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 company policy and process documentation updates

• Liaise with internal stakeholders (Talent Experience, Finance) on Colombia headcount changes and compliance questions as they arise.

Benefits & Pension Administration

• Process day-to-day benefit administration: new enrollments, life event updates, and terminations. Liaise with providers for ID cards and coverage confirmations.

• Reconcile monthly invoices against active enrollment data — creating journal entry reports for lead review.

• Support employees with benefit related questions across all countries in partnership with our broker relationships.

• Support leave management (maternity, medical, and other statutory leaves) in partnership with HR and payroll leadership. Assist in coordinating wellness initiatives and tracking participation.

• Maintain employee records and documentation in relevant systems.

• Support new hire and open enrollment logistics (distributing materials, scheduling info sessions).

• Support pension administration including creating and uploading pension contribution files to various providers

• Maintain time off accruals including vacation, borrowing time, time off in lieu management etc. Conduct routine audits and sync between systems.

HRIS & Data and Systems Integrity

• Maintain accuracy and synchronization between Slack, HRIS, payroll, and benefits systems.

• Maintain time off accruals including vacation, TOIL, and borrowed time — conduct routine audits and sync between systems.

• Support in generating requested reports on headcount, payroll costs, benefit utilization, and leave balances.

• Identify process inefficiencies and bring them to the lead before changing how something is done — not after.

• Prepare routine data for government filings (without taking responsibility for submission).

• Assist in gathering data for audits and internal reviews.

• Identify process inefficiencies, issues, or concerns and work with HR and Payroll/Benefits leadership in improvement implementation

Required Qualifications

• Diploma or post-secondary degree in Human Resources, Accounting, Payroll, Business Administration or related field.
• 3–5 years of direct experience in full-cycle payroll, benefits and pension administration across Canada and the US.

• Working knowledge of payroll legislation, tax compliance, and employment standards across Canadian provinces and US states.
• Experience using payroll/HRIS systems (e.g., ADP, BambooHR, or similar).
• Experience with communications systems such (ex. Slack and Sharepoint)

Assets

• Obtained or working towards Payroll Compliance Practitioner (PCP) designation (or equivalent) not required but considered an asset.
• High attention to detail, accuracy, and organization.
• Strong analytical and problem-solving abilities.
• Excellent interpersonal and customer service skills -- leading with empathy and support.
• Proactive communication — you flag errors the same day you find them, you confirm completions without being asked, and you raise process questions before making changes, not after.

• Process discipline — you follow documented processes until there's a reason to change them, and you have that conversation first.
• Discreet and professional in handling sensitive payroll and employee data.
• Ability to manage competing deadlines and maintain composure under pressure.
• Strong technical proficiency in Excel
• Collaborative mindset with a willingness to support cross-functional teams.

Where this role goes

As the function matures and integrations come online, the administrator who built their knowledge on the manual process becomes the subject matter expert on what the automation needs to replicate — and what it needs to do better. This is a role that grows with you. The ceiling is your curiosity.

Originally posted on Himalayas