Specialty Transportation

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A partnership of winning

The Skyward Specialty approach is to craft trucking liability and damage coverage to make insurance more affordable for our insureds, and easier for our distribution partners. Finding this balance is key, and it takes a partnership built on trust and a drive to think outside what is expected. That’s why we partner with only a handful of producers across the country. Agents and their insureds count on Skyward Specialty because we stand by their side no matter what. We take extra steps to educate them on ways to run safer and mitigate expensive losses.

Cutting edge independent contractor solutions

The trucking industry and the recent gig economy boom continue to make their mark on the independent contractor landscape. As these industries mature and more independent contractors enter the market, the insurance industry is challenged to create solutions to benefit both the overseeing company and the contractors. Skyward Specialty’s occupational accident (OccAcc) coverage is essential for independent contractors and should be a key component of any organization’s risk management program. Our deeply experienced OccAcc underwriters are dedicated to crafting custom solutions for independent contractors that address the most complex risks in this sector.

The Future of Driving Sucess

SkyDriveTM is Skyward Specialty’s award-winning, proprietary innovative loss control program that delivers integrated, real-time intelligence to improve driving performance, lower risk and potentially save lives. All specialty trucking clients have access to powerful data analytics that provide key insights into safety – giving clients greater control over managing risk. Click here to learn more about SkyDrive and how it can help you shape the future of driving success.


We offer liability and damage insurance packages to help provide strong and affordable coverage to commercial trucking customers.

  • Occupational Accident
    • Domestic trucking & logistics firms
    • Final mile logistics companies (including PPVs, Sprinter/Cargo vans)
    • Workforce companies
    • National & Regional rideshare and delivery platforms
    • Gig/On-demand platform companies
  • A.M. Best rated A-IX (Excellent) carrier(s)
  • Exclusive distribution channel
  • Dedicated claims staff
  • Emergency response & quick strike claims teams
  • Proprietary SkyDriveTM technology for risk management
  • OccAcc: AM Best rated A-IX (Excellent) carriers; Broad definition of “dispatch;”  Flexible rating models / User-based pricing options; Admitted/non-admitted paper in most states
  • Regional Trucking Coverage:
  • Auto Liability
  • Auto Physical Damage
  • General Liability
  • Occupational Accident Insurance
  • General Liability – up to $1M occurrence/$2M aggregate
  • Auto Liability – $1M CSL

Trucking / Last Mile Occupational Accident Coverage:

  • Up to $1 million – Occupational Accident policy limits per occurrence
  • Statutory Contingent Liability – WC limits (may be subject to $1 million sublimit in some states)
  • Corporate WC and Fleet WC available (OccAcc coverage must be in place)
  • Optional enhanced OccAcc benefit riders:
    •  Passenger accident
    • Truck payment reimbursement
    • Critical burn
    • Vocational retraining
    • Non-medical repatriation & return of remains

Gig Economy / On Demand Coverage:

  • Usage-based premium
  • Flexible & customized coverages
  • Optional enhanced benefits
    • Smartphone/ tablet repair and replacement
    • Sexual and felonious assault coverage
  • Contingent liability & workers compensation available (non-IC exposure)
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