Vice President, Customer Experience

Swooped · United States · 3 days ago

RemoteRemoteCustomer ServiceFull-time

About the Role

The organization powers the experiences industry, serving businesses from museums and attractions to tours and activities. With billions in bookings, its AI-powered platform has assisted thousands of merchants in increasing revenues, saving time, and delivering seamless guest experiences. The company has secured significant funding from institutional investors and is recognized as a leading startup employer and a best place to work. This is a transformation mandate for an experienced post-sales leader to unify customer operations across three leading brands, less than a year after acquisition.

The successful candidate will own the entire post-sales operating model, including Onboarding, Customer Success, and Technical Support. This involves integrating best practices from each brand to design a new, world-class customer experience organization. Key activities include architecting new organizational structures, defining role clarity and accountability, and establishing scalable processes and metrics. AI and automation will be central to enabling exceptional service and guiding clients through the AI era.

The role's mandate encompasses retention, expansion, and upsell. It will shape operational approaches with every client account, define key metrics, and align Sales, Marketing, Product, and Engineering around ideal customer outcomes. Expected outcomes include revenue growth, churn reduction, improved cost-to-serve, and elevated quality across all three teams.

Scope of Role

This VP will lead three distinct functions, unified under one CX operating model:

Onboarding & Implementation: Responsible for end-to-end client onboarding from contract close through go-live. This includes refining a segmented approach that delivers high-touch, white-glove onboarding for enterprise clients while deploying scalable, automation-enabled processes and one-to-many resources for smaller clients. The goal is to reduce time-to-first-value and cost-per-onboarding without sacrificing satisfaction.
Customer Success: Oversight of retention, net dollar retention (NDR), and lifetime value optimization. This function will be instrumented with data and AI to proactively identify churn risk and expansion signals in real time, allowing the team to focus on high-impact conversations. Expansion, cross-sell, and upsell will be positioned as primary drivers of revenue growth alongside retention.
Technical Support: Management of ticket resolution, escalations, knowledge management, and SLA compliance. This involves re-thinking key metrics and efficiency targets, re-architecting workflows to leverage automation, cross-training teams to operate effectively across geographies and time zones, and systematically surfacing themes, risks, and insights that inform product and success strategy.

Responsibilities

Team Leadership & Org Design
- Lead a multi-brand team of Directors, Managers, and individual contributors, developing talent and building bench strength across the unified organization.
- Foster a culture of operational rigor, data-driven decision-making, and leverage to enable the team to focus on high-impact work rather than low-value toil.
- Hire and mentor senior operators who understand both team leadership and how to amplify their impact with AI and modern tools.
- Partner with existing functional leadership to ensure customer relationships remain strong and institutional knowledge is preserved during the post-acquisition transition.
Unification & Operational Design
- Assess the operating model across all three functions and three brands, identifying best practices and prioritizing unification opportunities.
- Build standardized processes, playbooks, and workflows that allow teams to operate with consistency and clarity, while learning from each brand's strengths.
- Apply structured methodologies to continuously improve how teams work together and for clients.
- Lead cross-brand strategic initiatives to ensure changes land smoothly with clear outcomes.
AI & Automation as Operating System
- Identify opportunities where AI and automation can reduce manual toil and free up team members for work requiring human judgment and/or relationships.
- Enable onboarding teams with AI-assisted tools that help customers achieve value faster while freeing the team to focus on complex implementations and customer outcomes.
- Equip support teams with AI agents and improved knowledge systems so live agents can focus on tickets requiring human judgment and relationship-building, rather than routine requests.
- Instrument Customer Success with data and automation that surfaces early signals of risk and opportunity, allowing CSMs to focus their conversations on accounts where they can drive meaningful retention and growth.
- Leverage internal tools and infrastructure where appropriate. Thoughtfully navigate build vs. buy decisions and avoid vendor lock-in.
Metrics, Data & Reporting
- Define and own the KPI framework for Onboarding, Success, and Support across all three brands, establishing clear baselines, targets, and accountability.
- Work with internal teams to build dashboards and reporting that surface cost-to-serve, team efficiency, and customer satisfaction metrics with executive-level visibility.
- Use data and analytics to identify improvement opportunities and drive root-cause resolution.
- Track and improve NDR, time-to-value, CSAT, NPS, renewal rates, churn, and support resolution metrics across all brands.
- Measure the impact of new tools and workflows to ensure they improve team efficiency and customer outcomes.
Voice of the Customer & Cross-Functional Influence
- Own the customer feedback loop across the organization, as the teams are the primary conduit between clients and Product, Engineering, Marketing, and Executive Leadership.
- Translate customer sentiment and data into structured recommendations that inform the product roadmap.
- Champion the principle that current customers are the organization's most valuable asset and ensure their needs are heard and acted upon at every level, by every function.

Requirements

10+ years in Customer Success, Onboarding, and/or Support, with VP/Senior Director ownership of at least two functions.
Track record of transforming how a function operates, having personally architected team workflows.
Hands-on experience with AI and automation, understanding their capabilities and limitations in real workflows, including failure modes and iteration.
Demonstrated measurable impact on cost-to-serve or CX efficiency metrics (e.g., headcount-to-revenue, time-per-ticket) without sacrificing satisfaction.
Data fluency to build metrics frameworks, interpret dashboards, and drive decisions from data.
Direct hands-on experience with AI tools and agentic workflows.
SaaS experience across both complex enterprise post-sales operations and high-velocity SMB/Mid-market.
Player-coach mentality, willing to work at every level and understand front-line operational details.
Bachelor's degree required; MBA preferred.

Preferred Qualifications