The Zebra · 1 month ago
Director of Customer Experience, Retention & Service
United States
Full-time
Remote
Senior Level, Lead/Staff
8+ years expThe Zebra is a leading independent insurance comparison site that aims to revolutionize how consumers shop for insurance. The Director of Customer Experience, Retention & Service will be responsible for owning the strategy and execution of customer experience initiatives while building a retention operating system ahead of future initiatives.
InsuranceMarketplacePrice ComparisonSearch Engine
Responsibilities
Own the end-to-end existing customer experience, leading improvements across our servicing team and digital channels (chat/self-serve) to increase CSAT and reduce friction
Build the Retention operating system ahead of early 2026 initiatives, including strategy, roadmap, segmentation inputs, playbooks, governance, and cross-functional execution with our Re-engagement group
Lead and scale a customer feedback engine by managing our Voice of the Customer (VOC) Manager, establishing closed-loop processes that turn insights into product, training, and operational change
Define and operationalize CX measurement with CSAT as the primary near-term success metric; evolve scorecards as retention measurement (e.g., policies in force) matures
Partner with Product/Engineering and Operations to drive digital servicing improvements, including containment/deflection strategy, response/resolution standards, and contact reduction initiatives
Build and develop the team over time, including planning for and hiring a Retention Manager as the retention program scales
Qualification
Required
8+ years in Customer Experience, Retention, Service Operations, or Contact Center leadership, with demonstrated success driving measurable CX outcomes
Deep understanding of digital servicing experiences (chat, messaging, self-serve journeys) and how to improve them through process, tooling, and cross-functional partnership
Proven ability to build and execute programs from scratch, including retention readiness, operational cadences, and performance scorecards
Strong analytical and storytelling skills—comfortable translating customer and operational data into clear priorities and executive-ready narratives
Experience leading and developing teams (managers/analysts) and influencing senior stakeholders to drive organizational change
Comfort operating in a regulated or high-accountability environment; insurance/insurtech experience is a plus
Preferred
Experience in insurance/insurtech is a plus; experience operating in a regulated industry (e.g., financial services, healthcare) is also strongly preferred
Experience with VOC platforms (Qualtrics/Medallia), BI tools (Looker), and CRM/contact center data sources
Benefits
Competitive Compensation & Stock Option Offering
Health, Dental, Vision & Disability Coverages
End early Fridays (wrap up work at 2pm CST on Fridays!)
Sabbatical program for tenured employees
HSA offering + employer contribution
Fertility support through Carrot
$100 monthly wellness perk
$300 pet reimbursement program
401k with match
Unlimited PTO (paid time off)+ flexibility to enjoy it
Paid Parental Leave Program
Learning & Development Opportunities
Company
The Zebra
The Zebra is an online insurance comparison platform providing real-time rates and educational resources for various insurance types.
201-500 employees
H1B Sponsorship
The Zebra has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (90)
2024 (73)
2023 (74)
2022 (124)
2021 (80)
2020 (49)
Funding
Current Stage
Late StageTotal Funding
$258.63MKey Investors
HedosophiaAccelBallast Point Ventures
2024-08-06Series Unknown· $2.1M
2022-01-01Series Unknown
2021-04-12Series D· $150M
Leadership Team
Keith Melnick
CEO
Brett Little
Chief Financial Officer
Recent News
The Fintech Times
2025-04-26
2025-04-24
GlobalFinTechSeries
2025-04-23
Company data provided by crunchbase