Vice President of eCommerce and Loyalty

Ascend Wellness Holdings•Chicago, IL

4d•Remote

About The Position

Ascend Wellness Holdings ("AWH") is seeking a growth-minded and results-driven Vice President, eCommerce to shape the future of Ascend's digital commerce experience. This leader will define and execute the strategy behind a best-in-class omnichannel platform that unites our retail stores, brand portfolio, and digital ecosystem, delivering seamless experiences that drive meaningful, measurable growth. As Ascend continues to expand its retail and digital presence, the VP, eCommerce will play a pivotal role in scaling our platform, deepening customer connection, and elevating how we engage across every touchpoint. This leader will also oversee the evolution of Ascend's Loyalty program, driving customer retention, personalization, and advocacy through a seamless connection between digital and in-store experiences. This is a highly engaged leadership role, actively involved in day-to-day operations while setting long-term vision, guiding execution, and collaborating closely with executive leadership to influence enterprise strategy and priorities. The ideal candidate brings proven expertise in eCommerce digital merchandising and loyalty strategy within established, performance-driven organizations and thrives at the intersection of strategy, technology, and customer experience. Accountable for KPIs tied to conversion, transaction value, repeat purchase, and customer lifetime value, this leader ensures every decision keeps the customer at the center while driving Ascend's next stage of digital growth.

Requirements

Bachelor's Degree in Marketing, Business, or a related field; MBA preferred.
10+ years of specialized leadership experience overseeing eCommerce, digital merchandising, and loyalty functions end-to-end within established, performance-driven retail or consumer organizations, bringing deep functional expertise rather than broader marketing leadership experience, and demonstrating both strategic acumen and hands-on executional excellence.
Proven ability to build and empower high-performing eCommerce and Loyalty teams through mentorship, inclusion, and accountability.
Demonstrated success scaling digital revenue channels, improving customer retention, and implementing omnichannel strategies that drive engagement and lifetime value.
Deep understanding of digital merchandising, UX optimization, SEO/SEM, CRM, and loyalty integration.
Strong customer-centric orientation with the ability to translate insights into strategies that enhance satisfaction, loyalty, and advocacy.
Analytical mindset with proficiency in eCommerce and data visualization tools (Google Analytics, Shopify or similar platforms, Tableau, etc.).
Deep customer-centric orientation with the ability to translate insights into strategies that enhance satisfaction, loyalty, and advocacy.
Exceptional executive communication skills with the ability to present performance insights and strategic recommendations to senior leadership in clear, actionable terms.
Proven success managing eCommerce P&L performance and optimizing ROI across digital and loyalty channels.
Deep understanding of omnichannel strategy and the connection between digital engagement, in-store experience, and customer lifecycle value.
Experience leading digital transformation or platform migration projects (e.g., Shopify, Adobe Commerce, Salesforce Commerce Cloud).
Highly organized, adaptable, and able to manage multiple priorities in a rapidly evolving environment.
Strong collaboration and influence skills across AWH teams and vendors.
Experience managing budgets, forecasting, and vendor partnerships.
Operates with discretion, sound judgment, and confidentiality when handling sensitive business information and executive communications.
Ability to travel occasionally to AWH sites for collaboration and strategic alignment, with reasonable accommodations provided.

Nice To Haves

MBA preferred.

Responsibilities

Own the eCommerce and Loyalty strategy and execution, connecting acquisition, engagement, and retention to create a seamless, customer-focused experience across digital and retail channels.
Lead and continually enhance the omnichannel customer journey, overseeing platform operations, UX/UI, digital merchandising, CRM, and rewards activation to drive customer satisfaction, loyalty, and lifetime value.
Use customer insights and behavioral data to shape segmentation, personalization, and lifecycle strategies that strengthen connection, advocacy, and repeat business.
Collaborate with Marketing, Retail, and Design to ensure every digital and in-store touchpoint reflects a consistent, rewarding customer experience.
Define and manage KPIs: conversion, average order value (AOV), repeat purchase, loyalty engagement, and customer acquisition cost (CAC), linking every initiative to measurable customer and business outcomes.
Stay actively involved in daily execution, partnering with cross-functional teams to ensure product assortment, pricing, and promotions align with customer expectations and brand standards across POS, mobile apps, and digital platforms.
Partner with the Directors of Loyalty and eCommerce Digital Merchandising to align product presentation, rewards, and communications into a cohesive experience that deepens customer engagement and builds long-term loyalty.
Oversee paid and organic traffic strategies (SEO/SEM, listings, and menu visibility), ensuring customers can easily discover and engage with Ascend's offerings online.
Manage key vendor partnerships (Dutchie, Surfside, and others), ensuring all platforms and tools integrate seamlessly to enhance the customer experience and data visibility.
Drive continuous innovation of the D2C platform, scaling digital capabilities that elevate ease, access, and personalization.
Own eCommerce and Loyalty P&L performance, budgets, and forecasting, ensuring investments and initiatives deliver strong ROI and align with enterprise financial goals.
Report on customer and business performance metrics to executive leadership, translating insights into actionable strategies that advance loyalty and growth.
Lead, mentor, and inspire a high-performing team spanning eCommerce, Loyalty, and digital merchandising, operations, and analytics.
Serve as an active, visible leader, collaborating with the team in daily operations, guiding decision-making, and modeling accountability, collaboration, and excellence.
Establish clear performance objectives, provide ongoing coaching and feedback, and support professional development to strengthen team capabilities.
Foster a culture of accountability, collaboration, and innovation that drives measurable business impact, customer satisfaction, and loyalty engagement.