AI Automation & Internal Systems Engineer (GPT/RAG Systems)

Job Description

Role: AI Automation & Internal Systems Engineer (GPT / RAG Systems)  

Location: Remote (Philippines)

Type: Full-Time (Initial 3–6 Month Engagement, with Potential Long-Term Opportunity)  

Working Hours: Must overlap with Pacific Daylight Time (at least 4–6 hours)

Monthly Rate: To Be Disclosed

About Us

Winning Assistants helps doctors and healthcare businesses scale by placing highly trained, HIPAA-compliant virtual assistants into their operations.

We are growing fast and are now looking to build internal systems powered by AI to streamline operations, improve client success, and eliminate repetitive work across the company.

What This Role Is

This is NOT a typical developer role.

We are looking for someone who can think in systems, automate workflows, and implement AI into real business operations.

Your main objective is to help us build an internal “Company Brain” — an AI-powered system that allows our team to instantly access knowledge, past solutions, and SOPs.

Additionally, we see AI as a major opportunity for our business long-term. Beyond internal systems, we would value your input and consulting on how we could potentially introduce AI-driven offerings or services to our clients in the future.

Engagement Structure

This role will begin as a 3–6 month engagement focused on building and implementing core internal AI systems.

Based on performance and company needs, there is strong potential to:

• Extend into a full-time role, and/or  
• Transition into an ongoing AI consultant / strategic partner as we expand into AI-driven offerings

What You’ll Be Responsible For

• Build an internal AI assistant trained on company data (fires, SOPs, client issues, documentation)
• Extract and structure data from tools like Monday.com, Google Drive, Slack, and Front
• Implement RAG (Retrieval Augmented Generation) systems to make company knowledge searchable and actionable
• Create automations that reduce manual work across departments (Client Success, Ops, Sales)
• Set up and optimize workflows within tools like GoHighLevel (CRM), including automations for leads, follow-ups, and internal processes
• Continuously improve internal workflows using AI
• Identify bottlenecks and proactively suggest AI-driven solutions
• Provide strategic input on potential AI-based products, services, or enhancements we could offer to clients

Example Project You’ll Own

We log all internal “fires” (issues) in Monday.com along with how they were resolved.

You will build a system where:

• A team member can ask: “How do we handle this type of issue?”
• The AI provides:
• Similar past cases
• What actions were taken
• Suggested next steps

Requirements

Required Skills and Experience (Must-Haves)

• Experience working with OpenAI API / LLMs (GPT, etc.)
• Strong understanding of RAG systems (vector databases like Pinecone, Weaviate, etc.)
• Proficiency in Python or Node.js
• Experience integrating APIs and connecting different tools
• Ability to structure messy data into organized, usable systems
• Strong problem-solving skills and systems thinking mindset
• Good written and verbal English communication

Nice to Have (Bonus)

• Experience with Zapier, Make, or other automation tools
• Experience building internal tools or dashboards
• Familiarity with CRM/project management tools (Monday.com, ClickUp, GoHighLevel, etc.)
• Experience working with customer support or operations teams
• Exposure to building or launching AI-based products or services

Who This Is NOT For

• Someone who only knows basic ChatGPT prompting
• Someone who needs step-by-step instructions for everything
• Someone without real implementation experience
• Someone who cannot think independently or solve problems

What Success Looks Like

• We reduce repetitive manual work across teams
• Our Client Success Managers can instantly access solutions to problems
• Internal knowledge is centralized and easily accessible
• AI becomes embedded into our day-to-day operations
• Our CRM and internal systems become more automated and efficient
• We uncover opportunities to expand into AI-driven services or offerings

Compensation

• Competitive based on experience (Philippines market)
• Performance-based growth opportunities

How to Apply

Please include:

1. A brief Loom video (2–5 minutes) explaining:
   (a) A system or automation you built using AI, and (b) The problem, your approach, and the outcome.
2. Links to any relevant projects or tools you’ve built
3. Your expected monthly salary

Final Note

We are looking for someone who wants to grow with us long-term.

This role starts as a focused build phase but has the potential to evolve into a key strategic role within the company as we scale AI across our operations and offerings.

If you’re someone who enjoys building systems, solving problems, and using AI to create real impact — we’d love to hear from you.

Basic requirements

• Must be proficient in speaking and writing English very clearly
• Must have relevant work experience
• Be able to submit an NBI clearance and/or Local Police Clearance background check before onboarding [mandatory]
• Must be available for video meetings with your camera on (when needed)

Technical requirements

• Device: Reliable laptop or desktop computer.
• Internet: High-speed connection (minimum 15 Mbps).
• Audio: Noise-canceling headset.
• Video: Webcam for virtual meetings.
• Workspace: Quiet, professional environment