Director - Account Management (Hospitality)

Milestone Inc.; Canada; Hybrid; CAD 180,000 - 240,000; Full time

Job summary

Milestone Inc. is seeking a Director of Account Management for the Hospitality vertical to own retention, expansion, and customer outcomes across strategic enterprise accounts. This senior role carries a personal book of business and may include a small number of direct reports as the team evolves.

The Director serves as the primary executive-facing partner and quarterback for their accounts. This is a revenue-adjacent role focused on GRR, NRR, churn reduction, and value realization, requiring

Qualifications

• Strong omnichannel search experience including technical SEO and schema.
• Hospitality experience with hotels, resorts or multi-location brands.
• Hands-on AI/MarTech with CDPs, CRMs, personalization and attribution.
• Data/analytics fluency for adoption, journey, retention, and search data.
• Proven enterprise account management with retention and expansion.

Responsibilities

• Own GRR, NRR, churn, expansion ARR, and cohort health for a strategic portfolio.
• Forecast a multi-million-dollar book and maintain accountability.
• Execute end-to-end lifecycle playbooks across onboarding, adoption, renewal, expansion.
• Maintain QBRs, executive business reviews, health scoring, churn reviews.
• Drive systematic expansion within accounts to grow ARR yearly.
• Build executive relationships and orchestrate cross-functional teams.

Skills

Omnichannel search

Hospitality vertical experience

AI/MarTech experience

Data and analytics

Account management

Tools

CDPs

CRMs

Personalization tooling

Attribution

Campaign orchestration

Job description

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:

• Strong 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
• Follow clear playbooks, SLAs, and governance, and contribute improvements back to the broader CS motion
• Bring deep, direct experience serving hospitality clients (hotels, resorts, restaurants, travel, or multi-location brands)
• Understand hospitality-specific dynamics: multi-location and franchise structures, brand vs. property priorities, loyalty, direct-booking, and local/near-me discovery
• Apply strong omnichannel searchexpertise: technical SEO, structured data and schema, AI answer engines, generative engine optimization (GEO), and the digital strategy connecting them
• Apply working knowledge ofMarTechecosystems: CDPs, CRMs, personalization, attribution, ABM, and campaign orchestration
• Translate platform capabilities into hospitality-specific business outcomes
• Partner with senior client stakeholders such as CMOs, CDOs, and 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, and renewal/expansion forecasting
• Leverage automation across the CS stack, including CRM, ticketing, in-app guidance, chatbots, and knowledge bases, to work more efficiently across a large book
• Improve time-to-value and personal productivity through effective use of tooling
• Provide feedback on AI tools and workflows to help the broader CS andMarTechtoolingevolve

5. Hybrid SaaS + Services Delivery

• Manage accounts across recurring SaaS (land-and-expand, usage-driven) and Services (projects, retainers, SOWs, campaigns)
• Define clear value, scope, and success metrics for blended offerings within each account
• Partner with CS Ops / Rev Ops and Delivery on clean handoffs and 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, and usage patterns influence product evolution
• Partner with Product, Engineering, and GTM teams to inform roadmap priorities and improve customer experience
• Translate customer pain points and industry trends into recommendations for platform enhancements and AI-powered experiences
• Operate with a data-driven approach,leveragingadoption metrics, journey insights, retention analytics, and voice-of-customer signals

Ideal Candidate Profile

We areseekinga data-driven, execution-focused senior individual contributor who:

• Has strong account-management skills and thrives inside large, complex, multi-stakeholder customer organizations
• Buildstrust and credibility with senior and C-suite buyers, and keeps relationships multi-threaded
• Thinks in outcomes, revenue, and value, not just relationships
• Knows the hospitality industry well and can speak the language of hospitality buyers
• Is technically fluent in omnichannel search (technical SEO, structured data, GEO) and comfortable in detailed search and analytics conversations
• Understands SaaS economics and services margin
• Gets results through influence and cross-functional orchestration rather than positional authority
• Is highly self-directed, organized, and accountable for their own book of business
• Brings a strong learning mindset

Required Experience & Qualifications

• 7-10 years in SaaS,MarTechplatforms, agencies, or high-growth B2B environments
• Agency andMarTechexperience
• Direct, substantial experience serving the hospitality vertical (required)
• Strong omnichannel search experience across
• Technical SEO, CMS, Platform, Websites,Content, Schema, Local and near-me discovery, Paid, analytics, Generative Engine Optimization (GEO),and the digital commercial omnichannel strategy that ties them together.
• Hands-on AI andMarTechexperience: CDPs, CRMs, personalization, attribution, campaign orchestration, and AI-driven engagement tools (required)
• Strong data and analytics skills, using adoption, journey, retention, and search/performance data to drive decisions (required)
• Proven account-managementtrack recordowning retention and expansion for a book of enterprise accounts as a trusted executive partner (required)
• Strong command of CS economics: GRR, NRR, churn, expansion, payback period, and cohort health
• High-growth or startup experience strongly preferred
• Comfortable coordinating across distributed, multi-time-zone teams

Key Focus Areas (2026 Lens)

• Omnichannel search performance and digital strategy for hospitality accounts
• Revenue retention and expansion predictability
• Lifecycle playbook standardization at scale
• AI-powered CS workflows and automation
• Deep, multi-threadedexecutive relationships across enterprise accounts
• Margin improvement across SaaS + Services
• Supporting partnership / agency programs

KPI & Metrics Ownership

• Gross Revenue Retention (GRR)
• Net Revenue Retention (NRR)
• Expansion ARR
• Customer Lifetime Value (CLV)
• Time-to-Value
• Renewal Forecast Accuracy
• CS Productivity & Margin
• Customer Sentiment (NPS / CSAT)

What Success Looks Like (First 12 Months)

• Measurable improvement in GRR, NRR, and churn reduction across the assigned book
• Consistent, disciplined lifecycle execution account by account
• More predictable renewal and expansion forecasting for owned accounts
• Effective use of AI-driven CS workflows to work efficiently at scale
• Deep, multi-threadedrelationships across top accounts
• A reputation as a trusted executive partner to enterprise customers