Founding Head of AI Engineering (Co-Founder)

AI Engineer & Technical Co-Founder — Owlera
About Owlera
Owlera is an AI-powered career and professional experience platform built to solve one of the biggest challenges facing students and early-career talent: you need experience to get opportunities, but you need opportunities to gain experience.
We turn real company work into immersive virtual simulated internships where students complete professional missions, work with company resources, interact with AI managers, receive feedback and evaluation, and build verified evidence of what they can actually do.
Our vision goes beyond courses and traditional job simulations. We are building an AI-powered environment where people can build experience, prove their abilities, and prepare for a rapidly changing world of work.
About the Opportunity
We are looking for an exceptional AI Engineer to join Owlera as a technical co-founder/founding technical partner and take ownership of the AI intelligence behind the platform.
This is not a role focused on simply connecting an application to an LLM API. We need someone who can architect and build production AI systems that become core parts of the Owlera experience.
You would work directly with the founder to transform our validated MVP into a scalable AI-powered platform and help shape both the product and technical direction of the company.
What You'll Do
You will design and build Owlera's AI architecture and core AI product capabilities, including:
• AI agents and multi-step agentic workflows
• AI Managers and Supervisors that guide students through realistic work experiences
• AI evaluators that assess student submissions, provide feedback, score performance, and identify skills and professional behaviors
• RAG systems that allow AI agents to understand company documents, resources, processes, and internship context
• LLM integrations, orchestration, tool calling, memory, context management, and structured outputs
• Conversational AI and intelligent chat experiences
• AI-powered internship and mission generation from real company information
• Career intelligence and personalized AI guidance
• Reliable evaluation pipelines, guardrails, monitoring, testing, and AI quality improvement
• Backend integrations required to connect these AI systems with the wider Owlera product
You will also help determine what should be handled by agents, traditional software, retrieval systems, workflows, or other AI approaches as the platform scales.
What We're Looking For
We are looking for someone who is both a strong AI engineer and a builder. You should have hands-on experience with LLM applications, AI agents, agentic workflows, RAG, embeddings/vector databases, tool calling, structured outputs, prompt and context engineering, and production AI systems.
Experience with Python and modern backend development is important. Full-stack experience is a major advantage because this is an early-stage company where technical ownership will extend beyond isolated AI models.
Most importantly, we want someone who thinks like a founder: someone comfortable with ambiguity, fast experimentation, technical ownership, product decisions, and building from an early stage.
Experience in EdTech, HRTech, Future of Work, assessment systems, recommendation systems, or AI evaluation is valuable but not required.
Important: This Is a Co-Founder Opportunity
This is not a salaried position at this stage. Owlera is currently pre-seed and raising capital. We are looking for a technical partner who believes in the problem and wants to help build the company from the ground up in exchange for co-founder equity, with compensation becoming possible as the company raises funding and grows.
This opportunity is best suited for someone who wants more than their next engineering job. We are looking for someone who wants to help build the technology, product, team, and company alongside the founder.
Learn more about Owlera: www.owlera.online

Work arrangement
No