Head of Digital | Toronto-based | Onsite | Entertainment, Events & Hospitality | $95k-$125k

The Company

They are a leading hospitality and entertainment organization with a diverse portfolio spanning restaurants, nightlife, music, festivals, live events, and lifestyle experiences across North America. Their brands combine hospitality, culture, entertainment, and technology to create memorable experiences for their audiences. They operate in a fast-paced, highly collaborative environment where creativity, innovation, and commercial thinking are highly valued.

The Role

They are seeking a Head of Digital to lead the digital strategy across their portfolio of hospitality and entertainment brands. This senior leadership role will oversee the organization's digital ecosystem, including websites, CRM, paid media, SEO, analytics, marketing technology, AI, and customer experience. They will work closely with Marketing, Creative, Operations, Events, Partnerships, PR, and Technology leadership to drive customer growth, revenue, and digital innovation. They will also lead and mentor the digital team, including Social Media.

The Responsibilities

• Develop and execute the organization's overall digital strategy and long-term roadmap.
• Lead digital transformation initiatives that improve customer experience and business performance.
• Drive reservations, ticket sales, memberships, loyalty, gift card sales, and online revenue.
• Oversee CRM, email, SMS, lifecycle marketing, audience development, and customer retention.
• Lead paid media, SEO, performance marketing, conversion optimization, and digital acquisition.
• Manage digital agencies, media partners, budgets, and technology vendors.
• Oversee websites, reservation platforms, ticketing experiences, and other digital products.
• Develop digital strategies for concerts, festivals, nightlife, and major live events.
• Support sponsorship and brand partnership activations through digital campaigns.
• Use analytics, attribution, testing, and reporting to guide business decisions.
• Identify opportunities to leverage AI, automation, personalization, and emerging technologies.
• Lead, mentor, and develop the digital team while fostering a culture of innovation and accountability.

The Requirements

• 8+ years of progressive digital marketing experience, including leadership experience.
• Experience within hospitality, entertainment, live events, music, lifestyle, retail, or consumer brands.
• Strong expertise across paid media, SEO, CRM, analytics, marketing automation, websites, and digital strategy.
• Experience managing multi-brand digital ecosystems.
• Strong understanding of customer acquisition, digital commerce, retention, and lifecycle marketing.
• Proven experience managing agencies, budgets, vendors, and cross-functional teams.
• Strong commercial, analytical, strategic, and communication skills.
• Experience with ticketing, event marketing, sponsorship activations, or entertainment marketing is an asset.
• Familiarity with GA4, Google Ads, Meta Ads Manager, TikTok Ads, CRM platforms, CMS platforms, and AI marketing tools.
• Experience with Tradable Bits or similar marketing technology is an asset.

If you're a digital leader who combines commercial thinking, creativity, technology, and customer experience, this is an opportunity to shape the digital direction of an exciting hospitality and entertainment portfolio. Candidates who thrive in fast-moving environments and want meaningful ownership are encouraged to apply.

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