VP, Customer Experience & Success

Title: VP, Customer Experience & Success

Location: SF Bay Area

Reports to: President

Team Size: 50 (CS, Professional Services, Support, CS Ops)

Company: Milestone Inc.

About Milestone:

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, and MarTech-driven organizations, operating a hybrid SaaS Services business model at scale.

VP - CS Role Overview:

Milestone is seeking a strategic, revenue-oriented VP of Customer Experience & Success to own retention, expansion, partnerships, and customer outcomes across a global customer base.

This is a revenue-adjacent executive role, accountable for GRR, NRR, churn reduction, expansion ARR, payback period, and customer lifetime value—not just customer satisfaction.

The VP - CS will design and operate a modern, AI-powered Customer Success engine, spanning onboarding through expansion, while leading distributed teams across the US, India, Canada, and Mexico.

Problems We Are Looking to Solve:

The VP - CS will be entrusted with solving systemic, enterprise-level challenges including:

• Lifecycle execution challenges across onboarding, adoption, renewal, and expansion
• Limited predictability in churn risk, renewals, and expansion forecasting
• Scalability and repeatability in CS playbooks
• Fragmentation across SaaS Services delivery models
• Underutilization of AI and automation in CS workflows
• Weak executive-level customer relationships in complex verticals

Key Responsibilities:

1. Strategic Customer Success & Revenue Ownership

• Own and improve GRR, NRR, churn, expansion ARR, CLV, and cohort health
• Operate and forecast a multi-million-dollar global book of business
• Design and run end-to-end scalable and repeatable lifecycle playbooks:
• Onboarding → Adoption → Value Realization → Renewal → Expansion
• Establish a rigorous operating cadence:
• QBRs, executive reviews, health scoring, churn risk models, expansion pipelines
• Directly align CS outcomes with Company OKRs and board-level metrics
• Own the creation of systematic, built-in expansion engines so that customers adopting the Milestone product stack have defined, automatic ARR growth year over year.

2. Global Leadership & Operating Rigor

• Lead and scale 60 global team members across CS, PS, Support, and CS Ops
• Implement clear playbooks, SLAs, escalation models, and governance
• Drive tight cross-functional alignment with Sales, Product, Marketing, Engineering, and Delivery
• Lead change management for:
• New processes
• Pricing & packaging shifts
• AI-enabled workflows and tooling

3. MarTech, Hospitality & Banking Domain Leadership

• Bring deep expertise in MarTech ecosystems:
• CDPs, CRMs, personalization, attribution, ABM, campaign orchestration
• Demonstrate direct experience serving hospitality and banking / financial services clients:
• Translate platform capabilities into vertical-specific business outcomes
• Act as an executive partner to CMOs, CDOs, Heads of Digital & Loyalty

4. AI, Automation & CS Technology Leadership

• Deploy AI-driven Customer Success capabilities, including:
• Predictive health scoring
• Churn and risk signals
• Automated play triggers & next-best-action systems
• Renewal and expansion forecasting
• Drive automation across the CS stack:
• CRM, ticketing, in-app guidance, chatbots, knowledge bases
• Improve:
• Time-to-value
• CS productivity
• Margin and scalability
• Continuously evaluate and optimize AI tools across CS and MarTech ecosystems

5. Hybrid SaaS Services Model Excellence

• Operate seamlessly across:
• Recurring SaaS (land-and-expand, usage-driven models)
• Services (projects, retainers, SOWs, campaigns)
• Define clear value, scope, and success metrics for blended offerings
• Partner with CS Ops / Rev Ops to standardize:
• Handoffs
• Capacity planning
• Margin and profitability tracking
• Replace hero-driven delivery with repeatable, scalable execution models

6. Executive, Entrepreneurial & Culture Leadership

• Bring an entrepreneurial mindset suited for ambiguity and scale
• Build a strong CS leadership bench in the Bay Area while leveraging global teams
• Demonstrate executive presence through:
• Board-level storytelling
• Strategic customer engagement
• Partner and ecosystem leadership
• Serve as a culture carrier, reinforcing:
• Ownership over activity
• Accountability over intent
• Customer obsession over internal comfort

Ideal Candidate Profile:

We are seeking a strategic, data-driven, and execution-focused CS leader who:

• Thinks in outcomes, revenue, and systems, not just relationships
• Operates comfortably with C-suite buyers in complex enterprises
• Understands SaaS economics and services margin deeply
• Can design scalable operating models and still drive execution
• Is equally credible with boards, customers, and frontline teams
• Strong learning mindset

Required Experience & Qualifications:

• 15–20 years in SaaS, MarTech platforms, agencies, or high-growth B2B environments
• Proven VP or Sr Director experience owning retention and expansion outcomes
• Previous high growth/startup experience is must have
• Strong command of CS economics:
• GRR, NRR, churn, expansion, payback period, cohort health
• Deep exposure to hospitality and/or banking verticals
• Global leadership experience across multi-time-zone teams
• Bay Area presence preferred

Key Focus Areas (2026 Lens):

• Revenue retention and expansion predictability
• Lifecycle playbook standardization at scale
• AI-powered CS workflows and automation
• Executive-level customer partnerships
• Margin improvement across SaaS Services
• Establishing and Growing Partnership /Agency Programs

KPI & Metrics Ownership:

• Gross Revenue Retention (GRR)
• Net Revenue Retention (NRR)
• Churn Rate (Logo & Revenue)
• Expansion ARR
• Customer Lifetime Value (CLV)
• Time-to-Value
• Renewal Forecast Accuracy
• CS Productivity & Margin
• Customer Sentiment (NPS / CSAT)
• AI Automation Adoption & Efficiency Gains

What Success Looks Like (First 12–18 Months):

• Measurable improvement in GRR, NRR, and churn reduction
• Globally adopted lifecycle playbooks
• Predictable renewal and expansion forecasting
• AI-driven CS workflows delivering efficiency gains
• Strong executive relationships across top accounts
• A scalable, high-performing global CS leadership team

Why Milestone:

• Founder-led, award-winning, AI-first platform
• Deep focus on GEO, AI visibility, and customer outcomes
• Opportunity to shape Customer Success as a true growth engine
• Certified Great Place to Work