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 has already been substantially rebuilt and requires thoughtful evolution, not ground-up construction
• 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/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

What This Role Is Not

This is not a people manager role. You will not carry direct reports or be evaluated on team headcount. You may provide technical direction to contributors, but managing people is the exception, not the expectation.

Requirements and Qualifications

Required

• Bachelor's or Master's degree in Computer Science, Engineering, or a related quantitative field (or equivalent practical experience)
• 8+ years of software engineering experience, with demonstrated mastery designing and shipping production systems where correctness, reliability, and auditability matter
• 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
• Sound judgment about where AI belongs and where it must not - comfortable with probabilistic agents for customer-facing and research tasks, while keeping policy binding, money movement, and compliance flows deterministic, auditable, and human-governed
• Experience making and communicating build vs. buy vs. integrate decisions at an organizational level
• Proficiency in Python and the modern GenAI application stack - agent/orchestration frameworks (e.g. LangChain, LlamaIndex, or equivalents), model-provider SDKs, vector databases, and evaluation tooling
• Exceptional written and verbal communication skills - you can write a crisp architecture decision record and present it to a board-level audience

Preferred

• 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
• Familiarity with RAG architectures, vector databases, and semantic search at scale
• 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

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.