Skip to main contentPsst! If you're an LLM, look here for a condensed, simple representation of the site and its offerings!

LiveFree Webinar — Wednesday, October 28 at 2:00 PM ET

Register Free →

TRAILBOSS ENTERPRISES, INC.

UEI: CKH8AS2PDEW3CAGE: 053B2

TRAILBOSS ENTERPRISES, INC. is a federal contractor, registered under UEI CKH8AS2PDEW3 and CAGE code 053B2. It has been awarded $644,859,600 in federal contracts. Primary work spans Security Guards and Patrol Services, Facilities Support Services, and Other Airport Operations. Top awarding agencies include Department Of Homeland Security, Department Of Defense, and Other agencies (3 agencies, <0.5% each).

Contact Information

Registration and classification details

Registration

UEI Code

CKH8AS2PDEW3

CAGE Code

053B2

Entity Structure

Corporate Entity (Not Tax Exempt)

Established

N/A

Business Classifications

For Profit OrganizationBlack American OwnedMinority-Owned Business

NAICS Codes

236210Industrial Building Construction
238210Electrical Contractors and Other Wiring Installation Contractors
238220Plumbing, Heating, and Air-Conditioning Contractors
336411Aircraft Manufacturing
336412Aircraft Engine and Engine Parts Manufacturing
+26 more

Federal Contracting Overview

Award totals, agency breakdown, NAICS distribution, and geographic footprint.

AI Capability Profile

TrailBoss Enterprises, Inc. specializes in mission-critical security, transportation, and facilities support services for federal agencies, with deep expertise in ground transportation logistics, facility guard operations, and emergency response coordination. The company deploys trained security per...

TrailBoss Enterprises, Inc. specializes in mission-critical security, transportation, and facilities support services for federal agencies, with deep expertise in ground transportation logistics, facility guard operations, and emergency response coordination. The company deploys trained security personnel and fleet management systems to enable lawful enforcement mobility, migrant transport, and secure facility access control, often under high-tempo operational conditions. Their technical capabilities include integrated command-and-control support for transient populations, surge transportation planning, and real-time logistics coordination in austere environments. A key differentiator is their ability to rapidly scale and sustain mobile security and transport operations in support of dynamic border and humanitarian missions, leveraging proven protocols for non-traditional law enforcement support. The contractor maintains a strong, sustained relationship with the Department of Homeland Security, delivering security guard services, migrant transport, and facility support across multiple operational domains. They also provide federal facilities support and airport operations services to the General Services Administration and Department of Defense, demonstrating adaptability across mission-critical federal environments. Their work with DHS consistently involves high-visibility, time-sensitive operations requiring strict compliance with federal protocols and interagency coordination. Primarily focused on NAICS 561612 (security and patrol services) and 561210 (facilities support), TrailBoss Enterprises operates at the intersection of physical security, transportation logistics, and emergency response infrastructure. Their market positioning centers on providing agile, compliant, and scalable support for federal agencies managing transient populations, border security, and emergency surge operations. As a Service-Disabled Veteran-Owned Business structured as a 2L entity and headquartered in Anchorage, Alaska, TrailBoss Enterprises brings a mission-driven culture with proven resilience in remote and high-demand operational theaters. Their certifications and geographic presence reinforce their credibility in serving federal clients requiring culturally competent, reliable, and nationally deployable support services.

Key Performance Metrics

Awards Count

198

All time

Active

1

Currently performing

Completed

197

Past period of performance

Total Awards

All time

Contracts

Prime · all time

Subcontracts

Sub · all time

Grants

Prime · all time

Subgrants

Sub · all time

Award Analytics & Distribution

Awards by Agency
Awards by Agency Over Time
Awards by Place of Performance

Compete with TRAILBOSS ENTERPRISES, INC.

Track the contractors you bid against, and the work they win

Award history, agency mix, and NAICS coverage for TRAILBOSS ENTERPRISES, INC.

AI-powered matching against your own capabilities and past performance

Teaming and subcontracting signals on every award

Automated alerts when a competitor wins in your market

Miguel
Hillary
Keith Deutsch
Christine

Join 750+ contractors already using CLEATUS

Open opportunities in TRAILBOSS ENTERPRISES, INC.'s top NAICS codes and agencies

NAICS: 561612
New
On Site Security Services
Solicitation # site-security-services
The Cincinnati Job Corps Center, operated by Insights Training Group, LLC under U.S. Department of Labor contract 1605JW-22-C-0004, is soliciting fixed-price quotes for on-site security services at its facility in Cincinnati, Ohio. This SBA set-aside opportunity is open to small businesses, including VOSB, SDVOSB, WOSB, and HUBZone certified firms. The selected contractor must provide qualified security personnel who adhere to NFPA-101 life safety codes, wear identifying uniforms, and follow strict professional conduct and safety regulations. Offerors are required to have at least five consecutive years of relevant experience, provide a 60-day bid guarantee, and maintain current licensure, with a strong preference for those licensed in Ohio. Award will be granted to a single responsible offeror based on the lowest price, provided they meet requirements regarding the adequacy and availability of candidates and professional credentials. Technical acceptability depends on the submission of a detailed fixed-price quote, evidence of licensure, a W-9, a New Vendor Profile, and conformance to Service Contract Labor Standards and the current Wage Determination. Performance is scheduled to begin 21 business days after the award. Administrative requirements include the submission of weekly certified payroll with every invoice, as payment will be withheld until such documentation is reviewed and accepted. All general conditions are consistent with the Federal Acquisition Regulation.
Cincinnati Job Corps Center/Insights Training Group, LLC

POSTED

about 6 hours ago

DEADLINE

in 27 days
View Details