Ashley Digital - Director of AI Enablement & Applications
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. • What We Offer (subject to eligibility requirements):
Responsibilities
• 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. • The responsibilities described above are not exhaustive. You may be asked, from time to time and as reasonably required by business needs, to perform other duties consistent with your skills and role, including work for or on behalf of our related entities. This job description does not constitute a contract of employment and may be modified at any time, subject to applicable law.
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! • If you reside in a state or location where pay transparency laws or regulations have been adopted please read the following: The salary for this position is $110,000 - $130,000. We carefully consider a wide range of compensation factors, including your background, skills, qualifications, experience, geographic location and other non-discriminatory factors. These considerations can cause your compensation to vary. [Additionally, this role might be eligible for discretionary bonuses or commission payments]. For more information regarding the pay range applicable for this position, please contact us at [email protected] • 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. The Company will provide advance notice of such events and will cover approved, reasonable business travel expenses in accordance with Company policy. • Resident is a privately held US-based Company with remote employees in the US and the UK, and an office in Tel Aviv, Israel. Learn more at: https://www.residenthome.com • Resident is committed to a policy of equal employment opportunity, and will not discriminate against an applicant or employee on the basis of race, color, religion, creed, national origin, ancestry, sex, gender, age, physical or mental disability, veteran or military status, genetic information, sexual orientation, gender identity, gender expression, marital status, or any other legally recognized protected basis under federal, state, or local law. • Resident Home participates in E-Verify
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