Technology trainer Jobs in Chicago, IL

Why Harvey

At Harvey, we're transforming how legal and professional services operate. By combining frontier agentic AI, an enterprise-grade platform, and deep domain expertise, we're reshaping how critical knowledge work gets done for decades to come.

This is a rare chance to help build a generational company at a true inflection point. With 2400+ customers in 70+ countries, strong product-market fit, and world-class investor support, we're scaling fast and defining a new category in real time. The work is ambitious, the bar is high, and the opportunity for growth personal, professional, and financial is unmatched.

Our team moves fast, takes ownership, and is deeply committed to the mission operating with intensity, staying close to our customers, and pushing each other for excellence. We live by three values: Decisiveness, Simplicity, and Job's Not Finished. We act quickly on clear judgment over perfect information, we believe simplicity is what scales, and we're never satisfied with where we are. If you want to do the best work of your career alongside people who share that drive, we'd love to build with you.

At Harvey, the future of professional services is being written today and we're just getting started.

Role Overview

The Technology Enablement Analyst joins Harvey's Technical Program Management team to drive how internal teams adopt, integrate, and realize value from enterprise technology platforms. The team's mission is to ensure Harvey's rapidly scaling workforce has frictionless access to the tools and systems that power their work, bridging the gap between BizTech and organizational productivity. This role is accountable for turning complex technical programs into clear, actionable enablement plans that different teams can execute against. They will own stakeholder alignment, rollout strategy, and ongoing iteration based on feedback and metrics. They will partner closely with product, engineering, customer success, and go-to-market teams to ensure that documentation, training, and communications effectively support behavior change at scale.

What You'll Do

• Own the end-to-end enablement strategy for major internal technology initiatives, with an emphasis on internal AI tooling and related workflows
• Monitor adoption, usage, and feedback, and use those insights to iterate on enablement plans, documentation, and training content
• Plan and execute change management activities (e.g., communications, training, office hours) that drive adoption and sustained usage of new tools and processes
• Build and maintain dashboards and reports that provide leadership with visibility into technology health, utilization, and ROI
• Partner with all BizTech teams to evaluate new tools, drive integrations, and ensure smooth rollouts
• Develop process documentation, runbooks, and training materials to support technology onboarding and change management

What You Have

• At least 5 years of experience in technology-enabled program delivery, technical training, or organization change management
• Demonstrated track record leading change across multiple teams or functions (e.g., rolling out new tools, workflows, or processes)
• Background in technology enablement, organization change management, or as a technical trainer, with comfort translating complex concepts for non-technical audiences
• Experience designing and maintaining program documentation or enablement materials as a single source of truth for diverse stakeholders
• Strong stakeholder management skills, including partnering with product, engineering, operations, and go-to-market teams to drive measurable outcomes (e.g., higher adoption of internal AI tooling and new workflows, reduced support tickets, improved time-to-proficiency for end users)

Compensation

$99,200 - $148,800 USD

Harvey is an equal opportunity employer and does not discriminate on the basis of race, gender, sexual orientation, gender identity/expression, national origin, disability, age, genetic information, veteran status, marital status, pregnancy or related condition, or any other basis protected by law.

We are committed to providing reasonable accommodations to applicants with disabilities, and requests can be made by emailing accommodations@harvey.ai