Senior AI Engineer

• We’re hiring a Senior AI Engineer to join the team here in Boston. This is an opportunity to have a significant impact on the product. Come help us scale to the next level!
• You will have the opportunity to make a huge impact on a small yet growing team and culture. In this role, you will work directly on a cross-functional engineering team, reporting to the VP of Engineering
• Build AI Agent and Chat Capabilities – Develop AI-powered assistants using cutting-edge technologies and tooling that help our customers run their small businesses
• Deploy & Scale AI Features – Build infrastructure and pipelines to support real-time AI interactions in a production environment
• Experiment & Iterate – Prototype new AI applications, evaluate their performance, and continuously refine them based on user feedback
• Partner with engineering and product leaders – Contribute strategically and play a key role in the product development process

Benefits

• Health & Wellness: Comprehensive medical, dental, and vision plans. plus a Platinum tier Wellhub membership, fully covered by Topline Pro.
• Top tier tools: The tech, equipment, and workspace setup you need to do your best work.
• In-Office Energy: State-of-the-art offices in the heart of downtown Boston and the historic Domino Sugar Factory in Brooklyn, plus late-night Uber Eats coverage and a fully stocked kitchen and pantry so you’re never running on empty.
• 401(k) plan: Retirement savings available through Vestwell, with flexible employee contributions.
• Team Retreats & Pod Culture: Company offsites, inter-office travel, team events, and coffee chat budgets designed to build connection across teams.
• Learning & AI Budget: Monthly AI tool funding and annual professional development support to help you keep learning.- Experience with coded agentic frameworks such as Pydantic AI, LangChain/LangGraph, or similar
• Experience deploying AI-powered applications in production environments (e.g., cloud-based APIs, real-time processing)
• Experience working on an empowered team with Product and Design as equal counterparts
• 5+ years of experience in AI, ML, or NLP-related engineering roles
• Experience with end-to-end MLOps practices: monitoring, deployment, and evaluation
• Familiarity with LLMs and NLP techniques, including prompt engineering, fine-tuning, and evaluation
• Real-world experience with Retrieval Augmented Generation (RAG) and similar practices, including vector embeddings and vector databases
• Proficiency in Python, with preferred experience in Django, React, and PostgreSQL
• Hands-on experience with OpenAI and Anthropic APIs
• Experience in an Agile Scrum environment
• Confidence to make decisions with best-available rather than perfect information
• A drive to understand why your systems behave the way they do, not just that they work, but how
• Low ego, high energy
• A team-first mentality and a love of learning
• Sharp problem-solving instincts, especially in fast-moving, ambiguous situations
• We believe “great candidates” do not come about simply from a check mark next to past experience. We believe in hiring people, not just skills. Even if you do not check every box but find excitement at the prospect of working with us in this capacity, please apply
• Excellent written and verbal communication skills