Engagement Manager, Mid Market
$148,000–$175,000 year
On-site · Chicago, Illinois, United States
Job Summary
Engagement Manager for mid-market SaaS customers, driving end-to-end client journeys from rollout to adoption, expansion, and renewal. Responsible for building tailored success plans, enabling adoption through trusted advisory relationships, surfacing relevant AI-enabled use cases, leading renewals and growth conversations, monitoring health metrics to preempt risk, and collaborating with cross-functional teams (Legal Engineering, Product) to translate client feedback into product and engagement insights. The role requires 5+ years in client-facing, B2B SaaS, or legal-adjacent settings, a proven ability to drive adoption and retention, strong stakeholder management across all levels, comfort with AI-driven automation, and a collaborative, in-person work style at the West Loop office. Benefits include comprehensive medical plans, 401(k) with match, unlimited PTO, parental leave, and extensive supplemental programs. Location is Chicago, IL, USA with in-person work expected.
Required Qualifications
- 5+ years in management consulting, client advisory, a customer-facing role in B2B SaaS, or the legal field, owning client relationships.
- Track record of driving measurable adoption, retention, and expansion.
- Strong stakeholder instincts and EQ — comfortable engaging at all levels of a client organization, from hands-on teams to senior leaders.
- Exposure to legal teams, regulated industries, or legal tech a plus; curiosity to learn complex environments fast is essential.
- A builder who automates — fluent with AI, you create leverage for yourself and the team by building and automating workflows, not just using them.
- Strong data instincts and a metrics-driven read on customer health and outcomes, with clear, confident communication.
- Energetic about a fast-paced, early-stage environment — you help build the playbook, not just follow it, and mentor Associates along the way.
- A passion for in-office collaboration — in-office 5 days per week in our West Loop office, building together.
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