Software Engineer - AI Systems

Description

Are you Ready to Change the Industry Together?

Milestone is a technology-driven platform modernizing aggregate distribution. We connect customers, carriers, and suppliers through real-time visibility to deliver the service standard the industry has always needed. Operating across Florida, Texas, and South Carolina, we're committed to raising the standard of service in aggregate distribution. 

Milestone is powered by NewMile, the technology behind everything we do. NewMile builds the products and services that run our operations, from dispatch and real-time visibility to the AI-driven tools that will shape what comes next. It's a fast-growing team that embraces technology and elevates the experience for our customers, carriers, and team members. 

We are seeking an experienced, AI-first Software Engineer to be a pivotal player in building what lies ahead. Based in Jacksonville, FL and reporting to the Chief Technology Officer, you will design, build, and ship AI-powered products and agent workflows across the NewMile platform, including our web, mobile, and API services. You're a seasoned engineer who uses AI as a force multiplier every day: you pair with AI coding tools to move faster, you know when to trust the output and when to rewrite it, and you're excited about putting LLMs and agents to work on real problems in aggregate transportation. Whether it was building an agent workflow last month or testing a new model last weekend, your curiosity and enthusiasm make you the right fit. 

• Mission: We are a family of brands committed to raising the standard of service in the aggregate distribution industry. 
• Vision: Accelerating the world’s infrastructure. 

Our Values 

• 1% Better, Every Day: Continuous growth is a part of who we are as professionals and people. We are committed to being better today than yesterday, so we are ready for who our organization needs us to be tomorrow. 
• Promise & Deliver: Pick up the phone, respond, then get it done. We are reliable in every sense of the word and deliver quality work and customer service no matter our role. We own our areas and are accountable to ourselves and each other to build trust. 
• Find a Way or Make a Way: There is no problem we can’t solve. We work together and do hard things to simplify the lives of clients, haulers and each other. We find the best way and are open-minded to innovation, technology and new ways of working because we are building an organization to change our industry. 
• Candid, but Kind: We tell each other the truth and challenge when we don’t agree. We build real relationships rooted in kindness and thoughtfulness. Our people will always be our #1 unique and we will never lose sight of that. 
• Rev it Up: Positive energy fuels us to get us to our vision. Each of us contribute to our culture by bringing consistent energy and passion that ripples through our teams like a fire. We celebrate and praise each other’s contributions and strive to create a place we all want to be. 

Who You Are  
You're a builder who thinks like an engineer, an architect, and a product owner. You have a strong software engineering foundation: you've designed systems, shipped production code, and owned what you built. And you've leaned hard into AI. You use AI coding tools to accelerate development without sacrificing quality, and you can design, build, and evaluate AI-based systems, including LLM integrations, agent workflows, retrieval and data pipelines, and the guardrails that keep them reliable. You're language-agnostic and pick up new stacks quickly (we build in Elixir/Phoenix, Flutter/Dart, and SQL). In a small team, you work independently: you take a problem from idea to production with minimal oversight, translate business needs into technical solutions, and communicate clearly with technical and non-technical partners. Experience moving between engineering and product, architecture, or solution design is a big plus. 

Why This Role Matters  

NewMile is building the future of aggregate transportation, and AI is how we'll get there faster. In this role, you'll turn that ambition into working software: finding where AI can remove manual work, sharpen decisions, and improve the experience for haulers, customers, and our internal teams, and then building it. You'll own the design and delivery of AI-powered features and agent workflows across NewMile while keeping the core platform performant, secure, and scalable. On a small, fast-moving team, your ability to architect sound solutions, ship independently, and use AI to multiply your output directly expands what our technology team can deliver. Join us in shaping the future of logistics technology, where your skills and dedication matter every day. 

Who Your Internal Customers Are and How This Role Delivers Value to Them: 

• Leadership Team: You translate strategic priorities into practical AI and technology solutions, giving leadership clear options, honest tradeoffs, and working tools that drive better decisions and move NewMile toward its vision. 
• Operations & Growth Teams: You partner with dispatch, sales, finance, and growth services teams to find repetitive, manual work and automate it with AI agents and integrated workflows, freeing people up for higher-value work. 
• End Users: Haulers, customers, and team members experience your work every day. By building AI-enhanced features that are fast, reliable, and easy to use, you create products that meet and exceed their expectations. 

Your Impact: 

Build AI-powered products and agent workflows that move the business. 

• Design, build, and deploy AI agents and LLM-powered workflows that automate manual processes and improve decision-making across NewMile. 
• Integrate AI capabilities (LLM APIs, retrieval/RAG, tool use, Model Context Protocol and similar frameworks) into our web, mobile, and API services. 
• Build in evaluation, monitoring, and guardrails so AI features are accurate, secure, cost-effective, and trustworthy in production. 

Architect a robust, scalable, AI-ready platform. 

• Design and develop server-side functionality and data access (Elixir/Phoenix, Ecto, SQL) that supports both core platform needs and AI use cases. 
• Shape system architecture and data structures so NewMile's data is clean, accessible, and ready to power AI. 
• Ensure new functionality meets internal standards for performance, quality, security, and scalability. 

Use AI as a force multiplier to ship faster without cutting corners. 

• Leverage AI coding assistants and agentic development tools to accelerate design, coding, testing, and documentation. 
• Review, test, and own AI-generated code with the same rigor as your own, knowing when to trust the output and when to rewrite it. 
• Triage and resolve technology issues promptly to keep users and operations running smoothly. 

Bring a product mindset to every build. 

• Partner with business stakeholders to understand problems, scope solutions, and prioritize the work with the highest impact. 
• Rapidly prototype, test, and iterate on AI-driven ideas, then take the winners from concept to production. 
• Own work items end to end with minimal oversight, keeping the CTO and stakeholders informed along the way. 

Lead AI adoption and continuous learning. 

• Stay current on emerging AI models, tools, and practices, and recommend where they can give NewMile a competitive edge. 
• Share knowledge, document patterns, and help raise the AI fluency of the tech team and the broader organization. 

Requirements

• Bachelor's degree in Computer Science, Software Engineering, or related field preferred (or equivalent experience). 
• 5+ years of professional software engineering experience building and shipping production applications, ideally in a small-team SaaS or similar environment. 
• Strong full-stack fundamentals: back-end development, APIs, data modeling, and SQL, plus front-end experience. Proficiency in at least one modern language; Elixir/Phoenix experience is a plus (or the ability to ramp up quickly). 
• Hands-on experience building AI-based systems: integrating LLMs, designing agent workflows, prompt engineering, retrieval/RAG, and evaluating AI output for accuracy and reliability. 
• Daily, practical use of AI coding tools (e.g., Claude Code, Cursor, GitHub Copilot) with sound judgment on code quality, testing, and security. 
• Experience with systems design or software architecture; a background in technical product management, solution architecture, or product development is a strong plus. 
• Experience with mobile app development (Flutter + Dart, React Native, or similar) is a plus. 
• Experience with AWS or other cloud platforms, including deploying and monitoring services. 
• Proven ability to work independently, own projects from concept to production, and troubleshoot complex issues without heavy guidance. 
• Strong analytical and problem-solving abilities, with a pragmatic bias toward shipping effective solutions over perfect ones. 
• Excellent written and verbal communication skills, including explaining technical and AI concepts to non-technical partners. 
• Experience with Git, Agile development practices, and basic project management. 
• Understanding of data privacy, security, and responsible AI practices. 
• Collaborative, curious, and committed to continuous learning. 
• Based in or willing to relocate to Jacksonville, FL.