Director, Proposals

Connection

Director of Proposals leading enterprise IT RFP, bid, and contract responses for Connection, an IT solutions provider. Driving proposal strategy, deal governance, process improvement, and team leadership.

Posted 8/21/2026full-timeRemote • Illinois • 🇺🇸 United StatesLead💰 $138,000 - $179,670 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in leading full lifecycle proposal development, managing cross-functional teams, and implementing governance and compliance standards. Proven ability to drive proposal strategy, enhance process efficiency, and mentor high-performing teams to achieve business growth.

Highest-signal resume keywords

Full Lifecycle Proposal DevelopmentTeam Leadership and ManagementProposal Strategy and ExecutionNegotiation SkillsProcess Improvement

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Proposal DevelopmentRFP ManagementBid ManagementProposal WritingPerformance AnalysisContract NegotiationSolution DevelopmentProposal Tools and TemplatesOral Presentation ManagementDetail Orientation

Soft Skills

Excellent Communication SkillsInterpersonal SkillsProblem-SolvingDecision-MakingCollaboration

Industry Keywords

Governance StandardsCompliance StandardsProposal Knowledge BaseWin/Loss MetricsWorkforce PlanningSuccession PlanningBudget OwnershipDeadline-Driven EnvironmentCross-Functional CollaborationTechnical Solutions

About the role

Key responsibilities & impact

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 and ensure 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
Implement governance, compliance standards, and post-deal review processes
Lead proposal kickoff meetings, coordinate deliverables, and manage timelines and resources
Track win/loss metrics, analyze performance, and identify improvement areas
Develop and mentor a high-performing proposal team
Serve as the central leader for proposal strategy, cross-functional collaboration, process standardization, solution positioning, and business growth

Requirements

What you’ll need

Must have experience managing direct reports with full authority and responsibility for hiring, firing, performance management, coaching, compensation decisions, employee relations, workforce planning, succession planning, and budget ownership
Experience leading teams of staff writers and subcontractors in a complex, deadline-driven environment
Proven experience managing private business and state and federal contract proposals throughout the entire proposal development life cycle
Experience managing proposal resources, internal personnel across the company, and subcontractors
Experience leading full lifecycle proposal development, including pre-RFP solution development, proposal outlines, schedules, writing assignments, past performance, deal reviews, and proposal submission
Experience working with growth leads, technical staff, division sales leaders, subject matter experts, external consultants, and writing support
Negotiation skills with ability to secure favorable contracts
Process improvement experience or inclination
Experience working with Solution Architects to develop technical solutions for proposals
Experience managing oral presentations, technical demonstrations, and/or video proposals
Experience developing standardized proposal tools, templates, and processes
Excellent written and verbal communication skills
Excellent interpersonal skills and ability to build collaborative relationships
Detail-oriented with meticulous attention to detail and proofreading accuracy
Strong problem-solving and decision-making capabilities
Ability to handle and prioritize multiple proposals
Must be authorized to work for any employer in the U.S.; employment visa sponsorship is unavailable

Benefits

Comp & perks

Competitive compensation
401k plans
Medical insurance
Free therapy visits
Mental health coaching and tools
Meditation resources
Paid vacation time
Paid sick time
Wellness Time Off days
Volunteer Time Off days