Top Tech Jobs & Startup Jobs in Chicago, IL

Reviews client contracts and fee schedules, configures billing items and GL revenue routing, processes billing requests, reconciles revenue accounts, supports month-end close, maintains audit documentation, and coordinates with Sales, Implementation, Client Services, and Accounting to ensure accurate billing and revenue recognition.

Manages end-to-end benefit plan implementations from pre-sale consultation through post-sale administration. Serves as the primary client contact, coordinates stakeholders, develops project plans, tracks issues and deadlines, resolves implementation challenges, evaluates exceptions, manages costs, and supports complex account and benefit structure recommendations. The role also represents implementation services in finalist meetings and identifies cross-selling opportunities.

Leads the West region’s Mid-Market and Small Group sales team, managing approximately 10–12 direct reports. Responsibilities include coaching sellers, improving pipeline discipline, forecasting revenue, progressing deals, setting CRM and activity standards, supporting broker relationships, recruiting, onboarding, and addressing performance issues. The manager owns the region’s combined new-business target, develops sellers across consultative and transactional sales motions, and travels periodically for field coaching, client meetings, and industry events.

Leads the East region’s Mid-Market and Small Group sales team, coaching sellers, managing pipeline and forecasts, driving quota attainment, and developing talent. The role oversees approximately 10–12 direct reports, supports broker and consultant relationships, attends client and industry events, contributes to sales-model improvements, and partners cross-functionally on hiring, onboarding, performance management, and seller development.

Owns the enterprise AI engineering foundation, including shared AI platforms, semantic routing, model hosting, gateways, operations, agentic pipelines, and multi-agent orchestration. The role establishes architecture and standards, delivers secure production AI services, develops evaluation and governance capabilities, manages AI economics, prototypes emerging technologies, mentors senior engineers, and partners with security, risk, compliance, and data governance teams in a regulated financial and healthcare benefits environment.

Leads enterprise new-business growth for health and benefits solutions, including go-to-market strategy, sales team development, pipeline discipline, consultant and broker relationships, strategic employer pursuits, forecasting, and cross-functional coordination. Owns enterprise revenue targets, competitive intelligence, sales operating standards, and performance KPIs while personally supporting complex, executive-level opportunities and consultant-led RFPs.

Leads and builds a dedicated Retirement & Wealth marketing organization spanning product, segment, brand, communications, demand generation, lifecycle engagement, sales enablement, creative, and marketing operations. Develops integrated B2B, B2C, and B2B2C strategies, drives demand and asset growth, oversees customer engagement and marketing technology, and connects investment to measurable revenue, pipeline, retention, and brand outcomes. Partners with executive leadership and cross-functional teams in a regulated financial-services environment.

The Senior Security Engineer supports application security, vulnerability assessments, penetration testing, code reviews, security training, and secure SDLC practices. Responsibilities include third-party risk assessments, audit evidence collection, policy and compliance support, vulnerability research, incident response, security metrics, and remediation tracking. The role also administers security-system access, collaborates cross-functionally, guides junior engineers, responds to inquiries, and participates in a rotating one-week-per-month on-call schedule.

Leads the Level 1 Partner Support Services function, overseeing support operations, staffing, budgets, service-level performance, incident triage, escalations, workforce planning, and continuous improvement. Manages supervisors, team leads, and frontline staff while developing support processes, documentation, knowledge management, automation, self-service, and governance. Partners with Technical Operations, Engineering, Account Management, Relationship Management, and Operations leadership to improve issue resolution and partner satisfaction.

Designs, administers, maintains, and supports hybrid cloud infrastructure across Azure, VMware, networks, operating systems, databases, and security appliances. Builds CI/CD pipelines and Infrastructure-as-Code deployments, manages Kubernetes and AKS environments, configures cloud-native services, supports disaster recovery, and troubleshoots infrastructure and SQL Server issues. The role also maintains Active Directory, mentors engineers, improves reliability and cost efficiency, supports business applications, and collaborates with technical and business teams.