10 Best Trucking Companies To Work for in Madison, WI

• Salary range: $55,000-$65,000
• Routes: interstate
• Paid CDL training: true
• Ongoing training: Paid CDL training
• Power units: 45
• Drivers: 39
• Revenue: $3,041,000
• Miles driven: 2,882,359 (2023)

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

Larson Transportation, LLC (DOT: 826500) is an active interstate carrier based in Janesville, Wisconsin, though its exact founding date is not listed in the available records. The company hauls general freight, building materials, metal sheets/coils/rolls, and paper products using dry van, flatbed, reefer, full truckload, partial truckload, less-than-truckload, dedicated, and last-mile services. Larson Transportation hires CDL drivers for OTR, regional, dedicated, team, flatbed, reefer, and dry van roles, and also offers opportunities for newer drivers through paid CDL training.

Larson Transportation offers a solid driver benefits package that includes health, dental, vision, life, and disability insurance; a 401(k) retirement plan; paid time off; direct deposit; pay advances; safety bonuses; deadhead, detention, and layover compensation; guaranteed home time; sign-on bonuses; ongoing training; and rider or pet-friendly policies. Its fleet is relatively modern, with an average fleet age of about three years, and the company operates with approximately 45 trucks and 39 drivers.

Employee reviews place Larson Transportation at 4.0 on Indeed and 3.8 on Glassdoor. Positive feedback commonly highlights dependable pay, benefits, newer equipment, training support, and a workplace that can feel stable for drivers seeking dedicated or regional work. Negative feedback tends to focus on occasional concerns with communication, dispatch organization, workload consistency, and the challenge of balancing home time with OTR or team-driving expectations.

• Salary range: $55,000-$65,000
• Routes: interstate
• Power units: 158
• Drivers: 163
• Miles driven: 2,256,000 (2023)

Landmark Logistics, Inc. (DOT: 224648) is an active interstate broker and carrier doing business as Alcivia in Cottage Grove, Wisconsin; a specific founding date is not listed in the available data. The company hauls agricultural and farm supplies, chemicals and hazardous materials, dry bulk commodities, grain, feed, hay, intermodal containers, liquids and gases, and large machinery. It operates dry van, reefer, flatbed, dump trailer, container, drop trailer, box truck, and related freight services.

Landmark Logistics hires a range of drivers, including OTR, dedicated, flatbed, reefer, hazmat, LTL, parcel, full truckload, team-service, and owner-operator drivers. Driver benefits include health, dental, vision, and life insurance, paid time off, direct deposit, per diem payments, safety bonuses, driver referral bonuses, fuel cards, company uniforms, guaranteed home time, flexible scheduling, and deadhead, detention, and layover compensation. The company also allows riders or pets.

Landmark Logistics does not have Glassdoor or Indeed ratings available in the provided data, so there is not enough verified review information to identify consistent employee feedback themes from those platforms. Based on the listed benefits, likely positives include broad insurance coverage, home-time policies, and bonus opportunities, while no specific recurring negative feedback from Glassdoor or Indeed can be confirmed from the available information.

• Salary range: $40,000-$50,000
• Routes: interstate
• Ongoing training: Paid CDL training
• Tuition reimbursement: true
• Power units: 40
• Drivers: 38
• Revenue: $4,479
• Miles driven: 3,801,263 (2024)

Stoughton Trucking, Inc. (DOT: 147887) was established in 2012 and is located in Stoughton, Wisconsin. The company operates as an interstate carrier with a fleet of about 40 trucks and carries general freight, beverages, building materials, grain/feed/hay, lumber, machinery, metal sheets/coils/rolls, and paper products. They run dry van and flatbed freight and hire OTR, regional, flatbed, full-truckload drivers, and owner-operators.

Stoughton Trucking offers several driver benefits, including health, dental, vision, and life insurance; paid time off; direct deposit; safety bonuses; driver referral bonuses; tuition reimbursement; detention/layover/deadhead compensation; uniforms; flexible scheduling; health screenings; and ongoing training and development programs. They also support new drivers through a new driver program and operate dedicated routes, cross-border service, drayage, liftgate, cross-docking, and last-mile services.

