Proposal Writer

Join to apply for the Proposal Writer role at Skyward
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5 days ago – Be among the first 25 applicants.

This range is provided by Skyward. Your actual pay will be based on your skills and experience—talk with your recruiter to learn more.

$90,000.00/yr – $/yr

We are Skyward, a people-centered business dedicated to serving others and improving human advancement through information technology. We are diverse, collaborative, and committed to our values:
Integrity, Compassion, Inquiry, Unconventional, and Authentic.

• Write clear, compliant, and compelling proposals (RFPs, RFQs, RFIs, Sources Sought) for federal agencies, especially DoD and DHS.
• Collaborate with capture managers, BDs, solution architects, and SMEs to weave win themes, discriminators, and evidence-backed stories.
• Craft pricing narratives, management approaches, technical solutions, past performance, and executive summaries that tell a persuasive story.
• Work smart with AI tools such as Grok, Claude, Visible Thread, Grammarly Pro, and Skyward’s custom AI stack to accelerate content creation while maintaining authenticity.
• Build compliance matrices, run Pink/Red/Gold reviews, and enforce best practices throughout the proposal lifecycle.
• Monitor FAR, DFARS, HSAR, Section 508, CMMC, TAA, and other relevant regulations to ensure compliance.

• Bachelor’s in English, Communications, Journalism, Business, or related field (or equivalent experience).
• 8+ years of 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 and understanding cost realism, labor categories, and basis of estimate.
• Track record of winning $25M+ opportunities.
• Fluency in tools such as Gov Win, Visible Thread, Loopio, Proposal Tech, Qvidian, or Privia.
• Experience working with or inside AI tools, including editing and reviewing generated content.
• Calm, collaborative energy even under tight timelines and high stakes.

• Prior DHS-specific vehicle experience (Alliant 2, OASIS+, or GSA 8(a) STARS III).
• Public speaking, writing, or webinar experience on proposals, AI in federal contracting, or best practices.

• Medical, dental, vision insurance (fully paid for employees).
• 15 days of paid leave.
• 7 days sick leave.
• 2 days bereavement leave.
• 11 paid Federal holidays.
• Up to 40 hours jury duty pay.
• 401(k) with 4% employer contribution (no vesting period).
• Up to 4 weeks 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 d voluntary benefits.
• Opportunity to work in a collaborative, motivated team focused on modernizing government services with cutting‑edge technology.

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, but hiring decisions are ultimately made by humans.