Principal AI Productivity Engineer

Plansource

2d • Remote

About The Position

At PlanSource, a leading cloud-based provider of benefits administration technology and services, we are on a mission to simplify how people choose, use, and manage benefits through cutting-edge, AI-powered experiences. This is an incredible time to launch your career with us!
We are hiring a Principal AI Productivity Engineer to directly build, iterate, and deploy AI powered workflows that materially improve how our Product, Engineering, Test, and Operations teams work.
This is a hands on builder role, not a research, strategy, or standards first position. Your primary focus will be identifying high leverage workflow bottlenecks and rapidly shipping AI agents and skills - primarily using Claude - to help teams move faster without sacrificing quality.
You will partner closely with product leaders, engineers, testers, and operations teams, releasing improvements weekly, learning from real usage, and iterating based on feedback. Standardization and broader enablement come after value has been proven in practice.
This role reports directly to the CTO and operates with high visibility and broad autonomy.

Requirements

• 8+ years experience in software engineering, developer productivity, test enablement, platform engineering, or similar roles.
• Hands on experience building with modern LLMs (Claude strongly preferred).
• Strong workflow and systems thinking.
• Ability to read, reason about, and lightly modify code.
• Comfort working across disciplines and influencing without authority.
• Strong bias toward action, experimentation, and iteration.

Nice To Haves

• Experience building agent based systems or tool using LLM workflows.
• Familiarity with engineering and test automation pipelines.
• Background in DevEx, internal platforms, or productivity tooling.
• Exposure to operations or business process automation.

Responsibilities

• Design, build, and deploy AI agents and workflow automations embedded into day to day work.
• Ship improvements weekly (or faster), gather feedback, and iterate quickly.
• Focus on outcomes: throughput, cycle time, quality, and reduced manual effort.
• Work side by side with Product, Engineering, Test/QA, and Operations teams.
• Observe real workflows and identify where AI meaningfully helps.
• Co-create solutions rather than building in isolation.
• Determine which tasks benefit from AI and which should remain human driven.
• Design human in the loop patterns where appropriate.
• Balance judgment, safety, reliability, and speed.
• Identify patterns that consistently deliver results.
• Help converge and scale what works.
• Create lightweight guidance and reusable components without slowing experimentation.

Benefits

• Great benefits package, including a full suite of health benefits, a generous 401(k) Plan, unlimited PTO, paid parental leave, a strong rewards and recognition program, and a focus on mental health and well-being.
• An inclusive environment with Employee Resource Groups to join, volunteering days and the ability to donate to organizations of your choice through our recognition platform.
• The opportunity to work for a growing, established technology company, but work side-by-side with a small, dynamic team of talented professionals.
• Fast-paced environment with big goals and the opportunity to make a big impact.

What This Job Offers

• Job Type: Full-time
• Career Level: Principal
• Education Level: No Education Listed
• Number of Employees: 251-500 employees