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, Skilled 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-lo

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