Milestone Inc · 2 weeks ago
VP, Customer Experience & Success
United States
Full-time
Remote
Director/Executive
15+ years expMilestone Inc. is a leading Digital Experience Software and Services company focused on AI-first discovery, personalization, and conversion across all digital touchpoints. They are seeking a strategic, revenue-oriented VP of Customer Experience & Success to own retention, expansion, partnerships, and customer outcomes across a global customer base.
ConsumerMarketingWeb Design
Hiring Manager
Kishankumar P.
Responsibilities
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
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
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
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:
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
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
Qualification
Required
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
Preferred
Bay Area presence preferred
Benefits
Certified Great Place to Work
Company
Milestone Inc
Milestone drives online leads and customer acquisition for over 2,000 companies by seamlessly integrating “Experiences” and “Discovery” into its AI-First Digital Experience Platform.
201-500 employees
Funding
Current Stage
Growth StageLeadership Team
Anil Aggarwal
CEO
Benu Aggarwal
President and Founder
Recent News
Sourcery
2025-11-21
2025-11-15
2025-11-14
Company data provided by crunchbase