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Proposal Content Manager
We are seeking a dynamic Proposal Content Manager to join our team and play a pivotal role in creating, managing, and organizing content for RFIs, RFPs, and oral presentation materials. This position is essential to ensuring that our proposal process is followed rigorously and that all internal milestones are met. All proposal content, including final deliverables, will be maintained in our document management system (Microsoft Teams).
Key Responsibilities
•Content Development & Management:
Develop, curate, and maintain high-quality proposal content and supporting materials, ensuring accuracy, consistency, and compliance with client requirements.
•Collaboration:
Work closely with our capture management team to develop, refine and deliver the most current and relevant proposal/orals content, including the development of new content and diagrams tailored to specific opportunities.
•Service Integration:
Partner with delivery teams to define and draft content for new services and unique solutions for inclusion in upcoming proposals.
•Process Adherence:
Ensure all proposal content and graphics are following established review processes and internal toll gates, maintaining a high standard of proposal content quality and organization.
•Content Organization:
Maintain all proposal content in an organized, easily accessible manner within Microsoft Teams.
Required Experience & Skills
•Experience:
o Minimum 5 years in content management, proposal writing, or technical sales writing roles.
o Direct experience writing SaaS proposals or hands-on experience as a
SaaS implementer is required.
o Experience writing proposals for State, Local Government, Higher Education, or Federal clients is highly desirable.
•Education:
o Bachelor’s degree in Business, Journalism, English, Marketing, or a related field, with a strong emphasis on writing.
•Industry Knowledge:
o Deep understanding of the SaaS industry and terminology; preferred experience with HCM and ERP systems, especially in the public sector.
•Writing & Editorial Skills:
o Exceptional written English skills, with demonstrated ability in proofreading, editing, and developing persuasive technical sales content.
•Technical Proficiency:
o High level of proficiency with Microsoft Office and Adobe Acrobat.
o Familiarity with proposal automation tools, AI-driven solutions, and content databases.
•Project Management:
o Strong organizational and project management skills, with the ability to manage multiple deadlines and priorities.
Additional Information
•This position reports to Highstreet’s EVP of Strategy & Solutioning.
If you are passionate about crafting compelling proposals, thrive in a collaborative environment, and have a background in SaaS or public sector proposal writing, we encourage you to apply!
Why Join Us?
•Make an Impact: Your work will directly influence our company’s success and growth.
•Grow Your Career: Collaborate with industry leaders and expand your skills in a supportive, innovative environment.
•Be Recognized: We celebrate initiative, creativity, and results, your contributions will never go unnoticed.
•Specialize in Oracle Cloud: Join a team at the forefront of implementing Oracle Cloud solutions for state, local government, and higher education customers.
•Progressive Work Environment: Experience a modern, flexible workplace that values your ideas and encourages continuous learning.
•Career Development & Advancement: We are committed to your professional growth, offering clear pathways for development and advancement within the organization.
•Comprehensive Benefits: Enjoy a full range of competitive benefits—including medical, dental, vision, 401(k) matching, and more. We also offer unlimited paid time off to support your well-being and work-life balance.
•Competitive Salary & Bonus Plan: Receive a market-leading compensation package with performance-based bonuses.
If you are ready to take your Proposal Content Manager career to the next level and help us win the future, we want to hear from you!
Apply today and join a team that’s as ambitious as you are.
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory


