Director, Digital Marketing - Drew Estate

Applicants are required to provide a cover letter that addresses three key areas: (1) how your marketing approach aligns with Drew Estate’s bold and disruptive brand identity; (2) examples of how you have led digital strategy and transformation; and (3) your personal career vision and why this role at Drew Estate is the right next step for you.  Candidates who do not provide this information will not be considered.

Summary 

Drew Estate is seeking a Digital Marketing Director to lead the strategy, execution, and performance of our digital marketing function. This is a senior leadership role with full accountability for the vision, team, platforms, performance, and evolution of digital at Drew Estate.

We’re looking for a proven leader who can build and manage a team, guide agency partners, structure and interpret data, and effectively communicate results and opportunities across the business. This individual will play a critical role in ensuring that digital marketing is positioned not just as a support function, but as a strategic driver of consumer engagement, business growth, and long-term brand equity.

This position is based in Doral, Florida with a hybrid work schedule consisting of 3 days in-office (Tues – Thurs) and remote work on Mondays and Fridays.  The candidate must be willing to live in the South Florida area (Miami-Dade or Broward counties).  Relocation allowance may be considered for qualified candidates.  This position requires flexibility to travel 20% of the time to various trade shows, experiential events, customer visits, and external partner meetings.

Reporting Relationships

The Digital Marketing Director reports to the Senior Vice President of Marketing.

Compensation

Total target cash compensation (base salary plus target bonus) approximates $210k.

 Roles & Responsibilities

Digital Strategy & Leadership (40%) 

• Develop and lead Drew Estate’s comprehensive digital marketing strategy to align with Brand, Consumer Engagement, Innovation and company-wide strategic objectives
• Translate business and brand goals into integrated, insight-driven digital initiatives that drive awareness, engagement, and emotional connection with consumers and trade
• Build, mentor, and manage a high-performing digital marketing team. Provide clear goals, education, coaching, and performance accountability
• Direct agency relationships to ensure alignment with internal priorities, high-quality execution, and strong return on investment
• Own and manage the digital marketing budget, ensuring optimal allocation of resources to maximize ROI
• Advocate for Digital Marketing within the organization by regularly presenting plans, results, and insights to the Operating Team and Executive Leadership

Operational Discipline & Execution (25%) 

• Design and implement workflows, campaign calendars, approval processes, QA standards, and team processes to drive productivity and quality
• Lead the planning, launch, and optimization of digital marketing campaigns across email, social, paid media, CRM, and owned web properties
• Ensure consistent application of brand voice, identity, and messaging across all digital channels
• Align digital execution timelines with product launches, trade events, retailer programs, marketing campaigns, and Innovation initiatives
• Establish clear deliverables, deadlines, and performance metrics for internal teams and external partners

Performance Marketing, Data & Analytics (20%) 

• Define and monitor digital KPIs tied to business outcomes such as consumer acquisition, retention, engagement, and ROI
• Build and maintain dashboards and reporting systems that provide real-time visibility into campaign performance and digital health
• Establish a structured approach to marketing database management from collection to segmentation and the resulting insights reporting
• Drive a culture of testing, learning, and continuous optimization across all digital activities
• Partner with Legal and IT to ensure all digital marketing practices are compliant with data privacy and industry-specific regulations

Platform Management & Martech Infrastructure (15%) 

• Oversee the performance and evolution of key digital platforms including CRM/email systems, CMS, analytics tools, and marketing automation
• Ensure platform reliability, security, user experience, mobile optimization, and SEO/AEO best practices
• Evaluate and implement new tools and technologies that enhance personalization, targeting, automation, and data visualization
• Work cross-functionally to integrate digital systems with broader business operations and future innovation initiatives

Skills & Abilities 

• Proven ability to recruit, mentor, and retain top digital talent. Leads with clarity and empathy, setting a high bar for performance, accountability, and culture
• Strong project management and process development skills to drive campaign execution, streamline workflows, and ensure on-time, on-budget delivery across teams and external partners
• Operates with the fast-paced mindset of a startup while executing with the structure, polish, and discipline expected of a premium, global brand
• High attention to detail and critical thinking skills, with a strong ability to hold self and others accountable for high-quality execution
• Strong storytelling ability and creative judgment to ensure content is culturally relevant, on-brand, and resonates with cigar consumers and trade alike
• Proficient in Microsoft Office including PowerPoint and Excel to communicate strategic initiatives and results to key stakeholders and executive leadership
• Experienced in web platforms and CMS systems (e.g., WordPress) with a strong grasp of UX/UI and web optimization
• Skilled in CRM platforms (e.g., Mailchimp, Klaviyo, HubSpot), including A/B testing, deliverability, automation, and personalization
• Comfortable managing martech stacks and collaborating with Innovation, IT, and external agencies to evaluate and implement new tools and platforms
• Asks the right questions to uncover deeper insights, challenge assumptions, and fuels digital innovation from ideation through execution

Education & Experience Requirements 

• Bachelor’s degree in Marketing, Business or related field
• 8+ years of digital marketing experience, including 3+ years in leadership capacity preferably at the director level or above

• Demonstrated success building and leading digital marketing teams and agency partnerships
• Track record of translating brand and business objectives into high-performing digital programs
• Experience in tobacco, spirits, luxury, lifestyle and/or regulated goods preferred
• Genuine interest in or passion for premium cigars is highly desirable but not required
• Must be comfortable working in a cigar smoking environment

To be considered for this role, candidates must submit both a resume and a cover letter with information as stated above.

Drew Estate’s Core Values

1. Trust and Respect

• Does not ascribe malintent to others.
• Does not cultivate a culture of fear nor engage in retribution towards others.
• Maintains confidences.
  
  

2. Accountability and Integrity

• Follows through on one’s commitments.
• Takes personal responsibility for one’s actions, behaviors, comments, & results.
• Does not blame others or throw others under the bus.
  
  

3. Collaboration and Teamwork

• Works with others to solve problems and achieve outcomes in a constructive manner.
• Engages rather than fights or flees when interacting with others.
• Seeks to understand before seeking to be understood.
  
  

4. Self-Awareness

• Is aware of the impact that one’s interpersonal style has on others.
• Avoids and eliminates the drama.
• Maintains grace under pressure.
  
  

5. Communication

• Communicates respectfully – no personal attacks, disparaging language, or snarky tone/attitude.
• Provides constructive feedback to others.
• Goes directly to the source for information and explanations.
  
  

6. Innovation

• Teaches and inspires others to develop new ideas without fear of retribution.
• Disrupts the status quo in a constructive manner.
• Contributes knowledge / skills that enable the company to generate breakthroughs.