Location: REMOTE / Toronto, Ontario
This job allows you to work remotely.
PathPilot is on a mission to help millions of people unlock their potential by navigating and optimizing their careers through the power of AI. We’ve secured 7-figures in non-dilutive funding and established key partnerships to help us scale our impact. Our AI Career Companion is already helping people clarify goals, access opportunities, and grow through personalized support. Now, we’re looking to take things to the next level—and that’s where you come in.
We’re looking for a Founding AI Engineer to join us on this journey. You’ll be instrumental in bringing our roadmap to life, working closely with the founder and team to design and build intelligent, user-friendly, and scalable systems. Think of this as a hybrid between a systems thinker, full-stack engineer, and data-centric AI builder —with strong coding instincts and a love for crafting elegant solutions, fast.
Why join PathPilot?
- Work on something meaningful and mission-driven
- Be a founding team member with real ownership and product influence
- Build systems that support people’s careers and lives in transformative ways
- Collaborate with a team that values vibe coding for rapid feature development and the intelligent use of tools like Cursor or Aider to boost developer productivity
- Enjoy flexibility, autonomy, and the opportunity to work remotely
- Shape the future of AI-powered career tools while being backed by major partners and 7-figures of funding
What are we looking for in a Founding AI Engineer?
You’re an engineer with a strong ownership mindset. You know how to go from ideas to production-ready solutions—and enjoy the messiness and thrill of early-stage building. You’re comfortable switching between big-picture architecture and in-the-trenches implementation. You likely already use AI tools to speed up your workflow and build with velocity.
What will you be doing?
- Architect and implement core AI product features from end to end
- Design backend and frontend systems using Node.js, React, and TypeScript
- Integrate with and optimize the use of LLMs (OpenAI, Claude, etc.) for user interaction
- Design and leverage agentic workflows for improved outputs and user experiences
- Build vector search capabilities using Pinecone, Supabase, or similar
- Fine-tune models and/or run RLHF experiments to improve user personalization
- Lead or contribute to data ingestion pipelines and user context models
- Collaborate with the founder and product team on scoping, prototyping, and iterative development
- Push the limits of what's possible with AI in a career-focused product
- Prioritize shipping value fast—without sacrificing long-term integrity
How will you spend your time?
45% coding and system design (React/Node/TS + AI integration)
20% LLM experimentation (prompting, agents, fine-tuning, evals, vector DBs)
15% data engineering and embedding strategies
10% product iteration and user feedback loops
10% collaboration, planning, and roadmap refinement
In your first 30 days, you will:
Ship core feature improvements and test new LLM workflows
Implement a scalable vector search using Supabase or Pinecone
Pair with the founder to refine product and tech roadmap
Take ownership of AI tooling, prompt design, and experimentation environments
In your first 90 days, you will:
Launch new AI modules that unlock personalized career guidance
Improve our fine-tuning and RLHF workflows to drive better user outcomes
Scale our data systems to support upcoming B2B pilots
Lead key decisions around architecture and product experience
Our Hiring Process:
Intro Call – We’ll connect over a quick call to share more about PathPilot, and learn what excites you.
Tech Interview – Deep dive into your skills, system design, and AI experience.
Practical Challenge – A short async build or discussion task using your favorite AI dev environment.
Final Call – Chat with the founder and discuss team fit, product vision, and next steps.
Offer – If it feels right on both sides, we move fast.
Must Have Skills:
You might be the person we’re looking for if you:
- Have 5+ years of full-stack engineering experience, ideally with JS/TS and Python
- Are fluent in modern frameworks like React, Node.js, and backend APIs
- Have worked with LLMs, embeddings, vector databases, RLHF and fine-tuning techniques
- Use tools like Cursor, Aider, or GPT-based pair programming tools daily and are interested in vibe coding backed by strong systems design
- Have used tools like LlamaIndex, AutoGen, OpenAI Agents SDK, CrewAI or siimlar to build agentic workflows into software products
- Are strong at systems design and thinking about scale and modularity from day one
- Are excited by fast iteration, lean experimentation, and building things that matter
- Have experience with data pipelines and/or ML deployment workflows
- Thrive in environments with autonomy, ambiguity, and high ownership
Bonus: You’ve worked on early-stage teams or launched a product from scratch
