Title: Director, Account Management Hospitality Vertical
Location: US, Remote
Company: Milestone Inc.
Role Type: Primarily an individual-contributor role; may include a small number of direct reports
About Milestone
Milestone Inc. is a leading Digital Experience Software & Services company focused on AI-first discovery, personalization, & conversion across all digital touchpoints. Our platform enables brands to be visible in search engines & AI answer engines through structured data, entity intelligence, & AI-driven orchestration.
We serve complex, multi-location enterprises across hospitality, banking/financial services, & MarTech-driven organizations, operating a hybrid SaaS + Services business model at scale.
Role Overview
Milestone seeks a hands-on, revenue-focused Director, Account Management – Hospitality to drive retention, expansion, & customer success for strategic enterprise accounts. This senior individual contributor role owns GRR, NRR, churn reduction, & growth while serving as the executive partner for customers. The ideal candidate brings strong enterprise account management skills & expertise in SEO, CMS, websites, schema, GEO, local search, AI search, & omnichannel digital strategy.
Strong understanding of search strategies: Technical SEO, CMS, Platform, Websites, Content, Schema, Local & near-me discovery, Generative Engine Optimization (GEO), & the digital commercial omnichannel strategy that ties them together.
Must-Have Qualifications
Must demonstrate strength in all five areas:
- Strong omnichannel search experience: technical SEO, structured data/schema, local & near-me discovery, AI answer engines, & 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 / MarTech experience: hands-on familiarity with modern MarTech (CDPs, CRMs, personalization, attribution, campaign orchestration) & AI-driven engagement technologies
- Data & analytics: fluency with adoption, journey, retention, & search/performance data to drive decisions & prove value
- Account management: proven ownership of enterprise accounts, retention, & expansion as a trusted executive partner
Problems We Are Looking to Solve
The Director of Customer Success will help solve enterprise-level challenges including:
- Own strategic accounts & relationships
- Lifecycle execution gaps across onboarding, adoption, renewal, & expansion
- Limited predictability in churn risk, renewals, & expansion forecasting
- Create & follow Scalability & repeatability in CS playbooks
- Fragmentation across SaaS + Services delivery models
- Underutilization of AI & automation in CS workflows
- Weak or single-threaded executive relationships across complex enterprise accounts
Key Responsibilities
1. Enterprise Account Ownership & Revenue Outcomes
- Personally own & improve GRR, NRR, churn, expansion ARR, CLV, & cohort health across an assigned book of strategic enterprise accounts
- Operate & 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, & expansion
- Maintain a rigorous operating cadence: QBRs, executive business reviews, health scoring, churn-risk reviews, & expansion planning
- Identify & 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 & maintain multi-threaded, executive-level relationships across large, complex customer organizations
- Navigate enterprise buying & decision-making dynamics across procurement, security, legal, & multiple lines of business
- Orchestrate internal resources across Sales, Product, Marketing, Engineering, Professional Services, & Support to deliver for accounts, without direct authority over those teams
- Own escalations end-to-end, mobilizing the right people & communicating clearly to senior customer stakeholders
- Follow clear playbooks, SLAs, & governance, & contribute improvements back to the broader CS motion
3. Hospitality, Omnichannel Search & MarTech Expertise
- Bring deep, direct experience serving hospitality clients (hotels, resorts, restaurants, travel, or multi-location brands)
- Understand hospitality-specific dynamics: multi-location & franchise structures, brand vs. property priorities, loyalty, direct-booking, & local/near-me discovery
- Apply strong omnichannel search expertise: technical SEO, structured data & schema, AI answer engines, generative engine optimization (GEO), & the digital strategy connecting them
- Apply working knowledge of MarTech ecosystems: CDPs, CRMs, personalization, attribution, ABM, & campaign orchestration
- Translate platform capabilities into hospitality-specific business outcomes
