Skyward · 4 hours ago
Proposal Writer
Rockville, MD
Full-time
Hybrid
Senior Level
6+ years expSkyward is a people-centered business committed to human advancement through information technology. They are seeking a Proposal Writer who can blend creativity with compliance to author compelling proposals for federal agencies, particularly in the Department of Defense and Department of Homeland Security.
Information TechnologyProject ManagementUX Design
No H1B
U.S. Citizen Only
Responsibilities
Write to win. Author clear, compliant, and compelling proposals (RFPs, RFQs, RFIs, Sources Sought) for a range of federal agencies (with a sweet spot in DoD and 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 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, HSAR, and all the other acronyms that matter. Track compliance with Section 508, CMMC, TAA, and more
Qualification
Required
A bachelor's in English, Communications, Journalism, Business, or related field (or the equivalent in lived experience and great writing)
6+ years writing and coordinating federal proposals, with strong experience supporting DHS agencies (CBP, FEMA, TSA, etc.)
APMP Practitioner or higher (or Shipley-equivalent mastery)
Experience contributing to pricing volumes – you get how cost realism, labor categories, and basis of estimate actually play out
A track record of winning $25M+ opportunities
Fluency in tools like GovWin, 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
Applicants must have the ability to obtain and maintain a Public Trust security clearance due to the nature of our work as a government contractor
Preferred
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
Company
Skyward
We are Skyward. That is, a love for people, for improvement, for human advancement through information technology.
51-200 employees
Funding
Current Stage
Growth StageRecent News
Skyward IT Solutions
2025-05-29
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