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Skyward IT Solutions

Federal IT services and modernization

Overview

Skyward IT Solutions provides federal IT services to modernize U.S. government agencies, focusing on agile software development, AI/ML, data science, and human-centered design. It works as a prime contractor for agencies, delivering secure, scalable digital solutions, DevSecOps, data architecture, and AI governance, with projects like CMS payment system modernization and SBA’s Capital Access Financial System. The company differentiates itself through its 8(a) small-business status, civic-technology focus, and Sky Labs that pilot responsible AI for the public sector, serving agencies such as CMS, SBA, DOT, SEC, and FAA. Its goal is to transform federal contracting and civic technology by openly sharing expertise to benefit society and improve government operations for millions of Americans and small businesses.

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About Skyward IT Solutions

Simplify's Rating
Why Skyward IT Solutions is rated
B-
Rated B on Competitive Edge
Rated B on Growth Potential
Rated C on Differentiation

Industries

Data & AnalyticsGovernment & Public SectorCybersecurityAI & Machine Learning

Company Size

51-200

Company Stage

N/A

Total Funding

N/A

Headquarters

Rockville, MD

Founded

2013

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Simplify's take

What believers are saying

  • CMS pilots cut administrative processing time by over 70% in May 2025.
  • The September 2026 FEC award adds $327,661 and extends through 2027.
  • SEWP VI's $20 billion ceiling expands agency access starting November 2026.

What critics are saying

  • Skyward depends on federal contracting cycles, protests, and recompetes for growth.
  • If CMS or SEWP VI stall, Skyward loses its growth engine.
  • A failed flagship AI deployment would damage credibility with every federal buyer.

What makes Skyward IT Solutions unique

  • SkyAI Hub pairs secure agentic AI with CMS workflows and audit-ready controls.
  • New FEC FOIA work and CMS programs show deep federal compliance expertise.
  • NASA SEWP VI places Skyward inside a decade-long federal procurement channel.

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Benefits

  • Health Insurance
  • Dental Insurance
  • Vision Insurance
  • Paid Vacation
  • Paid Sick Leave
  • Bereavement Leave
  • Paid Holidays
  • Life Insurance
  • Disability Insurance
  • Health Savings Account/Flexible Spending Account
  • Remote Work Options
  • Flexible Work Hours

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