Data, AI & Automation Leader (Early Career)

The Role

We’re looking for a curious, entrepreneurial systems thinker early in their career: someone who wants to understand how a whole business works and then rebuild it to work better. This is a rare first job for someone equally drawn to finance and technology. You’ll help build our data lake, drive our AI efforts, and automate manual work across every Prairie business. Every project is judged by one standard: measurable financial impact. You’ll learn how three very different businesses make and lose money, then use data and AI to improve margins, cash flow, and decisions. You’ll spend real time in our operations, so the tools you build solve real problems for drivers, technicians, crews, and managers.

This is fresh territory. There’s no existing team, playbook, or system to inherit. We need someone willing to jump in headfirst, learn fast, and build as they go. As your results grow, so will the role, with a clear path into leadership.

How You’ll Work

This is a build-from-scratch role with far more responsibility than a typical first job. You’ll report to the CFO, work closely with the CEO and our operating company COOs, get regular mentoring, and have: • Freedom to set your own priorities and roadmap. Leadership agrees on goals rather than managing tasks. • Real resources to buy the tools, platforms, and outside help your projects need. • Direct access to leaders, employees, systems, and data across every Prairie business. • Freedom to test ideas quickly, kill what doesn’t work, and scale what does. • Room to shape the role and grow into a leader as the function expands. In exchange, we expect clear results. You’ll report regularly on what you’ve delivered, what it’s worth financially, and what’s next.

What You’ll Do

Financial Impact • Help build unit economics for every business, such as revenue and margin per truck, per load, per job, per technician, and per piece of equipment. • Produce timely, accurate financial and KPI reporting for each company and a consolidated view for Prairie leadership. • Write the business case for every data, AI, and automation project, with costs, expected return, and payback period, then verify actual results after launch. • Find margin leaks, such as unbilled work, fuel and labor variances, idle equipment, and pricing gaps, and quantify the fix. • Support budgeting, forecasting, cash flow, and job and customer profitability analysis. • Support acquisition and capital decisions with analysis. Data Lake • Inventory critical data across all businesses: ◦ PFS: dispatch/TMS, run tickets, ELD and telematics, fuel, maintenance, and customer volumes. ◦ One Call SWFL: CRM and leads, scheduling, work orders, technician performance, and reviews. ◦ Miller Brothers: job costing, bids, equipment hours, and project schedules. ◦ Shared: accounting, payroll, HR, insurance, safety, and fixed assets. • Help design and build the architecture, pipelines, and access controls, keeping each company separate where needed and consolidated where useful. • Set data quality rules and common definitions for shared measures like revenue, labor hours, and margin. • Work closely with finance and accounting so the data lake becomes the trusted source for financial reporting. AI Leadership • Help shape the AI roadmap for The Prairie Companies, ranking use cases by measurable return. • Build and test practical applications, such as dispatch and route optimization, automated ticket and invoice processing, predictive maintenance, lead scoring and call handling, bid estimating, and internal AI assistants. • Research and evaluate AI tools and vendors, and recommend whether to build or buy. • Draft AI usage guidelines covering data privacy, security, accuracy, and acceptable use. • Train employees and leaders across all businesses to use AI tools effectively. Automation • Map manual, repetitive processes across all businesses, such as ticket entry, billing, payroll prep, scheduling, and reporting, and rank them by time and cost savings. • Design and deploy automations and integrations that remove double entry between systems. • Standardize workflows where the businesses share needs, such as accounting, HR, and safety. • Document every automation and assign ownership so it keeps working after launch. Field Presence • Spend regular time at PFS terminals, One Call SWFL operations, and Miller Brothers job sites. • Interview and work side by side with people at every level, from leadership to drivers, technicians, and crews, to understand their real pain points and design solutions they’ll actually use. • Support the users of core systems so incoming data stays clean and adoption sticks. • Coordinate with our managed IT providers and software vendors.

What You Bring

We care more about what you’ve actually built and done than about your GPA or a traditional résumé. Nontraditional paths are welcome, such as a gap year spent working, starting a business, or building something on your own. The strongest candidates will show: Relevant Experience • Real-world work experience, whether internships, a startup, a family business, a gap-year job, or running something of your own, ideally touching finance, data, operations, or technology. • A completed data project you can show and explain, ideally a data lake, data warehouse, or database that pulls together data from multiple sources. Class, internship, research, and personal projects all count. • Personal or side projects where you used AI tools like ChatGPT, Claude, or Copilot to automate a task, analyze data, or build something useful. • Hands-on work with SQL, Python, Excel, Power BI, or similar tools, shown through real projects rather than coursework alone. • Experience turning data into a business recommendation, such as cost savings, pricing, or profitability analysis. Education • A bachelor’s degree, completed recently, in engineering, finance, economics, data analytics, information systems, computer science, or a related field, or equivalent hands-on experience.

Who You Are

• Deeply curious. You take things apart to see how they work, whether that’s a machine, a process, or a business. • A systems thinker. You see how people, processes, data, and money connect, and you look for the root cause rather than the quick patch. • Entrepreneurial. You’ve started, built, or fixed something without being asked, and you act like an owner. • A fast self-teacher who is comfortable with ambiguity and figures things out without a playbook. • Someone who follows through. You take ownership, ask good questions, and finish what you start. • A clear communicator with people at every level, from drivers to executives. • Willing to travel regularly between Minnesota, Utah, the western basins, and Southwest Florida.

Nice to Have

• Experience with cloud data platforms like Azure, AWS, Snowflake, or Databricks. • Automation tools like Power Automate or Zapier, or experience connecting systems through APIs. • Work, internship, or family exposure to trucking, oilfield services, construction, or home services. How to Apply Along with your résumé, send a short description of, or link to, your most relevant project, such as a data lake, dashboard, financial model, or AI automation. Tell us what problem it solved, what you built, and what you’d do differently. We also want to hear about the thing you’re proudest of having figured out on your own, at work or anywhere else. Finalists will walk us through it in the interview.

Compensation & Benefits

Competitive salary and benefits, with compensation that grows with your results and responsibilities. We also support travel, relocation, professional development, and certifications.

The Prairie Companies is an equal opportunity employer.