Top Tech Jobs & Startup Jobs in Chicago, IL

Sell commercial insurance to small business customers through inbound and outbound calls. Responsibilities include qualifying prospects, setting appointments, maintaining lead systems, understanding customer needs, partnering with underwriting, presenting policies, closing deals, and building customer relationships. The role is remote within the United States and requires strong communication, coordination, adaptability, and problem-solving skills.

Lead total rewards strategy and execution for compensation, incentives, equity, benefits, and wellness. Partner with People Partners, Talent Acquisition, and executives to maintain job architecture, audit pay equity, manage benefits programs, and support annual compensation and performance cycles.

Reviews and analyzes commercial insurance submissions, quote revisions, bind reviews, endorsements, and policy updates within delegated authority. Communicates with underwriters, agency partners, and internal teams; verifies business information; identifies risk concerns; requests additional details; and supports accurate, timely policy processing. Maintains knowledge of workers’ compensation and commercial auto coverage, forms, ratings, and manuals while managing high-volume work across multiple states.

Conducts quality audits across underwriting, premium audit, and customer service departments; analyzes review data to identify trends and training opportunities; helps develop and deliver training; maintains process, authority, and governance documentation; facilitates calibration and quality meetings; coaches employees on procedures, systems, regulations, and expectations; and supports process improvement and implementation of new workflows.

Own end-to-end sourcing and procurement activities, including RFx processes, spend analysis, benchmarking, bid evaluations, and vendor recommendations. Manage Claims vendor relationships, performance scorecards, stewardship meetings, escalations, onboarding documentation, contract compliance, and billing reviews. Support negotiations, cost optimization, audit coordination, and defense counsel panel oversight while producing accurate, leadership-ready outputs independently.

Serve as in-house commercial counsel by drafting and negotiating contracts, managing the LinkSquares contracting workflow, advising internal stakeholders, and maintaining contract records. Lead legal collections through demand letters, outside counsel coordination, and dispute resolution. Support corporate governance, regulatory compliance, subpoena responses, policy development, and other legal matters. The role requires independent judgment, strong organization, and the ability to communicate legal concepts clearly to business teams.

Leads customer service operations and external vendor partnerships, including performance management, SLA and KPI tracking, forecasting, risk remediation, escalations, reporting, automation, and process improvement. Develops team members, builds operational business cases, partners with Product and Engineering, and drives scalable workflows and self-service capabilities. Requires customer service or insurance operations expertise, BPO vendor management, strong metric analysis, and P&C insurance experience.

Leads end-to-end billing and collections operations, owning bad debt recovery, litigation and settlement outcomes, vendor and BPO performance, compliance, KPIs, and allowance processes. Manages and develops collections staff, establishes procedures and service levels, partners with Accounting, Legal, Product, and Engineering, and drives automation and continuous improvement. Oversees escalations, disputes, vendor scorecards, financial close documentation, and risk-based collection strategies.

Manage workers’ compensation medical-only claims from setup through closure, including investigations, compensability decisions, reserves, medical benefits, utilization review, lien resolution, and claim mitigation. Provide guidance to agents and insureds, maintain regulatory compliance, identify claims requiring indemnity conversion, and support improvements to claims processes and customer service. The role is remote within the United States.

Provides timely customer service and issue resolution for payroll partners and insureds through email and platform channels. Handles policy issuance, billing and agency questions, cancellations, renewals, escalations, and complex requests while meeting service-level agreements. Builds partner relationships, advocates for customer needs, identifies process improvements, and supports onboarding, peer training, system testing, and maintenance of standard operating procedures and training resources.