Conversational AI Operations Specialist

Key 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.
• Execute content updates and audits, proactively identifying stale or inaccurate information.
• Translate complex internal operations, supplier policies, and platform updates into clear, concise, and well documented internal processes and advisor facing content.
• Partner with Support to gather feedback and identify patterns in advisor questions and resolution gaps.
• Collaborate with teams including Tour Operations, Booking Platform, and Advisor Integrity to coordinate destination specific guidance, supplier data ingestion, and policy updates.
• Coordinate with Product and Engineering on Sidekick updates tied to new feature rollouts and quality assurance.
• Act as a keeper of truth for advisor-facing knowledge by independently researching, fact checking, and validating information across multiple sources.

Requirements

• 1-3 years of experience in content operations, support operations, customer success, technical writing, or a related field.
• Demonstrated experience building or improving operational systems or processes that drove measurable improvements.
• Proven AI power user who uses AI tools daily in a current or recent role and can speak concretely about workflows built with those tools.
• Exceptional writing skills with the ability to communicate complex or technical concepts clearly and concisely for both internal and advisor facing audiences.
• Strong research instincts with a track record of independently validating information and synthesizing findings into actionable guidance.
• Systems thinker who can design repeatable frameworks and scalable processes rather than one off solutions.
• High attention to detail with the ability to consistently execute, follow through, and close loops.
• Ability to quickly learn new tools and platforms, including customer support and knowledge base systems.
• Strong empathy for users and a genuine commitment to ensuring advisors feel understood and supported.
• Ability to work in the United States and be based in or willing to relocate to New York City.

Strongly Preferred

• Experience with AI chatbots, conversational design, or prompt writing.
• Experience building QA programs, testing frameworks, or structured audit processes.
• Hands-on experience with platforms such as Intercom, Zendesk, Notion, or other knowledge base and support tools.
• Experience building advanced workflows or automations within support or content systems.
• A writing portfolio that demonstrates clear, structured, and user centric communication.

Compensation & Benefits

• Indicative range of $60K–$90K + equity
• Unlimited vacation
• Health Insurance (including an option completely covered by Fora)
• Dental & Vision Insurance
• Wellhub Memberships
• 401k plan with company match
• Commuter Benefits
• Supplemental Life Insurance
• Stock Options