Conversational AI Operations Specialist

About Fora

Fora is the modern travel agency empowering travel enthusiasts to build thriving advisory businesses. We’re modernizing the $100B+ travel industry by combining technology, data, and community to enable thousands of entrepreneurs to launch and scale on our platform. Our business-in-a-box platform provides tools, personalized training, a vibrant community, and exclusive partnerships. Our mission is to help the next generation of travel entrepreneurs turn their love of travel into a fulfilling career, whether full-time or part-time. We were founded in 2021 and now have 200+ full-time employees based in New York City. In 2025, we announced $60 million Series B and C rounds, led by Thrive Capital and Insight Partners, with participation from prior investors. We have been recognized as a LinkedIn Top Startup 2024, Fast Company Most Innovative Companies (2023, 2025), and Built In Best Places to Work (2025). We are building the first truly unified platform for all travel needs—combining human expertise and technology to transform how people plan and book travel.

About The Role

We are seeking a Conversational AI Operations Specialist to maintain, optimize, and improve Sidekick, our AI advisor support chatbot. Join our Conversational AI team to scale Sidekick and deliver exceptional instant support experiences for advisors. 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 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.

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, 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 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.
• Experience building or improving operational systems or processes that drove measurable improvements.
• Proven AI power user who uses AI tools daily and can discuss workflows built with those tools.
• Exceptional writing skills with the ability to communicate complex or technical concepts clearly for 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 varies based on experience, with an indicative range of $60K–$90K plus equity. Final compensation depends on the level at which the candidate is hired, as multiple levels are being considered for this role.

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

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

Our Values

We’re forging our own path

Fora drives change within the industry and challenges the status quo.

We’re stronger together

Community is our cornerstone; collective power helps us unlock better opportunities for advisors, partners, and travelers.

We believe in technology

Technology, AI advancements, and a world-class data infrastructure transform advisory work and travel experiences.

We’re here to serve

We empower our community and prioritize advisors’ best interests at every step.

We mean business

We combine meaningful work with travel entrepreneurship to deliver high-quality experiences at scale.

WORK AUTHORIZATION

Authorization to work in the United States is required for full-time roles based in New York City. Fora does not sponsor U.S. work authorization for this role. Roles outside 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 do not discriminate and will take action to ensure equality in employment, recruitment, compensation, promotions, and other conditions of employment on the basis of race, color, gender, national origin, age, religion, creed, disability, veteran status, sexual orientation, gender identity or any other characteristic protected by law.