# Jerry.ai — AI Product Engineer

- Generated: 2026-09-02 05:35:09 PM EDT
- Original JD posting: https://www.indeed.com/viewjob?jk=5a1637248238efa7
- Independently corroborated posting: https://builtin.com/job/ai-product-engineer/10972514
- Work model/location: Remote; Massachusetts is explicitly eligible
- Compensation: $160,000-$210,000 base plus potential equity
- Travel: Not disclosed
- Posting time: Alert received September 2, 2026 at 3:26 PM EDT; provider page said just posted
- Applicants: Not disclosed
- Positioning track: Technical IC
- Fit outcome: PASS — 88%

## Fit decision

PASS. Keith has direct, recent evidence for production LLM systems, agents, workflow automation, model orchestration, evaluation, observability, latency/cost tradeoffs, failure handling, AWS deployment, and end-to-end product delivery. Massachusetts is explicitly eligible and the range reaches Keith's $200,000 threshold. The principal caveat is that his recent application stack is Python/FastAPI rather than TypeScript/NestJS; the JD presents that as the current stack, not an explicit must-have qualification.

## Weighted evidence map

| Requirement | Weight | Evidence score | Evidence |
|---|---:|---:|---|
| Build production LLM and agent systems | 3 | 3 | AssistX, customer-service agents, RAG, tools, agent orchestration, and managed AWS agent deployment. |
| Own products end to end from ambiguity to production | 3 | 3 | IDW commercial release in eight months plus repeated product/platform delivery across prior roles. |
| Evaluation, regressions, reliability, and failure handling | 3 | 3 | Direct evaluation, observability, guardrail, feedback, and operational-quality work. |
| Model and architecture selection | 3 | 3 | OpenAI/Anthropic integration, Bedrock, model routing, architecture reviews, and cost/latency judgment. |
| AWS production infrastructure | 2 | 3 | Deep AWS architecture plus ECS, EKS, Lambda, CDK, Docker, Kubernetes, and platform operations. |
| Chatbot, voice, document, and workflow automation | 2 | 2 | Direct chatbot and workflow automation; voice and computer-use depth are adjacent rather than fully documented. |
| TypeScript/NestJS, React, and GraphQL stack | 2 | 1 | React and GraphQL evidence exists; recent TypeScript/NestJS delivery is not documented. |
| Startup builder operating mode | 2 | 3 | Technical co-founder who built product, team, architecture, platform, and operations from scratch. |

Weighted result: 58 of 66 possible points = 87.9%, rounded to 88%.

## Material gaps and caveats

1. Recent TypeScript and NestJS implementation is not documented; recent backend work is primarily Python/FastAPI.
2. Direct production voicebot and computer-use-agent depth is lighter than chatbot, RAG, and workflow-agent evidence.
3. Insurance-domain experience is not documented, but the posting does not require it.
4. Applicant count and travel are not disclosed.

## Full normalized job description

Jerry.ai is hiring a remote AI Product Engineer to lead the next generation of AI automation for insurance quoting, customer support, document validation, voice interactions, and external-system navigation. The role sets the technical bar for chatbot systems, helps shape prompt-engineering direction, evaluates new AI technologies, and builds selected approaches through production deployment. Core responsibilities include new automation for record disputes, document validation, email and call reduction, voicebot expansion, and computer-use agents; partnership with OpenAI is part of the mandate. Required evidence includes 5+ years in software engineering, end-to-end product ownership, deep hands-on AI experience, rapid experimentation with new models, and production LLM operations covering evaluation, regressions, latency, cost, reliability, and failure handling. The published stack is TypeScript/NestJS, React, GraphQL, AWS ECS/EKS/Lambda, OpenAI, Anthropic Claude, and Google Gemini. The employer explicitly permits full-time salaried hiring in Massachusetts and states that it is fully remote. Base compensation is $160,000-$210,000 plus possible equity.

## Artifacts

- Resume: https://bit.ly/3T5wuNU
- Cover letter: https://bit.ly/4zRRacR
- Direct resume: https://files.keithsteward.com/Jerry_ai/Keith_Steward_AI_Product_Engineer_5a1637248238efa7_Resume.pdf
- Direct cover letter: https://files.keithsteward.com/Jerry_ai/Keith_Steward_AI_Product_Engineer_5a1637248238efa7_Cover_Letter.pdf
- Validation: 2-page resume (954 words); 1-page cover letter (243 words); profile 71 words; 42 supported technologies; PDF content, geometry, annotations, text extraction, and rendered pages validated.
- Google Drive used: No