We are DeweyLearn, an education technology startup building AI systems that capture expert judgment and turn it into authentic assessment. We're small and early, and the work is real from day one.

In your cover letter, tell us about a time an AI coding tool produced something that looked correct but wasn't — how you caught it, and what you changed afterward.

Tasks

• Build and maintain production backend services and APIs in Python (FastAPI)
• Implement retrieval workflows (RAG, embeddings, vector search)
• Work closely with other engineers and stakeholders to make good technical trade-offs
• Help keep our systems clean, reliable, and easy to extend

Requirements

General

• You’re a curious technologist at heart. You like understanding how things work, and you enjoy exploring new tools, approaches, and ideas
• You are a fast self-learner and enjoy dialog
• You have proven software engineering fundamentals and can build reliable systems that others can understand, maintain, and extend
• You are a good communicator and can ask the right questions, explain trade-offs in a straightforward way, and collaborate with stakeholders
• You enjoy collaborating with other team members
• 4–8 years of professional software engineering experience. This is a deliberate band, not a minimum — we want engineers who learned the fundamentals the hard way and then rebuilt how they work around AI
• You have experience working with ML/AI systems in a production environment.
• You have native/fluent proficiency in English
• Experience in early-stage startups is a plus
• You work agentically. AI is your primary authoring tool, not an autocomplete you tolerate, and you can say precisely where you let a model run unsupervised and where you don't
• You read AI output critically. You've caught it being confidently wrong, and you still know what's underneath — when an agent writes something that breaks, you can debug it
• You must be legally authorized to work in the United States without sponsorship, now and in the future, and be physically located in the US while working. Eastern time zone strongly preferred — we need at least six hours of daily overlap with 9:00–17:00 ET

Technical

• Exceptional command of the Python language is a must
• Exceptional command of FastAPI and related topics is a must
• Production API work backed by PostgreSQL is a must
• Good command of Docker in dev and deployment use cases
• Understanding of Infra as code is a plus
• Exceptional understanding of “engineering basics” (version control, CI/CD, environments, debugging)
• Familiarity with retrieval workflows (RAG) and embedding-based search
• Experience with Natural Language Processing is a plus
• Familiarity with at least one front-end framework is a plus

Benefits

• Flexible remote work arrangement
• Collaborative, innovation-focused environment
• Opportunity to shape the future of education

Join us in building the future of education technology. If you're passionate about creating innovative solutions and want to be part of something groundbreaking, we want to hear from you.

Requires 4–8 years of software engineering experience, production ML/AI experience, fluent English, US work authorization without sponsorship, and expertise in Python, FastAPI, PostgreSQL, Docker, APIs, and retrieval workflows.

Key Responsibilities

• building services
• implementing workflows
• debugging systems

Skills & Tools

Python, FastAPI, RAG, PostgreSQL, Docker, CI/CD, Natural Language Processing

Job Details

• Category: Software Development
• Seniority: Senior Level
• Commitment: Full Time
• Workplace: Remote — New York City, New York, United States
• Salary: USD 140,000 – 165,000 / year
• Languages: English

About DeweyLearn

An education technology startup building AI systems that capture expert judgment and create authentic assessments. — Industry: Education