Senior Manager of Loyalty

Ascend Wellness Holdings, Inc.
Chicago, IL

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, 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.

Key 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.

Supervisory Responsibilities

  • 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.

Qualifications & Skills

  • 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.

Work Environment

This position primarily performs duties in a remote office setting. This position will also be onsite in retail and manufacturing settings.

Physical Requirements

While performing the duties of this job, this position is regularly required to sit and use hand(s) to handle, grasp, feel, and/or touch. The position is occasionally required to stand, walk, and reach with hands and arms. The position is required to speak and listen regularly and may occasionally need to lift or move materials, event supplies, or equipment weighing up to 25 pounds.

Company Overview

Ascend Wellness Holdings ("AWH") is a vertically integrated cannabis cultivator, processor and provisioning center operator with assets in Illinois, Maryland, Massachusetts, Michigan, New Jersey, Ohio and Pennsylvania. We seek to foster a robust and inclusive cannabis industry through a premium, unmatched customer‑focused retail experience. We are looking to build a world‑class team that will help carry out our mission of helping to shape the future of cannabis as a leading healthcare solution. We are committed to improving the quality of our patient's lives by offering unrivaled quality, consistency and meticulously curated products that satisfy our customers unique, individual needs. When it comes to customer service experience, our dispensaries will set a new standard of excellence, emphasizing health and wellness by a highly knowledgeable team. A team that is committed to our values, our people, and our communities; we are looking for people who are inspired by our vision and stay dedicated to our mission as we continuously expand.

EEO Statement

Ascend Wellness Holdings, INC., ("AWH") and its subsidiaries is an equal opportunity employer and celebrate the population of differences and does not discriminate in its hiring / hiring practices, regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law.

Nothing in this job specification restricts management's right to assign or reassign duties and responsibilities to this job at any time. Critical features of this job are described under various headings above. They may be subject to change at any time due to reasonable accommodation or other reasons. The above statements are strictly intended to describe the general nature and level of the work being performed. They are not intended to be construed as a complete list of all responsibilities, duties, and skills required of employees in this position.

This job description in no way states or implies that these are the only duties to be performed by the employee(s) incumbent in this position. Employees will be required to follow any other job‑related instructions and to perform any other job‑related duties requested by any person authorized to give instructions or assignments. All duties and responsibilities are essential functions and requirements and are subject to possible modification to reasonably accommodate individuals with disabilities.

To perform this job successfully, the incumbents will possess the skills, aptitudes, and abilities to perform each duty proficiently. Some requirements may exclude individuals who pose a direct threat or significant risk to the health or safety of themselves or others. The requirements listed in this document are the minimum levels of knowledge, skills, or abilities. This document does not create an employment contract, implied or otherwise, other than an "at will" relationship.

#LI-REMOTE

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Posted 2026-01-15

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