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Selected role

Managing Engineer, Applied Generative AI

SquareTrade San Francisco, CA, US

$185k - $250k Senior Full-time

Company Description

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.

Job Description

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

Qualifications

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

Additional Information

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.

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 status as a veteran by refusing to employ an applicant on the basis that they are a veteran of the armed forces of the United States, a member of the Indiana National Guard or a member of a reserve component.

For jobs in San Francisco, please click “here” for information regarding the San Francisco Fair Chance Ordinance.

For jobs in Los Angeles, please click “here” for information regarding the Los Angeles Fair Chance Initiative for Hiring Ordinance.

To view the “EEO Know Your Rights” poster click “here”. This poster provides information concerning the laws and procedures for filing complaints of violations of the laws with the Office of Federal Contract Compliance Programs.

To view the FMLA poster, click “here”. This poster summarizing the major provisions of the Family and Medical Leave Act (FMLA) and telling employees how to file a complaint.

SquareTrade is proud to be an Equal Employment Opportunity employer. We are committed to creating an inclusive work environment for all employees. We celebrate diversity and encourage applications from all qualified individuals regardless of race, religion, color, national origin, sex, gender identity, gender expression, sexual orientation, age, marital status, veteran status, or ability status. It is the Company’s policy to employ the best qualified individuals available for all jobs. Therefore, any discriminatory action taken on account of an employee’s ancestry, age, color, disability, genetic information, gender, gender identity, gender expression, sexual and reproductive health decision, marital status, medical condition, military or veteran status, national origin, race (include traits historically associated with race, including, but not limited to, hair texture and protective hairstyles), religion (including religious dress), sex, or sexual orientation that adversely affects an employee's terms or conditions of employment is prohibited. This policy applies to all aspects of the employment relationship, including, but not limited to, hiring, training, salary administration, promotion, job assignment, benefits, discipline, and separation of employment.

Beware of Recruitment Fraud. For more information, please click “here”.

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