Top Tech Jobs & Startup Jobs in Chicago, IL

Lead pre-sales solution design for large self-funded employer benefits clients. Analyze populations and savings projections, configure plan-design and engagement levers, assess carrier and TPA implementation constraints, present recommendations, and coordinate handoffs to Client Success. Partner closely with Sales, Product, Clinical Affairs, Operations, and Client Success while translating market feedback into implementation guides, technical requirements, and roadmap priorities.

Leads Leap’s technical implementation organization and a large portfolio of healthcare client launches. Responsibilities include managing implementation leaders, setting delivery processes and escalation paths, overseeing eligibility, claims, prior authorization, SFTP, and platform configuration work, resolving off-track implementations, improving QA and data integrity, and partnering with Engineering, Finance, Client Success, TPAs, health plans, and carriers to deliver accurate, on-time go-lives.

Leads and develops a senior client success team while building scalable operating systems, escalation paths, account coverage models, playbooks, health scoring, and renewal workflows. Owns executive relationships with employers, TPAs, PBMs, and benefits consultants; oversees retention, utilization, satisfaction, and resolution metrics. Partners cross-functionally to improve service delivery, manage portfolio risks, support renewals and expansion, and deliver a high-touch client experience during rapid growth.

Build and operate Leap’s post-sale client delivery engine. Responsibilities include designing scalable delivery processes, forecasting activation, savings, and revenue, automating client reporting with AI, defining analytics requirements, measuring lifecycle campaigns, supporting drug sourcing strategy, and identifying opportunities for client engagement and account expansion. The role partners closely with Sales, Operations, Analytics, Marketing, Pharmacy, and Growth Strategy teams.

Drive enterprise sales for employer groups of 5,000+ by building relationships with brokers, TPAs, PBMs and other partners, managing pipeline, presenting proposals, and closing deals to meet quota and grow revenue.

The Strategic Client Success Manager ensures client satisfaction and retention within a portfolio of strategic relationships, focusing on operational excellence and value delivery. The role involves account management, data-driven performance discussions, and cross-functional collaboration to drive growth and mitigate risks.

Lead enrollment strategy for a portfolio of large employer and health-plan clients: diagnose engagement gaps using data, design and run client-specific activation plans, influence stakeholders, coordinate cross-functional execution, and build the Enrollment Marketing function and playbooks to scale enrollment and activation.

Lead Leap's engineering function: hire and scale a high-performing team, own the technical roadmap and architecture, build AI-native data and production ML systems (LLMs/agents), and deliver correct, auditable healthcare workflows for drug identity, causal attribution, and intervention automation.