Lead AI Engineer

At InsCipher, our commitment to our customers is what drives us. Ours is a culture of innovation and progress. We are a creative team of doers constantly striving to develop value-driven products and services for our customers. Our ultimate goal is to become the trusted authority and leading partner for state departments of insurance, surplus lines associations, and brokers nationwide. We’re achieving that goal by enhancing every facet of our customers reporting and tax filings through education and innovative, streamlined compliance solutions. We’re growing fast and want you to be a part of it! We are seeking a Lead AI Engineer to serve as our organization's foremost technical authority on artificial intelligence strategy, architecture, and adoption. At InsCipher, that means shaping how AI is built and scaled across a compliance-critical platform – one that serves surplus lines brokers, state departments of insurance, and associations nationwide through tax filing, state reporting, and regulatory workflow automation. This is not a people management role – it is a systems leadership role. You will act as the connective tissue between engineering, product, and business leadership, making and owning the high-stakes technical decisions: build vs. buy, platform selection, architectural patterns, and AI tooling standards. You will bring structure and discipline to our AI practice while operating with the urgency and adaptability of a fast-moving, mission-driven company. Key Responsibilities Technical Strategy & Direction Define the AI engineering roadmap and architecture standards across the organization Lead build vs. buy vs. integrate decision-making for AI systems and platforms – and be accountable for articulating how you arrived at those decisions Evaluate emerging tools, frameworks, and models; provide clear, defensible recommendations to leadership Serve as the ultimate technical escalation point for complex AI/ML system design challenges Enterprise Systems & Scaling Architect AI solutions for our enterprise platform – which is actively being upgraded and requires someone comfortable working across both the process layer and the underlying platform architecture as a normal part of the role, not just layering AI on top of stable infrastructure Design systems for scale, reliability, and cost-efficiency in production environments Establish LLMOps practices – evaluation and regression suites for LLM-powered features, cost and quality observability, versioned prompts and configs with staged rollout and rollback, and production guardrails Ensure AI systems integrate cleanly with existing product and engineering infrastructure Cross-Functional Collaboration Partner closely with Product and Engineering leadership to align AI capabilities with business outcomes Receive operational support to help initiate and coordinate cross-functional engagement, allowing you to stay focused on technical leadership and decision-making Provide clear guidance on resource allocation – who owns what, who should be engaged, and in what sequence Translate complex technical concepts for non-technical audiences, including executives and business stakeholders Challenge direction constructively and push back on approaches that compromise long-term system health AI Coding & Process Transformation Champion and introduce AI-assisted coding practices and developer tooling across the engineering organization Define standards for responsible AI development including guardrails, evaluation frameworks, and security considerations Drive continuous improvement in how the organization builds and ships AI-powered features Required to perform other duties as requested, directed, or assigned Requirements and Qualifications Required Bachelor's or Master's degree in Computer Science, Engineering, or a related quantitative field, or equivalent practical experience 5+ years of software engineering experience with a meaningful portion in production AI/ML or LLM/GenAI systems – strong judgment and vision at the 5–6 year mark will not be screened out on tenure alone 2+ years building production LLM/GenAI and agentic systems, plus fluency with AI-assisted coding tooling and the judgment to set org-wide standards, evals, and guardrails for AI-generated code Demonstrated track record of taking an existing business process apart and rebuilding it with AI at the core within an existing enterprise environment – shipped to production and owned the outcome Production experience with LLM/GenAI and agentic systems – agent orchestration, tool calling, RAG, structured outputs – with the fluency to set org-wide standards, evals, and guardrails for AI-generated code Sound judgment about where AI belongs and where it must not – comfortable with probabilistic agents for customer-facing and research tasks, while treating policy binding, money movement, and compliance flows as deterministic, auditable, and human-governed; this framing is non-negotiable in an insurance context Experience making and communicating build vs. buy vs. integrate decisions at an organizational level Proficiency in Python and the modern GenAI application stack – agent and orchestration frameworks, model-provider SDKs, vector databases, and evaluation tooling; screened for fluency with the stack generally, not a specific checklist of tools Exceptional written and verbal communication skills – you can write a crisp architecture decision record and present it to a board-level audience Preferred Direct evidence of legacy-process redesign with real latitude to alter underlying platform architecture – not just process work layered on top of stable infrastructure Enterprise or regulated-domain experience, ideally in a business context closer to insurance or financial services Experience in a technical lead or principal engineer role with broad organizational influence Background working closely with product engineering teams in a dual-track agile model Experience with AI cost management, observability, and governance frameworks Perks Health, dental, and vision plans Amazing work-life balance with 4 weeks of Paid Time Off 10 Paid Company Holidays with 2 floating holidays 401K Programs with employer match Personal assistance programs for support in a healthy personal and work life Why InsCipher? At InsCipher, you'll join a team of disruptors, innovators, and forward-thinkers. We're not just changing the game; we're creating a new one. We offer a dynamic, inclusive work environment where your ideas are valued, and your contributions lead to real change. With us, you'll have the opportunity to: Work on cutting-edge projects that are reshaping an industry Collaborate with a team of passionate, like-minded professionals Enjoy a culture that values flexibility, innovation, and personal growth Compensation Range: $200k/yr - $220k/yr + 10% Bonus We are proud to be an equal-opportunity employer. We are committed to providing equal opportunities to all qualified applicants, regardless of race, color, religion, sex, national origin, disability, or any other legally protected characteristics. If you need accommodation, please let us know during the interview process.