Payroll & Benefits Administrator

Robots and Pencils is a global AI-first technology company with employees and contractors across Canada, United States, Colombia, and Ukraine. We run payroll and benefits across two ADP environments, multiple benefits platforms, and a set of manual processes that connect them — because the integrated system we're building toward isn't fully there yet. This role is for someone who wants to understand how everything works deeply, own it end-to-end, and be part of building the automated, integrated environment that makes this function scalable. If you want to join a function where the work is already solved, this isn't it. If you want to be the person who helps solve it — read on. Why This Role What you'll build toward We're moving toward a fully integrated payroll and HRIS environment. The person in this role will help design and test the workflows that make that possible — and when integration arrives, your deep knowledge of the manual process is what makes you the expert on whether it's working. What you'll learn right now You'll touch every system — ADP Canada, ADP US, Employee Navigator, Empower, Canada Life, BambooHR/Rippling, Harvest, and more. Understanding how data flows between them manually means you'll instinctively know what to automate first and why. The honest environment This is a manual-intensive role today. Data flows between systems are largely handled by hand — which means you'll develop an unusually deep understanding of where the work actually lives and what breaks when something goes wrong. When integration arrives, you'll be the person who knows the process better than anyone — and that's a career-defining position to be in. What You'll Own This is an ownership role, not a support role. You will be responsible for end-to-end execution across the following areas — and for flagging proactively when something isn't working so we can fix it together. North American & Colombia Payroll You will own payroll across three jurisdictions — Canada, the United States, and Colombia. Canada and the US are established and running. Colombia is newer, currently owned entirely by the Payroll & Benefits Manager, and will transition to this role as you build familiarity with the environment. This is an opportunity to grow into genuinely global payroll ownership. Process semi-monthly payroll in ADP Canada (multiple provinces) and ADP US (23+ states) — entering all changes, running pre-payroll reports, validating entries, ensuring accuracy and compliance with local laws and submitting for lead review. Manage all manual data entries across both countries: new hires, terminations, address changes, salary changes, direct deposit updates, and off-cycle adjustments. Prepare ROEs within CRA timelines. Support T4, W-2, and year-end compliance including the annual data audit reconciling BambooHR/Rippling and ADP. Assist with account setup for new US states — registering accounts, saving credentials, configuring in ADP. Support government agency responses: UI requests, workers compensation filings, SUI accounts, and CRA/IRS correspondence. Assist with collecting and validating timesheets/hours worked. Support routine payroll reconciliations (checking for missing hours, duplicate entries, etc.). Support routine payroll reconciliations (checking for missing hours, duplicate entries, etc.). Generate standard payroll reports, including the creation of journal entry reports for review by the Payroll & Benefits Lead. Respond to employee payroll-related inquiries promptly and professionally. Colombia — Transitioning to This Role Colombia is our newest payroll jurisdiction, currently managed entirely by the Payroll & Benefits Manager. As you settle into the role and develop confidence in the Canada and US environments, Colombia will transition to you. Learn and take ownership of Colombia payroll processing — cycle, platform, and compliance requirements to be documented as part of onboarding. Manage Colombia-specific holiday and PTO time Support…