Recently named one of Entrepreneur magazine’s Top 100 Cannabis Leaders, Cresco Labs is one of the largest vertically-integrated multi-state cannabis operators in the United States. Cresco is built to become the most important company in the cannabis industry by combining the most strategic geographic footprint with one of the leading distribution platforms in North America. Employing a consumer-packaged goods (“CPG”) approach to cannabis, Cresco’s house of brands is designed to meet the needs of all consumer segments and includes some of the most recognized and trusted national brands including Cresco, Remedi and Mindy’s, a line of edibles created by James Beard Award-winning chef Mindy Segal. Sunnyside*, Cresco’s national dispensary brand is a wellness-focused retailer designed to build trust, education and convenience for both existing and new cannabis consumers. Recognizing that the cannabis industry is poised to become one of the leading job creators in the country, Cresco has launched the industry’s first national comprehensive Social Equity and Educational Development (SEED) initiative designed to ensure that all members of society have the skills, knowledge and opportunity to work in and own businesses in the cannabis industry. 


At Cresco, we aim to lead the nation’s cannabis industry with a focus on regulatory compliance, product consistency, and customer satisfaction. Our operations bring legitimacy to the cannabis industry by acting with the highest level of integrity, strictly adhering to regulations, and promoting the clinical efficacy of cannabis. As Cresco grows, we will operate with the same level of professionalism and precision in each new market we move in to.



Cresco seeks a VP of Loyalty and Engagement Program Engineering capable of owning, leading, supporting and implementing our technology road-map for a robust Loyalty platform to support our Engagement program as we continue to grow and expand as a company, making necessary adjustments for success, along the way.  This role reports directly to the CIO and is based out of our headquarters in Chicago, IL.



  • Provides overall leadership in the evaluation, solutioning, development, implementation, and oversight of software development, delivery and management of the Loyalty platform. Directs, supervises, and evaluates the work of staff. Holds staff accountable for achieving plans and performance targets. Develops staff to ensure continued professional growth and to provide the competencies the company needs to support its growth and long-term success.
  • Directs the development and integration of new and innovative operations and/or services by providing leadership that maximizes management staff contributions and assures timely decision-making reflective of the mission, vision, and values of the system.
  • Overall delivery accountability; provide leadership to delivery teams, lead planning and budgeting; manage delivery teams to ensure quality, completeness and timeliness of solution delivery
  • Responsible for the design, implementation and operations aligned to the Loyalty platform need
  • Influence and inspire teams to collaborate effectively and promote a platform and service mindset for the Loyalty platform
  • Responsible for overseeing and implementing continual delivery excellence initiatives
  • Supports the CIO to develop short term and long term Strategic Technology Roadmap.
  • Manage a multi-million dollar annual budget
  • Clearly communicate the connection between the Loyalty platform and the company’s overall strategy, objectives and priorities to staff. Ensure staff understands their place in the company strategy
  • Provide oversight and leadership in evaluating build vs. buy decisions
  • Provide oversight and leadership in vendor and product evaluation and selection


  • 12+ years of service delivery experience in implementing and maintaining real-time, high-volume transactional systems, leading a high performing, globally distributed delivery teams.
  • Matured understanding of the Retail industry and Loyalty function and their role in driving P&L improvements
  • Experience in build vs. buy decisions and TCO evaluation against company objectives
  • Experience building and running a multi-tenancy platform with multiple active tenants
  • Delivery Management experience in Loyalty and Marketing Technology space (Loyalty / CRM / Email / Marketing Ops)
  • Strong experience in engagements that span tracks of work including User Experience, Technology, Project Management, Business Analysis, Systems Integration, Migration and Infrastructure (Cloud and Data Center)
  • Strong background in modern technology architecture, process and solutions from cloud technologies: test driven development; API and SOA; CI / CD; Swagger, AWS, etc.
  • Solid experience and understanding of how a robust ecosystem of systems and functions interact as an integrated Omni-Channel experience along with understanding the critical elements, KPIs and success measures with Loyalty, CRM, GLs, 3rd Party Integrations, Multi-tenant Integrations, eCommerce, Brick and Mortar Store POS, Multi-Channel Marketing (email, online messaging, targeted interactions, A/B testing, etc.)
  • Experience managing highly available systems and key KPIs of a mission critical system
  • Deep understanding and experience with customer experience and customer journey centric platform development and approaches
  • Excellent people management skills, ability to develop and motivate diverse teams. Should have directly managed a global team of 40+ associates;
  • Expertise in managing contracting and consulting service providers
  • Minimum of 15 years of experience in a managerial position in a technology group with a proven track record for development talent, including managing other leaders (e.g., Directors, Senior Managers, Managers, etc.)
  • Experience leading key initiatives against strict timeline and multiple priorities
  • Experience working in a consultative manner with key business leaders and serving as a key advisor and partner
  • Strong executive presence, demonstrated history of working with internal business partners at the executive level (e.g. VP, SVP, CXO)
  • Experience with measurable and reliable agile delivery approaches that can be adapted to different industries and work environments
  • Experience of driving large scale, enterprise wide transformation, including the culture and mindset of a group to embrace new and improved ways of using technology.
  • Demonstrated competency in owning a multi-tenant Platform as a Service (PaaS) with multiple external companies / entities concurrently using the platform
  • Ability to learn, pivot and change as business priorities change to adapt to new executive priorities
  • Experience with Digital Transformation and customer experience improvement initiatives a plus.
  • Experience negotiating MSAs and SOWs for technology vendors and service providers


  • Must be 21 years of age or older to apply
  • Must comply with all legal or company regulations for working in the industry 

Cresco Labs is an Equal Opportunity Employer and all applicants will be considered without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran, or disability status.

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