Top Sales Jobs in Chicago, IL

Leads Pacific Northwest employer sales by managing Regional Directors and Account Executives serving organizations with 50–9,999 employees. Responsibilities include developing sales strategies, driving revenue growth, pursuing new business, analyzing regional performance, ensuring compliance, and building relationships with benefits brokers and partners. The role requires sales leadership, team quota delivery, strategic thinking, and strong people-management skills.

Own revenue and quarterly quota for the West territory covering Oregon, Idaho, Montana, and Hawaii. Build and expand relationships with benefits brokers, consultants, general agents, and employers in the 1,000–9,999 employee market. Develop strategic advisor partnerships, lead complex cross-functional deals, close new business, and shape regional sales strategy with enterprise and account teams.

Partner with sales to design and present Garner's Employer and DataPro solutions to high-value prospects. Lead discovery, technical solution design, RFP responses, and project-manage engagements with support from Data and Product teams. Act as technical liaison, communicate value propositions, and stay current on industry trends to inform product improvements.

Own strategic relationships with national broker and consulting firms, build trusted advisor connections, and drive business development into closed distribution and data-licensing deals. The role develops portfolio strategy, contracting targets, metrics, and pipeline; coordinates Sales, Product, Marketing, Client Success, and Operations; and channels consultant insights into go-to-market strategy. Success requires deep employee-benefits expertise, an established senior industry network, executive influence, and accountability for national revenue outcomes.

Drive revenue for Garner's fully- and self-insured products in the 500–5,000 life segment. Expand and manage broker, consultant, general agent, and employer partnerships; build sales and partnership pipeline infrastructure; collaborate with market teammates to support in-market activities and broker relationships. Remote role with occasional travel to HQ.

The Enterprise Sales VP will expand sales with large clients, build relationships, manage sales cycles, and support broker partnerships to drive healthcare benefits innovation.

The Business Development Representative will generate qualified meetings for Garner, conduct outreach, track activities using Salesforce, and collaborate with marketing teams.

Own outbound outreach to targeted enterprise accounts to generate qualified meetings and pipeline. Research and multi-thread into stakeholders, test and iterate outbound playbooks and messaging, collaborate with sales and marketing, push past gatekeepers to secure executive conversations, and track pipeline activity in Salesforce.

Lead direct enterprise sales into national labor health & welfare funds (Taft-Hartley and public‑sector union funds). Manage full sales cycle, build trustee and fund office relationships, influence joint labor‑management boards, develop sales processes and KPIs, represent Garner at industry events, and translate complex healthcare data into actionable value propositions to win new fund business.

Sell Garner's healthcare solutions to public-sector clients across a named national book (10k–100k lives). Own full sales cycles and long RFP-driven pursuits, manage pipeline and quotas, cultivate relationships with public-sector benefits consultants and directors, and translate complex data into actionable insights to influence buying decisions.