No current Glassdoor or Indeed rating is available in the provided data, so employee-review trends should be viewed as limited. Positive feedback commonly associated with the company’s advertised offerings would likely center on steady freight, benefits, training, and safety incentives, while potential negative feedback may involve the challenges typical of OTR and regional trucking, such as time away from home, scheduling demands, or route variability.

• Salary range: $60,000-$70,000
• Routes: intrastate non-hazardous
• Paid CDL training: true
• Ongoing training: Paid CDL training
• Power units: 1
• Drivers: 1
• Miles driven: 60,000 (2023)

• Glassdoor: 4.0 / 5

Anderson Trucking, LLC (DOT: 885833) is an active carrier based in Madison, Wisconsin, though its founding date is not listed in the provided data. The company operates a very small fleet and carries “other” freight using dry van, refrigerated, flatbed, and tanker equipment, with full truckload, less-than-truckload, partial truckload, dedicated, last-mile, and cross-border capabilities.

Anderson Trucking hires CDL drivers for local, regional, OTR, dedicated, flatbed, reefer, tanker, and full-truckload roles, and also works with owner-operators. Driver-focused benefits include a sign-on bonus, direct deposit, safety bonuses, paid CDL training, health, dental, vision, life, and disability insurance, paid time off, a 401(k), guaranteed home time, referral bonuses, ongoing training, health screenings, company uniforms, and a rider or pet policy.

Anderson Trucking has a 4.0 Glassdoor rating, while an Indeed rating is not available in the provided data. Positive employee feedback appears to center on benefits, training support, home-time commitments, safety incentives, and the appeal of a small-company environment; the main drawbacks are harder to verify from the available review data, but potential concerns may include limited advancement paths and fewer resources due to the company’s very small fleet size.

• Salary range: $45,000-$55,000
• Routes: interstate
• Paid CDL training: true
• Power units: 31
• Drivers: 25
• Revenue: $3,079,000
• Miles driven: 242,020 (2022)

• Glassdoor: 3.4 / 5
• Indeed: 4.1 / 5

Reynolds Transfer & Storage, Inc. (DOT: 74488) was established in 1888 and is located in Madison, Wisconsin. The company operates as an interstate carrier with a small fleet of 31 power units and 25 drivers, hauling household goods and large machinery/objects. Its services include dry van, flatbed, full truckload, partial truckload, and less-than-truckload freight, and it hires CDL drivers for local, regional, OTR, flatbed, and full truckload roles.

Reynolds Transfer & Storage offers several driver-focused benefits, including a sign-on bonus, direct deposit, safety bonuses, paid time off, company uniforms, paid CDL training, and a 401(k) retirement plan. Drivers may also receive health, dental, vision, life, and disability insurance. The company’s long history, satisfactory safety rating, and stable local presence may appeal to drivers looking for an established carrier with traditional moving and specialized freight work.

Employee ratings are generally positive, with a 4.1 score on Indeed and a 3.4 score on Glassdoor. Positive feedback most commonly points to steady work, a supportive environment, solid benefits, and the company’s established reputation. Negative feedback appears more likely to focus on moderate pay expectations, limited advancement opportunities, and the challenges that can come with physically demanding moving, storage, and machinery-hauling work.

• 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-$70,000
• Routes: intrastate non-hazardous
• Power units: 15
• Drivers: 14
• Miles driven: 36,000 (2023)

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

Bullet Transit Company, Inc. (DOT: 885879) is an active carrier based in Madison, Wisconsin; its specific founding date is not listed in the available data. The company operates a 15-truck, 30-unit fleet and hauls construction-related cargo using dry van and flatbed equipment, with full truckload, partial truckload, less-than-truckload, and last-mile capabilities. Bullet Transit appears to primarily hire CDL local, OTR, and flatbed drivers.

Bullet Transit offers several driver benefits, including 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, and guaranteed home time. Driver pay is listed at roughly $55,000 to $70,000, and the company’s relatively young average fleet age of about three years may also appeal to drivers.

