Job Description
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
At PlanSource, benefits are at the core of what we do, and we understand their impact on our employees and their families. That’s why we’ve designed our benefits program to support overall wellbeing across health, financial security, career growth, and work‑life balance.
- Comprehensive health coverage with multiple medical plan options - all covering 100% of in-network preventive care.
- Employer‑funded Health Savings Account (HSA) - up to $1,000 annually for family coverage.
- Dental & Vision plans with 100% coverage for routine dental care and $250 vision frame allowance, plus employee-only vision premiums at $0.
- 401(k) with immediate vesting and a 50% company match up to 6% of contributions.
- Generous paid parental leave, adoption assistance, and fertility benefits.
- Flexible PTO, paid holidays, a strong culture of work‑life balance and Flex Fridays in the summer.
- Mental health & wellbeing support, including Employee Assistance Program (EAP), movement and wellness resources.
- Rewards and recognition programs that celebrate employees through peer recognition, awards, and quarterly recognition initiatives.
Top 5 Reasons to join PlanSource
#5: Be part of what’s next in benefits technology
Join a company redefining how benefits work. Backed by Vista Equity Partners, PlanSource is continuously investing in innovation, bringing together AI, automation, and human insight to simplify complex processes and deliver real outcomes. This is your opportunity to build the future of benefits at scale.
#4: Make an impact with technology our customers trust
Our platform powers some of the most complex benefits programs in the market, and our customers rely on us to get it right. From a unified benefits ecosystem to AI-driven decision support, everything we build is designed to deliver clarity, confidence, and measurable impact for the people who use it every day.
#3: Be recognized, supported, and set up to thrive
We believe great work deserves recognition and real support. From meaningful rewards and recognition programs to a comprehensive approach to employee support, we invest in helping our people perform at their best and feel valued along the way.
Recognized as a top workplace, PlanSource has earned multiple Great Place to Work certifications and numerous awards, including Best Company for Culture, Work-Life Balance, and Compensation, reinforcing our commitment to an exceptional employee experience.
#2: Grow your career with intention
At PlanSource, career growth doesn’t happen by accident. With a strong track record of internal mobility, structured development paths, and opportunities to take on new challenges, you’ll have the support and flexibility to build a career that evolves with you.
#1: Be part of a culture built on connection and impact
Our culture is rooted in connection, inclusion, and shared success. Guided by our S.O.U.R.C.E. values, we lead with service by putting others first, approach challenges with optimism, and act with urgency to drive meaningful outcomes. We hold ourselves accountable through reliability, continuously grow through curiosity, and operate with efficiency to maximize the impact of our work. Here, diverse perspectives are valued and they directly shape how we collaborate, innovate, and deliver an exceptional experience for our customers.
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.
REF 4815
Other similar titles: AI Engineer – Productivity Applied AI Engineer - AI Systems Engineer - AI Automation Engineer - AI Workflow Engineer
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.
At PlanSource, benefits are at the core of what we do, and we understand their impact on our employees and their families. That’s why we’ve designed our benefits program to support overall wellbeing across health, financial security, career growth, and work‑life balance.
- Comprehensive health coverage with multiple medical plan options - all covering 100% of in-network preventive care.
- Employer‑funded Health Savings Account (HSA) - up to $1,000 annually for family coverage.
- Dental & Vision plans with 100% coverage for routine dental care and $250 vision frame allowance, plus employee-only vision premiums at $0.
- 401(k) with immediate vesting and a 50% company match up to 6% of contributions.
- Generous paid parental leave, adoption assistance, and fertility benefits.
- Flexible PTO, paid holidays, a strong culture of work‑life balance and Flex Fridays in the summer.
- Mental health & wellbeing support, including Employee Assistance Program (EAP), movement and wellness resources.
- Rewards and recognition programs that celebrate employees through peer recognition, awards, and quarterly recognition initiatives.
Top 5 Reasons to join PlanSource
#5: Be part of what’s next in benefits technology
Join a company redefining how benefits work. Backed by Vista Equity Partners, PlanSource is continuously investing in innovation, bringing together AI, automation, and human insight to simplify complex processes and deliver real outcomes. This is your opportunity to build the future of benefits at scale.
#4: Make an impact with technology our customers trust
Our platform powers some of the most complex benefits programs in the market, and our customers rely on us to get it right. From a unified benefits ecosystem to AI-driven decision support, everything we build is designed to deliver clarity, confidence, and measurable impact for the people who use it every day.
#3: Be recognized, supported, and set up to thrive
We believe great work deserves recognition and real support. From meaningful rewards and recognition programs to a comprehensive approach to employee support, we invest in helping our people perform at their best and fee