Senior Software Engineer, AI

About Lilypad Learning:

Lilypad Learning helps public schools evaluate students for learning disabilities by remotely connecting them with school psychologists.

There is a nationwide shortage of school psychologists and schools face an critical problem: their budgets are being strained by legal challenges for missing federally mandated special education timelines and there aren’t enough school psychologists available to provide the support schools need.

All students in special education must receive something called a psycho-educational evaluation every three years for the school to remain compliant. Today, these evaluations take a psychologist 10-12 hours per student, with 70% of that time spent on laborious report writing.

We help bridge the gap between psychologists and schools who need help. We leverage LLMs to automate laborious parts of the reporting process, enabling school districts to remain compliant while their students get the support they need fast.

Today, we are supporting more than 15 public school districts, and have received backing from top VCs, such as XYZ Venture Capital. We are eager to scale quickly across the 13,700 districts in the US as we help schools everywhere support students with learning disabilities.

Who you are:

You’re an experienced senior software engineer with a backend tilt. You’re well-versed in all things web and have experience building LLM applications end-to-end. You follow the AI/LLM space closely, play with new technologies as they come out, and are excited to use these technologies to build safe, reliable educational AI systems. Using your expertise in Large Language Models (LLMs), Natural Language Understanding (NLU), and conversational design, you can craft effective AI workflows, ensuring quality, performance, and seamless operation.

What you will do:

• Lead the development of new AI-driven projects, encompassing ideation, prototyping, research, infrastructure design, scalability, monitoring, and evaluation.
• Analyze individual student evaluation requirements and craft precise LLM prompts to generate assessment summaries, IEP recommendations, and progress insights.
• Decompose complex special-education processes into clear, machine-digestible tasks so our AI agents can automate and accelerate them effectively.
• Enable seamless API orchestration between our AI modules, Supabase backend, and external SIS/EHR systems to power real-time data exchange.
• Collaborate closely with other engineers to embed AI-powered evaluation flows into our Next.js interface, ensuring a unified, intuitive experience for end users.
• Research and apply best practices in terms of knowledge graphs, embeddings, vector and graph RAG search, fine-tuning, and model optimization.
• Write clean, efficient, and well-documented code, following industry best practices.
• Collaborate with clinical experts to validate performance and accuracy.

What you’ll bring:

• 5+ years software development experience with a focus on backend software engineering
• 2+ years of experience in conversation design and AI agent development
• Deep understanding of distributed systems, event-driven architectures, and building APIs with TypeScript and Python
• Proficiency in applying advanced prompt engineering techniques
• Ability to analyze customer requirements and craft LLM prompts that align with desired outcomes
• Strong project and stakeholder management skills, with passion for meeting milestones and effective communication
• Strong understanding of data structures and how information is stored and transmitted across different systems
• Exceptional attention to detail and logical thinking, with a proven ability to identify and address subtle nuances in conversational flows, ensuring a seamless and engaging user experience

Highly desired:

• Prior experience in working at an EdTech and/or HealthTech startup with HIPAA/FERPA compliance requirements
• Experience in an high growth, early stage startup environment
• Professional experience building end-to-end LLM-powered applications

Why you should join us:

• Join a small, high-impact team building the future of student psychological evaluations
• Work with cutting-edge LLM tools that support school districts across the United States
• Shape core technical architecture in an emerging field
• Work remotely (or meet up with team members in New York City and Washington D.C.)
• Earn competitive salary with equity package and benefits
• Enjoy generous PTO with company holidays
• Medical, dental, and vision coverage for you and your family
• Get access to tools like Cursor, Claude, and Linear to help you move fast

Compensation:

• $145K - $175K/year
• 0.25% - 1% equity

Our tech stack:

• TypeScript
• Backend; Docker, Turborepo, Node, Supabase, Drizzle, tRPC, AI SDK, Inngest, Render
• Frontend: Next.js, TanStack, Tailwind, Zustand, Shadcn UI

Interview process:

1. Application form
2. Conversation with our Lead Engineer
3. Technical Interviews:
4. Coding interview focused on a real-world application relevant to the role (e.g., LLMs, backend engineering)
5. Architecture/whiteboarding interview focused on discussing general application-design relevant to the role
6. Conversation with our CEO