Director of AI Enablement – Customer Experience

🕒 April 28

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Resident

WebsiteLinkedInAll Job Openings

201 - 500 employees

🛒 Retail

🛍️ eCommerce

Retail • eCommerce

Resident is a company that creates a house of brands focused on providing high-quality, comfortable, and stylish home furnishings. Known for its award-winning mattress brand Nectar, Resident partners with technology and retail giants to inspire great sleep and enhance home comfort. The company has demonstrated substantial growth, achieving significant sales and profitability, and has been recognized in prestigious media outlets. Resident operates in over 2500 locations and embraces a culture dedicated to comfort and innovation in home living.

📋 Description

• 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

• 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

• 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!