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 solid 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

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