Senior Director Enterprise - Travel & Hospitality

Senior Director Enterprise - Travel & Hospitality Company: Milestone Inc. Department: Enterprise Customer Success Reports To: VP of Customer Success Location: United States (Flexible / Remote-Friendly – Hybrid in San Jose ideal) Type: Full-Time About Milestone Milestone Inc. is a leading AI-powered Digital Experience Platform company that empowers location-based businesses to enhance their omnichannel presence and accelerate revenue growth. Serving over 2,000 brands across Hospitality, Financial Services, Retail, and Automotive, Milestone delivers award-winning innovation across every digital touchpoint. Our mission: pioneer the discovery and visibility of content through an AI-native platform—combining SEO/GEO-first CMS, Local Listings, Schema Management, AI Content Studio, AI Agents, and Performance Marketing services to drive discovery, personalization, and conversion at scale. We are a founder-led, Certified Great Place to Work with a collaborative, high-bar leadership culture deeply committed to customer outcomes and continuous innovation. Role Overview Milestone is seeking a Senior Director, Enterprise Travel & Hospitality to own strategic growth, retention, and expansion of high-value accounts within the travel, hospitality, and tourism sectors. This role sits at the intersection of enterprise account leadership, digital marketing expertise, and technical platform enablement—making it one of the most impactful customer-facing roles in the company. You will serve as a trusted executive advisor to CMOs, Heads of Digital, Revenue Managers, and senior operators at leading hotel chains, travel brands, and hospitality management companies. You will translate Milestone's AI-first platform capabilities into measurable business outcomes—direct bookings, digital discoverability, guest acquisition, and loyalty—while driving account growth through strategic consulting, ABM execution, and value-based relationship management. The ideal candidate is a rare blend: technically fluent in SaaS platforms and digital marketing stacks, deeply experienced in hospitality or travel verticals, and a skilled marketer who understands what it takes to drive enterprise pipeline and revenue. What You Will Own (Outcome Ownership) 1. Strategic Account Ownership & Revenue Growth

• Own and grow a portfolio of high-ARR strategic accounts across hospitality, travel, and outdoor tourism verticals.
• Drive measurable improvement in Net Revenue Retention (NRR), Gross Revenue Retention (GRR), and expansion ARR within your book of business.
• Develop and execute strategic account plans aligned to customer OKRs and Milestone platform capabilities—onboarding through expansion.
• Establish a rigorous operating cadence: quarterly business reviews, executive check-ins, renewal forecasting, and expansion pipeline management.
• Lead contract renewals and upsell negotiations, identify and close expansion opportunities.

2. Enterprise Marketing & ABM Leadership

• Design and execute Account-Based Marketing (ABM) strategies to deepen engagement, drive product adoption, and create upsell momentum within strategic accounts.
• Translate digital marketing best practices—SEO, GEO, content strategy, omnichannel campaigns—into actionable playbooks for hospitality clients.
• Act as a thought leader and strategic advisor on digital marketing trends relevant to travel and hospitality: AI search, voice, local discovery, and direct booking optimization.
• Partner with the Milestone marketing team to develop hospitality-specific content, case studies, and success stories that amplify brand visibility and pipeline.
• Support demand generation through participation in industry events, webinars, and speaking engagements (HSMAI, AAHOA, ITB, etc.).

3. Technical Platform Enablement & Digital Advisory

• Develop deep technical fluency across Milestone's full platform suite: AI-native CMS, Local Listings, Schema Manager, GEO/AI Search, AI Content Studio, Events Calendar, and Analytics.
• Guide clients through platform adoption, integration best practices, and website optimization strategies to drive maximum ROI.
• Advise enterprise clients on CMS governance, multi-location digital management, structured data strategy, and AI-readiness across their digital footprint.
• Stay ahead of technology trends shaping hospitality distribution: OTAs, metasearch, direct booking, AI-powered guest journeys, and generative search.
• Serve as a conduit between customer needs and Milestone's Product and Engineering teams, advocating for

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