Remote AI Support Operations Lead

15Five; Oregon; Hybrid; USD 98,000 - 115,000; Full time

Benefits offered by this job

Medical, dental, vision

Disability coverage

Inclusive benefits stipend

Mental health resources

Flexible time off

Parental leave

Military leave

Paid holidays

Sabbatical program

401K with 4% matching

Job summary

15Five is an AI-powered performance management platform built to help managers lead with impact. The AI Support Operations Manager owns the day-to-day performance of our customer-facing AI agent and the related Help Center content.

You will own content quality, publish and verify knowledge, triage AI-failure reports, and ensure release readiness. This role blends operations, content engineering, and analytics in a remote, US-wide role.

Qualifications

• 3–5+ years in support operations, CX operations, knowledge management, or conversational AI operations, with hands-on ownership of a production AI agent (Intercom Fin strongly preferred; Ada, Forethought, Decagon, or similar also relevant).
• A proven content engineer: customer-facing help content you owned end to end, plus taxonomy, content verification workflows, structured authoring, and writing for AI retrieval, not just human readers.
• An experimenter's method: hypothesize, test small, measure, then scale. Comfortable with AI-assisted workflows as a daily practice.
• Strong analytical habits: you can trace a wrong AI answer through retrieval, content, and product behavior to root cause, and you show your work.
• Collaboration as a first-class skill: you raise concerns early, directly, and through agreed channels; you disagree openly, commit fully, and treat peers' domains with the respect you expect for yours.
• You build systems, not dependencies: your instinct when you become the only person who can do something is to document it and train a second.

Responsibilities

• Owns Fin/AI agent operations, ensuring correct resolutions and quality-adjusted automation month over month, including prompts and escalation design.
• Help Center content ownership: accountability for every published article, taxonomy, and AI-retrieval writing standards.
• The content flywheel: triage AI-failure reports, root-cause analysis, and track gap-closure velocity.
• Launch readiness: ensure release content is ready and coordinate with teams to prepare Help Center articles and topics.
• Operability: maintain runbooks, configuration docs, and ensure trained backups for critical systems.

Skills

Support operations

CX operations

Knowledge management

Conversational AI operations

Tools

Intercom Fin

Ada

Forethought

Decagon

Job description

15Five is an AI-powered performance management platform built to help managers lead with impact. The AI Support Operations Manager owns the day-to-day performance of our customer-facing AI agent and the related Help Center content.

You will own content quality, publish and verify knowledge, triage AI-failure reports, and ensure release readiness. This role blends operations, content engineering, and analytics in a remote, US-wide role.