Senior Director, Marketing Technology

Join Trulieve, where passion meets purpose in one of the nation's fastest-growing industries. Recognized on TIME's America's Best Companies 2026 List, Trulieve stands out for employee satisfaction, financial strength, and sustainability transparency—one of only two cannabis companies to receive this honor. We are dedicated to bringing patients relief through trusted, hand-grown products cultivated in carefully controlled environments to ensure natural quality.

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 enhance customer experience, operational efficiency, and marketing effectiveness at scale. You will own end-to-end workflow infrastructure, architect smarter processes, accelerate throughput, and embed AI-enabled personalization into our marketing operations. Additionally, this role oversees customer experience insights from Medallia and Google.

The ideal candidate is a strategist, operator, architect, and change leader with deep experience in building marketing technology roadmaps, leading enterprise platform implementations, managing vendor partnerships, enabling AI-driven capabilities, and driving organization-wide adoption of new technologies. This leader will shape the future-state marketing architecture supporting Trulieve's growth, modernization, and customer-centric transformation.

Responsibilities

• Marketing Technology Strategy & Roadmap
  • 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.
• Enterprise Transformation Leadership
  • 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 with adjacent tools.
  • Identify bottlenecks in the 4,000+ monthly asset pipeline and design scalable solutions that reduce cycle time without sacrificing quality.
• AI, Automation & Innovation
  • Identify and implement AI-driven solutions that 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.
• Platform Architecture & Integrations
  • Partner closely with IT, Data, Delivery, and Enterprise Architecture teams.
  • 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.
• Vendor Management & Governance
  • Own vendor evaluation, selection, contract negotiations, renewals, and ongoing performance management.
  • Develop business cases and ROI frameworks for technology investments.
  • Ensure vendors deliver against contractual obligations, timelines, and business outcomes.
• Adoption & Change Management
  • Drive platform adoption across marketing and cross-functional teams.
  • Develop change management strategies, training programs, communication plans, and success metrics.
  • Establish scalable processes that maximize utilization and business value.
• Customer Experience Insights
  • Own insights from customer experience platforms like Medallia, Google reviews, Yelp, and Weedmaps to capture, share, 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

• Opportunity to shape the future of digital marketing and lead enterprise-wide transformation initiatives.
• Comprehensive benefits package including paid time off.