To be considered for this remote opportunity, you must reside and be authorized to work within the United States.

About the Role:

Great AI conversations don't happen by accident, they're designed, measured, and continuously improved. As our AI Conversation & Knowledge Manager, you'll own the performance of our customer-facing AI experiences across Ashley Digital's brands. You'll combine customer insights, conversation design, analytics, and knowledge management to ensure every interaction helps customers achieve the right outcome quickly while driving measurable business results.

This role is equal parts strategist, analyst, writer, and systems thinker. You'll define how customers interact with AI, establish success metrics, analyze performance, identify optimization opportunities, and continuously improve conversational experiences through experimentation and iteration.

You'll partner closely with Product, Customer Support, Operations, CRM, QA, Legal, Brand, and AI Enablement teams to ensure our AI experiences remain accurate, conversational, on-brand, and continuously optimized using customer sentiment, behavioral insights, and business performance metrics.

Success in this role isn't measured by the number of knowledge articles but through improvements in customer satisfaction, resolution quality, conversion, retention, operational efficiency, and the overall customer experience.

What You'll Be Doing:

• Own the end-to-end performance of Ashley Digital's AI customer experience, defining customer intents, desired outcomes, success metrics, and conversation strategy across all AI workflows.
• Design, test, and continuously improve conversational experiences through prompts, response logic, routing, escalation strategies, and system instructions, ensuring every interaction feels natural, helpful, and true to the Ashley Digital brand.
• Balance automation with customer experience by determining when AI should resolve customer needs independently and when human support delivers the best outcome.
• Monitor customer sentiment, conversation quality, and behavioral analytics to continuously improve tone, clarity, empathy, resolution quality, and overall customer experience.
• Analyze AI performance using KPIs such as CSAT, One-Touch Resolution, Total Resolution Time, containment, escalation, retention, conversion, and AOV to identify optimization opportunities and prioritize the roadmap.
• Build and maintain a continuous improvement framework by leveraging customer sentiment, QA findings, conversation analytics, operational data, and experimentation to optimize AI performance and customer outcomes.
• Conduct recurring conversation reviews to identify friction points, underperforming workflows, emerging customer trends, and knowledge gaps, translating insights into actionable improvements.
• Partner closely with Customer Support, Product, Engineering, QA, Operations, CRM, Legal, and Brand teams to align AI experiences with evolving customer needs, business priorities, and operational processes.
• Own and maintain the enterprise knowledge base, ensuring it serves as the trusted source of truth for both AI and human support.
• Establish scalable knowledge management practices, including taxonomy, metadata, governance, content lifecycle management, templates, and authoring standards that keep information accurate, AI-ready, and easy to maintain.
• Continuously improve the knowledge base using conversation insights, customer feedback, and operational changes to ensure content remains current, relevant, and effective.
• Communicate performance trends, business impact, and strategic recommendations to stakeholders through clear reporting, dashboards, and data-driven insights.

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.

What Success Looks Like:

• Improve customer experience by increasing customer sentiment, CSAT, and One-Touch Resolution while reducing Total Resolution Time.
• Optimize AI performance by increasing successful AI containment and reducing unnecessary escalations caused by knowledge or workflow gaps.
• Drive business impact by improving customer conversion, Average Order Value (AOV), and customer retention where AI supports the customer journey.
• Establish a measurable continuous improvement program that uses analytics, experimentation, customer feedback, and operational insights to identify issues, prioritize opportunities, and drive ongoing optimization.
• Deliver consistent, conversational, on-brand AI experiences across every customer touchpoint.

Skills & Qualifications:

• 5+ Experience in LLM prompting, Conversation Design, UX Writing, Linguistics, or related CX operations
• Deep understanding of conversation AI workflows and data integrations.
• Strong writing and communication skills with exceptional attention to detail
• Experience analyzing customer conversations and identifying operational trends
• Strong problem-solving and cross-functional collaboration skills
• Experience with Intercom Fin or similar conversational AI platforms.
• Experience with BI and analytics platforms such as Looker, Tableau, Sigma, or similar reporting tools.
• Familiarity with experimentation frameworks
• Experience managing enterprise knowledge bases, preferably in Notion.
• Expertise with prompt engineering and Large Language Model (LLM) best practices.

What We Offer (subject to eligibility requirements):

• Remote-first workplace (since 2016!)
• Competitive Salary
• Health, Vision & Dental Insurance
• HSA company contributions
• 401K with company match component
• Take what you need Paid Time Off
• 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 $90,000 - $110,000. 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 [redacted]

Ashley Digital is a privately-held company headquartered in Tampa, FL with offices in New York City, London and Tel Aviv. Learn more at: https://www.residenthome.com

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