Founding Engineer, AI

Overview

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 future 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. We’re looking for a systems-savvy generalist with a data-first mindset, someone who values scale, modularity, and performance as much as iteration speed. You know when to let the model take the first pass—and when human logic needs to take over. You’ve worked with LLMs and agents and have fine-tuned models, or RLHF workflows, and are excited about applying that expertise in real-world products that make a difference. This role is ideal for someone who wants to move fast, own major decisions, and build AI-native software that couldn’t exist 2 years ago.

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 use AI tools to speed up your workflow and build with velocity, but with a mind toward scalability, modularity and high quality secure code.

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 (AI-first coding in 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

You might be the person we’re looking for if you

• Have 5+ years of full-stack development experience, ideally with JS/TS and Python
• Are fluent in modern frameworks like React, Node.js, and backend APIs
• Are strong systems designer and thinking about scale, modularity and speed
• Have deep comfort with LLMs, embeddings, vector DBs, agentic frameworks, fine-tuning, and RLHF
• Have AI-native mindset - you lean heavily into tools like Cursor, Aider, RooCode, Cline by default backed by strong systems design
• Have used tools like LlamaIndex, CrewAI, AutoGen, Pydantic, OpenAI Agents SDK or similar to build agentic workflows into software products
• Are excited by fast iteration, lean experimentation, and building things that matter
• Have a data-centric approach to product building with experience in data pipelines and/or ML deployment workflows
• Are comfortable in environments with fast-paced iteration, autonomy, ambiguity, and high ownership
• Have a customer-centric development mindset and are thinking in advance of ways to leverage the latest in AI to drive our mission

Bonus: Early-stage experience or having shipped 0•1 products

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

In your first 180 days, you will

• Build and ship agent-based tools that personalize user journeys in real-time
• Expand and productionize our LLM stack with continuous evals and active learning
• Drive improvements across our data and ML pipelines
• Build agent-centric custom course creation and delivery engines
• Mentor new contributors or collaborators as the team expands
• Own key aspects of our AI infrastructure and establish scalable design patterns

Our hiring process

1. Intro Call – We’ll connect to align on the mission, values, and your goals
2. Async Challenge – You’ll complete a small AI-focused task using tools you prefer
3. Technical Interview – We’ll review your code and extend the challenge into real-world scenarios
4. Final Call – A deeper conversation with the founder to ensure alignment on vision, culture, and contribution
5. Offer – If it’s a fit, we move quickly and collaboratively to bring you on board

#J-18808-Ljbffr