Proposal Writer

Skyward IT Solutions•Rockville, MD

6d•Hybrid

About The Position

We are Skyward, a people-centered business passionate about human advancement through information technology. We are a diverse, unified, creative, and collaborative team driven by a civic tech mission. Our values of Integrity, Compassion, Inquisitiveness, Unconventionality, and Authenticity guide our actions. We are looking for a Proposal Writer who is a storyteller, a compliance expert, and a collaborative powerhouse, capable of blending creativity with compliance to turn requirements into compelling narratives and RFPs into real-world impact. If you thrive in a fast-paced environment, embrace smart technology like AI tools, and believe in the power of storytelling to win contracts, you are the ideal candidate. 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 practical experience and writing skills.
5+ years of experience writing and coordinating federal proposals, with significant experience supporting DHS agencies (USCIS, CBP, FEMA, TSA, etc.).
Proven ability to manage multiple requirements against competing deadlines.
APMP Practitioner certification or higher, 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 key proposal sessions (kick-off, partnership, strategy, solutions).
A track record of winning opportunities valued at $25M+, preferably with DHS and other law enforcement agencies.
Fluency in proposal support tools such as GovWin, sam.gov, VisibleThread, Loopio, ProposalTech, Qvidian, or Privia.
Experience working with or within AI tools, including the ability to critically evaluate and edit generated content.
A calm and collaborative demeanor, especially under pressure with tight timelines and high stakes.

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 industry 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 various 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-based stories.
Craft persuasive pricing narratives, management approaches, technical solutions, past performance sections, and executive summaries.
Utilize GenAI tools (Grok, Claude, VisibleThread, Grammarly Pro, Skyward’s custom AI stack) to enhance content creation while maintaining an authentic human touch.
Build compliance matrices, conduct Pink/Red/Gold reviews, and enforce best practices throughout the proposal lifecycle.
Monitor and stay current with relevant regulations such as FAR, DFARS, GSAR, HSAR, and compliance requirements like Section 508, CMMC, TAA.

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.