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 solid 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

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