Conversational AI Operations Specialist

Fora Travel; New York (NY); On-site; USD 60,000 - 90,000; Full time

Benefits offered by this job

Unlimited vacation

Health Insurance

Dental & Vision Insurance

Wellhub Memberships

401(k) plan with company match

Commuter Benefits

Supplemental Life Insurance

Stock Options

Job summary

Fora is seeking a Conversational AI Operations Specialist to maintain and improve Sidekick, our AI advisor support chatbot. You will design systems for QA, testing infrastructure, content operations, and feedback loops, and own content across Sidekick surfaces.

You will collaborate with Support, Product, Engineering, and other teams to ensure Sidekick delivers accurate and empathetic guidance at scale from our New York City office.

Qualifications

• 1–3 years of experience in content operations, support operations, customer success, technical writing, or related field.
• Demonstrated experience building or improving operational systems or processes.
• Proven AI power user who uses AI tools daily in a current or recent role.
• Exceptional writing skills with ability to communicate complex concepts clearly.
• Strong research instincts with a track record of validating information.
• Systems thinker who can design repeatable frameworks.
• High attention to detail with strong execution and follow‑through.
• Ability to quickly learn new tools and platforms.
• Strong empathy for users and ensuring advisors feel understood.
• Willingness to work in New York City or relocate.

Responsibilities

• Design and operationalize repeatable systems for Sidekick QA, testing infrastructure, content operations, and feedback loops.
• Own content and knowledge management across Sidekick surfaces (Help Center, prompts, macros).
• Conduct regular QA reviews with rubrics and escalation protocols to maintain quality.
• Build use case testing frameworks for new features and workflows before launch.
• Execute content updates and audits to remove stale or inaccurate information.
• Translate internal operations and policies into clear internal processes and advisor content.
• Gather feedback from Support and identify patterns in advisor questions.
• Coordinate with Product and Engineering on feature rollouts and QA.
• Collaborate with Tour Operations, Booking Platform, and Advisor Integrity on guidance and data ingestion.
• Research and validate information across multiple sources to keep advisor knowledge accurate.

Skills

Content operations

Writing skills

Research instincts

Empathy for users

Tools

Intercom

Zendesk

Notion

Knowledge base systems

Job description

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 at scale. This 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.

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

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.

Benefits

• Unlimited vacation
• Health Insurance (including an option completely covered by Fora HQ)
• Dental & Vision Insurance
• Wellhub Memberships
• 401(k) plan with company match
• Commuter Benefits
• Supplemental Life Insurance
• Stock Options

Work Authorization

Authorization to work in the United States is required for full‑time roles based in our New York City office. Fora is unable to sponsor or assist with U.S. work authorization. Roles based outside of the United States are not subject to this requirement.

Equal Opportunity

Fora is committed to an equitable hiring process and an inclusive work environment. BIPOC and traditionally underrepresented candidates are strongly encouraged to apply. We will not discriminate and will take action to ensure against discrimination in employment, recruitment, advertisements for employment, compensation, termination, upgrading, promotions, and other conditions of employment against any employee or job applicant on the bases of race, color, gender, national origin, age, religion, creed, disability, veteran's status, sexual orientation, gender identity, gender expression or any other characteristic protected by law.