AI Chatbot Specialist

About FlySquid

FlySquid specializes in developing and managing AI-powered assistants deployed across WhatsApp, social media direct messages, SMS, and web chat platforms tailored for clients including clinics, hospitals, educational institutions, and service businesses throughout the UAE, Lebanon, and North America. Each deployment is customized with system prompts, structured knowledge bases, CRM automations, and a continuous feedback mechanism to ensure live, effective assistance. Missing a scheduled booking directly impacts client revenue, emphasizing the importance of reliable chatbot performance.

Location and Working Hours

The position is based onsite in Beirut, Lebanon, exclusively for candidates residing in Lebanon. The role demands a 40-hour workweek, requiring at least four hours of overlap with Gulf standard business hours (09:00 to 18:00).

Role Responsibilities

• Develop and refine system prompts to enhance client assistant performance.
• Create comprehensive knowledge bases and FAQ compilations using onboarding forms, websites, price lists, and voice recordings.
• Implement client-specific operational rules, including pricing policies, escalation procedures, human handover conditions, language adaptation, and tone management.
• Design and debug CRM automation workflows to ensure smooth functionality.
• Conduct systematic testing to diagnose issues in prompts, knowledge repositories, or platform integrations.
• Manage client onboarding processes, including data collection, follow-up on incomplete information, and identifying gaps that may hinder project launch.
• Translate client feedback—sometimes ambiguous—into actionable improvements in prompts and knowledge content.
• Maintain detailed documentation for each client, tracking prompt iterations, change histories, and current project status.

Candidate Requirements

• Proficiency in both written English and Arabic to create and review chatbot dialogue, including making decisions regarding communication style and register.
• Demonstrated experience crafting prompts for large language model (LLM) assistants and understanding common causes of instruction failures.
• A methodical approach to problem-solving, focusing on isolated changes for effective debugging.
• Strong skills in spreadsheet management for handling FAQs, pricing details, and tracking information gaps.
• Professionalism and poise in client interactions, especially when engaging with high-expectation clients such as medical professionals, avoiding technical jargon.

Preferred Qualifications

• Familiarity with platforms and tools such as GoHighLevel, n8n, Zapier, or Make.
• Basic knowledge of scripting in Python or JavaScript.
• Ability to communicate in French.
• Experience in healthcare or dental industry settings.
• Exposure to voice AI technologies, including ElevenLabs.

Work Environment and Expectations

The role entails managing multiple concurrent chatbot builds, requiring agility in handling varying client requirements and changes. Work is predominantly asynchronous; however, client feedback often arrives as WhatsApp voice notes that must be addressed within the same business day.

Probation Period

The position includes a 90-day probation period with full salary. Performance reviews occur on day 30 and day 90. Either party may terminate the engagement during probation with a two-week notice.

Application Instructions

Interested candidates should submit their CV along with a brief work sample demonstrating prompt writing skills. The sample should be a system prompt tailored for a bilingual dental clinic in Dubai that (a) refuses to disclose prices via chat, (b) requires the collection of name, service, and preferred appointment time before providing a booking link, and (c) operates from Saturday to Thursday, between 10:00 and 20:00. The work sample should not exceed one page. Applications will be reviewed starting with the work sample prior to CV evaluation.