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Executive Director, Enterprise Proposal Development & Events

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Chicago, IL Full time 06/25/2026 R0052451 Compensation: $146,700.00 - $272,400.00

At HCSC, our employees are the cornerstone of our business and the foundation to our success. We empower employees with curated development plans that foster growth and promote rewarding, fulfilling careers.

Join HCSC and be part of a purpose-driven company that will invest in your professional development.

This position is responsible for leading the team that partners closely with our Sales and Account Management teams and develops and writes proposals, manages proposal content across various areas and Network information requests for the Enterprise along with providing support to Dearborn National on Blue branded quotes for certain membership thresholds; managing a separate team that supports Enterprise National Accounts Meetings that host internal and external guests based on business objectives; managing a team that supports Open Enrollment requests to support Enterprise National Accounts, Oklahoma, and Illinois/Texas local/mid markets.

Required Job Qualifications

  • Bachelor Degree and 15 years experience in progressive marketing/benefits administration, proposal development, or insurance operations OR
  • Bachelor Degree and 15 years experience in managing proposal development professionals in a deadline-driven environment, preferably with employees in multiple locations including but not limited to professional writing, marketing, business development, etc.
  • 7 years experience in leadership, communications, and management skills.
  • Self-starter able to develop and maintain focus on strategic marketing objectives.
  • Process minded, ability to think about people, process, and technology to gain efficiencies in the Proposal Management process, leveraging data and insights. Organized and detail oriented.
  • Knowledge of proposal development methodologies/trends,
  • Experience in balancing short term deadlines against long-term goals for self and staff.
  • Interpersonal, negotiation and engaging communication skills for all levels within the organization including senior leadership.
  • Overseeing the annual budget and allocating resources for various projects and operational needs.
  • Translating needs and initiatives into compelling business cases.
  • Conducting cost-benefit analyses to justify investments and ensure ROI.

Preferred Job Qualifications

  • Bachelor Degree in Business, Marketing Communications, or English.
  • Leader in the proposal industry with proven best practices, including the value of AI and content management strategies
  • Knowledgeable of health care industry trends to incorporate messaging in all communications, meetings and events to ensure consistency in messaging.
  • Knowledge of HCSC product offerings, competitors’ capabilities, and the BCBS System.
  • Demonstrated ability to design knowledge management practices and disciplines for development of the team, as well as stakeholders who engage in the process of RFP development.
  • Experience in managing teams to support onsite events for clients as well as meeting and planning support, preferably with employees and events in multiple locations.
  • Creative problem-solver, strategic critical thinker with operational discipline, team player with leadership qualities.
  • Proactive mindset looking at industry best practices around analytics/automation, ways to balance standardization with unique responses for critical growth opportunities.
  • Achievements within deadline driven environment and pressure related to these activities/roles within the organization.

Compensation: $146,700.00 - $272,400.00

Exact compensation may vary based on skills, experience, and location

HCSC Employment Statement:

We are an Equal Opportunity Employment employer dedicated to providing a welcoming environment where the unique differences of our employees are respected and valued. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, protected veteran status, or any other legally protected characteristics.


To learn more about available benefits, please click https://careers.hcsc.com/totalrewards

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