Senior Director, Marketing Transformation & Operations

Join Trulieve, where passion meets purpose. Recognized on TIME's America's Best Companies 2026 List, Trulieve is one of only two cannabis companies to receive this distinction based on employee satisfaction, financial strength, and sustainability transparency. We bring patients relief through hand-grown, carefully controlled products designed to minimize unwanted chemicals and pests.

About the role

Trulieve is seeking a Senior Director of Marketing Transformation & Operations to lead the vision, strategy, and execution of our enterprise marketing technology ecosystem. This role bridges Marketing, Technology, Data, Product, and Retail Operations to drive digital transformation initiatives that improve customer experience, operational efficiency, and marketing effectiveness at scale. The ideal candidate is equal parts strategist, operator, architect, and change leader with deep experience in marketing technology roadmaps, enterprise platform implementations, vendor partnerships, AI-driven capabilities, and driving organization-wide adoption.

Responsibilities

• Define and maintain the enterprise marketing technology vision and multi-year roadmap.
• Evaluate current-state capabilities, gaps, and opportunities across marketing platforms and workflows.
• Prioritize technology investments that improve customer acquisition, personalization, retention, and operational efficiency.
• Align technology initiatives with business objectives and marketing growth strategies.
• Lead large-scale digital transformation initiatives across Marketing, Digital, Data, and Technology teams.
• Establish governance frameworks and operating models supporting long-term scalability.
• Own and evolve Monday.com as the organization’s workflow management platform, including board architecture, automation rules, dependency mapping, and integrations.
• Identify bottlenecks in the 4,000+ monthly asset pipeline and design scalable solutions to reduce cycle time without sacrificing quality.
• Identify and implement AI-driven solutions to increase productivity, content velocity, personalization, and business intelligence.
• Drive enterprise modernization efforts, including platform consolidation, process optimization, and capability expansion.
• Evaluate emerging technologies and recommend future-state capabilities.
• Lead the integration strategy across key platforms including CDP (CRM), Rewards/Loyalty, eCommerce, CMS, Mobile, Analytics, DAM, PIM, and Marketing Automation.
• Ensure scalable, secure, and compliant data flows across the organization for both medical and recreational markets.
• Own vendor evaluation, selection, contract negotiations, renewals, and ongoing performance management.
• Develop business cases and ROI frameworks for technology investments.
• Drive platform adoption across marketing and cross-functional teams through change management strategies, training programs, and communication plans.
• Own insights from customer experience platforms like Medallia, Google reviews, Yelp, and Weedmaps to capture and capitalize on the voice of the patient/customer.

Requirements

• 15+ years of experience in Marketing Technology, Digital Transformation, Enterprise Platforms, or related disciplines.
• 5+ years leading enterprise-scale marketing technology teams.
• Proven track record implementing and optimizing marketing technology ecosystems.
• Experience managing large budgets, vendor relationships, and technology contracts.
• Strong understanding of customer data platforms (CDP), CRM, marketing automation, analytics, CMS, personalization, loyalty, and digital commerce ecosystems.
• Experience leading cross-functional teams through organizational and technology change.
• Exceptional communication and executive presentation skills.

Preferred Qualifications

• Experience with Adobe Experience Cloud, SAP, AEM, EDS, CDP, AJO, ACO, SEO, GEO or similar enterprise platforms (Salesforce, Braze, Segment, Amperity, Tealium, Bloomreach, etc.).
• Experience leading AI and automation initiatives across marketing organizations.
• Background in retail, consumer packaged goods, healthcare, or highly regulated industries.
• MBA or advanced degree (not required based on experience).

Benefits

• Comprehensive benefits package including paid time off.