Who are we?

Trucker Path is a leading technology platform in the freight and logistics industry, trusted by over a million drivers and carriers for navigation, load planning, and operational efficiency tools. With deep insight into the commercial trucking ecosystem, Trucker Path continues to expand its offerings to better serve the evolving needs of its users. 

Trucker Path Insurance (TPI) is the newest subsidiary of Trucker Path, created to provide innovative and accessible insurance products tailored specifically for truckers, fleets, and owner-operators. TPI aims to revolutionize how commercial drivers access insurance—streamlining processes, delivering value, and driving long-term customer relationships. As we rapidly grow our national footprint, we are building a world-class sales team focused on supporting the trucking industry with best-in-class insurance solutions. 

What’s the job?

We’re looking for a Data Analytics / Data Science Intern who’s excited to roll up their sleeves and make data come alive. In this role, you won’t just maintain dashboards—you’ll shape how we see and run our business. You’ll dig into BigQuery, craft dashboards in Looker, and partner with teams across sales, operations, service, and marketing to give them the insights they need to move faster and smarter.

• Own and evolve our data dashboards: Build, maintain, and continuously improve Looker dashboards that provide mission-critical visibility into how we run and scale a trucking insurance brokerage.
• Turn raw data into business impact: Use SQL and BigQuery to dig into large datasets and translate them into clear insights that inform decision-making across sales, service, operations, and marketing.
• Be the go-to for insights: Partner closely with cross-functional teams to understand their needs, then deliver dashboards and reports that unlock faster, smarter decisions.
• Experiment and explore: Design and run independent data experiments to uncover new ways of measuring performance, efficiency, or customer behavior.
• Support strategy and storytelling: Provide clean, reliable reporting that powers business strategy discussions and client-facing deliverables.
• Raise the bar for data at Trucker Path Insurance: Help shape how a startup builds a data-driven culture inside a fast-growing division of a company with national scale.

What’s the work location?

This is a hybrid (one day in-office per week) internship based in Chicago, designed for someone who wants to apply classroom skills to real-world challenges at the intersection of trucking, insurance, and startup growth. The internship averages 2–3 hours per day (approximately 10 hours per week) and offers flexible scheduling—making it ideal for students or professionals working full-time who want to gain hands-on experience. Preferred availability is in the late afternoon, but we can accommodate flexibility during the workday as needed.

What's the earning potential ($$$)? 

The internship offers a competitive hourly rate of $20–$25, with final compensation based on experience, skills, and impact potential. 

What's the estimated internship length?

This is a 3-month internship with the possibility of extension for high-performing interns who demonstrate strong results and initiative.

What are we looking for?

• Currently pursuing a Master’s in Data Analytics, Data Science, or a related field (exceptional undergraduates also considered).
• Strong SQL skills, with hands-on experience in BigQuery preferred.
• Familiarity with BI tools, especially Looker.
• Analytical mindset with attention to detail—able to connect raw data to business impact.
• Comfort working with multiple teams and adapting to startup pace.
• Curiosity and creativity to test new ideas and approaches.

Anything else? Absolutely! Benefits and Perks: 

This is a place where every day we are inspired by our teammates, encouraging each other to be our best. The environment is friendly and supportive! And we feel it’s important to reward our team with competitive pay and benefits. Here are some of the highlights: 

• Team Building: We may work across time zones and countries, but we’re still united. We host a monthly schedule of team activities, open Q&A sessions, and other special events…so many fun ways for us to connect and support one another. 
• Growth Opportunities: When our people grow…we grow! We offer leadership training, development journeys for core teams, and coaching/mentoring opportunities. Constant growth and development are inherent in our culture. 
• Tools To Do The Job: We ensure you are hooked up with the tools, equipment, and systems you need. We begin the process prior to your start date, so you are ready to rock ‘n roll on your first day.  

Join our growing team and let’s have fun building this business together!