Payroll & Benefits Administrator

Robots & Pencils is an applied AI engineering firm building the next frontier of business architecture. We design and ship AI co-workers that integrate into enterprise operations and deliver measurable results for our clients. We're all in on AWS, combining deep UX capability with senior engineering talent to get AI into production fast and keep it there. 
We’ve earned the trust of leaders across Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, and Manufacturing and more, and earned a reputation as the nimble alternative to traditional global systems integrators. Founded in 2009, with delivery centers in Canada, the United States, Eastern Europe, and Latin America, we are smaller, faster, and more senior by design. Our teams average 15+ years of experience. We move fast, sweat the details, and build things that actually ship. 

Position Overview 

We're looking for a Payroll & Benefits Administrator to keep semi-monthly payroll accurate and on time across Canada and the U.S. You'll own the day-to-day mechanics of the job — entering and verifying employee data in the HRIS and payroll systems, processing benefits and pension transactions, and staying compliant across multiple jurisdictions — plus the reporting, reconciliations, and year-end filings that keep the business audit-ready. 

You'll report to the Payroll & Benefits Manager, North America, and work closely with the Talent (HR) Manager, Talent Engagement Specialist, IT, and Finance. This role is remote-first and detail-heavy — you'll manage a high volume of sensitive data without losing accuracy, and you'll do well here if you're precise, discreet, and energized by making a fast-moving payroll operation run cleanly. 

Why This Role Matters 

At Robots & Pencils, we design AI systems for a human world. Our name says it all. Robots and pencils means engineering paired with creativity, because every agent we ship has to work for real people in real workflows. That balance is baked into how we operate. 
 
Every role here contributes directly to that mission. Here, you shape how AI systems integrate into enterprise operations, how teams move at real velocity, and how products create measurable impact for clients and the people they serve. We ship production-ready AI in 30 to 45 days. That pace demands people who take ownership, lead with craft, and care deeply about what they put their name on. 

What You’ll Do 

Craft & Delivery 

• Enter and verify employee data changes in the HRIS/payroll system — new hires, terminations, address changes, direct deposit details, and tax forms 

• Coordinate and administer semi-monthly payroll for salaried and hourly employees across Canada and the U.S., ensuring accuracy and compliance with local laws 

• Run pre-payroll reports for regular and off-cycle payrolls, and prepare termination documentation, for review by the Payroll & Benefits Lead 

• Validate timesheets and hours worked, and run routine payroll reconciliations to catch missing hours or duplicate entries 

• Prepare annual tax documents (T4s, W-2s, ROEs) and support year-end reporting, journal entries, and payroll tax reconciliation across both countries 

• Process benefits and pension transactions — new enrollments, life event updates, terminations — and support pension contribution file uploads to providers 

• Balance and reconcile benefit invoices for Canada and U.S. group plans, and maintain time-off accrual accuracy through routine audits and system syncs 

• Maintain accurate, synced employee and compensation data across HRIS, payroll, and benefits systems, and generate regular headcount, cost, and leave reporting 

Collaboration & Communication 

• Respond to employee payroll and benefits inquiries promptly and professionally, escalating complex issues to the Payroll & Benefits Lead when needed 

• Liaise with benefits providers on day-to-day requests — ID cards, coverage confirmations — and support wellness program communications and participation tracking 

• Support new hire and open enrollment logistics, and partner with HR and Payroll/Benefits leadership on leave management, including maternity and medical leave 

• Prepare responses to Unemployment Insurance requests and support workers' compensation reporting, filings, and audits in both Canada and the U.S. 

Leadership & Influence 

• Flag process inefficiencies and gaps as you find them, and work with HR and Payroll/Benefits leadership to fix them 

• Maintain strict confidentiality and data-privacy discipline as the person closest to sensitive payroll and benefits data 

• Support audits and internal reviews by pulling accurate, well-organized data on request 

 

What You’ll Bring 

• Diploma or degree in Human Resources, Accounting, Payroll, Business Administration, or a related field 

• 3–5 years of hands-on payroll and benefits administration experience, ideally spanning both Canada and the U.S. 

• Working knowledge of payroll legislation, tax compliance, and employment standards in Canadian and U.S. jurisdictions 

• Experience with payroll/HRIS systems such as ADP or BambooHR, and full-cycle payroll processing 

• Experience administering benefits, wellness programs, and pension plans 

• High attention to detail and strong reconciliation instincts — you catch the missing hour and the duplicate entry before anyone else does 

• Discretion and professionalism handling sensitive payroll and employee data 

• Strong Excel skills and comfort working across HR and payroll systems 

• Ability to manage competing deadlines and stay composed under pressure 

 

Helpful Extras and Unique Skills 

• Payroll Compliance Practitioner (PCP) designation, obtained or in progress 

• Experience with Slack and SharePoint, including Slack workflow builder 

 

You’ll Do Well Here if You Are 

• A doer. You see something broken and fix it. You'd rather move on clarity than wait for certainty. 

• A fast learner who knows you don't know everything. The AI landscape changes weekly. You're senior enough to know better and curious enough to keep learning anyway. 

• Direct in a way that makes the work better. You give honest feedback. You'd rather have the hard conversation than blow smoke. 

• Obsessed with craft. You know genius is in the details. You ship exceptional, not perfect, and you don't put your name on work you wouldn't stand behind. 

• Built for ownership. You honor commitments, admit mistakes fast, and back your teammates when a decision costs something. No handoffs, no finger-pointing. 

• All in. You treat clients' businesses like your own. You take the work seriously without taking yourself seriously. 

• Resourceful when the budget, timeline, or team is tight. Constraints don't slow you down. They sharpen you. 

• Glad to be in the room with people who care as much as you do. Our teams average fifteen-plus years of experience. We hire people who push each other to do better work.