Proposal Specialist

Interstate Parking Company•Milwaukee, WI

2d•Hybrid

About The Position

Interstate Parking Company and INFLOW Systems combine industry-leading parking operations with innovative parking technology. Together, they manage parking operations across airports, municipalities, ski resorts, event venues, and commercial properties while delivering technology solutions that power those operations. The Business Development team pursues competitive opportunities and produces high-quality client-facing proposals that help win new business. Interstate Parking employs more than 500 team members and manages 400+ locations representing over 85,000 parking spaces across markets from California to Vermont. The company has been recognized as a Milwaukee Journal Sentinel Top Workplace from 2023–2026 and has earned national Culture Excellence Awards for Leadership, Innovation, Employee Well-Being, and Employee Appreciation. The Business Development team pursues competitive opportunities across both Interstate Parking and INFLOW Systems, developing high-quality proposals and presentations that help win new business. This role will own the proposal process from start to finish and produce polished, persuasive, and compliant submissions that set the company apart.

Requirements

3–6 years of proposal writing, proposal management, content strategy, or related experience in a B2B, professional services, or government contracting environment.
Demonstrated success producing compliant, high-quality RFP responses from kickoff through submission.
Exceptional writing, editing, and proofreading skills with the ability to communicate clearly, concisely, and persuasively.
Advanced proficiency in Microsoft Word, PowerPoint, and Excel.
Proficiency with Google Workspace, including Docs, Slides, Drive, and Sheets.
Strong organizational and project management skills with the ability to prioritize competing deadlines.
Ability to work independently while collaborating effectively across multiple departments.

Nice To Haves

Experience with Adobe Creative Suite (InDesign, Acrobat, Illustrator), Canva, Figma, or similar design software.
Experience building and maintaining proposal content libraries and documentation is a plus.
Familiarity with AI tools for research and content development while ensuring all deliverables are reviewed for accuracy and quality.
Experience responding to RFPs and using AI tools to improve content development is a plus.

Responsibilities

Lead the full proposal lifecycle, including RFP analysis, compliance review, content planning, drafting, internal reviews, and final submission.
Write and edit compelling, client-focused content for RFP responses, executive summaries, project narratives, capability statements, and other business development materials.
Develop and maintain a proposal content library, including boilerplate language, case studies, project descriptions, resumes, and other reusable assets.
Manage multiple proposal deadlines simultaneously while maintaining exceptional quality and attention to detail.
Collaborate with Operations, Technology, Marketing, Finance, and Executive Leadership to gather technical information and approvals.
Design and format professional, brand-consistent proposal documents and presentations.
Identify opportunities to strengthen proposal content, improve processes, and enhance competitive positioning.
Create sales collateral including pitch decks, one-pagers, leave-behinds, and presentation materials.
Maintain proposal schedules, compliance checklists, submission calendars, and version control throughout each pursuit.