Founder Collaboration

• Work directly with the founder on daily AI operations and improvements.
• Communicate issues, findings, and recommendations clearly.
• Take ownership of problems from identification through resolution.
• Move quickly while maintaining high standards for customer-facing AI output.

Required Experience & Skills

Must-Have

• Proven experience running LLM or AI systems in production.
• Hands-on experience monitoring and improving production AI outputs.
• Experience with prompt engineering and system prompt optimization.
• Strong understanding of LLM behavior, failure modes, and iterative testing.
• Experience analyzing AI-generated conversations or customer-facing outputs.
• Ability to work with webhooks, APIs, knowledge bases, or similar integrations.
• Strong analytical and problem-solving skills.
• Excellent written English — required for editing customer-facing AI messages and documenting system changes.
• Strong attention to detail.
• Ability to work independently and take ownership of production systems.

What Makes You a Strong Fit

• You've actually operated AI systems in production rather than only experimenting with ChatGPT.
• You are comfortable reviewing hundreds or thousands of AI interactions to identify patterns and problems.
• You think in terms of outcomes and conversion, not just whether the AI response sounds good.
• You are methodical about testing changes and measuring their impact.
• You can quickly identify why an AI system is behaving incorrectly and determine how to improve it.
• You communicate clearly and document your work thoroughly.
• You enjoy working directly with a founder in a fast-moving environment.

What Does a Typical Day Look Like?

You'll begin by reviewing the performance of live AI conversations and looking for unusual patterns, failures, or opportunities for improvement.

You may spend part of the day onboarding a new telehealth client, configuring their knowledge base and integrations, and setting up their campaigns.

You'll also review conversation transcripts, identify issues with AI responses, update prompts or system instructions, test your changes, and monitor the resulting conversion performance.

Throughout the day, you'll work directly with the founder to discuss findings, prioritize improvements, and make sure production systems continue performing effectively.

Interview Process

1. Initial Recruiter Screening
2. Client Interview
3. Offer Stage

Originally posted on Himalayas