- Partner with senior client stakeholders such as CMOs, CDOs, & 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, & renewal/expansion forecasting
- Leverage automation across the CS stack, including CRM, ticketing, in-app guidance, chatbots, & knowledge bases, to work more efficiently across a large book
- Improve time-to-value & personal productivity through effective use of tooling
- Provide feedback on AI tools & workflows to help the broader CS & MarTech tooling evolve
5. Hybrid SaaS + Services Delivery
- Manage accounts across recurring SaaS (land-&-expand, usage-driven) & Services (projects, retainers, SOWs, campaigns)
- Define clear value, scope, & success metrics for blended offerings within each account
- Partner with CS Ops / Rev Ops & Delivery on clean handoffs & 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, & usage patterns influence product evolution
- Partner with Product, Engineering, & GTM teams to inform roadmap priorities & improve customer experience
- Translate customer pain points & industry trends into recommendations for platform enhancements & AI-powered experiences
- Operate with a data-driven approach, leveraging adoption metrics, journey insights, retention analytics, & voice-of-customer signals
Ideal Candidate Profile
We are seeking a data-driven, execution-focused senior individual contributor who:
- Has strong account-management skills & thrives inside large, complex, multi-stakeholder customer organizations
- Builds trust & credibility with senior & C-suite buyers, & keeps relationships multi-threaded
- Thinks in outcomes, revenue, & value, not just relationships
- Knows the hospitality industry well & can speak the language of hospitality buyers
- Is technically fluent in omnichannel search (technical SEO, structured data, GEO) & comfortable in detailed search & analytics conversations
- Understands SaaS economics & services margin
- Gets results through influence & cross-functional orchestration rather than positional authority
- Is highly self-directed, organized, & accountable for their own book of business
- Brings a strong learning mindset
Required Experience & Qualifications
- 7–10 years in SaaS, MarTech platforms, agencies, or high-growth B2B environments
- Agency & MarTech experience
- Direct, substantial experience serving the hospitality vertical (required)
- Strong omnichannel search experience across
- Technical SEO, CMS, Platform, Websites, Content, Schema, Local & near-me discovery, Paid, analytics, Generative Engine Optimization (GEO), & the digital commercial omnichannel strategy that ties them together.
- Hands-on AI & MarTech experience: CDPs, CRMs, personalization, attribution, campaign orchestration, & AI-driven engagement tools (required)
- Strong data & analytics skills, using adoption, journey, retention, & search/performance data to drive decisions (required)
- Proven account-management track record owning retention & expansion for a book of enterprise accounts as a trusted executive partner (required)
- Strong command of CS economics: GRR, NRR, churn, expansion, payback period, & 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 & digital strategy for hospitality accounts
- Revenue retention & expansion predictability
- Lifecycle playbook standardization at scale
- AI-powered CS workflows & automation
- Deep, multi-threaded executive relationships across enterprise accounts
- Margin improvement across SaaS + Services
- Supporting partnership / agency programs
KPI & Metrics Ownership
- Gross Revenue Retention
- Net Revenue Retention
- Churn Rate (Logo & Revenue)
- Expansion ARR
- Customer Lifetime Value
- Time-to-Value
- Renewal Forecast Accuracy
- CS Productivity & Margin
- Customer Sentiment (NPS / CSAT)
- AI Automation Adoption & Efficiency Gains
What Success Looks Like (First 12 Months)
- Measurable improvement in GRR, NRR, & churn reduction across the assigned book
- Consistent, disciplined lifecycle execution account by account
- More predictable renewal & expansion forecasting for owned accounts
- Effective use of AI-driven CS workflows to work efficiently at scale
- Deep, multi-threaded relationships across top accounts
- A reputation as a trusted executive partner to enterprise customers
Why Milestone
- Founder-led, award-winning, AI-first platform
- Deep focus on GEO, AI visibility, & customer outcomes
- Opportunity to help shape Customer Success as a true growth engine
- Certified Great Place to Work
Featured Benefits
OKRs Bonus, Phantom Stock, Medical insurance, Vision insurance, Dental insurance, 401(k)