Top Tech Jobs & Startup Jobs in Chicago, IL

Develop new business, close sales to meet revenue goals, and manage an assigned book of business. Partner with marketing, account management, and service teams to nurture leads, oversee renewals, client retention, contract negotiations, compliance, and client wellness programs. Manage pipeline in Microsoft CRM and represent the company at events and networking opportunities.

Manage a book of benefits clients as primary contact, coordinate with internal teams and consultants, handle renewals, enrollments, and compliance (5500 filings), advise on cost-saving benefit strategies, grow accounts via cross-selling, and deliver high-level client service and relationship management.

Own the sales technology strategy and roadmap, integrating tools (ZoomInfo, Outreach, Seismic, intent platforms, AI) into seller workflows. Drive adoption, measure ROI, align sales and marketing data, lead vendor negotiations, and manage a Sales Technology Manager. Partner cross-functionally with Sales, Marketing, IT, Legal, and L&D to operationalize AI-enabled selling and link technology adoption to pipeline and revenue outcomes.

Manage a book of client accounts for employee benefits: build relationships, coordinate PBM implementations, analyze plan performance, run RFP/onboarding, maintain CRM and client documentation, lead meetings and communications, and support internal projects and process improvements. Minimal travel.

Coordinate post-sale implementation and onboarding of stop loss, captive, level-funded, and self-funded benefit programs. Manage project plans, stakeholder communications, claims submissions, reimbursement tracking, and carrier reporting while maintaining databases (including D365) and ensuring timely vendor payments and documentation.

Support M&A diligence and integration by migrating systems, documenting infrastructure, resolving escalated helpdesk issues, mentoring team members, identifying integration risks, and ensuring smooth onboarding of acquired offices into OneDigital environments.

Produce polished, on-brand creative assets across presentations, video, social, email, and print. Drive visual storytelling and brand integration for announcements, M&A, and internal communications. Collaborate cross-functionally, use AI and digital tools to accelerate workflows, and ensure consistent brand application across channels.

Manage stop loss and TPA (ASO) marketing and renewal cycles for assigned self-funded clients. Secure competitive quotes, provide financial analysis and recommendations, maintain partner relationships, and support SFCOE leadership and field offices.

Manage a book of employer benefits clients as the primary contact: advise on benefits strategy, lead renewals, ensure compliance (e.g., 5500 filings), coordinate internal service teams, conduct enrollments and client meetings, and grow business through cross-sales.

Manage a portfolio of clients using isolved HCM, provide ongoing support, troubleshoot system issues, deliver training, advise on payroll/HR/benefits/time & attendance, document interactions in CRM, and identify upsell opportunities to increase platform adoption.