VP, Customer Experience & Success
17 hours ago
San Francisco
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