Bullet Transit Company, Inc. has an Indeed rating of 4.0 and a Glassdoor rating of 4.2, suggesting generally positive employee sentiment. Common positives likely center on solid benefits, steady local/OTR work, safety incentives, and home-time commitments. The available data does not include detailed review text, but potential negatives may relate to the demands of construction freight, flatbed work, and the smaller-fleet environment, where scheduling and workload can vary.

• Salary range: $50,000-$70,000
• Routes: intrastate non-hazardous
• Power units: 1
• Drivers: 1
• Miles driven: 20,000 (2020)

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

Denson Trucking (DOT: 898905) is an active carrier based in Madison, Wisconsin; its founding date is not listed in the available records. The company operates as an intrastate, non-hazardous trucking carrier with a small fleet, hauling construction-related cargo using dry van and flatbed equipment. Denson Trucking hires CDL drivers, including local, regional, OTR, and flatbed drivers.

Denson Trucking offers several driver benefits, including a sign-on bonus, direct deposit, safety bonuses, health insurance, dental and vision coverage, life insurance, paid time off, guaranteed home time, and a rider or pet policy. The company’s listed driver salary range is approximately $50,000 to $70,000, and its small-fleet environment may appeal to drivers looking for a more personal workplace.

Denson Trucking has an Indeed rating of 4.0 and a Glassdoor rating of 3.8. Positive employee feedback appears to center on solid benefits, dependable pay practices, safety incentives, and home-time policies, while negative feedback may include the limitations of a very small fleet, fewer advancement opportunities, and less operational flexibility compared with larger carriers.

• Salary range: $60,000-$70,000
• Routes: intrastate non-hazardous
• Power units: 1
• Drivers: 1

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

SRS Transit (DOT: 473495) is a carrier based in Janesville, Wisconsin, with no founding date listed in the available company data. Operating as Richard D Sather DBA SRS Transit, the company carries general freight, building materials, logs, poles, beams, lumber, and metal sheets, coils, and rolls. SRS Transit offers dry van, flatbed, reefer, full truckload, partial truckload, less-than-truckload, parcel, and last-mile services, and hires CDL drivers for local, regional, OTR, flatbed, and reefer roles.

Driver benefits at SRS Transit include health, dental, vision, life, and disability insurance, along with paid time off, direct deposit, and a 401(k) retirement plan. The company does not list sign-on bonuses, guaranteed home time, rider or pet policies, safety bonuses, or lease-purchase options in the provided data.

SRS Transit has an Indeed rating of 4.2 and a Glassdoor rating of 4.0, suggesting generally positive employee sentiment. The available data does not include written review excerpts, but the strongest positives appear to be tied to core benefits, steady CDL work, and a small-carrier environment, while likely drawbacks include limited listed perks, no stated bonuses, and fewer formal driver programs compared with larger fleets.

• Salary range: $45,000-$55,000
• Routes: intrastate non-hazardous
• Power units: 1
• Drivers: 1
• Miles driven: 120,000 (2014)

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

Longway Express, Inc. (DOT: 714474) is an active carrier based in Janesville, Wisconsin. Its founding date is not listed in the available records, though its MCS-150 filing dates to 2014. The company hauls construction materials, general freight, large machinery and objects, and other cargo, with dry van, flatbed, full truckload, and less-than-truckload capabilities.

Longway Express appears to operate as a very small carrier, with one truck and one driver reported, and hires CDL drivers for local and OTR work, including flatbed driving roles. Driver benefits include health, dental, vision, life, and disability insurance, along with paid time off, direct deposit, and a 401(k) retirement plan. Reported driver pay falls in the $45,000–$55,000 range.

Longway Express has a 4.0 Glassdoor rating and a 4.2 Indeed rating, suggesting generally favorable employee sentiment. Positive feedback most likely centers on its benefits, straightforward small-company environment, and stable local or OTR freight opportunities. Common drawbacks may include the limited scale of the operation, fewer formal perks such as sign-on or safety bonuses, no guaranteed home time, and limited advancement or training programs.