We are Skyward. That is, a love for people, for improvement, for human advancement through information technology. We are a people-centered business with a desire to serve others. We are diverse and unified; creative and collaborative; a collection of complementary, not competing talents. And though on the surface we remain relaxed, beneath, a torrent of energy links us to our civic tech mission. We stand by our values, and we won’t compromise on any of them. Integrity: We’re conscientious, intentional, and empathetic. Our words and actions align. That’s our character. Please don’t ask us to play another part, we’re poor actors. Compassionate: If we may borrow a quote from Theodore Roosevelt: “No one cares how much you know until they know how much you care.” Because our team is thoughtful and supportive, caring deeply for each other, our clients, and our work, this comes naturally. Inquisitive: We remain students by failing openly and turning lessons into solutions. Unconventional: For us, life isn’t what happens outside of work. Work happens inside of life and our culture erases the line often dividing the two. Authentic: Made possible only because we embody the values listed above. We’re relaxed and fun yet intensely curious and driven. Team members are placed with thought, care, and precision to ensure that Trust, Truth, and Transparency continue to represent our brand. Because of that, we continue Onward, Upward, and Skyward.

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, embraces smart tech (hello, AI tools), and believes storytelling can win hearts and contracts, then you’re exactly who we are looking for.

Come join us if you're motivated to learn from others, to learn from mistakes, to be part of a future-looking and growth-oriented team.

Let's go Skyward together.

What You'll Do

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.

What we'd like you to have:

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.

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.

Even if you don’t meet 100% of the qualifications, we encourage you to apply. At Skyward, we’re focused on hiring individuals with the right skills and passion to grow, not just checking off every box. And now the important part. What we offer you:

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. Who says government work can't be exciting!

$90,000 - $110,000 a year

We believe great work deserves great pay. That’s why we ensure our compensation is not only competitive but also fair and transparent, as required by Maryland law. Expect a salary that matches your skills, experience, and the value you bring to the table — because you’re worth it!

At Skyward, we support flexible working hours and remote opportunities to help maintain a healthy work-life balance for all employees. Offers of employment with Skyward are contingent upon acceptable results of a background investigation. 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.We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

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Proposal Writer