1

Director Proposal Development Jobs in Chicago, IL

Proposal & RFP Specialist

Chicago, IL · On-site

$70K - $80K/yr

This direct hire opportunity is ideal for an experienced proposal professional who thrives in a ... Partner with Sales leadership on pricing strategy and proposal development * Prepare proposal ...

Director of Marketing

Chicago, IL · On-site

$105K - $120K/yr

The Director ensures consistency, operational efficiency, and scalability within the marketing ... ESSENTIAL FUNCTIONS Proposal Development & Pursuit Management * Lead and oversee the full proposal ...

Director-Engineering

Chicago, IL · Remote

$170K - $200K/yr

Director (Engineering) Location: Remote Hire Type: Direct Compensation: $170,000 - $200,000 Must ... Supports proposal development, project scoping, estimating, and staffing strategies. * Maintains ...

next page

Showing results 1-20

Director Proposal Development information

See Chicago, IL salary details

$52K

$95.1K

$132.4K

How much do director proposal development jobs pay per year?

As of Aug 3, 2026, the average yearly pay for director proposal development in Chicago, IL is $95,072.00, according to ZipRecruiter salary data. Most workers in this role earn between $82,400.00 and $114,900.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a Director of Proposal Development, and why are they important?

To thrive as a Director of Proposal Development, you need expertise in proposal management, strategic planning, and persuasive writing, often supported by a bachelor’s or master’s degree in business, communications, or a related field. Familiarity with proposal automation tools (like RFPIO or Loopio), CRM systems, and certifications such as APMP are commonly required. Strong leadership, attention to detail, and exceptional organizational and interpersonal skills set top performers apart in this role. These competencies are crucial for leading teams, producing compelling proposals, and securing business opportunities in competitive environments.

What does a Director of Proposal Development do?

A Director of Proposal Development oversees the creation, management, and submission of proposals, typically for business development or government contracts. They lead a team of proposal managers and writers, coordinate with subject matter experts, and ensure proposals meet requirements and deadlines. Their role involves strategic planning, quality control, and often working closely with sales and executive leadership to align proposal efforts with organizational goals. Success in this role requires strong leadership, project management, and communication skills.

How does a Director of Proposal Development typically collaborate with cross-functional teams during the proposal process?

A Director of Proposal Development regularly works with subject matter experts, sales teams, project managers, and executives to gather the necessary information and create compelling, compliant proposals. This role involves coordinating input from various departments, leading meetings to align on strategy, and ensuring deadlines are met. Effective communication and project management skills are essential, as the director must balance multiple priorities while ensuring consistency and quality in every submission. Building strong relationships across departments is key to streamlining the proposal process and improving win rates.

What is the difference between Director Proposal Development vs Proposal Manager?

AspectDirector Proposal DevelopmentProposal Manager
ResponsibilitiesOversees proposal strategy, manages teams, and ensures alignment with organizational goalsCoordinates proposal efforts, manages proposal timelines, and ensures compliance with RFP requirements
Required CredentialsTypically requires a bachelor’s degree, extensive proposal experience, and leadership skillsUsually requires a bachelor’s degree and experience in proposal coordination
Work EnvironmentStrategic, leadership-focused, often in corporate or government sectorsOperational, detail-oriented, often in government contracting or consulting firms

The main difference is that the Director Proposal Development focuses on strategic leadership and overseeing proposal teams, while the Proposal Manager handles day-to-day proposal coordination and compliance. Both roles require strong proposal experience, but the director role involves higher-level planning and management responsibilities.

What are the most commonly searched types of Proposal Development jobs in Chicago, IL? The most popular types of Proposal Development jobs in Chicago, IL are:
What are popular job titles related to Director Proposal Development jobs in Chicago, IL? For Director Proposal Development jobs in Chicago, IL, the most frequently searched job titles are:
What cities near Chicago, IL are hiring for Director Proposal Development jobs? Cities near Chicago, IL with the most Director Proposal Development job openings:

Executive Director, Enterprise Proposal Development & Events

Health Care Service Corporation

Chicago, IL

$146K - $272K/yr

Full-time

Medical, Life, Retirement, PTO

Re-posted 8 days ago


Job description

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.

Job SummaryThis 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.

Are you being referred to one of our roles? If so, ask your connection at HCSC about our Employee Referral process!

Pay Transparency Statement:

At Health Care Service Corporation, you will be part of an organization committed to offering meaningful benefits to our employees to support their life outside of work. From health and wellness benefits, 401(k) savings plan, pension plan, paid time off, paid parental leave, disability insurance, supplemental life insurance, employee assistance program, paid holidays, tuition reimbursement, plus other incentives, we offer a robust total rewards package for employees. Learn more about our benefit offerings by visiting https://careers.hcsc.com/totalrewards.

The compensation offered will vary depending on your job-related skills, education, knowledge, and experience. This role aligns with an annual incentive bonus plansubject to the terms and the conditions of the plan.

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.

Base Pay Range$146,700.00 - $272,400.00

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