Principal AI Productivity Engineer

Summary

Join Us at PlanSource: Your Exciting Career Awaits!

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.

 

What You’ll Do

Build First, Iterate Constantly

• 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.

Partner Across Product, Technology, and Operations

• 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.

Apply AI Pragmatically

• 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.

Standardize After Value Is Proven

• Identify patterns that consistently deliver results.
• Help converge and scale what works.
• Create lightweight guidance and reusable components without slowing experimentation.

In Your First 30 Days, You Would Have…

• Embedded directly with Product, Engineering, Test, and Operations teams to understand real workflows.
• Identified multiple high leverage opportunities for AI acceleration.
• Built and released at least one AI agent or automation used in live workflows.
• Partnered closely with principal engineers and domain leaders already experimenting with AI.
• Established a weekly build release learn cadence.
• Begun to surface early signals of measurable productivity gains.

In Your First 90 Days, You Would Likely…

• Be shipping AI powered workflow improvements weekly across multiple functions.
• Help teams reclaim meaningful time from repetitive or low leverage work.
• Increase adoption of Claude and agentic workflows without becoming a bottleneck.
• Establish a clear roadmap for expanding impact through nearshore and/or offshore support roles.

About You

Required

• 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 Have

• 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.

What This Role Is Not

• Not a research or model training role.
• Not a pure architecture or standards first role.
• Not a program management or advisory role.

This role exists to build, deploy, and iterate on AI powered workflows that deliver real productivity gains.

 

Why This Role Matters

AI is becoming a structural advantage - or disadvantage - based on how effectively it is embedded into real work. This role exists to continuously increase throughput and efficiency across the company without increasing headcount.

What We Offer

• 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.

Top five reasons to come to PlanSource:

 

#5: Join the Vista Family. In March 2019, Vista Equity Partners acquired PlanSource, marking a new phase of growth. Vista’s portfolio of technology and software companies collectively make up the 4th largest software ecosystem in the world.

 

#4: PlanSource is highly rated with our customers. Be proud of our sophisticated cloud-based technology that meets the needs of even the most complex benefit programs.

 

#3: Success is rewarded. With more than just a pat on the back, your success is recognized and rewarded. We take care of our employees in every way we can, with comprehensive benefits, employee recognitions, and a commitment to wellbeing.

 

#2: You can grow and develop professionally. PlanSource has a great track record of internal promotions within the company and offering development plans and tracks to pursue your personal and professional goals.

 

#1: Share our values. Be part of a team that values diversity and representation in all levels of the organization. Be part of a team that gives back to local communities and is actively aware of their social and environmental impact.

PlanSource is committed to fostering, cultivating, and preserving a culture of diversity and inclusion. Our employees are the most valuable asset we have. The collective sum of the individual differences, life experiences, knowledge, inventiveness, innovation, self-expression, unique capabilities and talent that our employees invest in their work represents a significant part of not only our culture, but our reputation and company’s achievement as well.

 

We celebrate and support our employees’ diversity in age, color, disability, ethnicity, cultural beliefs, family or marital status, gender identity or expression, language, national origin, physical and mental ability, political affiliation, race, religion, sexual orientation, socio-economic status, veteran status and other characteristics that make our employees unique.

 

NOTE: We will consider a remote employee for approved cities PlanSource can accommodate.

 

If you’re selected, you’ll receive your offer and be asked to complete a background check. This will include a drug screen, criminal record search and verification of previous employment and/or education.

 

Recruiting Scams: Unfortunately, scams targeting job seekers are common. To protect our candidates, we want to remind you that authorized representatives of PlanSource will only contact you from an email address ending in @plansource.com.  PlanSource will never ask for personally identifiable information such as Date of Birth (DOB), Social Security Number (SSN), banking/direct/tax details, etc. via email or any other non-secure system, nor will we instruct you to make any purchases related to your employment. If you believe you’ve encountered a recruiting scam, report it to the Federal Trade Commission and your state’s Attorney General.

 

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