Proposal Writer

Skyward

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

Posted 6/3/2026full-timeRockville • Maryland • 🇺🇸 United StatesMid-LevelSenior💰 $90,000 - $110,000 per yearWebsite

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

proposal writingfederal proposalspricing narrativescompliance matricescost realismlabor categoriesbasis of estimatecontent creationproject managementdeadline management

Soft Skills

collaborationcommunicationstorytellingstrategic thinkingcalm under pressureteamworkproblem-solvingadaptabilityattention to detailleadership

Tools & Technologies

GrokClaudeVisibleThreadGrammarly ProSkyward AIGovWinsam.govLoopioProposalTechQvidian

Certifications & Qualifications

APMP PractitionerShipley-equivalent mastery

Industry Keywords

DHSFARDFARSGSARHSARSection 508CMMCTAARFPRFQ

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.