Head of Enterprise Accounts – Travel & Hospitality (Digital Marketing/SEO)

Milestone Inc. is a leading AI-powered Digital Experience Platform company that empowers location-based businesses. They are seeking a Head of Enterprise Accounts – Travel & Hospitality to lead strategic growth and customer success across their key accounts in the hospitality sector.

Responsibilities:

• Own the overall health, growth, retention, and commercial success of Milestone’s enterprise travel and hospitality portfolio
• Lead and mentor a team of Enterprise Account Managers and Customer Success Managers responsible for strategic customer engagement, renewals, adoption, and expansion
• Directly manage a select portfolio of high-value strategic accounts and serve as the executive relationship owner
• Own revenue performance across the portfolio, including:
• Net Revenue Retention (NRR)
• Gross Revenue Retention (GRR)
• Expansion ARR
• Renewal forecasting
• Customer growth plans
• Commercial expansion strategy
• Drive measurable customer outcomes tied to direct bookings, AI discoverability, guest acquisition, and digital performance. Develop and operationalize strategic account plans aligned to customer business goals and Milestone platform capabilities
• Establish executive operating cadence across the portfolio:
• QBRs
• Executive business reviews
• Renewal planning
• Expansion pipeline reviews
• Escalation management
• Success forecasting
• Lead complex commercial conversations including renewals, upsells, cross-sells, and strategic growth negotiations
• Build a high-performance enterprise customer success function focused on customer value realization, adoption, retention, and long-term strategic growth. Drive platform adoption and product success across Milestone’s AI-first platform ecosystem including:
• CMS
• GEO / AI Search
• Local Listings
• Schema Manager
• AI Content Studio
• Events & Local Experience Solutions
• Analytics & Reporting
• Ensure customers achieve measurable ROI and business impact through proactive success planning and operational rigor. Develop scalable playbooks for onboarding, adoption, expansion, executive engagement, and risk mitigation
• Partner closely with Product and Engineering teams to ensure customer feedback directly influences platform evolution and roadmap priorities. Drive customer health visibility, adoption metrics, executive alignment, and proactive risk management across the portfolio
• Design and execute strategic Account-Based Marketing (ABM) programs to deepen engagement and accelerate growth within enterprise accounts
• Act as a strategic advisor on:
• SEO & GEO (Generative Engine Optimization)
• AI search visibility
• Omnichannel digital strategy
• Local discovery
• Structured data & entity optimization
• AI-first digital experiences
• Direct booking optimization
• Translate hospitality digital marketing best practices into actionable customer growth strategies and measurable business outcomes. Partner with Marketing to develop hospitality-focused thought leadership, customer stories, executive content, and strategic campaigns. Support demand generation and industry visibility through events, executive roundtables, webinars, and speaking engagements
• Develop deep expertise across Milestone’s AI-first platform ecosystem and evolving AI search landscape
• Advise enterprise clients on:
• CMS governance
• Multi-location digital management
• Structured data & entity strategy
• AI readiness
• GEO optimization
• Digital experience modernization
• AI-powered discovery and conversational search
• Stay ahead of technology trends shaping hospitality and travel including:
• AI agents
• Conversational commerce
• OTAs
• Metasearch
• Revenue management evolution
• Generative search
• Direct booking transformation
• Act as a strategic bridge between customers and Milestone Product, Engineering, and GTM teams
• Lead, coach, and scale a world-class enterprise account and customer success organization
• Create a culture of:
• Ownership
• Accountability
• Customer obsession
• Operational excellence
• Commercial thinking
• Proactive leadership
• Drive alignment across Sales, Product, Marketing, Professional Services, Engineering, and Support teams to ensure exceptional customer outcomes
• Build scalable operational frameworks for forecasting, customer health, escalation management, expansion planning, and executive communication
• Serve as the executive voice of the customer internally

Requirements:

• 12–18+ years of experience in enterprise account management, customer success, or commercial leadership roles
• Strong experience within hospitality, travel, tourism, or enterprise martech/SaaS environments
• Proven success leading enterprise account management and/or customer success teams
• Demonstrated ownership of enterprise portfolio revenue, renewals, retention, and expansion ARR
• Strong executive presence with experience engaging CMOs, CDOs, Revenue Leaders, and senior hospitality executives
• Deep expertise in digital marketing including SEO, GEO, AI search, omnichannel strategy, ABM, and content strategy
• Strong understanding of SaaS platforms, CMS, analytics, structured data, AI search, and digital experience ecosystems
• Experience managing strategic enterprise accounts directly while also leading teams
• Commercial mindset with strong negotiation and forecasting capabilities
• Strong cross-functional leadership and operational execution skills
• Hospitality technology ecosystem experience is a strong plus: PMS, CRS, OTAs, metasearch, loyalty systems, and revenue management platforms
• Experience speaking at industry events or contributing to hospitality thought leadership is a plus
• Bachelor's degree in Business, Marketing, Hospitality, or related field; MBA preferred