Milestone Inc

Compensation

Full Description

Title: VP, Customer Experience & Success Location: USA (Bay Area preferred) 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