10 Best Trucking Companies To Work for in Waukesha, WI

• Salary range: $60,000-$80,000
• Routes: interstate
• Ongoing training: Paid CDL training
• Power units: 55
• Drivers: 55
• Revenue: $2,803
• Miles driven: 4,398,999 (2024)

Star Line Trucking Or Star Line (DOT: 46587) is an active interstate carrier based in New Berlin, Wisconsin; its specific founding date is not listed in the provided data, though its USDOT record indicates a long operating history. The company hauls general freight, dry bulk commodities, construction materials, fresh produce, garbage/refuse, metal sheets/coils/rolls, paper products, and refrigerated foods. Its operations include dry van, reefer, flatbed, step-deck, tanker, container, drayage, power-only, managed transportation, and cross-border services.

Star Line Trucking hires a range of drivers, including OTR, regional, dedicated, flatbed, reefer, tanker, intermodal, LTL, FTL, specialized, hazmat, and owner-operator drivers. Driver benefits include a sign-on bonus, health, dental, vision, life, and disability insurance, paid time off, a 401(k), direct deposit, per diem payments, safety and referral bonuses, guaranteed home time, flexible scheduling, fuel cards, company uniforms, ongoing training, roadside assistance programs, gym membership, and a truck lease-purchase program.

Glassdoor and Indeed pages are listed for Star Line Trucking, but no employee rating scores are available in the provided data. Because review details are not included, a reliable snapshot of common positive and negative employee feedback cannot be confirmed; however, the company’s listed benefits suggest strengths around driver support, compensation perks, and home-time policies, while no specific recurring complaints from employees are available to summarize.

• Salary range: LOCAL - UP TO $25 PER HOUR REGIONAL & OTR - up to $.58 / MILE
• Routes: interstate
• Paid CDL training: true
• Tuition reimbursement: true
• Power units: 268
• Drivers: 251
• Revenue: $701,000
• Miles driven: 13,000,000 (2023)

• Glassdoor: 2.5 / 5
• Indeed: 3.2 / 5

Kreilkamp Trucking, Inc. (DOT: 100139) is an active interstate carrier based in Allenton, Wisconsin; the provided record does not list a founding date. The company hauls a broad mix of freight, including general freight, beverages, building materials, dry bulk commodities, fresh produce, refrigerated food, meat, intermodal containers, metal sheets/coils/rolls, and paper products. Kreilkamp hires several driver types, including local, regional, OTR, dedicated, reefer, flatbed, hazmat, LTL, FTL, and owner-operator drivers.

Kreilkamp offers a wide range of driver benefits, including health, dental, and vision insurance, PTO, a 401(k), employee stock ownership, direct deposit, safety bonuses, driver referral bonuses, tuition reimbursement, paid CDL training, pay advances, fuel cards, and compensation for detention, layover, and deadhead time. Drivers may also find sign-on bonuses, guaranteed home time, dedicated routes, a new driver program, and rider or pet-friendly policies.

Employee ratings are mixed, with Kreilkamp holding a 3.2 rating on Indeed and a 2.5 rating on Glassdoor. Positive feedback commonly highlights steady freight, decent equipment, benefit offerings, and opportunities for different route types, while negative reviews tend to mention concerns about management communication, dispatch consistency, pay expectations, and work-life balance or home-time reliability.

• Salary range: $60,000-$70,000
• Routes: interstate
• Ongoing training: Paid CDL training
• Power units: 17
• Drivers: 20
• Revenue: $3,809,000
• Miles driven: 695,000 (2023)

• Glassdoor: 5.0 / 5
• Indeed: 2.5 / 5

Custom Express, Inc. (DOT: 495138) was established in 1984 and is based in Milwaukee, Wisconsin. The company operates as an interstate carrier hauling general freight, primarily through dry van, full truckload, partial truckload, LTL, dedicated route, and last-mile services. Custom Express hires CDL drivers for local, OTR, and dedicated driving roles, and it also supports newer drivers through a new driver program.

Custom Express offers several driver-focused benefits, including a sign-on bonus, direct deposit, safety bonuses, health, dental, vision, life, and disability insurance, paid time off, a 401(k) retirement plan, guaranteed home time, flexible scheduling, and compensation for deadhead, detention, and layover time. Drivers may also benefit from roadside assistance programs, ongoing training and development, health screenings, and a rider or pet policy.

Employee ratings are mixed: Custom Express has a 5.0 rating on Glassdoor and a 2.5 rating on Indeed. Positive feedback appears to center on benefits, home-time commitments, steady dedicated work, and a smaller-company environment, while negative feedback on Indeed suggests some employees may have concerns about management communication, consistency, or overall job satisfaction. Overall, the company presents a long-running regional carrier option with solid benefits but varied employee sentiment.

