Director - Account Management (Hospitality)

Milestone Inc. is a leading Digital Experience Software and Services company focused on AI-first discovery, personalization, and conversion across all digital touchpoints. Our platform enables brands to be visible in search engines and AI answer engines through structured data, entity intelligence, and AI-driven orchestration.We serve complex, multi-location enterprises across hospitality, banking/financial services, andMarTech-driven organizations,operatinga hybrid SaaS + Services business model at scale.

Role Overview

Milestone isseekinga hands-on, revenue-orientedDirector, AccountManagementHospitality Verticalto own retention, expansion, and customer outcomes across a portfolio of strategic enterprise accounts in the hospitalityvertical.It is primarily a senior individual-contributor role in which the Director carries their own book of business and is measured on the outcomes they drive within it, and it may over time include a small number of direct reports as the teamevolves.The Director serves as the primary executive-facing partner and quarterback for their accounts.

This is a revenue-adjacent role, accountable for GRR, NRR, churn reduction, expansion, time-to-value, and customerdelight, not just customer satisfaction. Success depends on strong account-management skills: navigating complex, multi-stakeholder organizations, building trust with senior and C-level buyers, orchestrating cross-functional resources without formal authority, and translating capability into measurable business value. Because Milestone's platform makes brands visible across search engines and AI answer engines,



the Director must bring a strong technical understanding of omni-channel searchstrategies:Technical SEO,CMS, Platform, Websites,Content, Schema,Local and near-me discovery,GenerativeEngineOptimization (GEO),and the digitalcommercialomnichannelstrategythat ties them together. The Director works closely withglobal teamsincludingCS, Professional Services, and Support teams across the US, India, Canada, and Mexico

Must-Have Qualifications

Candidates mustdemonstratestrength in all five areas:

- Solid omnichannel search experience:technical SEO, structured data/schema, local and near-me discovery, AI answer engines, and 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 /MarTechexperience: hands-on familiarity with modernMarTech(CDPs, CRMs, personalization, attribution, campaign orchestration) and AI-driven engagement technologies
- Data and analytics: fluency with adoption, journey, retention, and search/performance data to drive decisions and prove value
- Account management: proven ownership of enterprise accounts, retention, and expansion as a trusted executive partner

Problems We Are Looking to Solve

The Director of Customer Success will help solve enterprise-level challenges including:

- Ownstrategicaccountsandrelationships




- Lifecycleexecution gaps across onboarding, adoption, renewal, and expansion
- Limited predictability in churn risk, renewals, and expansion forecasting
- Create andfollowScalabilityand repeatability in CS playbooks
- Underutilization of AI and automation in CS workflows
- Weak or single-threaded executive relationships across complex enterprise accounts

Key Responsibilities

- Personally own and improve GRR, NRR, churn, expansion ARR, CLV, and cohort health across an assigned book of strategic enterprise accounts
- Operate and 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, and expansion
- Maintain a rigorous operating cadence: QBRs, executive business reviews, health scoring, churn-risk reviews, and expansion planning
- Identifyand 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 andmaintainmulti-threaded, executive-level relationships across large, complex customer organizations
- Navigate enterprise buying and decision-making dynamics across procurement, security, legal, and multiple lines of business
- Orchestrate internal resources across Sales, Product, Marketing, Engineering, Professional Services, and Support to deliver for accounts, without direct authority over those teams
- Own escalations end-to-end, mobilizing the right people and communicating clearly to senior customer stakeholders
- Fol

📌 Director - Account Management (Hospitality) (Canada)
🏢 Milestone
📍 Canada