Government Proposal Specialist (Remote, Flexible Hours)

Government Proposal Specialist (Remote, Commission-Based)About Win Win Operations

Win Win Operations is a rapidly growing, woman- and minority-owned company specializing in staffing, technology, government contracts, and business development. We foster a diverse, innovative, and family-oriented team culture and are on track for exponential growth. We’re excited to offer a flexible and dynamic opportunity to join our expanding team.

Job Overview

We are seeking a motivated and detail-oriented Government Proposal Specialist to support our team in developing high-quality responses to RFPs, RFIs, RFQs, and Sources Sought solicitations on Sam.gov and other federal, state, county, and city platforms. This is a commission-based remote position with the potential for a competitive salary and benefits as the company secures more contracts.

The ideal candidate has a strong understanding of information technology, project management, and government contracting and possesses excellent communication and writing skills.

Key Responsibilities
• Develop and write compelling proposals in response to RFPs, RFIs, RFQs, and Sources Sought solicitations.
• Collaborate with contracting officers, partners, vendors, and job candidates to gather and organize necessary documentation.
• Break down and simplify technical content related to Cloud computing, cybersecurity, data storage, AI, and IT services for proposal submissions.
• Create clear and effective ChatGPT prompts to refine and simplify technical language.
• Participate in virtual meetings twice per week, with occasional evening and weekend availability.
• Ensure high accuracy and attention to detail in proposal submissions, deadlines, and compliance requirements.
• Manage communications via email, calendars, and virtual meeting platforms (Google Meet, Teams, Zoom).
• Stay updated on government contracting procedures and solicitation changes.

Qualifications

? IT & Technical Expertise: Knowledge of Cloud, cybersecurity, data storage, AI, and resilience.
? Government Contracting Knowledge: Understanding of federal, state, or local government proposal writing (preferred but not required).
? Writing & Communication Skills: Ability to write clear, concise, and persuasive content.
? Project Management & Organization: Experience with consulting, Agile methodology, or handling multiple deadlines is a plus.
? Software Proficiency: Familiarity with Microsoft Office, Google Suite, CRM platforms (Podio, HubSpot, etc.), and online meeting tools.
? Tech-Savvy: Must have a strong internet connection, a high-quality virtual camera, and the ability to present professionally in remote settings.
? No college degree required, but practical experience in proposal writing, IT, or government contracting is highly preferred.
? Must pass a basic background check (No drug test required).

Preferred (Not Required) Skills
• Experience with business development or customer service.
• Basic knowledge of IT infrastructure, software development, or SDLC.
• Understanding of relationship-building and networking in government or private sectors.
• Prior experience with military procurement.

Why Join Us?

? Remote & Flexible: Work from anywhere with flexible hours.
? Support & Training: Hands-on guidance for candidates eager to learn and grow.
? Growth Opportunities: Be part of a fast-growing company with plans for

competitive salaries, benefits, and career advancement.
? Team Culture: A family-friendly, diverse, and team-oriented work environment.

Who Should Apply?

We strongly encourage applications from:
? Stay-at-home parents, individuals with limited mobility, expats, military veterans, and recent graduates.
? Those passionate about diversity, innovation, and making an impact in government contracting.

How to Apply

Submit your resume and a brief cover letter highlighting your experience in government contracting, IT, or proposal writing.

For questions, email [email protected] with the subject line: Government Proposal Specialist Application.

Job Type: Contract

Benefits:
• Flexible schedule

Schedule:
• Choose your own hours
• Monday to Friday
• Weekends as needed

Application Question(s):
• Do you have experience writing proposals for government contracts (federal, state, or local)? If so, please describe.
• Are you familiar with IT services such as Cloud, cybersecurity, AI, and data storage? Please provide specific examples of your experience.
• Have you worked with prompt-based AI tools like ChatGPT? If yes, how have you used these tools in your work?
• Can you describe a time when you successfully met a tight deadline for a proposal? What was the outcome?
• Do you have experience using CRM platforms like Podio, HubSpot, or similar systems?
• Are you comfortable working in a remote environment and participating in virtual meetings?
• What is your expected compensation (commission-based to start)?
• Have you or are you planning to submit the documentation listed in the "Required Submittals" section of the job listing? You can do so by submitting documents on Indeed or sending them directly to [email protected] (Subject: Government Proposal Specialist).

Experience:
• AI: 1 year (Required)
• Contracts: 1 year (Required)
• Project management: 1 year (Required)

Work Location: Remote

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