Conversational AI Operations Specialist

About Fora Fora is the modern travel agency, empowering the next generation of entrepreneurs to build thriving travel advisory businesses. We’re modernizing the $100B+ travel industry with AI woven through every part of the advisor’s workflow, plus global supplier relationships, personalized training, and a vibrant community, all in one place. That’s what lets advisors build businesses that scale, while their taste and service create trips no algorithm alone could plan. At the heart of it all is our mission: to help the next generation of travel entrepreneurs turn their love for travel into a fulfilling career, whether full-time or part-time. We’re mission-driven and obsessed with our customers, and we believe humans and AI are both essential: the best work here comes from people and technology at their best, together. That’s not just a philosophy about our product, it’s how we build our team. Everyone at Fora gets hands-on with frontier AI tooling as part of the job. At Fora, you’ll learn to be AI-fluent, with real experience applying AI to solve problems day to day, wherever you sit in the company.

Founded in 2021, Fora has grown to a team of 250+ full-time employees based in downtown New York City . In 2026, we closed a $60 million Series D led by Forerunner and Tactile Ventures, with continued backing from Thrive Capital, Insight Partners, and Heartcore Capital. We’ve been named a LinkedIn Top Startup (2024), one of Fast Company’s Most Innovative Companies (2023 and 2025), and one of TIME’s 100 Most Influential Companies (2026).

Come build something that hasn’t existed before.

About The Role Fora is seeking a Conversational AI Operations Specialist to maintain, optimize, and improve Sidekick, our AI advisor support chatbot. Join our Conversational AI team and play a critical role in scaling Sidekick to deliver exceptional instant support experiences for our advisors. In this role, you’ll 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.

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 b…