Senior Manager of Loyalty

Ascend Wellness Holdings•Chicago, IL

5d•Remote

About The Position

Ascend Wellness Holdings ("AWH") is building a hands-on, customer-obsessed Loyalty organization designed to elevate the Ascenders Club into a premier brand experience. Reporting to the Chief Commercial Officer, the Senior Manager of Loyalty will serve as the architect and active working leader of this new function. The Senior Manager, Loyalty is responsible for setting strategy, driving execution, and measuring success against clear KPIs. This leader will be in the paint, building, optimizing, and executing initiatives that strengthen customer connection, retention, and long-term loyalty while directly interfacing with executive leadership to influence enterprise priorities. Every decision starts and ends with the Customer. The Senior Manager bridges creative strategy and analytical insight to define how Ascend connects with its most loyal customers through personalized communications, omnichannel experiences, and exclusive moments that reinforce Ascend's commitment to community and care.

Requirements

Bachelor's degree in Marketing, Business Administration, Communications, or related field; MBA or advanced degree preferred.
8+ years of experience in Loyalty, CRM, or Customer Experience roles within retail, CPG, or hospitality sectors.
Proven success as a working leader who both sets strategy and executes, delivering measurable results tied to customer KPIs.
Strong understanding of customer behavior and passion for building programs that create emotional connection and long-term advocacy.
Demonstrated ability to develop and implement omnichannel loyalty strategies that drive quantifiable business outcomes.
Exceptional analytical and storytelling skills with the ability to turn insights into action.
Hands-on experience leveraging CRM, customer analytics, and marketing automation to optimize engagement and retention.
Ability to collaborate cross-functionally with Marketing, Retail, Operations, and Technology to create seamless customer experiences.
Proven leadership in developing and inspiring teams through feedback, coaching, and empowerment.
Excellent communication and presentation skills; confident engaging with executive stakeholders and board-level audiences.
High degree of emotional intelligence, adaptability, and resilience in a dynamic, growth-focused environment.
Ability to travel periodically to retail locations and member events as business needs require.

Responsibilities

Serve as a hands-on, working leader who shapes strategy and executes in the day-to-day, ensuring progress is measured against defined KPIs for engagement, retention, and customer lifetime value.
Develop and own the enterprise loyalty strategy from concept through execution, covering program design, optimization, and innovation roadmap.
Champion the customer voice in every initiative, ensuring loyalty drives genuine connection, satisfaction, and repeat engagement.
Lead the evolution of the Ascenders Club, creating tiered, experiential benefits that deliver measurable business impact.
Act as a cross-functional connector across Brand, Marketing, Retail, Digital, and Operations, embedding loyalty into the broader customer experience and commercial strategy.
Collaborate closely with field and retail teams to bring loyalty to life at dispensary level, ensuring every in-person interaction reinforces program value and customer delight.
Translate complex data into clear, actionable insights that inform strategy, optimize campaigns, and guide investment decisions.
Monitor and report performance against KPIs, providing transparency, accountability, and proactive recommendations to the Executive Team.
Serve as a trusted advisor to senior leadership communicating insights through compelling narratives and influencing long-range planning and resource allocation.
Identify and evaluate emerging technologies, partners, and platforms to enhance loyalty innovation and future-proof the program.
Foster a continuous improvement mindset through agile testing, customer feedback loops, and analytics-driven iteration.
Drive consistent brand storytelling across all loyalty touchpoints, ensuring tone, visuals, and experience align with Ascend's premium identity.
Manage vendor and technology relationships (CRM, automation, app, or loyalty platform partners).
Perform additional projects that advance Ascend's loyalty, customer engagement, and retention goals.
Build and lead a high-performing team of strategists and experience designers, fostering a culture of innovation, accountability, and excellence.
Directly manage and mentor team members, providing coaching, feedback, and professional development opportunities.
Foster a culture of innovation, collaboration, and accountability within the team.
Partner with Human Resources to recruit, train, and retain high-performing talent within the Loyalty organization.