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
Top Skills:
- Enterprise Proposal / RFP Leadership
- Healthcare / Insurance Expertise
- Sales & Account Management Partnership
- Process Optimization & Operational Excellence
- Team Leadership (multi-location)
- Content & Knowledge Management
- Open Enrollment & Event Operations
- Executive Stakeholder Engagement
- Budgeting & ROI Analysis
- AI / Automation in Proposal Strategy
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