Manager of Payroll and Benefits (Global)

TAKE YOUR CAREER TO NEW HEIGHTS WITH the company! 🚀✨

The company is seeking a global Manager of Payroll and Benefits to ensure the accurate and timely payment of our employees and the effective administration of our benefits programs across all of our regions. In this role, you will own the payroll and benefits function end to end, with the autonomy to manage day-to-day execution in a fast-paced, AI-forward environment. You will champion a positive employee experience and support and promote our competitive total rewards strategy.

You will report to the Chief People Officer and work closely with the Senior Director of Finance. As a member of the People team, you will at times work closely with Sales and Revenue Operations, especially for Variable compensation planning.

We run payroll in-house for employees in Canada, India, the UK and the US. You will have a strong working knowledge of payroll processing and statutory compliance in each of these jurisdictions, including tax withholding, remittances, and year-end reporting.

Note: This is an existing vacancy on the team

💻 WHAT YOU’LL BE DOING

• Payroll

• Prepare, process and review payroll accurately and on time for employees in Canada, the UK, India and the US, in line with the regulations of each country

• Own and manage payroll operations end to end across all four jurisdictions, including pay calendars, data changes, off-cycle payments, terminations and final pay

• Resolve pay issues quickly and handle sensitive conversations with employees and leaders with care and discretion

• Own statutory remittances, filings and year-end reporting in every jurisdiction, including: Canada: CRA remittances, T4s and ROEs, provincial requirements such as Ontario EHT and workers’ compensation

• UK: PAYE and National Insurance, HMRC Real Time Information (RTI) submissions, P60s, and workplace pension auto-enrolment

• India: TDS and quarterly returns, Provident Fund, ESI, Professional Tax and Form 16

• US: federal, state and local withholding, payroll tax deposits and quarterly filings, W-2s, and state unemployment

• Ensure we meet every deadline and statutory obligation in each jurisdiction, and manage any government notices, registrations and audits

• Complete and make all Commission and variable compensation plan calculations and payments (monthly and quarterly)

• Benefits

• Oversee the day-to-day administration of our health and benefits plans, including enrolments, carrier invoices and reconciliations, and renewals with our broker

• Be the go-to expert for People Operations and employees on benefits questions, and provide a great Looper experience

• Month-end close and variable compensation

• Prepare and post payroll, bonus and commission accruals and other compensation and benefits journal entries each month

• Reconcile payroll and benefits activity to the general ledger, across currencies and entities

• Calculate variable compensation plans and commission accruals monthly, working closely with Sales and Revenue Operations

• Reporting

• Prepare monthly, quarterly and annual payroll and benefits reporting for People, Finance and GTM leaders (including ad hoc reports)

• Controls, compliance and audit

• Establish and maintain controls, payroll guidelines and procedures that keep us compliant with payroll and employment legislation

• Support quarterly reporting and annual audit requests from external auditors

• Stay current on changes to payroll legislation and tax law, and act on them before they affect our people

• Continuous improvement

• Look for ways to simplify and automate processes and reporting, including where AI can improve accuracy and speed

• Create an updated Payroll & Benefits playbook, and contribute to various dashboards across People ops, Finance and at times other teams.

• Take on ad hoc accounting projects and requests as needed

• Ensure data is kept up to date for all Loopers on our internal sites and for all New Hires

✨ WHAT YOU’LL BRING TO THE TEAM

• Must have

• 7 years of experience managing payroll and benefits with global exposure/experience (Canada, ideally with exposure to India, UK and US)

• Tech industry experience, preferably in

• A Canadian Payroll Association designation (PCP or CPM) and up-to-date knowledge of Canadian payroll legislation and tax law

• Experience with calculating and paying commissions and variable compensation

• A thorough understanding of compensation and benefits regulations in Canada

• Hands-on experience with month-end close, journal entries, accruals and supporting external audits

• Advanced Google Sheets or Excel skills

• Experience calculating commissions and variable compensation in a SaaS or sales-led business

• Strong written and verbal communication, and the relationship skills to manage difficult conversations with empathy, honesty and confidentiality

• The ability to meet deadlines in a fast-paced environment without sacrificing accuracy

• Curiosity about using automation and AI to improve payroll and reporting processes

• Nice to have / Preferred experience

• Experience with Dayforce, BambooHR, and Deel

• Working knowledge of payroll and benefits requirements in the UK, US and India, or experience managing them through EOR and vendor partners

WHERE YOU’LL WORK 📍

• We are currently looking only for candidates who live in the Greater Toronto Area and surrounding areas, where you can access our co-working space in Downtown Toronto for the occasional Team get-together.

