Conversational AI Operations Specialist

About The Role

Fora is seeking a Conversational AI Operations Specialist to maintain, optimize, and improve Sidekick, our AI advisor support chatbot. In this role, you will design and implement systems to enable quality assurance, testing infrastructure, content operations and feedback loops.

You will report to the Conversational AI Data Scientist and partner closely on conversational design, automation, and prioritization. You will work cross‑functionally with teams across Fora, including Support, Booking Platform, Tour Operations, Product, and Engineering, to ensure Sidekick delivers accurate, clear, and empathetic guidance s is a highly execution focused role with meaningful ownership and autonomy.

This role is based in our beautiful New York City office (Tribeca/Fidi) with lots of natural light and great views.

• 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.

• 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.

• 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 for this role varies based on experience, with an indicative range of $60,000–$90,000 + equity. Final compensation will depend on the level at which the candidate is hired, as we’re considering multiple levels for this role.

• Unlimited vacation
• Health…