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Harper (YC W25) · 1 day ago

Head of Customer Experience

San Francisco, CA

Full-time

Onsite

Director/Executive

$185K/yr - $250K/yr

Harper is a rapidly growing company in the insurance technology sector, focusing on transforming commercial insurance distribution through AI. The Head of Customer Experience will own the entire service lifecycle, collaborating closely with Product and Engineering to build scalable systems and enhance customer interactions during hypergrowth.

Artificial Intelligence (AI)FinTechInsurance

Responsibilities

Own end-to-end customer experience — COIs, endorsements, renewals, claims coordination, billing escalations, carrier follow-ups, quality, and trust

Partner deeply with Product + Engineering — Surface problems, translate to requirements, prioritize, validate solutions in production

Drive productization of service — Customer portal, self-serve flows, internal routing/triage tooling, automation guardrails

Build scalable systems — Map workflows into AI → self-serve → human → escalation; instrument everything

Establish the defect loop — Weekly cadence with Product/Eng so recurring issues get fixed upstream

Ship quick wins — Immediately reduce repeat contacts and rework while building the long-term model

Qualification

Scaling CX/OpsPartnering with Product/EngineeringSoftware development cyclesBuilding scalable modelsHands-on leadershipAI/automation experienceBackground in regulated industriesStartup experience

Required

Proven experience scaling CX/Ops through hypergrowth (10x+ volume)

Track record partnering deeply with Product/Engineering on ops tooling, workflows, or self-serve

Fluency in software development cycles: prioritization tradeoffs, edge cases, testing, iteration

Experience building scalable operating models (tiers, routing, escalation paths, QA/calibration)

Hands-on leadership style—you'll work real tickets/escalations to learn the operation

Based in San Francisco or willing to relocate immediately

Preferred

Background in regulated, high-stakes industries (insurance, fintech, healthcare)

Ex-founder who owned ops end-to-end

Experience with AI/automation in customer operations

Prior startup or high-growth company experience

Benefits

Health, dental, and vision insurance

Commuter benefits

Team meals and snacks

Company

Harper (YC W25)

Harper is a commercial E&S insurance brokerage.

Founded in 2024

San Francisco, California, USA

11-50 employees

https://www.harperinsure.com/

Funding

Current Stage

Early Stage

Total Funding

$0.5M

Key Investors

Y Combinator

2025-03-12Pre Seed· $0.5M

Company data provided by crunchbase