Director of AI Enablement – Customer Experience

Resident

Director of AI Enablement overseeing AI applications within Customer Experience teams at Resident. Driving measurable improvements in customer satisfaction and operational efficiency.

Posted 4/28/2026full-timeRemote • 🇺🇸 United StatesLead💰 $110,000 - $130,000 per yearWebsite

About the role

Key responsibilities & impact

Owns CX-facing AI enablement across pre-purchase, post-purchase, and service recovery journeys, in partnership with Product on model configuration, intent design, and platform capabilities.
Translate customer insights and agent workflows into AI use cases, intents, escalation logic, and experience standards.
Partner with Product and Engineering to influence AI roadmaps while championing responsible, brand-safe AI practices.
Evaluate and recommend AI platforms, tools, and vendors through a CX and scalability lens.
Owns configuration, optimization, and business performance of CX tooling (telephony, WFM, messaging), while partnering with Product & Engineering on architecture, integrations, and platform decisions.
Lead tool evaluation and optimization to improve agent productivity, queue management, and CX quality.
Own WFM configuration, including channel-based forecasting and staffing across voice, chat, sales, and support.
Hold vendors accountable to performance, delivery timelines, and scalability requirements.
Own day-to-day AI performance across channels, including containment, deflection, CSAT, resolution quality, and efficiency impact.
Define success metrics and reporting that connect AI performance to CX outcomes and financial results.
Lead root-cause analysis on performance gaps and drive cross-functional improvements.
Partners with Product and Engineering to define integration requirements, success criteria, and prioritization for CX AI capabilities.
Owns AI-readiness and structure of CX knowledge systems (taxonomy, retrieval quality, governance), in partnership with Content and Product teams who own underlying CMS platforms.
Partner with Quality, Training, and Knowledge teams to align human and AI learning standards.
Establish governance and quality standards for AI prompts, responses, and knowledge updates.
Lead AI and technology initiatives from scoping through launch, adoption, and optimization.
Serve as the primary CX owner for AI and tooling initiatives across Product, Engineering, Data, Operations, and vendors.
Develop project plans, communication cadences, and success metrics to drive alignment and execution.

Requirements

What you’ll need

7+ years of experience in CX technology, systems enablement, automation, or related fields, with 2+ years in a leadership or program ownership role.
Proven track record of delivering AI or technology-driven initiatives in complex, multi-channel customer environments.
Hands-on experience designing and optimizing LLM/AI-powered solutions, including prompt engineering, RAG, or workflow orchestration—not just tool usage.
Strong analytical and experimentation mindset, with experience leveraging A/B testing and performance data to drive measurable improvements in CX, efficiency, and cost.
Experience in high-growth DTC or eCommerce environments strongly preferred.
Solid understanding of CX systems architecture, including integrations across CRM, telephony, order management, and data platforms, with the ability to evaluate build vs. buy decisions.
Demonstrated success leading change management and driving adoption of new technologies across frontline teams and cross-functional stakeholders.
Deep understanding of conversational AI across voice and chat, including escalation models and human-in-the-loop workflows.
Strong cross-functional leadership with experience influencing Product, Engineering, Operations, and CX teams.
Excellent program and vendor management skills in fast-paced, high-growth environments.
Clear and effective communicator, comfortable engaging both technical and non-technical audiences.
High ownership mindset with a bias toward action and continuous improvement.

Benefits

Comp & perks

Remote-first workplace (since 2016!)
Competitive salary
Annual bonus potential
Health, Vision & Dental Insurance
HSA company contributions
401K with company match component
“Take what you need” PTO
Wellness benefits
WFH office and cell phone/internet stipend
A FREE MATTRESS plus an awesome Friends and Family discount!

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

AI enablementmodel configurationintent designAI platformsWFM configurationprompt engineeringRAGworkflow orchestrationA/B testingCX systems architecture

Soft Skills

analytical mindsetchange managementcross-functional leadershipprogram managementvendor managementcommunication skillsownership mindsetcontinuous improvementinfluencing skillscollaboration