Engagement Associate (AI)

Location: Chicago, United States; on-site

Salary: OTE $112,000–$128,000 per year, plus equity

Company

Legora provides an AI-native workspace that helps legal professionals analyze documents, streamline end-to-end workflows, and adopt new ways of working.

What you will do

• Support adoption playbooks, stakeholder maps, change-management plans, and target outcomes for strategic and enterprise accounts.
• Own discrete workstreams from initial rollout through firm-wide adoption, adapting plans as client needs and AI capabilities evolve.
• Prepare success plans, training resources, enablement sessions, stakeholder check-ins, and value reviews.
• Track account health, product usage, risks, opportunities, measurable outcomes, and ROI.
• Coordinate with GTM, Product, Legal Engineering, Engineering, Marketing, and Support teams to maintain account continuity.
• Surface expansion signals and customer feedback while developing toward ownership of an account book.

Requirements

• 1–3 years of experience in management consulting, customer success, account management, client advisory, B2B SaaS, or a related field.
• Experience supporting client-level projects and driving measurable outcomes with enterprise clients or senior stakeholders.
• Strong organizational, project management, communication, and stakeholder-management skills.
• Experience with legal, compliance, regulated, or otherwise complex industries, or the ability to learn complex domains quickly.
• Comfort with metrics, customer health, data-driven decision-making, and fast-paced environments.
• Interest in AI and using automation tools to improve personal and client-facing work.

Culture & Benefits

• In-person work environment in the Chicago office, with company-provided lunch daily.
• Collaboration with teams and clients across Stockholm, New York, London, and Sydney.
• Medical, dental, and vision plans, with HSA or Healthcare FSA options.
• Generous parental leave, Maven Clinic access, dependent care FSA, and One Medical membership.
• 401(k) with company match, unlimited PTO, commuter benefits, life insurance, and short- and long-term disability coverage.