Part Time Ai Chatbot Trainer Jobs (NOW HIRING)

About Fora
Fora is the modern travel agency, empowering anyone with a passion for travel to build a thriving advisory business. We're modernizing the $100B+ travel agency industry by combining powerful technology, data, and community to enable thousands of entrepreneurs to build on our platform. Our business-in-a-box platform gives travel entrepreneurs everything they need to launch and scale, from cutting-edge tools and personalized training to a vibrant community and exclusive industry partnerships. 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 believe that everyone, from seasoned professionals to first-time advisors, can build something both profitable and personal.
Founded in 2021 by seasoned entrepreneurs, Fora has grown steadily since, expanding to a team of 200+ full-time employees based in downtown New York City. In 2025, we announced our $60 million Series B and C investment rounds, led by Thrive Capital and Insight Partners, with participation by previous investors including Forerunner and Heartcore Capital. We've also been recognized as a LinkedIn Top Startup 2024, Fast Company's Most Innovative Companies 2025 and 2023, and Built In 2025 Best Places to Work.
We're building the first truly unified platform for all travel needs-leveraging the best of human expertise and technology to transform how people plan and book travel.
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 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 $60K-$90K + 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 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 beautiful New York City office (Tribeca/Fidi) with lots of natural light and great views.
Our Values
We're forging our own path
Fora has always been about driving change within the industry. We're not interested in maintaining the status quo.
We're stronger together
Community is our cornerstone and collective power is our strength. We believe we can all go further when we operate together, using our combined leverage to unlock better opportunities and outcomes for our advisors, partners, and travelers.
We believe in technology
We believe technology is an answer to some of the most fundamental challenges the travel industry faces. We believe advancements in AI, bold investments in our platforms, and a world-class data infrastructure will transform the work of our advisors and our partners, while creating better travel experiences for travelers.
We're here to serve
We operate in service of our community and believe that when they're empowered to focus on what they do best, we all win. It's why we relentlessly advocate for our advisors and prioritize their best interest every step of the way.
We mean business
Fora is equal parts fun, meaningful work and serious travel business. We're unlocking opportunities for thousands of travel entrepreneurs, delivering a stream of high-quality guests at scale for our partners, and providing a superior travel experience for our travelers. It's a better equation for the future of our industry.
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.