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Director of Customer Success
Full-time
Title: Director, Account Management Hospitality Vertical
Location: US,
Remote
Company:
Milestone Inc.
Role Type:
Primarily an individual-contributor role; may include a small number of direct reports
About Milestone
Milestone Inc. is a leading Digital Experience Software & Services company focused on AI-first discovery, personalization, & conversion across all digital touchpoints. Our platform enables brands to be visible in search engines & AI answer engines through structured data, entity intelligence, & AI-driven orchestration.
We serve complex, multi-location enterprises across hospitality, banking/financial services, & MarTech-driven organizations, operating a hybrid SaaS \+ Services business model at scale.
Role Overview
Milestone seeks a hands-on, revenue-focused
Director, Account Management – Hospitality
to drive retention, expansion, & customer success for strategic enterprise accounts. This senior individual contributor role owns GRR, NRR, churn reduction, & growth while serving as the executive partner for customers. The ideal candidate brings strong enterprise account management skills & expertise in SEO, CMS, websites, schema, GEO, local search, AI search, & omnichannel digital strategy.
Strong understanding of search strategies: Technical SEO, CMS, Platform, Websites, Content, Schema, Local & near-me discovery, Generative Engine Optimization (GEO), & the digital commercial omnichannel strategy that ties them together.
Must-Have Qualifications
Must demonstrate strength in all five areas:
Strong omnichannel search experience:
technical SEO
, structured data/schema, local & near-me discovery, AI answer engines, & generative engine optimization (GEO), paired with digital strategy experience
Hospitality experience
: direct, substantial experience serving hospitality brands (hotels, resorts, restaurants, travel, or multi-location operators)
AI / MarTech experience: hands-on familiarity with modern
MarTech
(CDPs, CRMs, personalization, attribution, campaign orchestration) & AI-driven engagement technologies
Data & analytics: fluency with adoption, journey, retention, & search/performance data to drive decisions & prove value
Account management
: proven ownership of enterprise accounts, retention, & expansion as a trusted executive partner
Problems We Are Looking to Solve
The Director of Customer Success will help solve enterprise-level challenges including:
Own strategic accounts & relationships
Lifecycle execution gaps across onboarding, adoption, renewal, & expansion
Limited predictability in churn risk, renewals, & expansion forecasting
Create & follow Scalability & repeatability in CS playbooks
Fragmentation across SaaS \+ Services delivery models
Underutilization of AI & automation in CS workflows
Weak or single-threaded executive relationships across complex enterprise accounts
Key Responsibilities
1. Enterprise Account Ownership & Revenue Outcomes
Personally own & improve GRR, NRR, churn, expansion ARR, CLV, & cohort health across an assigned book of strategic enterprise accounts
Operate & forecast a multi-million-dollar portfolio, carrying individual accountability for the number
Run end-to-end lifecycle playbooks account by account across onboarding, adoption, value realization, renewal, & expansion
Maintain a rigorous operating cadence: QBRs, executive business reviews, health scoring, churn-risk reviews, & expansion planning
Identify & drive systematic expansion within accounts so customers on the Milestone product stack have defined ARR growth year over year
2. Enterprise Stakeholder Management & Cross-Functional Orchestration
Build & maintain multi-threaded, executive-level relationships across large, complex customer organizations
Navigate enterprise buying & decision-making dynamics across procurement, security, legal, & multiple lines of business
Orchestrate internal resources across Sales, Product, Marketing, Engineering, Professional Services, & Support to deliver for accounts, without direct authority over those teams
Own escalations end-to-end, mobilizing the right people & communicating clearly to senior customer stakeholders
Follow clear playbooks, SLAs, & governance, & contribute improvements back to the broader CS motion
3. Hospitality, Omnichannel Search & MarTech Expertise
Bring deep, direct experience serving hospitality clients (hotels, resorts, restaurants, travel, or multi-location brands)
Understand hospitality-specific dynamics: multi-location & franchise structures, brand vs. property priorities, loyalty, direct-booking, & local/near-me discovery
Apply strong omnichannel search expertise: technical SEO, structured data & schema, AI answer engines, generative engine optimization (GEO), & the digital strategy connecting them
Apply working knowledge of MarTech ecosystems: CDPs, CRMs, personalization, attribution, ABM, & campaign orchestration
Translate platform capabilities into hospitality-specific business outcomes
Partner with senior client stakeholders such as CMOs, CDOs, & Heads of Digital & Loyalty
4. AI-Powered Customer Success Execution
Use AI-driven CS capabilities in daily account work: predictive health scoring, churn/risk signals, next-best-action, & renewal/expansion forecasting
Leverage automation across the CS stack, including CRM, ticketing, in-app guidance, chatbots, & knowledge bases, to work more efficiently across a large book
Improve time-to-value & personal productivity through effective use of tooling
Provide feedback on AI tools & workflows to help the broader CS & MarTech tooling evolve
5. Hybrid SaaS \+ Services Delivery
Manage accounts across recurring SaaS (land-&-expand, usage-driven) & Services (projects, retainers, SOWs, campaigns)
Define clear value, scope, & success metrics for blended offerings within each account
Partner with CS Ops / Rev Ops & Delivery on clean handoffs & account-level margin
Drive consistent, repeatable execution rather than one-off, hero-driven delivery
6. Product Mindset & Voice of Customer
Bring a product mindset, understanding how customer feedback, adoption behavior, & usage patterns influence product evolution
Partner with Product, Engineering, & GTM teams to inform roadmap priorities & improve customer experience
Translate customer pain po
