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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, including agile software development, AI/ML, data science, and human-centered design. It acts as a prime contractor on federal programs, delivering secure, scalable digital solutions, DevSecOps, data architecture, and AI governance. It differentiates itself as an 8(a) small business with a mission-driven civic-tech focus and Sky Labs, an internal unit for responsible AI adoption. Its goal is to transform federal contracting and civic technology by sharing expertise to benefit society, serving agencies like CMS, SBA, DOT, SEC, and FAA and supporting 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, Maryland

Founded

2013

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Simplify's Take

What believers are saying

  • September 2026 DHS OHSS award added $3.0 million in new federal work.
  • Skyward’s STARS III recertification preserved access to a $50 billion vehicle.
  • CMS and DOT task orders signal continued demand for modernization execution.

What critics are saying

  • 8(a) graduation in May 2027 threatens recompete access on legacy contracts.
  • STARS III ordering ended July 1, 2026, forcing constant pipeline renewal.
  • A CMS or SBA contract loss would crush revenue concentration exposure.

What makes Skyward IT Solutions unique

  • Skyward won CMS, SBA, DOT, SEC, and FAA federal modernization work.
  • July 2026 STARS III recertification extends ordering eligibility through July 2029.
  • SkyAI Hub and Sky Labs package secure agentic-AI delivery for agencies.

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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

Parental Leave

Professional Development Budget

Employee Referral Bonus

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