Senior Engagement Manager (AI)

TL;DR

Senior Engagement Manager (AI/LegalTech): Owning complex enterprise account engagements from rollout through adoption and renewal with an accent on tailored adoption strategies and executive stakeholder management. Focus on driving measurable retention, identifying expansion opportunities, and building scalable engagement frameworks.

Location: On-site in Chicago (West Loop), 5 days per week

Salary: $180,000 – $204,000 OTE + Equity

Company

An AI-native workspace redefining legal work for the world's best legal teams.

What you will do

• Partner with enterprise accounts to own complex engagements end-to-end, driving adoption and value.
• Design and execute value strategies for every phase of the client relationship, from rollout to renewal.
• Maintain high-level executive relationships and use success planning to reframe how clients work.
• Lead commercial conversations to identify growth opportunities, upsells, and multi-team expansions.
• Proactively mitigate retention risks using data and health signals to activate client champions.
• Develop scalable engagement frameworks and coach junior Engagement Managers and Associates.

Requirements

• 7+ years in management consulting, client advisory, or a strategic client-facing field owning high-value accounts.
• Proven track record of driving measurable adoption, retention, and expansion.
• Experience building and sustaining trusted, executive-level relationships.
• Experience advising legal teams, regulated industries, or sophisticated professional services clients.
• Fluency with AI tools and the ability to build and automate workflows.
• Must be based in Chicago for full-time in-office collaboration (5 days/week).

Nice to have

• Specific experience in legal tech or working directly with law firms.

Culture & Benefits

• Comprehensive health package including Medical, Dental, and Vision (Aetna, Kaiser Permanente, MetLife).
• 401(k) with a generous company match.
• Unlimited PTO and generous parental leave.
• Daily company-provided lunch in the West Loop office.
• Family support perks including Maven Clinic and Dependent Care FSA.