Jobs · OTHR

Proposal Writer

Skyward · Rockville, MD · 1 mo ago
OTHR$25/hrFull-time

About the role

We need a Proposal Writer. Are you a storyteller, a compliance whisperer, and a collaborative powerhouse? Do you blend creativity with compliance, turn requirements into narratives and RFPs into real-world impact? If you’re someone who thrives in the fast lane, embrace smart tech (hello, AI tools), and believe storytelling can win hearts and contracts, then you’re exactly who we are looking for.

Responsibilities

  • 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

  • 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.

Qualifications

  • A calm, collaborative energy – even when timelines are tight and stakes are high.

What would blow us away

  • You have prior experience with DHS-specific vehicles like Alliant 2, OASIS+, or GSA 8(a) STARS III.
  • You have spoken or written about proposals, AI in federal contracting, or best practices at events, blogs, or webinars.

Benefits

  • 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

Pay

ESTIMATED: $100,756 per year

Schedule

Full time

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