
Job Overview
Location
New York, New York
Job Type
Full-time
Category
Engineering
Date Posted
June 24, 2026
Full Job Description
đź“‹ Description
- • Lead the development and scaling of Jerry.ai’s AI platform and customer-facing Agentic AI product, shaping how LLMs, agents, and internal APIs create a seamless, magical experience for over 5M+ customers.
- • Drive end-to-end ownership of AI systems including prompt strategies, evaluation frameworks, guardrails, and experimentation to improve answer quality, customer satisfaction, and automation rates across >70% of inbound sales and service requests (50k+ chats/month).
- • Partner with engineering and product teams to unify fragmented AI infrastructure, establish platform standards, and serve as the technical translator between technical and non-technical stakeholders.
- • Collaborate with OpenAI to evaluate and deploy next-generation voice models and workflow automation, pioneering new model capabilities integrated directly into the ChatGPT App.
- • Report directly to the COO in a flat, high-impact org chart, leading one of the company’s most critical growth levers with accelerated career growth opportunities.
- • Join a profitable, pre-IPO startup with $240M raised, 5M+ customers, and a mission to revolutionize car ownership through AI-powered automation of insurance, financing, maintenance, and repairs.
🎯 Requirements
- • 4+ years of experience in a technical role such as forward deployed engineering, technical product management, or similar at a fast-paced startup.
- • Deep passion and curiosity for AI systems, including modern LLMs, with hands-on experience building custom workflows and staying current with model releases.
- • Proven track record of taking complex, strategic AI concepts and turning them into scalable, production-grade products.
- • Comfort with SQL and data-driven experimentation to validate hypotheses and drive systematic improvements in AI performance.
- • Ability to navigate technical tradeoffs, lead by example in implementing AI platform standards, and communicate complex ideas clearly to diverse audiences.
🏖️ Benefits
- • Comprehensive health, dental, and vision coverage for regular employees.
- • Paid time off, paid parental leave, and 401(K) plan with employer matching.
- • Wellness benefits and equity opportunities as part of the total rewards package.
- • Opportunity to work directly with OpenAI on cutting-edge voice models and AI workflow automation.
- • Flat organizational structure with direct access to leadership and accelerated career growth in a profitable, pre-IPO startup.
Skills & Technologies
See exactly how your profile matches this role — strengths, skill gaps, and what to do about them.
About Jerry Technologies Inc.
Jerry Technologies offers a mobile-first AI platform that automatically compares insurance quotes, refinances auto loans, and shops for home and renters coverage. Users submit photos of existing policies, and the app retrieves and compares rates from carriers to find lower premiums or better terms. The company earns commissions from insurers when policies are switched or originated through its platform, serving consumers seeking to reduce recurring auto and home expenses without manual comparison shopping.
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