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Milestone Inc · 3 days ago

VP, Customer Experience & Success

United States

Full-time

Remote

Director/Executive

15+ years exp

Milestone 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 VP of Customer Experience & Success to own retention, expansion, partnership, and customer outcomes across a global customer base, with direct accountability for key revenue metrics and leading a large team.

ConsumerMarketingWeb Design

Hiring Manager

Kishankumar P.

Responsibilities

Own and improve GRR, NRR, churn, expansion, ARR growth, payback period, and cohort health

Operate a multi-million-dollar book of business, with accountability for renewals and expansion

Design, enhance and run end-to-end lifecycle playbooks (onboarding → adoption → value → renewal → expansion), directly tied to company OKRs

Establish a rigorous operating cadence including QBRs, executive reviews, customer advocacy health scoring, renewal forecasting, and expansion pipelines

Lead and scale 50+ global team members across Customer Success, Professional Services, Support, and CS Operations

Implement clear playbooks, SLAs, governance models, and escalation frameworks across time zones

Drive tight cross-functional alignment with Sales, Product, Marketing, Engineering, and Delivery to ensure one integrated customer journey

Lead change management initiatives when rolling out new processes, tooling, pricing models, or AI-driven workflows

Bring deep expertise in MarTech ecosystems: CDPs/CRMs, campaign orchestration, personalization, attribution, ABM, real-time decisioning

Demonstrate direct experience supporting hospitality and banking/financial services customers, including:

Acquisition, loyalty, guest/cardholder lifecycle

Compliance and governance expectations

Multi-location, enterprise digital environments

Translate platform capabilities into vertical-specific business outcomes (engagement, spend, retention, NPS, revenue lift)

Serve as an executive partner to CMOs, CDOs, Heads of Loyalty, and Digital leaders

Deploy AI-driven CS capabilities including:

Predictive health scoring and churn signals

Automated play triggers and next-best-action recommendations

Risk and expansion forecasting

Drive automation across the CS stack (CRM, ticketing, in-app guidance, chatbots, knowledge bases) to improve:

Time-to-value

Deflection rates

CS productivity and margin

Evaluate, integrate, and continuously optimize AI tools within the martech and CS ecosystem

Operate effectively across:

Recurring SaaS models (usage, adoption, land-and-expand)

Services / Agency models (projects, retainers, SOWs, campaigns)

Define clear value, scope, and success metrics when software and services are sold together

Partner with CS Ops / Rev Ops to standardize:

Handoffs and playbooks

Profitability tracking

Capacity and margin management

Eliminate hero-driven execution in favor of repeatable, scalable delivery models

Bring an entrepreneurial mindset —experience building or scaling teams, processes, or business lines in ambiguous environments

Build a strong CS leadership bench in the Bay Area while effectively leveraging global delivery hubs

Demonstrate executive presence with:

Board-level storytelling using data

Strategic customer engagement

Partner and ecosystem representation

Act as a culture carrier—setting high bars for ownership, accountability, and customer obsession

Qualification

Customer Success StrategyMarTech ExpertiseAI-driven AutomationGlobal LeadershipSaaS Business ModelData-driven Decision MakingChange ManagementExecutive PresenceCustomer EngagementCross-functional Collaboration

Required

15–20+ years across SaaS, MarTech platforms, agencies, and/or high-growth B2B companies

Proven VP / Sr Director experience owning retention and expansion outcomes

Strong command of CS economics and operating metrics

Deep familiarity with hospitality and/or banking verticals

Hands-on leader who can operate at strategy and execution levels

Global leadership experience required

Preferred

Bay Area presence preferred

Benefits

Collaborative, high-bar leadership culture

Certified Great Place to Work

Company

Milestone Inc

Glassdoor4.0

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.

Founded in 1998

Santa Clara, California, USA

201-500 employees