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Skyward

Proposal Writer

Skyward

Proposal Writer at Skyward creating compelling proposals for federal clients, collaborating with teams and using AI tools.

Posted 6/4/2026full-timeRockville • Maryland • 🇺🇸 United StatesMid-LevelSenior💰 $90,000 - $110,000 per yearWebsite

About the role

Key responsibilities & impact
  • Write to win. Author clear, compliant, and compelling proposals (RFPs, RFQs) and generate RFI and Sources Sought responses which demonstrate an understanding of the customers’ mission for a range of federal agencies with primary focus on DHS.
  • Team up. Collaborate with capture managers, BD pros, solution architects, and SMEs to weave together win themes, discriminators, and evidence-backed stories that resonate.
  • Bring the narrative. Craft pricing narratives, management approaches, technical solutions, past performance, and executive summaries that don’t just check boxes – they tell a persuasive story.
  • Work smarter with AI. Use GenAI tools like Grok, Claude, VisibleThread, Grammarly Pro, and Skyward’s custom AI stack to speed up content creation, while keeping that authentic human touch.
  • Keep it Shipley. Build compliance matrices, run Pink/Red/Gold reviews like a pro, and enforce best practices throughout the proposal lifecycle.
  • Stay sharp. Monitor FAR, DFARS, GSAR, HSAR, and all the other acronyms that matter. Track compliance with Section 508, CMMC, TAA, and more.

Requirements

What you’ll need
  • A bachelor’s in English, Communications, Journalism, Business, or related field (or the equivalent in lived experience and great writing).
  • 5+ years writing and coordinating federal proposals, with strong experience supporting DHS agencies (USCIS, CBP, FEMA, TSA, etc.) and managing multiple requirements against competing deadlines.
  • APMP Practitioner or higher (or Shipley-equivalent mastery).
  • Experience contributing to pricing volumes – you get how cost realism, labor categories, and basis of estimate play out.
  • Developing proposal schedules and facilitating kick-off, partnership, strategy, and solutions sessions.
  • A track record of winning $25M+ opportunities preferably with DHS and other Law enforcement agencies.
  • Fluency in tools like GovWin, sam.gov, VisibleThread, Loopio, ProposalTech, Qvidian, or Privia.
  • Experience working alongside or inside AI tools – and knowing when to trust, edit, or rewrite that generated content.
  • A calm, collaborative energy – even when timelines are tight and stakes are high.

Benefits

Comp & perks
  • Medical, dental, vision insurance (fully paid for employees)
  • 15 days of paid leave
  • 7 days of sick leave
  • 2 days bereavement leave
  • 11 paid Federal holidays
  • Up to 40 hours for jury duty
  • 401K with 4% employer contribution (and no vesting period)
  • Up to 4 weeks of paid paternity and maternity leave
  • Company provided laptop
  • $5,000 per year for professional development
  • $600 per year for technical supplies and equipment
  • $2,000 referral bonus
  • Life and disability insurance
  • HSA and FSA
  • Legal Shield and ID Shield Voluntary Benefits
  • Opportunity to work in a collaborative, motivated team focused on modernizing government services with cutting-edge technology and innovative solutions.

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
proposal writingfederal proposalspricing narrativescompliance matricescost realismlabor categoriesbasis of estimatecontent creationproject managementdeadline management
Soft Skills
collaborationcommunicationstorytellingstrategic thinkingcalm under pressureteamworkproblem-solvingadaptabilityattention to detailleadership
Certifications
APMP PractitionerShipley-equivalent mastery