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
- Lifecycle execution challenges across onboarding, adoption, renewal, and expansion
- Limited predictability in churn risk, renewals, and expansion forecasting
- Scalability and repeatability in CS playbooks
- 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
- 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.
- 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:
- AI-enabled workflows and tooling
3. MarTech, Hospitality & Banking Domain Leadership
- 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
- Operate seamlessly across:
- 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
- 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
- Margin improvement across SaaS + Services
- Establishing and Growing 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 12–18 Months)
- Measurable improvement in GRR, NRR, and churn reduction
- Globally adopted lifecycle playbooks
- Predictable renewal and expansion forecasting
- 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