Senior Software Engineer - AI (Remote)

Pair Team is looking for a builder to deliver value at the intersection of healthcare and artificial intelligence. In this role, you’ll focus on fast iteration—prototyping and launching zero-to-one AI-powered experiences that directly improve outcomes for patients and unlock scale for our care teams.

You’ll leverage your deep knowledge of AI models, tools, and best practices to design intelligent workflows, automate decision-making, and enhance user experience. From LLM-integrated features to behind-the-scenes intelligent routing, you’ll be a key agent of Pair’s AI strategy—helping us learn quickly, ship responsibly, and deliver high-quality results even in ambiguous or high-risk environments.

In this role, you will:

• Rapidly prototype, test, and ship AI-powered features that solve real problems for patients and care teams
• Optimize for speed-to-learning—working in tight loops to validate assumptions and improve outcomes
• Apply modern AI patterns (LLMs, embeddings, RAG, agents, fine-tuning, etc.) in creative, practical ways
• Collaborate closely with product, engineering, operations, and clinical stakeholders to align AI efforts with user needs
• Build robust evaluation pipelines and quality gates to ensure we ship AI features that are trustworthy and useful especially in high risk care delivery scenarios

This is a unique opportunity to build mission-critical AI in one of the most meaningful sectors—using cutting-edge tools to increase access to care for vulnerable populations.

• Impact & Growth: Operates with increasing scope and autonomy; Senior engineer is not a stopping point. Seeks feedback, takes on new challenges, and continues to grow.
• Technical Leadership: Drives technical design and direction. Leads design discussions, navigates trade-offs, and aligns the team around sound architectural decisions.
• System Design: Designs scalable solutions for moderate to high-complexity problems. Balances technical, operational, and cross-functional considerations (e.g., operations, medical).
• Highly Autonomous Execution: Owns projects end-to-end. Balances priorities effectively, delivers on proposals, and follows through with consistent, high-quality execution.
• Problem Solver: Thrives in ambiguous environments, able to deliver high quality products even amid chaos. Balances speed and quality, knowing when to cut corners and when to invest in long-term solutions.
• Technical Excellence & Range: Demonstrates expertise in at least one core area (frontend, backend, infrastructure), while also comfortable flexing beyond their specialty as needed to support broader goals.
• Cross-Functional Trust Builder: Sets clear expectations with non-technical partners and builds strong cross-functional trust. Aligns technical work with business and operational outcomes.
• Growing Team Leadership: Mentors junior and mid-level engineers, participates in technical reviews, improves team workflows or tooling, and helps drive technical standards through the team.
• Data-Driven Mindset: Able to select and implement metrics that drive meaningful operational improvements. Uses data to inform decisions and measure impact.
• Bias for Action: Delivers value iteratively, avoiding over-engineering. Breaks down complex problems into shippable steps and balances planning with execution.

• 2+ years of experience as a high-performing builder in a fast-paced startup environment
• Familiarity with modern AI tools and frameworks (e.g., OpenAI, Llama, etc)
• Proven ability to go from zero to one—rapidly prototyping and delivering AI-driven features and systems
• Able to translate complex user needs into creative AI-driven features
• Comfortable evaluating model performance, designing feedback loops, and managing trade-offs between speed, quality, and risk
• Comfortable working across the stack; experience with Ruby on Rails or similar backend frameworks is a plus
• Experience working in iterative environments, with a bias toward shipping value early and often
• Passionate about building technology that improves care for individuals navigating chronic health and social challenges—including homelessness, severe mental illness, and substance use disorder

• Lead with integrity: We keep our commitments and take responsibility for our actions. We are dependable and choose authenticity over perfection.
• Embrace challenges: We leave our egos at the door and step forward into discomfort instead of back into safety. We help each other to learn and provide feedback using candor and kindness.
• Break through walls: We go the extra mile for our patients, partners and one another, and we run toward hard things. We are resilient in our push for consistent improvement and challenge the status quo.
• Act beyond yourself: We build each other up and respect boundaries. We seek first to understand and assume positive intent.
• Care comes first: We hold ourselves to the highest standards for our patients. We are relentless in the pursuit of our mission, and ensure that we are taking care of ourselves in order to care for others.

• Competitive salary: $180,000 - $220,000
• Equity compensation package
• Flexible vacation policy – take the time you need to recharge
• Comprehensive health, vision & dental insurance
• $50 employer contribution to active HSA accounts
• 401k through Guideline
• Life insurance and AD&D
• Work entirely from the comfort of your own home
• Monthly $100 work from home expense stipend 
• We provide the equipment needed for the role
• Opportunity for rapid career progression with plenty of room for personal growth!