Sr. Director, Analytics and Insights

1400 Castlefield Ave, York, ON M6B 4C4, Canada

Sr. Director, Analytics & Insights

As a senior member of the leadership team, you will build and lead a best‑in‑class analytics function that drives commercial strategy, unlocks growth, and enables data‑driven decision‑making across all areas of the business. Reporting to the Chief Commercial Officer, you will shape how the organization identifies and pursues its biggest opportunities across channels, categories, customers, and markets.

Key Responsibilities

• Act as a strategic growth partner to the CCO and commercial leadership team — proactively identify 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 the company should grow, invest, and optimize.
• Champion a test‑and‑learn culture across commercial functions — develop experimentation frameworks, support A/B testing, and build the organization’s ability to make faster, evidence‑based decisions.
• Stay at the forefront of emerging analytics technologies and AI capabilities — evaluate 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.

Cross‑Functional Commercial Partnership

• Serve as the primary analytics partner to Ecommerce, Retail, Merchandising, and Marketing — embed 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 — segmentation, win‑back, personalization, and loyalty program optimisation.
• 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 optimisation, 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 the company, including the team’s operating model, prioritisation 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, prioritisation, SLA management, and the identification of recurring questions that should become standing reports or dashboards.

Data Infrastructure & BI Platforms

• 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.

Qualifications & Experience

• 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.

At Roots we appreciate that skills and expertise are cultivated through a range of experiences. We are committed to reflecting Canada’s diverse landscape in our products, team, and workplace culture. We value your unique perspective and encourage you to apply, even if you don’t meet every listed requirement. Accommodations are available for applicants throughout the recruitment process.

Please note: Roots uses technology‑assisted tools, including artificial intelligence, to support parts of the recruitment process. These tools may be used to help review applications, assess qualifications, and support interview documentation. All hiring decisions are reviewed and made by our Talent team and key leaders involved in the recruitment process.

The posted salary range is intended to reflect the competitive market value of this role and is provided to support transparency in our hiring process. Final compensation will be determined based on a variety of factors, including but not limited to internal equity, relevant skills, demonstrated knowledge, experience, and overall fit for the position.

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