting performance, but proactively identifying opportunities, shaping strategy, and influencing investment decisions through data.
Strong technical foundation with hands-on experience in SQL, data modelling, and BI platforms (experience with Snowflake is a strong asset); able to engage credibly with data engineers and evaluate technical approaches.
Exceptional executive communication and storytelling skills — able to distill complex analytical findings into compelling commercial narratives, present with confidence to the C-suite and Board, and drive alignment through insights.
Proven ability to operate in an embedded analytics model, building trusted relationships with functional leaders while maintaining centralized standards and a cohesive team culture.
Experience building and managing structured analytics operating rhythms, including regular reporting cadences, ad-hoc request processes, and roadmap planning.
Bachelor's degree in a quantitative field (Mathematics, Statistics, Computer Science, Economics, or related); Master's degree or MBA is an asset.
Demonstrated curiosity and working knowledge of AI and machine learning applications in a retail or commercial context — including experience evaluating or deploying predictive models, generative AI tools, or automation capabilities that have driven measurable business outcomes.

Nice To Haves

Master's degree or MBA is an asset.

Responsibilities

Act as a strategic growth partner to the CCO and commercial leadership team — proactively identifying opportunities to accelerate revenue, expand market share, improve margin, and deepen customer relationships across all channels.
Lead the development of commercially-driven analytics that go beyond performance reporting — surfacing white space, sizing opportunities, and informing investment decisions across Ecommerce, Retail, Merchandising, and Marketing.
Bring a forward-looking perspective to the business: translate trends in customer behaviour, channel performance, and competitive positioning into clear strategic recommendations for the senior leadership team.
Influence the annual planning process and long-range strategic plan with a data-driven point of view on where Roots should grow, invest, and optimize.
Champion a test-and-learn culture across commercial functions — developing experimentation frameworks, supporting A/B testing, and building the organization's ability to make faster, evidence-based decisions.
Stay at the forefront of emerging analytics technologies and AI capabilities — evaluating where tools such as generative AI, predictive modelling, and machine learning can be applied to accelerate insight generation, improve forecasting accuracy, and create competitive advantage for Roots.
Serve as the primary analytics partner to Ecommerce, Retail, Merchandising, and Marketing — embedding analytical thinking into their strategies, roadmaps, and operating rhythms.
Partner with Marketing and CRM to unlock customer analytics capabilities that drive loyalty, retention, and lifetime value growth — including segmentation, win-back, personalization, and loyalty program optimization.
Collaborate with Merchandising and Planning on assortment strategy, pricing architecture, and inventory investment decisions; bring an analytical lens to buying and open-to-buy processes.
Support Ecommerce in building a performance marketing and digital analytics capability that connects media spend to revenue outcomes, and identifies the highest-ROI levers for growth.
Partner with Retail to identify operational and commercial opportunities at the store level, including conversion improvement, traffic optimization, and comp store growth strategies.
Lead, coach, and develop a team of analytics professionals across central and embedded functions, fostering a culture of intellectual curiosity, commercial thinking, accountability, and continuous improvement.
Establish clear roles, responsibilities, and performance expectations for both central team members and business-embedded analysts; ensure alignment and collaboration across the full team.
Champion the professional growth of each team member through regular feedback, development planning, and exposure to enterprise-wide commercial priorities.
Build for the future — identify capability gaps, develop succession plans, and invest in the skills needed to grow the analytics function as the business scales.
Define and execute the analytics strategy for Roots, including the team's operating model, prioritization framework, and approach to self-serve analytics across the business.
Own the organization's reporting cadence — from daily revenue pulses to quarterly business reviews — ensuring that the business operates from a single, trusted source of truth.
Establish and govern standards for data definitions, metric frameworks, and analytical methodology across all functions to drive consistency and confidence in reported numbers.
Build and maintain the analytics roadmap, balancing short-term commercial priorities with longer-term infrastructure investments and capability development.
Champion a structured approach to ad-hoc analytics requests — including intake, prioritization, SLA management, and the identification of recurring questions that should become standing reports or dashboards.
Oversee the data engineering and BI function, ensuring that data pipelines, Snowflake data models, and dashboard infrastructure are reliable, scalable, and accessible to business users.
Partner with Technology and Finance to evaluate and evolve the analytics tech stack, including BI tooling, data pipeline infrastructure, and data governance platforms.
Champion data quality and integrity across all reporting; ensure issues are identified proactively and resolved with urgency.
Drive the adoption of self-serve analytics tools and capabilities that reduce dependency on the central analytics team for routine reporting needs.
Identify and evaluate opportunities to integrate AI and machine learning into the analytics stack — including demand forecasting, customer propensity modelling, personalization, and automated anomaly detection — and build a roadmap for adoption that is practical, scalable, and aligned to business priorities.