Principal Product Lead, AI

Job Description

Job Description

Principal Product Lead, AI

Department: Product

Reports To: VP of Product

The Principal Product Lead, AI is responsible for defining and executing the AI product strategy across Casepoint's full product portfolio, including AI agents, LLM-powered workflows, and AI-driven search and review capabilities embedded in our eDiscovery, legal hold, investigations, and compliance products. Reporting to the VP of Product, this role partners with Engineering, Data Science, and go-to-market teams to identify where AI can deliver practical, trusted value for customers working in high-stakes legal, regulatory, and compliance environments. The ideal candidate has a hands-on approach to AI product work, using prototyping and vibe coding as regular parts of their process, and understands what it takes to ship AI responsibly in regulated industries.

What You’ll Do (Key Responsibilities):

• Define and maintain the AI product roadmap across Casepoint's full product portfolio, prioritizing AI agents, LLM-powered workflows, and shared AI capabilities in a sequence that reflects customer value and business goals.
• Use AI-assisted development tools, LLMs, and vibe coding techniques to prototype solutions and produce working demonstrations for customers and internal stakeholders before committing to full engineering efforts.
• Lead AI feature delivery from discovery through launch by establishing evaluation standards and acceptance criteria that Engineering and QA can build to reliably in legal and compliance contexts where accuracy and auditability are required.
• Engage with customers directly to validate AI concepts, surface expectations around accuracy and explainability, and develop the kind of trust that supports adoption in enterprise environments with significant regulatory obligations.
• Work with Sales and Customer Success to articulate AI capabilities in terms that resonate with customers and prospects, supporting competitive evaluations and helping teams communicate value in clear, credible terms.
• Act as an AI product authority across the portfolio by establishing deployment standards, advising fellow product team members on AI integration, mentoring and coaching on AI product thinking and execution, and ensuring AI capabilities are built consistently and positioned coherently across Casepoint's platform.
• Define AI-specific performance metrics, including accuracy, adoption, and business impact, and use post-launch data to drive iterative improvement across all AI-powered features.

What You Bring to the Team:

• A background shipping AI or ML-powered features in enterprise B2B SaaS products, with direct experience taking AI capabilities from concept through production in environments where quality and reliability are non-negotiable.
• Working knowledge of modern LLM patterns and tradeoffs (e.g., retrieval-augmented generation, embeddings/vector search, tool/function calling), including how cost, latency, and accuracy considerations shape product decisions.
• Experience building and operating AI features responsibly in regulated environments, including partnering on privacy/security reviews, defining monitoring and human-in-the-loop workflows, and managing model behavior over time (drift, regressions, and changing customer expectations).
• Hands-on experience with LLMs, AI coding assistants, and prototyping tools, with a habit of using these tools actively in your product work to validate ideas quickly and generate working demonstrations.
• The ability to explain AI capabilities, their limitations, and how they work in accessible terms to a range of audiences, including legal and compliance professionals, technical engineers, and executive stakeholders.
• Experience or exposure to legal technology, eDiscovery, or regulated industry software, with enough domain context to understand where AI can be appropriately trusted and where it requires additional safeguards.
• Strong cross-functional collaboration skills, with a track record of aligning Engineering, Data Science, Sales, and Customer Delivery teams around a shared product direction.
• Experience mentoring and coaching colleagues and cross-functional partners, raising the quality bar for AI product discovery, evaluation, and delivery through guidance, reviews, and shared standards.
• Comfort operating in conditions of ambiguity, making reasonable decisions with incomplete information, and adjusting course as the technology, the market, and customer expectations continue to develop.

Who Thrives in This Role:

• This role is a strong fit for someone who thrives in a fast-paced, build-and-iterate environment where there is always more to do than time allows.
• You are comfortable owning outcomes, balancing competing inputs, forming a point of view, and acting on what matters most right now.
• You bring an entrepreneurial, startup mentality and a real appetite for improving how things work.
• You look for better approaches, push past “how it’s always been done,” and take thoughtful big swings when they can unlock meaningful customer value.
• You are a positive change agent who can educate, persuade, and drive adoption across internal teams and external stakeholders.
• You are comfortable presenting and demoing product to diverse audiences, and you speak up as the owner of your domain in meetings and written threads.
• You bring high energy, strong judgment, and a team-first attitude, staying open to feedback and new ways of working that help the team move faster and raise quality.

Work Location & Flexibility:

We are headquartered in Washington, D.C., and this role is eligible for remote work from the following states: AR, AZ, CA, CO, CT, D.C., DE, FL, GA, IL, IN, KS, KY, MA, MD, MI, MN, NC, NH, NJ, NY, OH, OR, PA, SC, TX, VA, WA, WI, WY. If you live outside these states, unfortunately we’re not able to consider your application at this time.

About Casepoint:

Casepoint empowers government agencies and enterprises to discover, secure, and activate defensible insights with confidence across their most critical legal, regulatory, and compliance workflows. From global enterprises to major federal agencies, including the Department of War, organizations rely on Casepoint to unify legal hold, eDiscovery, investigations, FOIA, regulatory, and compliance response together in one secure platform.

Built on an award-winning, cloud-native foundation with FedRAMP® High and DOD Impact Levels 5 (IL5) and 6 (IL6) authorizations, Casepoint combines purpose-built workflows with transparent, auditable AI and advanced analytics to help teams move faster, reduce risk, and maintain control under scrutiny. Through long-term partnership and responsive support, Casepoint works alongside customers to strengthen operations over time, ensuring lasting control, custody, and confidence in their data. For more information, visit

Casepoint is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or any other protected characteristic.