Director of AI Engineering

iManage•Chicago, IL

1d•$200,000 - $290,000•Hybrid

About The Position

We offer a flexible working policy that supports a healthy balance between personal and professional well-being. This role requires in-office presence on Tuesdays & Thursdays to collaborate, connect, and learn from peers - while also maintaining the flexibility for meaningful work-life balance. Being a Director of AI Engineering at iManage Means… We are looking for a Director of AI Engineering to own the production quality, cost efficiency, scalability, and feature expansion of our LLM services. This is a role where your architectural judgement directly shapes the system on how we serve models, how enrichment pipelines are built, and how our AI capabilities compose across the platform. You will partner closely with our Director of Data Curation and report to the VP of AI Engineering, leading a 15 person team responsible for turning AI powered features and capabilities into reliable, performant systems that our customers trust. In regulated industries like legal, AI must come to the data, not the other way around. iManage holds data for the worlds most sophisticated legal professionals, and this role is about producing the AI capabilities worthy of that position.

Requirements

Bachelor’s or master’s in computer science, machine learning, data science, or a related field preferred.
8+ years in software and ML/AI engineering, with 3–5+ years leading engineering teams delivering AI products to production at scale.
A track record in regulated or high-reliability environments (e.g. healthcare, fintech, insurance, legal tech, government) where production quality means real consequences.
Experience growing and managing multi-disciplinary teams through scaling phases, including managers as direct reports.
Proven success shipping LLM-powered products including RAG pipelines, agents, or personalization features with measurable business outcomes.
Strong system-level thinking: you architect services that compose well, degrade gracefully, expose clean interfaces, and partner effectively across data, product, and platform teams.
Fluency in the cost/quality/performance trade-offs of AI services. You have made real decisions about when to use a large, hosted model versus a fine-tuned smaller one.
Grounded experience in modern AI/ML infrastructure: model lifecycle, MLOps practices, evaluation frameworks, and cloud-native deployment (AWS/Azure/GCP).
Hands-on engineering background: comfortable going deep technically when the situation requires it.
Strategic fluency: you can articulate why we are building what we are building and make a compelling case to senior stakeholders.

Responsibilities

Building and leading a high-performing AI Engineering organization managing both individual contributors and engineering managers across ML, backend, and platform.
Scaling engineering practices (CI/CD, observability, on-call, release management) to match the team's growth, keeping velocity high as complexity increases.
Serving as a senior technical presence in London, fostering strong working relationships with the US team and leadership in Chicago.
Defining the end-to-end architecture for AI and GenAI applications, thinking across the full pipeline, integration layer, and data, not just the model.
Making pragmatic build/buy/partner decisions across the AI stack, with clear reasoning on the cost, quality, and performance trade-offs of each.
Setting engineering standards for evaluation, responsible AI, and system reliability, ensuring what ships to production handles edge cases and earns customer trust.
Designing how iManage AI capabilities are exposed to and composed with external systems, thinking in terms of protocols and interfaces, not just features.
Translating business priorities into multi-quarter technical roadmaps with clear milestones and ROI targets.
Collaborating with Product, Data, and GTM teams to prioritise high-impact AI initiatives. Communicating progress, risks, and value to executive leadership when needed.
Contributing to competitive strategy: understanding our landscape well enough to push back on roadmap priorities with data, not just opinion.

Benefits

Join a rapidly evolving, industry-leading SaaS company on an exciting journey of growth and scalability!
Take on meaningful, high-impact challenges by leveraging cutting-edge technologies and best-in-class protocols to drive innovation.
Own my career path with our internal development framework. Ask us more about this!
Expand my skill set and earn certifications with unlimited access to LinkedIn Learning courses and interactive Microsoft courses & training.
Be part of a supportive and experienced team within a dynamic, inclusive, and encouraging culture.
Enjoy flexible work hours that empower me to balance personal time with professional commitments.
Collaborate in a modern, open-plan workspace featuring a gaming area, free snacks and drinks, and regular social events.
Creating an inclusive environment where I can help shape the culture not just by fitting in, but by adding to it.
Providing a market competitive salary that is applied through a consistent process, equitable for all our employees, and regularly reviewed based on industry data.
Rewarding me with an annual performance-based bonus.
Offering comprehensive Health/Vision/Dental/Life Insurance, and a 401k Retirement Savings Plan with a company match up to 4%.
Granting enhanced leave for expecting parents; 20 weeks 100% paid for primary leave, and 10 weeks 100% paid for secondary leave.
Providing me with a flexible time off policy to take the time off that I need. Be it for vacation, volunteering, celebrating holidays, spending time with family, or simply taking time to recharge and reset.
Having multiple company wellness days each year to prioritize mental health and well-being.
Providing access to RethinkCare, a global behavioral health platform that enhances personal well-being, strengthens professional resilience, and empowers parental success through expert-led training and resources.