Conversational AI Operations Specialist

Tech Stack

Solid badges = required, outlined = preferred

Responsibilities

• Design and operationalize repeatable systems that drive continuous improvement for Sidekick, including QA frameworks, testing infrastructure, content operations processes, and structured feedback loops.
• Own content and knowledge management across Sidekick surfaces, including the Help Center, macros, prompts, and proactive messaging.
• Conduct regular QA reviews, establish rubrics and escalation protocols, and ensure consistent quality standards across conversational outputs.
• Build and maintain use case testing frameworks to validate new features, guidance prompts, and workflows before launch.
• Translate complex internal operations, supplier policies, and platform updates into clear, concise, and well documented internal processes and advisor facing content.

Soft Skills

Benefits

• 401k
• Commuter Benefits
• Dental
• Equity
• Health Insurance
• Life Insurance
• Mental Health
• Unlimited PTO
• Vision

Culture

Requirements