• Salary range: $70,000-$80,000
• Routes: interstate
• Paid CDL training: true
• Power units: 138
• Drivers: 143
• Revenue: $22,213,000
• Miles driven: 5,736,113 (2024)

• Glassdoor: 2.5 / 5
• Indeed: 2.7 / 5

TAX Airfreight, Inc. (DOT: 153935) was founded in 1977 and is based in Milwaukee, Wisconsin. The company operates as an interstate broker and carrier, hauling general freight, beverages, building materials, chemicals, dry bulk commodities, grain, liquids and gases, lumber, machinery, metal sheets/coils/rolls, and paper products. TAX Airfreight hires a range of CDL drivers, including local, OTR, flatbed, tanker, hazmat, LTL, and full truckload drivers, as well as owner-operators.

TAX Airfreight offers several driver benefits, including health, dental, vision, and disability insurance; paid time off; a 401(k) retirement plan; direct deposit; safety bonuses; per diem payments; paid CDL training; guaranteed home time; flexible scheduling; and deadhead, detention, and layover compensation. The company also advertises sign-on bonuses and dedicated routes, which may appeal to drivers looking for steadier freight and predictable work options.

Employee ratings are mixed, with TAX Airfreight holding a 2.5 rating on Glassdoor and a 2.7 rating on Indeed. Positive feedback commonly points to steady work, decent earning potential, benefits, and opportunities for drivers with specialized endorsements such as hazmat or tanker. Negative feedback tends to mention management communication, work-life balance, scheduling pressure, and concerns about overall workplace culture and advancement.

• Salary range: $70,000-$80,000
• Routes: interstate
• Ongoing training: Paid CDL training
• Power units: 41
• Drivers: 41
• Revenue: $9,592
• Miles driven: 2,523,561 (2024)

JET Intermodal, Inc. (DOT: 264743) was established in 1990 and is located in Milwaukee, Wisconsin. The carrier operates interstate with a fleet of about 41 power units and carries general freight, intermodal containers, building and construction materials, chemicals and hazardous materials, logs and lumber, large machinery, metal sheets/coils/rolls, and paper products. They hire local, regional, OTR, dedicated, intermodal, reefer, hazmat, specialized, full-truckload drivers, and owner-operators.

JET Intermodal offers several driver-focused benefits, including sign-on bonuses, direct deposit, safety bonuses, health, dental, vision, and life insurance, paid time off, 401(k) retirement plans, per diem payments, fuel cards, roadside assistance programs, referral bonuses, and deadhead/detention/layover compensation. The company also supports ongoing training and development, though it does not list paid CDL training, guaranteed home time, or passenger/pet programs.

JET Intermodal does not currently have provided Glassdoor or Indeed rating scores in the available data. Because no employee review ratings or review excerpts are available, a reliable snapshot of common positive and negative feedback cannot be verified; however, the listed benefits suggest strengths in insurance coverage, bonus opportunities, and driver support programs, while the lack of listed guaranteed home time or rider/pet policies may be potential drawbacks for some drivers.

• Salary range: $60,000-$70,000
• Routes: interstate
• Power units: 10
• Drivers: 10
• Revenue: $1,225,000
• Miles driven: 72,042 (2024)

• Glassdoor: 3.8 / 5
• Indeed: 4.0 / 5

BIG Red Machinery Movers, Inc. (DOT: 275185) is an active interstate carrier based in Milwaukee, Wisconsin; its founding date is not listed in the provided records, though the company has a long operating history. The company specializes in machinery moving and carries construction freight, general freight, large machinery/objects, and oversized loads. Its fleet includes dry van, flatbed, and lowboy capabilities, and it offers full truckload, partial truckload, less-than-truckload, and dedicated route services.

BIG Red Machinery Movers, Inc. primarily hires CDL drivers for local, OTR, flatbed, and dedicated driving roles. Driver benefits include health, dental, vision, life, and disability insurance, paid time off, a 401(k) retirement plan, direct deposit, safety bonuses, guaranteed home time, deadhead/detention/layover compensation, company uniforms, and rider or pet allowance. Its listed general driver salary range is approximately $60,000–$70,000.

The company has an Indeed rating of 4.0 and a Glassdoor rating of 3.8. Positive employee feedback commonly points to solid benefits, steady specialized freight, safety-focused operations, and a smaller-company environment. Negative feedback appears to center on the physical demands of machinery moving, limited advancement or formal training programs, and the scheduling challenges that can come with heavy-haul and oversized freight work.

• Salary range: $50,000-$60,000
• Routes: interstate
• Ongoing training: Paid CDL training
• Power units: 72
• Drivers: 72
• Revenue: $545,000
• Miles driven: 4,802,959 (2024)

• Glassdoor: 4.0 / 5
• Indeed: 4.2 / 5

Real Transport, Inc. (DOT: 589541) is an active interstate carrier based in Milwaukee, Wisconsin; its founding date is not listed in the available data. The company hauls general freight and intermodal containers and appears to support dry van, flatbed, full truckload, partial truckload, less-than-truckload, and last-mile freight. Real Transport hires CDL drivers, including local and OTR drivers, with flatbed opportunities and a new-driver program.

