About this role.
Oddball is seeking a Proposal Writer to lead content strategy and production for U.S. federal RFP, RFQ, RFI, and related opportunity-response materials. The role develops technical, management, staffing, corporate-experience, and oral-presentation content while coordinating closely with proposal, capture, business development, solutioning, and operations stakeholders. The successful candidate will interview subject-matter experts, convert complex technical concepts into persuasive and compliant narratives, and support graphics ideation and peer reviews. Strong federal contracting knowledge, including FAR, contract vehicles, and government technology practices such as Agile, HCD, DevSecOps, and cloud infrastructure, is central to the position. This is a remote U.S.-authorized role with potential citizenship, background investigation, or clearance requirements depending on the contract.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
4/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Sample interview questions
I begin by reviewing the solicitation, evaluation criteria, and compliance matrix to identify requirements, discriminators, and risks. I build a content plan with owners, milestones, and review gates; interview SMEs early; and maintain close coordination with capture and solution teams. Before submission, I conduct compliance, consistency, and executive-quality reviews to ensure the volume is both responsive and persuasive.
I prepare targeted questions tied to the customer problem, requirements, and evaluation criteria rather than simply documenting an SME discussion. I identify the technical approach, benefits, proof points, and operational outcomes, then shape them into a clear narrative with an appropriate graphic concept. I validate the draft with SMEs while retaining accountability for readability, accuracy, and proposal strategy.
I translate every applicable instruction and evaluation factor into a traceable compliance matrix and outline. I use annotations, page-budget controls, and structured reviews to confirm that each requirement is addressed in the required format and location. I also check for consistency among technical, management, staffing, pricing-adjacent, and past-performance claims.
I prioritize early decisions on strategy, outline, assignments, and reusable approved content so writing can begin immediately. I use concise daily status reporting to surface blockers, make tradeoffs visible, and protect time for reviews and final production. Under pressure, I focus on the highest-value evaluation criteria while maintaining compliance and version control.
I would use AI as a drafting and analysis aid, not as a substitute for subject-matter expertise, source validation, or professional judgment. Any generated content would be checked against solicitation requirements, approved corporate information, and SME-confirmed facts before use. I would also follow organizational security and data-handling rules and avoid placing sensitive customer or proposal data into unapproved tools.
Oddball believes that the best products are built when companies understand and value the things they are working on. We value learning and growth and the ability to make a big impact at a small company. We believe that we can make big changes happen and improve the daily lives of millions of people by bringing quality software to the federal space.
We’re looking for a Proposal Writer to join our dedicated Proposal team, where you’ll own the content strategy and production of our responses to government Requests for Proposals (RFPs), Quotes (RFQs), Information (RFI), and other external deliverables to support the opportunity lifecycle.
What you’ll be doing:
- Lead content planning, writing, graphics ideation, peer reviews, and editing across proposal volumes and artifacts, including but not limited to: technical approaches, management, corporate experience, staffing, vendor-written Performance Work Statements, oral presentations, and technical challenges.
- Work with the proposal, business development, capture, solutioning, and operations teams to clear blockers to developing compliant, responsive, and compelling proposals.
- Interview subject matter experts to extract (not simply transcribe) technical information and distill it into clear, persuasive, and differentiated narrative and concepts for graphics.
- Act as an ambassador of the Proposal team, Growth team, and of Oddball: manage peer, cross-functional, executive, and external relationships to ensure consistent input, alignment, and buy-in to the proposal process.
- Demonstrate disciplined and ethical use of AI as an extension of your own thinking and ability to produce winning content, never as a substitute for it: arguing against your own draft, shifting feedback left based on evaluation criteria and company standards, and running down sources so you can stand confidently behind every word on the page.
- Meaningfully contribute to improving the writing practice, proposal function, and broader Growth team at Oddball.
What you’ll bring:
- Proven experience leading proposal volumes for U.S. federal government clients across multi-phase and quick-turn efforts.
- Exceptional writing skills with the ability to sell complex technical concepts and our value proposition to all buyer personas/stakeholders.
- Familiarity with U.S. federal agencies (civilian and defense), with experience writing proposals for VA, CMS, SEC, and DoW preferred.
- Strong understanding of federal contracting including the FAR, contract vehicles, and the opportunity/business development lifecycle.
- Demonstrated fluency with key concepts in government technology today, including: agile, human-centered design, DevSecOps, cloud infrastructure, product management, etc.
- The drive to excel under deadline pressure and in collaborative cross-functional environments
- Communication and persuasion skills, whether you’re interviewing a SME from the driver’s seat, offering peer-to-peer feedback, or presenting to leadership.
- Intellectual curiosity about the work Oddball does and how we put Oddball in the best position to win more work.
- A genuine passion for how what we do as a company improves the lives of the people we serve.
Requirements:
- Applicants must be authorized to work in the United States. In alignment with federal contract requirements, certain roles may also require U.S. citizenship and the ability to obtain and maintain a federal background investigation and/or a security clearance.
Education:
- Bachelor’s degree
Benefits:
- Fully remote
- Tech Stipend
- Comprehensive Benefits Package
- Company Match 401(k) plan
- Flexible PTO, Paid Holidays
Oddball is an Equal Opportunity Employer and does not discriminate against applicants based on race, religion, color, disability, medical condition, legally protected genetic information, national origin, gender, sexual orientation, marital status, gender identity or expression, sex (including pregnancy, childbirth or related medical conditions), age, veteran status or other legally protected characteristics. Any applicant with a mental or physical disability who requires an accommodation during the application process should contact an Oddball HR representative to request such an accommodation by emailing hr@Oddball.io
Compensation:
At Oddball, it’s important each employee is compensated competitively and fairly. In alignment with state legal requirements. A range for the included position is listed below. Be advised, actual offer details are determined by job category, job location, and candidate skill level.
United States Wage Range: $110,000 – $140,000
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