Software Engineer, AI Systems

NewMile•Jacksonville, FL

About The Position

Milestone is a technology-driven platform modernizing aggregate distribution, connecting customers, carriers, and suppliers through real-time visibility. NewMile builds the products and services that power its operations, including dispatch, real-time visibility, and AI-driven tools. The company is seeking an experienced, AI-first Software Engineer to design, build, and ship AI-powered products and agent workflows across the NewMile web, mobile, and API services. The role is based in Jacksonville, Florida, and reports to the Chief Technology Officer. The engineer will build AI systems and workflows that automate manual processes, improve decision-making, and enhance experiences for haulers, customers, and internal teams. This includes integrating LLMs and retrieval capabilities, building evaluation and reliability guardrails, and maintaining a performant, secure, and scalable core platform. The role also calls for a product mindset: partnering with stakeholders to identify needs, prioritize high-impact work, prototype ideas, and take successful solutions from concept to production with minimal oversight. The position is part of a small, fast-moving team. The engineer is expected to use AI coding assistants and agentic development tools to accelerate work while reviewing, testing, and taking ownership of generated code. They will also help lead AI adoption by staying current with emerging tools, documenting patterns, and sharing knowledge across the technology team and broader organization.

Requirements

Bachelor's degree in Computer Science, Software Engineering, or a related field, or equivalent experience; the degree is preferred.
At least 5 years of professional software engineering experience building and shipping production applications.
Strong full-stack fundamentals, including back-end development, APIs, data modeling, SQL, and front-end experience.
Proficiency in at least one modern programming language.
Hands-on experience building AI-based systems, including LLM integration, agent workflows, prompt engineering, retrieval/RAG, and evaluation of AI output for accuracy and reliability.
Daily practical use of AI coding tools, with sound judgment about code quality, testing, and security.
Experience with systems design or software architecture.
Experience with AWS or another cloud platform, including deploying and monitoring services.
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.
Excellent written and verbal communication skills, including the ability to explain 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, Florida.

Nice To Haves

Experience building production applications in a small-team SaaS or similar environment.
Elixir/Phoenix experience, or the ability to ramp up quickly.
Experience moving between engineering and product, architecture, or solution design; technical product management, solution architecture, or product development background.
Experience with mobile app development using Flutter and Dart, React Native, or a similar framework.

Responsibilities

Design, build, and deploy AI agents and LLM-powered workflows to automate manual processes and improve decision-making.
Integrate LLM APIs, retrieval/RAG, tool use, Model Context Protocol, and similar capabilities into web, mobile, and API services.
Build evaluation, monitoring, and guardrails to make AI features accurate, secure, cost-effective, and trustworthy in production.
Design and develop server-side functionality and data access, including Elixir/Phoenix, Ecto, and SQL, for core platform needs and AI use cases.
Shape system architecture and data structures so company data is clean, accessible, and ready to support AI.
Ensure new functionality meets internal standards for performance, quality, security, and scalability.
Use AI coding assistants and agentic development tools to accelerate design, coding, testing, and documentation; review, test, and own AI-generated code.
Triage and resolve technology issues promptly to keep users and operations running smoothly.
Partner with business stakeholders to understand problems, scope solutions, and prioritize high-impact work.
Prototype, test, and iterate on AI-driven ideas, then move successful solutions from concept to production.
Own work items end to end with minimal oversight and keep the CTO and stakeholders informed.
Stay current on AI models, tools, and practices and recommend ways they can provide a competitive edge.
Share knowledge, document patterns, and help increase AI fluency across the technology team and broader organization.