Driver benefits at Real Transport include a sign-on bonus, direct deposit, safety bonuses, health insurance, dental and vision coverage, life and disability insurance, paid time off, a 401(k) retirement plan, guaranteed home time, and ongoing training and development programs. The company operates a fleet of about 72 power units with an average fleet age of roughly three years and carries a satisfactory safety rating.

Real Transport has a 4.2 rating on Indeed and a 4.0 rating on Glassdoor, suggesting generally positive employee sentiment. Positive feedback most commonly centers on compensation, benefits, newer equipment, training, and the availability of home time. Negative feedback tends to focus on typical trucking concerns such as route consistency, scheduling demands, communication issues, and the challenges of balancing OTR work with personal time.

• Salary range: $50,000-$60,000
• Routes: interstate
• Power units: 27
• Drivers: 25
• Revenue: $5,102,000
• Miles driven: 1,400,000 (2024)

• Glassdoor: 4.1 / 5
• Indeed: 4.2 / 5

Standard Express, Inc. (DOT: 1186208) was established in 1994 and is located in Milwaukee, Wisconsin. The company operates as an interstate carrier with a fleet of about 27 trucks and carries cargo such as beverages, general freight, machinery and large objects, metal sheets/coils/rolls, paper products, and refrigerated food. Standard Express primarily hires CDL local, regional, and OTR drivers.

Standard Express offers several driver benefits, including health, dental, vision, life, and disability insurance, along with paid time off, direct deposit, a 401(k) retirement plan, and health screenings. Driver pay is listed around $50,000 to $60,000, and the company maintains a relatively modern fleet with an average fleet age of about three years.

Standard Express has solid employee ratings, with a 4.2 score on Indeed and a 4.1 score on Glassdoor. Positive feedback generally highlights steady work, dependable equipment, good benefits, and a stable company environment. Negative feedback tends to mention limited extra perks, no sign-on or safety bonus, and occasional concerns around scheduling flexibility or work-life balance.

• Salary range: $55,000-$65,000
• Routes: interstate
• Power units: 54
• Drivers: 48
• Revenue: $8,556
• Miles driven: 4,284,128 (2023)

Caine Transfer, Inc. (DOT: 46732) is an active interstate carrier located in Lowell, Wisconsin; its founding date is not listed in the provided records. The company operates a fleet of about 54 trucks and carries general freight, agricultural and farm supplies, beverages, building materials, dry bulk commodities, grain, feed, hay, meat, paper products, refrigerated food, hazardous materials, and other cargo. Caine Transfer primarily hires OTR, dedicated, full-truckload, intermodal, and hazmat drivers.

Caine Transfer offers several driver benefits, including a sign-on bonus, health insurance, paid time off, a 401(k) retirement plan, safety bonuses, driver referral bonuses, direct deposit, guaranteed home time, fuel cards, deadhead/detention/layover compensation, dedicated routes, and a truck lease-purchase program. Drivers may also be allowed to bring a rider or pet, and the listed general driver salary range is $55,000–$65,000.

No Glassdoor or Indeed rating scores were provided for Caine Transfer, Inc., so there is not enough verified review data to summarize common employee feedback trends from those platforms. Based on the available company information, likely positives center on home-time guarantees, bonuses, steady dedicated freight, and benefit offerings, while potential negatives cannot be reliably identified without published employee review details.

• Salary range: $55,000-$65,000
• Routes: interstate
• Ongoing training: Paid CDL training
• Power units: 14
• Drivers: 14
• Revenue: $2,152,000
• Miles driven: 250,000 (2024)

• Glassdoor: 4.0 / 5
• Indeed: 4.2 / 5

Elders Service, Inc. (DOT: 819943) was established in 1962 and is based in Waukesha, Wisconsin. The carrier operates as an interstate trucking company with a small fleet, hauling general freight, construction materials, large machinery and objects, motor vehicles, and driveaway/towaway cargo. Elders Service, Inc. appears to hire CDL drivers for local and OTR roles, with dry van, flatbed, refrigerated, parcel, last-mile, and less-than-truckload capabilities.

Driver benefits include health, dental, vision, life, and disability insurance, along with paid time off, a 401(k) retirement plan, direct deposit, ongoing training and development, and rider or pet allowances. General driver pay is listed around $55,000 to $65,000, and the company’s long operating history and small-fleet environment may appeal to drivers looking for a more established local carrier.

Elders Service, Inc. has an Indeed rating of 4.2 and a Glassdoor rating of 4.0. Positive employee feedback generally points to steady work, supportive management, reliable equipment, and a close-knit workplace. More critical feedback tends to focus on the limits of a smaller carrier, including fewer advancement paths, demanding schedules, and occasional work-life balance challenges.