Remote Proposal Jobs in Milwaukee, WI (NOW HIRING)

Job Title: Proposal Specialist 
Location: Milwaukee, WI (preferred) | Remote considered 
Employment Type: Full-Time | Individual Contributor 
Compensation: Competitive salarycommensuratewith experience 
Schedule:Standard business hours, Monday–Friday 

Job Description  

Interstate Parking Company and INFLOW Systems combine industry-leading parking operations with innovative parking technology. Together, we manage parking operations across airports, municipalities, ski resorts, event venues, and commercial properties while delivering technology solutions that power those operations. Our Business Development team pursues competitive opportunities and produces high-quality client-facing proposals that help us win new business. 

Headquartered in Milwaukee, Wisconsin, Interstate Parking employs more than 500 team members and manages 400+ locations representing over 85,000 parking spaces across markets from California to Vermont. Our continued growth is driven by exceptional customer service, innovative technology, and a commitment to operational excellence. 

We're equally committed to our people. Interstate Parking has been recognized as a Milwaukee Journal Sentinel Top Workplace from 2023–2026 and has also earned national Culture Excellence Awards for Leadership, Innovation, Employee Well-Being, and Employee Appreciation. These awards are especially meaningful because they're based entirely on feedback from our employees. 

Our Business Development team pursues competitive opportunities across both Interstate Parking and INFLOW Systems, developing high-quality proposals and presentations that help us win new business. We're looking for a Proposal Specialist who can own the proposal process from start to finish and produce polished, persuasive, and compliant submissions that set us apart. 

Learn more about our Top Workplace recognition: 
https://topworkplaces.com/company/interstate-parking/ 

Our rapid growth means we’re always seeking to add highly talented and creative people to the Interstate team.  

What You’ll Do 

• 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 our 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. 

What We Are Looking For 

• 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. 
• Experience with Adobe Creative Suite (InDesign, Acrobat, Illustrator), Canva, Figma, or similar design software. 
• Strong organizational and project management skills with the ability to prioritize competing deadlines. 
• Ability to work independently while collaborating effectively across multiple departments. 
• 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. 

What We Offer 

• Competitive pay, bonus opportunity, and phone stipend 
• Medical, dental, and vision insurance 
• 401(k), PTO, and paid holidays 

• 3–6 years of experience in proposal writing, proposal management, or a related field.
• Excellent writing, editing, and proofreading skills with strong attention to detail.
• Strong project management and organizational skills with the ability to manage multiple deadlines.
• Proficiency with Microsoft Office, Google Workspace, and document design tools.
• Self-motivated team player who collaborates effectively across departments.
• Experience responding to RFPs and using AI tools to improve content development is a plus.