Managing Engineer, Applied Generative AI

SquareTrade 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, SquareTrade has headquarters in San Francisco and London. We are currently expanding in Europe and Asia Pacific, including Japan and Australia.

SquareTrade is seeking a hands-on Managing Engineer to lead the operationalization of Generative AI at enterprise scale. This role owns the delivery of production-grade, LLM-powered systems that enhance claims processing, customer support, and fraud detection.You will lead two squads—AI Platform Infrastructure and Applied AI Product—guiding solutions from architecture and experimentation through secure, cost-efficient production deployment. This is a player-coach role, with at least 50% hands-on contribution in design, coding, and technical execution using XP practices including test-driven development and pair programming.

What You’ll Do

• Own the end-to-end lifecycle of generative AI products, from architecture and prototyping to enterprise production
• Lead and mentor engineering teams, setting technical direction, expectations, and delivery standards
• Design and evolve scalable AI platforms, including LLM orchestration, vector search, evaluation frameworks, monitoring and observability
• Integrate modern AI capabilities into existing enterprise systems and workflows
• Establish and champion CI/CD, TDD, and DevOps best practices
• Partner closely with product managers and stakeholders to translate business needs into technical solutions
• Communicate technical trade-offs, risks, and outcomes clearly to executive and non-technical audiences
• Foster a culture of collaboration, feedback, and continuous learning

• Bachelor's Degree in Computer Science or related field
• 8 or more years of engineering experience
• Strong proficiency in Python and modern AI tooling
• Experience with vector databases, LLM frameworks, and agent orchestration (e.g.,Semantic Kernel, CrewAI, Google ADK)
• Hands-on experience with Azure or AWS, Docker, and Kubernetes

Nice to Have

• 2 or more years of management experience with full time software engineers
• Experience with fine-tuning, RLHF, evaluation frameworks (including “LLM-as-a judge”)
• Experience in insurance, warranty, fintech, or e-commerce domains
• Familiarity with hybrid cloud and on-prem environments
• Strong DevOps and GitHub collaboration experience

At SquareTrade 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 
• Various corporate perks and discounts 

This role is a hybrid role associated with our Bay Area Office.

SquareTrade estimates the possible base compensation for this role, if hired in the San Francisco Bay Area, California, to be in the range : $185K - 250K

The candidate(s) offered this position will be required to submit to a background investigation. 

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