Managing Engineer, Applied Generative AI
SquareTradeSan Francisco, CA$185k – $250kPosted 5 March 2026
Job Description
<p>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.</p><p>What You’ll Do</p><ul><li>Own the end-to-end lifecycle of generative AI products, from architecture and prototyping to enterprise production</li><li>Lead and mentor engineering teams, setting technical direction, expectations, and delivery standards</li><li>Design and evolve scalable AI platforms, including LLM orchestration, vector search, evaluation frameworks, monitoring and observability</li><li>Integrate modern AI capabilities into existing enterprise systems and workflows</li><li>Establish and champion CI/CD, TDD, and DevOps best practices</li><li>Partner closely with product managers and stakeholders to translate business needs into technical solutions</li><li>Communicate technical trade-offs, risks, and outcomes clearly to executive and non-technical audiences</li><li>Foster a culture of collaboration, feedback, and continuous learning</li></ul><p> </p>
<ul><li>Bachelor's Degree in Computer Science or related field</li><li>8 or more years of engineering experience</li><li>Strong proficiency in Python and modern AI tooling</li><li>Experience with vector databases, LLM frameworks, and agent orchestration (e.g.,Semantic Kernel, CrewAI, Google ADK)</li><li>Hands-on experience with Azure or AWS, Docker, and Kubernetes</li></ul><p>Nice to Have</p><ul><li>2 or more years of management experience with full time software engineers</li><li>Experience with fine-tuning, RLHF, evaluation frameworks (including “LLM-as-a judge”)</li><li>Experience in insurance, warranty, fintech, or e-commerce domains</li><li>Familiarity with hybrid cloud and on-prem environments</li><li>Strong DevOps and GitHub collaboration experience</li></ul>
<p>At SquareTrade you'll have access to:  </p><ul><li>Medical, dental and vision coverage with network optionality and the ability to contribute to a savings account (HSA or FSA)   </li><li>Up to 4% company match into 401(k) and contributions into your company-sponsored pension </li><li>$75/month budget to help prioritize your physical wellbeing </li><li>$80/month stipend to subsidize connectivity costs </li><li>Mental health resources including free 1:1 therapy, coaching sessions and digital resources </li><li>Supportive leave policies </li><li>Flexible Time Off Policy in addition to 9 Company Holidays </li><li>Tuition reimbursement up to $5,250 per year to further your personal educational advancement desires </li><li>Hybrid work arrangements with regular investment in gatherings/offsites to spend time together as team </li><li>Various corporate perks and discounts </li></ul><p>This role is a hybrid role associated with our Bay Area Office.</p><p>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</p><p>The candidate(s) offered this position will be required to submit to a background investigation. </p><p>Effective July 1, 2014, under Indiana House Enrolled Act (HEA) 1242, it is against public policy of the State of Indiana and a discriminatory practice for an employer to discriminate against a prospective employee on the basis of ... (truncated, view full listing at source)
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