15+ years in proposal development, marketing, or insurance operations
7+ years in leadership roles
Expertise in proposal development methodologies
Strong organizational and prioritization skills
Budget management experience
Effective communication and negotiation abilities
Responsibilities
Lead enterprise proposal strategy and respond to RFPs and bids
Partner with Sales and Account Management to enhance client relations
Standardize proposal processes and content management
Implement process optimization and technology initiatives
Oversee staffing for 1,000+ annual Open Enrollment meetings
Manage enterprise client meetings and external engagements
Lead cross-functional initiatives with various stakeholders
Enhance proposal content quality and market alignment
Conduct budget management and strategic resource allocation
Build and direct high-performance teams in fast-paced settings
Benefits
Hybrid work environment
Opportunity to lead high-impact initiatives
Access to advanced technology and automation tools
Engage with diverse stakeholders and large-scale events
Potential to influence enterprise-wide proposal strategy
Full Job Description
Location: Chicago, Illinois
Type: Contract
Job #104126
Job Title: Director, Enterprise Proposal Management Location: Chicago, IL. Hybrid Job Type: W2 Contract Expected Hours per Week: 40 hours per week Schedule: Monday-Friday, 8-5. Pay Range: $125 - 130 per hour. Position Description: Job Purpose: This position is responsible for leading enterprise proposal operations and strategy, partnering closely with Sales and Account Management teams to develop and deliver high-quality proposals, manage content, and support network information requests across Commercial, RX, and Group Medicare lines. The role also oversees teams supporting National Accounts meetings and large-scale Open Enrollment efforts.
Key Responsibilities:
Lead enterprise proposal strategy, responding to RFPs, bids, and unsolicited proposals while developing innovative, value-added client solutions
Partner with Sales and Account Management to drive new business acquisition and client retention
Establish and standardize proposal processes, tools, timelines, and content management practices across the enterprise
Drive operational excellence through process optimization and technology/automation initiatives
Oversee Open Enrollment support, managing staffing and coordination for 1,000+ annual meetings
Manage enterprise-level client meetings, events, and external engagements with key stakeholders (customers, brokers, consultants)
Lead cross-functional initiatives with internal teams and external partners (BCBSA, consortiums, consultants)
Evaluate and enhance proposal content quality to ensure alignment with market trends and competitive positioning
Manage budgets, allocate resources, and conduct cost-benefit analyses to support strategic initiatives
Build and lead high-performing, multi-location teams in a fast-paced, deadline-driven environment
Required Qualifications:
Bachelor's Degree
15+ years of experience in proposal development, marketing, benefits administration, or insurance operations OR
15+ years managing proposal teams in a deadline-driven environment (writing, marketing, business development)
7+ years in leadership roles with demonstrated team management experience
Strong knowledge of proposal development methodologies and best practices
Proven ability to manage competing priorities and balance short-term deadlines with long-term goals
Experience driving process improvements across people, process, and technology
Strong communication, negotiation, and stakeholder management skills (including senior leadership)
Experience managing budgets, resource allocation, and ROI-driven decision-making
Preferred Qualifications:
Bachelor's Degree in Business, Marketing, Communications, or English
Healthcare/insurance industry experience (Commercial, Medicare, RX)
Experience with AI, automation, and advanced content management strategies in proposal development
Knowledge of BCBS systems, products, and competitive landscape
Experience designing knowledge management and proposal governance frameworks
Experience supporting large-scale client events and enterprise meetings
Strong analytical mindset with ability to drive innovation and continuous improvement
