Director Subcontracting Jobs in Illinois (NOW HIRING)

What We Do

We calm the confusion of IT by guiding the connection between people and technology. If a customer is looking for a better way to manage their warehouse inventory, equip their workforce, or secure their data, we make it happen. All it takes is finding the right combination of tech hardware, software, cloud solutions, and support services. That’s what we do. We’re the IT Department’s IT Department.

Who We Are

Our team is made stronger by a multitude of backgrounds, experiences, and perspectives. It’s what makes Connection unique—what drives us to innovate and create technology solutions that stand apart from the crowd. We’d love for you to be a part of that fabric, to share your ideas and experiences with a team that thrives on fresh thinking, creativity, and helping others.

Why You Should Join Us

You’ll find supportive teammates and a rewarding career at Connection—plus great benefits. We take pride in supporting employees with a total rewards package that provides financial, emotional, and physical resources for you and your family. Our compensation, 401k plans, medical insurance, and other benefits are progressive and competitive. We value the importance of our employees’ emotional wellbeing. To support employees, we provide free therapy visits, mental health coaching and tools, and meditation resources. You’ll also enjoy a generous paid time off package that includes not only vacation and sick time, but also Wellness and Volunteer Time Off days.

Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment visa at this time.

We are seeking a strategic and results-driven Director of Proposals to lead and elevate our enterprise-wide proposal function. In this high-impact leadership role, you will oversee the development of compelling, compliant, and competitive responses to RFPs, bids, and other strategic pursuits across our Sales organization.

You will serve as the central leader guiding proposal strategy, driving cross-functional collaboration, and standardizing processes that improve efficiency, quality, and win rates. This role offers the opportunity to shape how we position our solutions, tell our story, and win business.

• Lead enterprise-wide responses to RFPs, RFIs, and large, complex bid opportunities
• Drive a consistent, scalable proposal development process across business units
• Own high-priority pursuits, ensuring submissions are accurate, compelling, and on time
• Partner with Sales, Solution Architects, and subject matter experts to develop winning strategies and narratives
• Establish and lead a Deal Desk to evaluate and shape high-value opportunities
• Build and maintain a centralized proposal knowledge base to improve efficiency and consistency
• Implement governance, compliance standards, and post-deal review processes to drive continuous improvement
• Lead proposal kickoff meetings, coordinate deliverables, and manage timelines and resources
• Track win/loss metrics, analyze performance, and identify areas for improvement
• Develop and mentor a high-performing proposal team, fostering a culture of collaboration, accountability, and excellence

USD $138,000.00/Yr.

USD $179,670.00/Yr.

• Proven experience managing private business and state and federal contract proposals with the demonstrated capability to take ownership and initiative over the entire proposal development life cycle, including managing proposal resources, teams of internal personnel from across the company, and subcontractors to deliver compliant, winning-quality, professionally designed proposal documents.
• Experience leading full lifecycle proposal development processes, including but not limited to: pre-RFP solution development; proposal outlines; schedule; writing assignments; past performance; deal reviews; and proposal submission.
• Experience working closely with growth leads and technical staff including division sales leaders, subject matter experts, external consultants, and other writing support to develop understanding of, create and persuasively articulate a winning solution.
• Negotiation skills with ability to secure favorable contracts.
• Process improvement inclinations and/or experience.
• Proven ability to lead teams, not just manage processes and schedules.
• Proven ability to manage teams with many writers and subcontractors.
• Experience working with Solution Architects to assist in development of technical solutions for proposals.
• Experience managing oral presentations, technical demonstrations, and/or video proposals.
• Experience working with and developing standardized sets of proposal development tools, templates, and processes.
• Excellent written and verbal communications skills with people at all levels of the company, internal personnel, and subcontractors.
• Excellent Interpersonal skills with ability to build collaborative relationships.
• Detail oriented with meticulous attention to detail with ability to proofread for accuracy.
• Strong problem-solving and decision-making capabilities.
• Flexible with ability to handle and prioritize multiple proposals.
• Self-motivated with ability to work independently with minimal supervision and in large teams ranging from Account Managers to senior level management.
• Strong organization skills and commitment to high-quality of work.
• Strong interpersonal and presentation skills for interacting with team members and clients.
• Working knowledge of Microsoft Office Suite and Salesforce.