Proposal Writer

Skyward IT Solutions, LLC•Rockville, MD

1d•$90,000 - $110,000•Remote

About The Position

We are Skyward, a people-centered business driven by a love for people, improvement, and human advancement through information technology. We are diverse, unified, creative, and collaborative, with a mission in civic tech. Our culture erases the line between work and life, fostering an environment where authenticity, integrity, compassion, inquisitiveness, and unconventional thinking are paramount. We are looking for a Proposal Writer who is a storyteller, a compliance whisperer, and a collaborative powerhouse, blending creativity with compliance to turn RFPs into real-world impact. If you thrive in a fast-paced environment, embrace smart tech like AI tools, and believe in the power of storytelling to win contracts, you are who we are looking for. Join us to learn from others, grow from mistakes, and be part of a future-looking, growth-oriented team.

Requirements

A bachelor's degree in English, Communications, Journalism, Business, or a related field, or equivalent experience.
5+ years of experience writing and coordinating federal proposals, with significant experience supporting DHS agencies (USCIS, CBP, FEMA, TSA, etc.).
Experience managing multiple requirements against competing deadlines.
APMP Practitioner or higher certification, or equivalent mastery (e.g., Shipley).
Experience contributing to pricing volumes, including understanding cost realism, labor categories, and basis of estimate.
Experience 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 proposal tools such as GovWin, sam.gov, VisibleThread, Loopio, ProposalTech, Qvidian, or Privia.
Experience working with AI tools and understanding how to trust, edit, or rewrite generated content.
A calm, collaborative demeanor, especially under tight timelines and high stakes.
Ability to obtain and maintain a Public Trust security clearance.

Nice To Haves

Prior experience with DHS-specific vehicles like Alliant 2, OASIS+, or GSA 8(a) STARS III.
Experience speaking or writing about proposals, AI in federal contracting, or best practices at events, blogs, or webinars.

Responsibilities

Write clear, compliant, and compelling proposals (RFPs, RFQs) and generate RFI and Sources Sought responses that demonstrate an understanding of customer missions for federal agencies, with a primary focus on DHS.
Collaborate with capture managers, BD professionals, solution architects, and SMEs to integrate win themes, discriminators, and evidence-backed stories.
Craft pricing narratives, management approaches, technical solutions, past performance sections, and executive summaries that are persuasive.
Utilize GenAI tools (Grok, Claude, VisibleThread, Grammarly Pro, Skyward's custom AI stack) to expedite content creation while maintaining an authentic human touch.
Build compliance matrices, conduct Pink/Red/Gold reviews, and enforce best practices throughout the proposal lifecycle, adhering to Shipley methodology.
Monitor and ensure compliance with FAR, DFARS, GSAR, HSAR, Section 508, CMMC, TAA, and other relevant regulations and requirements.

Benefits

Medical, dental, and 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 (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.