Description:
Are you curious about solving complex business challenges for a leading convenience retailer? Do you have a passion for cross functional collaboration? Then you may be the perfect addition to our team!

Position Summary:

We are seeking a highly experienced Senior Director of Loyalty & Digital Commerce, with a proven track record of business growth. You will serve as the strategic architect, P&L owner, and operational powerhouse driving the transformation of our national retail footprint. Operating at the intersection of consumer psychology, data science, and cutting-edge retail technology, you will be responsible for defining how millions of customers interact with our brand across all digital touchpoints. In an increasingly competitive landscape, this executive leadership role is charged with converting casual shoppers into lifelong brand advocates, ultimately driving sustained revenue growth, digital market share, and long-term enterprise value.

You will inherit a robust digital infrastructure and be expected to elevate it into a frictionless, unified omni-channel commerce engine. This requires total strategic ownership of our e-commerce platforms, native mobile applications, and emerging digital sales channels. Rather than managing a digital storefront in a vacuum, you will fundamentally redefine how our digital presence enhances, supports, and integrates with our nationwide brick-and-mortar stores. Your success will be measured by your ability to drive conversion rates, increase average order value (AOV), and pioneer seamless fulfillment models like Buy Online, Pick Up In-Store (BOPIS) and curbside delivery.

Simultaneously, you will spearhead the total evolution of our customer loyalty program, moving it beyond a traditional, transactional "points-for-purchases" model. You will architect a highly personalized, emotional, and experiential loyalty ecosystem that fosters deep brand devotion and top-of-mind awareness. By leveraging our massive first-party data warehouse and Customer Data Platforms (CDPs), you will oversee the deployment of hyper-targeted CRM strategies, predictive lifecycle marketing, and behavioral personalization engines that maximize Customer Lifetime Value (LTV), mitigate churn, and structurally lower our Customer Acquisition Costs (CAC).

You will manage a multi-million dollar budget and lead a diverse, high-performing organization of digital experts, CRM managers, loyalty specialists, and growth marketers. You will act as a critical cross-functional bridge between Technology, Marketing, Store Operations, and Merchandising, ensuring that digital and loyalty initiatives are deeply embedded into the DNA of the overall corporate strategy. This role demands a visionary leader who is comfortable navigating rapid market shifts, building data-driven corporate cultures, and championing the voice of the customer in every business decision.

Responsibilities:

1. Partnership Management

• Partner Acceleration: Foster strong relationships with DoorDash, GrubHub, Uber Eats and aggregator partners to ensure seamless integration and growth of delivery services. Negotiate favorable terms and conditions with partners to enhance profitability and customer
• Category Management: Implement category management strategies to optimize product offerings and promotions on delivery platforms, focusing on both packaged goods and food service items. This includes
• Product Assortment: Analyze sales data to optimize product assortment on third-party platforms, ensuring alignment with customer preferences and market trends.
• Pricing Strategies: Develop pricing strategies that balance profitability with competitiveness across different platforms.
• Promotional Planning" Plan and execute promotions and offers that drive sales and customer engagement for key categories.

2. First-Party Delivery Expansion

• Strategy Development: Develop and execute a strategic plan for expanding our first-party delivery capabilities, including market analysis, operational setup, and technology integration.
• Technology Integration: Oversee the integration of necessary technology solutions to support first-party delivery operations.

3. Loyalty & Customer Retention Strategy

• Modernize the Loyalty Program: Lead the strategic roadmap for our customer loyalty program, transitioning it from a transactional points system into a personalized, emotional, and high-value ecosystem.
• Boost Engagement & LTV: Utilize data-driven insights to increase active participation, reduce churn, and maximize customer lifetime value.
• Personalization & Lifecycle Marketing: Oversee the CRM and marketing automation teams to deliver hyper-targeted, personalized campaigns, offers, and content based on customer segments and purchasing behavior.

4. P&L Management

• Financial Oversight: Manage the P&L for both third-party and first-party delivery operations, ensuring both top and bottom-line performance to budget.
• Budget Planning: Develop and manage budgets for marketing activations, operational improvements, and technology investments.

5. Digital Partnerships

• Identify: Evaluate and identify the right external partners EGA needs to accelerate retail growth, digital performance and omni-channel customers.
• Negotiate: Partner with procurement and legal to negotiate best-in-class commercial terms for EGA.
• Implementation: Lead cross-functional teams to successful pilots, ensuring proper ROI, and national launch programming thereafter.

6. Stakeholder Management

• Internal Collaboration: Collaborate with cross functional teams including category teams, marketing, finance, and operations to align strategies and improve delivery services.
• External Relations: maintain strong relationships with external partners and stakeholders.

7. Must be able to perform the essential functions of this position with or without reasonable accommodation

Working Relationships: Partnerships, Marketing, Finance, Operations, Fuel & Category Management.

Requirements:
Minimum Education: Bachelor's degree in business, finance, economics or a related field

Preferred Education: Master's degree in business, finance, economics or a related Field

Minimum Experience:15 years' experience in managing loyalty and digital commerce businesses. Preferably in a retail or convenience store environment

Soft Skills/Competencies:

• Strategic Vision: The ability to anticipate retail trends and position the brand ahead of the digital curve.
• Customer Centricity: An unwavering focus on the end-consumer experience to drive brand advocacy.
• Agile Execution: Comfort navigating fast-paced environments, prioritizing effectively, and driving cross-functional alignment.
• Advanced analytics skills and ability to translate data into actionable insights
• Strong negotiation and partnership management skills.
• Excellent analytical and problem-solving abilities.
• Ability to drive lead through ambiguity and adapt to quick pivots
• Experience with P&L management and budget planning.
• Ability to work in a fast-paced environment with minimal supervision.
• Familiarity with category management principles and best practices.

Other Requirements:

Travel: 10% Travel

Hours & Conditions: Typically, Monday - Friday, 8+ hour days in office setting

Physical Requirements: Minimal physical effort required, sitting / standing at computer for long periods of time. Ability to maneuver and lift up to 10 lbs.

Additional Info:
At Cumberland Farms, it's important that our employees reflect the world we live in and the communities we serve. We celebrate our differences, so your unique background and skillset could bring a wonderful new perspective to our team. If you have a passion for delivering exceptional results, thrive in a fast-paced corporate environment, and bring experience in business management or related areas, we'd love to meet you - even if you don't meet every single requirement.

Consistent with Massachusetts Pay Transparency Law, we're sharing the base salary range for this position. Final pay within this range will be based on your skills, experience, and qualifications. Base pay represents just one part of our total rewards approach. We're proud to offer a variety of financial and non-financial benefits that invest in your overall growth, well-being, and career journey.