Lead AI-First Software Engineer (Remote)

FreeWill; Louisiana; Remote; USD 190,000 - 210,000; Full time

Benefits offered by this job

Work from home

Flexible hours

Competitive salary

Company stock options

401k

Medical/Dental/Vision

Paid parental leave

Job summary

FreeWill is seeking a Lead Software Engineer (AI-Native) to orchestrate AI development systems and rapidly evolve our products. You will operate in a lean 3–4 person pod, turning product requirements into spec-driven workflows and shipping production-ready code using Claude Code, Codex, Cursor, and other tools.

The role, reporting to the R&D organization, emphasizes building an AI-native playbook, mentoring peers, and delivering high-impact user experiences with fast, quality-focused delivery.

Qualifications

• 7+ years of experience as a software engineer with full-stack production systems.
• Experience mentoring engineers and sharing knowledge across teams.
• Experience building tools and workflows with quality baked in from the start.
• Familiarity with agentic coding tools in real development workflows.
• Knowledge of LLM behavior, evaluation, and prompt iteration techniques.

Responsibilities

• Lead AI-native software development workflows using Claude Code, Codex, Cursor.
• Mentor engineers within R&D on AI-native development practices.
• Translate product requirements into technical specs, prompts, and system instructions.
• Own end-to-end delivery from spec to production rollout.
• Develop repeatable AI coding playbooks and engineering patterns.
• Collaborate in a small pod to rapidly rebuild and improve product flows.
• Design systems to manage potential code comprehension and debt issues.
• Document patterns and lessons into a repeatable playbook.

Skills

AI-native systems

Mentorship culture

Full stack web stacks

Agentic codingTools

Prompt iteration

System debugging

Clear specs writing

Tools

Claude Code

Codex

Cursor

Copilot

Job description

FreeWill is seeking a Lead Software Engineer (AI-Native) to orchestrate AI development systems and rapidly evolve our products. You will operate in a lean 3–4 person pod, turning product requirements into spec-driven workflows and shipping production-ready code using Claude Code, Codex, Cursor, and other tools.

The role, reporting to the R&D organization, emphasizes building an AI-native playbook, mentoring peers, and delivering high-impact user experiences with fast, quality-focused delivery.