Director of AI Enablement & Applications

Director of AI Enablement & Applications - Customer Experience

Remote (USA)

About the Role

The Director of AI Enablement & Applications for Customer Experience owns how AI is applied, operationalized, and optimized across Resident's CX ecosystem. This role ensures AI-powered experiences across voice, chat, and messaging deliver measurable improvements in customer satisfaction, efficiency, and cost, while maintaining a high-quality, human-centered brand experience.

Serving as the connective tissue between Customer Experience, Product, Engineering, Data, and Operations, this role translates customer needs and agent workflows into actionable AI use cases, operating standards, and success metrics. It also oversees the full CS technology stack, ensuring tools are configured, integrated, and continuously improved to support team performance and operational goals.

What You'll Be Doing

AI Strategy & CX Enablement

• 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.

CS Technology & Tools

• 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.

AI Performance & Operational Excellence

• 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.

Knowledge, Content & AI Readiness

• 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.

Program Leadership & Cross-Functional Execution

• 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.

Skills & Qualifications

• 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.

What We Offer

• 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!

Compensation

The salary for this position is $110,000 - $130,000.

Additional Notes

While this role at Resident is remote, if hired, please note that Resident employees are expected to first notify the People Operations Team (HR) if they plan to move from the state in which they were hired. Additionally, from time to time, the Company may organize in-person meetings, trainings, team events, or other off-site gatherings that are important to business operations and team alignment. Attendance at these events is considered an essential function of the role, and Resident employees are expected to participate and travel as-needed.

Resident is a privately held US-based Company with remote employees in the US and the UK, and an office in Tel Aviv, Israel.