Job Description

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 wont compromise on any of them.

Integrity: Were conscientious intentional and empathetic. Our words and actions align. Thats our character. Please dont ask us to play another part were 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 isnt 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. Were 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 youre someone who thrives in the fast lane embraces smart tech (hello AI tools) and believes storytelling can win hearts and contracts then youre exactly who we are looking for.

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

Lets go Skyward together.

What youll do:

• 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 dont just check boxes they tell a persuasive story.
• Work smarter with AI. Use tools like Grok Claude VisibleThread Grammarly Pro and Skywards 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.

What wed like you to have:

• A bachelors in English Communications Journalism Business or related field (or the equivalent in lived experience and great writing).
• 8 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.

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 dont meet 100% of the qualifications we encourage you to apply. At Skyward were 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
• $5000 per year for professional development
• $600 per year for technical supplies and equipment
• $2000 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 cant be exciting!

$90000 - $110000 a year

We believe great work deserves great pay. Thats 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 youre worth it!

At Skyward we are committed to creating an environment where everyone regardless of gender race ethnicity sexual orientation disability or background can thrive. We support flexible working hours and remote opportunities to help maintain a healthy work-life balance for all employees including caregivers and those with unique needs.

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.

Job Tags

Full time, For contractors, Remote work, Flexible hours,

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