Senior Software Engineer – Applied Generative AI

Overview

Square Trade is the fastest growing company of its kind. We’re revolutionizing a $30b industry with service innovation and attention to customer satisfaction. We partner with some of the largest, most sophisticated retailers and carriers in the world (Amazon, Walmart, The Home Depot to name a few), consistently win industry awards, have received tens of thousands of 5-star reviews… and we’re just getting started.

A member of the Allstate family, Square Trade has headquarters in San Francisco and London. We are currently expanding in Europe and Asia Pacific, including Japan and Australia.

We’re looking for a Senior Software Engineer to help build and scale our Applied Generative AI ecosystem. You will work hands‑on across Agentic workflows, Retrieval‑Augmented Generation (RAG) systems, and production‑grade LLM integrations. This role blends deep engineering with practical AI application, contributing to systems that are secure, reliable, and built for enterprise scale. You will collaborate closely with technical leads, product partners, and data scientists to turn experimental AI ideas into robust production features.

• Technical Architecture & System Design
  • Contribute to the design of scalable GenAI systems, including RAG pipelines and autonomous agents integrated with core claims platforms.
  • Implement standards for agent orchestration using frameworks such as Semantic Kernel, Google ADK, or CrewAI.
  • Support decisions on model selection, vector storage, and cloud infrastructure to balance performance, reliability, and cost.
• Hands-on Engineering
  • Write high-quality Python code for production AI services, following strong testing and observability practices.
  • Develop backend logic and APIs that connect modern AI systems with existing Java/Spring services.
  • Optimize Kubernetes/Docker-based infrastructure to meet the concurrency and compute demands of LLM workloads.
• LLMOps & Production Excellence
  • Build components of LLMOps pipelines, including prompt versioning, evaluation workflows, and automated regression testing.
  • Implement observability tooling to track token usage, drift, latency, and error patterns.
  • Participate in incident response and root cause analysis to ensure high availability and reliability.
• Collaboration & Technical Influence
  • Collaborate with senior and lead engineers through code reviews and design discussions.
  • Translate product requirements into technical tasks and contribute to roadmap planning.
  • Promote experimentation and best practices while maintaining a focus on security and stability.

• Build real AI systems—not just chatbots that solve meaningful customer problems
• Work with cutting-edge agentic and RAG architectures
• Impact millions of customers through enterprise-scale AI
• Grow your career in a supportive, innovative engineering culture

• Bachelor’s Degree in Computer Science or related field
• 5+ years of software engineering experience, including backend development
• Strong proficiency in Python and API development
• Hands-on experience with Generative AI including RAG, vector databases, and LLM APIs
• Experience with agent frameworks such as Google ADK, Semantic Kernel, or CrewAI
• Experience building distributed systems on AWS or Azure using Kubernetes/Docker

• Ability to read/debug Java/Spring codebases
• Familiarity with fine-tuning or RLHF
• Background in fintech, insurance, or e-commerce

• At Square Trade you'll have access to:
  • Medical, dental and vision coverage with network optionality and the ability to contribute to a savings account (HSA or FSA)
  • Up to 4% company match into 401(k) and contributions into your company-sponsored pension
  • $75/month budget to help prioritize your physical wellbeing
  • $80/month stipend to subsidize connectivity costs
  • Mental health resources including free 1:1 therapy, coaching sessions and digital resources
  • Supportive leave policies
  • Flexible Time Off Policy in addition to 9 Company Holidays
  • Tuition reimbursement up to $5,250 per year to further your personal educational advancement desires
  • Hybrid work arrangements with regular investment in gatherings/offsites to spend time together as team
  • Variou…