Head of Customer Experience and Operations

About VacationRenter VacationRenter is the fastest growing vacation rental search engine. We love traveling, but not how time-consuming and complex it can be to find the right place to stay. So we reimagined a better way. We eliminated the need to search across several sites and scroll through pages of irrelevant results just to find the perfect home away from home. We aggregate accommodations from the top travel sites, giving travelers all the best options in one place. VacationRenter was born inside the startup studio Wilbur Labs. VacationRenter uses automation and AI to help travelers find the perfect stay. Be sure to check out our rebranded site, Vogo.com. Vogo is the same company travelers have come to love but under a new name. 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