Senior AI Product Manager (Context Engineering)

WEX • Chicago, IL

4d • $125,300 - $154,100

About The Position

At WEX, context engineering turns collective company knowledge, operational reality, and business logic into trusted, timely, permission-aware context for AI agents. The Senior AI Product Manager (Context Engineering) owns the enterprise context layer powering WEX’s global fleet of AI agents. This hands-on builder role within the Data, AI, Risk & Product organization bridges unstructured knowledge, governed semantic data, and agent execution workflows, partnering with global engineering, data, and business teams to ensure AI actions are grounded, authorized, and accurate.

Requirements

• Bachelor's degree in Computer Science, Engineering, Business, or a related field, or equivalent practical experience.
• Senior-level Product Management experience owning data platforms, enterprise search or retrieval systems, semantic layers, API products, or internal developer platforms consumed by engineering teams.
• Deep understanding of applied generative AI and agentic systems, including advanced RAG, embeddings, chunking, metadata management, grounding, and context window assembly.
• Strong experience with structured enterprise data, relational models, certified metrics, and failure modes of natural-language querying over raw database schemas.
• Comfort working directly with technical artifacts, including inspecting retrieval traces, reading SQL query plans, reviewing JSON/YAML configurations, and executing API calls.
• Track record of designing and running evaluation harnesses, golden benchmark datasets, error taxonomies, and quantitative quality gates.
• Working knowledge of enterprise controls, including authentication and identity, tenant isolation, Row-Level Security, audit logging, and data privacy.
• Exceptional written and verbal communication skills in English, with the ability to align and influence global engineering, security, compliance, and executive stakeholders without direct authority.

Nice To Haves

• Experience with knowledge graphs, ontologies, taxonomies, and enterprise entity resolution (MDM).
• Hands-on familiarity with headless BI, metric stores such as dbt Semantic Layer or Cube, or governed NL-to-SQL products.
• Domain background in payments, fintech, benefits, healthcare-adjacent platforms, or other highly regulated environments.
• Experience with vector databases, automated RAG evaluation frameworks such as Ragas or TruLens, or agent tool protocols such as Model Context Protocol (MCP).
• Track record of consolidating or replacing legacy enterprise knowledge management or search systems in active production.

Responsibilities

• Partner with global product, engineering, and business leaders to prioritize high-value context initiatives and sequence workflows based on business impact, agent demand, source readiness, and risk.
• Own the semantic object roadmap for core enterprise entities, defining certified measures, join graphs, and Row-Level Security to replace raw schema reasoning and reduce hallucinations.
• Establish enterprise standards for federated ingestion, chunking, caching, metadata, and citation enforcement, and consolidate legacy knowledge APIs into unified, multi-tenant interfaces.
• Design and deliver production-ready context packs for critical operational workflows and SOPs; partner with agent teams to inspect retrieval traces, debug failures, and optimize context consumption.
• Build and run evaluation harnesses, golden datasets, error taxonomies, and go/no-go quality gates to benchmark retrieval relevance, query precision, and agent containment.
• Embed auditability, data lineage, least-privilege access, and responsible AI guardrails into the context layer.
• Track return on investment through API cost reduction, task resolution lift, and operational risk mitigation.

Benefits

• Health, dental, and vision insurance
• Retirement savings plan
• Paid time off
• Health savings account
• Flexible spending accounts
• Life insurance
• Disability insurance
• Tuition reimbursement
• Quarterly or annual bonus eligibility for non-sales roles, based on role and applicable plan

What This Job Offers

• Job Type: Full-time
• Career Level: Senior