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Wilbur Labs is a startup studio.
The Role
The Head of Customer Experience and Operations will lead a unified support and sales operation, enhancing service quality and operational efficiency while managing customer engagement and brand protection.
Summary Generated by Built In
About VacationRenter
VacationRenter is a global travel platform that brings all types of accommodations into one place, making it easy for travelers to find the perfect stay.
From private homes and beachfront villas to city apartments and hotels, VacationRenter offers one of the most extensive selections of properties worldwide and simplifies the entire search experience. Behind the scenes, VacationRenter’s technology analyzes millions of listings and billions of data points to surface the best options for every trip.
Launched out of Wilbur Labs in 2018, VacationRenter quickly became one of the fastest growing travel startups ever, surpassing $1 billion in gross bookings in just two years. The company is led by a team of seasoned travel industry leaders.
About This Role
VacationRenter is seeking a rigorous, data-driven Head of Customer Experience and Operations with a strong focus on service quality, operational efficiency, and risk mitigation across the full customer lifecycle. This role will build and lead a unified customer support and sales operation across phone, chat, email, SMS, and reputation management, creating a scalable system that captures every interaction, resolves issues quickly, protects the brand, and supports revenue growth through professional sales engagement.
The ideal candidate is a strong operator who will work closely with product, engineering, legal, finance, and supply to create a seamless experience for travelers and partners. Success will be measured by improvements in conversion, complaint resolution, refund discipline, fraud reduction, and the strength of the company’s public trust signals.
This role will report directly to the COO. This is a full-time hybrid position, based in Dallas.
Role & Responsibilities:
- Build and operate a unified customer care system across all channels
- Implement routing rules that prioritize by topic, value, and urgency with consistent SLAs
- Define and document clear agent policies for all customer interactions that reduce ambiguity for agents and provide for a top-tier customer experience
- Define and manage escalation paths for supplier disputes, complex cases, fraud risk, and potential regulatory issues
- Own and drive improvements in critical operational metrics, with a strong focus on process efficiency and customer satisfaction
- Develop playbooks and scripts for inbound sales and assisted conversion, including chat and phone
- Integrate AI capabilities for classification, response suggestions, summarization, and automated tagging
- Own presence and strategy across review platforms with strong processes for proactive collection and fast responses
- Monitor social platforms and complaint sites and manage public replies in coordination with legal and communications
- Establish severity levels for reputation issues and ensure appropriate escalation on high-risk cases
- Lead fraud and chargeback workflows, including investigation, documentation, and root cause tracking to mitigate all forms of fraud
- Build dashboards for volume, SLA compliance, agent performance, refund trends, disputes, and complaint drivers
- Identify recurring issues and partner with product and supply to eliminate root causes
- Set quarterly operational targets and track progress against efficiency, cost per contact, conversion lift, and trust metrics
Minimum Qualifications:
- Bachelor’s degree (B.S. or B.A.) from an accredited college or university or equivalent career experience
- 8+ years in customer care, sales operations, CX leadership, or a comparable role
- Experience building or restructuring multi-channel customer support operations with phone and chat
- Proven ability to lead vendor-delivered teams, including BPOs, with measurable performance outcomes
- Strong understanding of policies, quality frameworks, and coaching programs
- Experience managing reputation risk and public complaint handling across multiple platforms
- Familiarity with fraud mitigation, chargeback processes, and financial risk controls
- Hands-on experience and familiarity with the newer technologies (e.g., AI chat, advanced ticketing systems)
- Analytical mindset with comfort using data to guide decisions
Preferred Qualifications & Prior Experience:
- Early-stage startup experienceLeadership experience at a high-growth consumer or travel company
- Prior oversight of both sales-assisted channels and service operations
- Experience designing or operating AI-assisted support workflows
- Background managing review platforms, reputation programs, or crisis response
- Experience with international support teams or multilingual operations
- Strong understanding of payment operations and advanced dispute analytics
Benefits & Perks:
- Competitive salary + equity
- Top-tier laptop provided100% company-paid health benefits for base plan coverage, with the option to upgrade to higher-tier plans
- 401(k) with company matchUnlimited, guilt-free vacation days
- Annual wellness stipend (gym + other wellness activities)
- Monthly house cleaning stipend
- Annual travel allowance
- Monthly cell phone & internet usage stipend
- Charity donation company match
- Employee referral bonus
- Team offsites/activities
Top Skills
Advanced Ticketing Systems
Ai Chat
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The Company
What We Do
The studio identifies big customer pain points and builds businesses to solve these problems. After an idea is validated in the lab, the studio brings in industry leaders with domain expertise to manage the company. Wilbur Labs continues to provide funding, shared resources, and operational support to ensure management is focused on solving problems that matter. Wilbur Labs was founded in 2016 by Phil Santoro and David Kolodny.
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