• the company is a remote-first workplace because we recognize the advantages of working flexibly. We are HQ’d in Canada, with established hub regions around the world where we hire from.

• Our employees (or Loopers, as we call ourselves!) live and work in 🇨🇦 Canada (British Columbia and Ontario), 🇺🇲 US, 🇮🇳 India (specifically in Gujarat, Maharashtra, and Bengaluru), and 🇬🇧 London.

• The majority of our team is based in ON and BC, which means these employees live and work remotely within a 300km radius of Toronto (within Ontario) and Vancouver (Within BC).

• We offer flexible co-working locations available to Loopers in ON and BC. Those based in ON have the option of working out of our convenient co-working space located in the heart of Downtown Toronto and a 12-minute walk from Union Station. BC Loopers have the option to work centrally in Vancouver. It is whatever works best for you!

• You’ll collaborate with your teams virtually across the UK, India, and North America (we’re just a Zoom call and Slack message away!) with core sync hours and focus time for headsdown work 🙇🏾 during the workday

• We encourage asynchronous collaboration to effectively work as a global #OneTeam!

WHY YOU’LL ♥️ WORKING AT the company

• Your manager supports your development by providing ongoing feedback and regular 1-on-1s, we leverage Lattice [link for members] for our 1:1s and performance conversations

• You will have the opportunity to elevate 🪄 your craft and the opportunity to explore your creativity, with a dedicated professional mastery allowance for more learning support! We encourage experimentation and innovative thinking to drive business impact.

• We offer a wide range of health and wellness benefits [link for members] to support your physical and mental well-being, starting day 1️⃣ with the company.

• We’ll set you up to work remotely with a MacBook laptop 🍏, a monthly phone and internet subsidy, and a work-from-home budget to help get your home office all set up.

• We’ll give you a Claude account to experiment with, automate your routine tasks, and build tools so you can work smarter every day.

• You’ll be joining a supportive culture that has thoughtfully built out opportunities for connections in a remote first environment.

• Participate in 🎤 townhalls, AMA (Ask-Me-Anything), and company celebrations to celebrate the big wins and milestones as #oneteam!

• Our four Employee Resource Groups [link for members] offer opportunities for employees to learn and connect year-round.

• You’ll be a part of an award-winning workplace 🏆with an opportunity to make a big impact on the business.

Questioning your qualifications? Read this ‼️ Hi there, we recognize that all too often, potential candidates don’t apply for a position simply because they don’t hit every single criteria included in the job description—particularly members of underrepresented groups.

Whether or not your experience ✅ checks off all the boxes on a job posting, we still encourage you to apply to ensure that your application receives a review from our team. We understand that a resume can only showcase so much during the applicant stage, so we've created prompts in the application for you to share more about yourself. If you've made a career transition (or a few!), you’re self taught in a new role, or you have skills/experience you’d like to highlight, we want to hear more about what you could bring to the table.

AI in Recruitment 👩🏻‍💻 At the company, we leverage  artificial intelligence (AI) technology to enhance our recruitment process. These tools assist with tasks such as resume screening, drafting preliminary job descriptions, generating initial interview questions, transcription and occasionally sourcing prospective candidates. However, AI is never used to make final hiring decisions; our use of AI  serves to support repetitive and administrative tasks in order to streamline our hiring and recruitment workflows. We are committed to the responsible use of AI in our hiring practices, prioritizing both  an improved candidate experience and operational efficiency. Our standardized hiring practices remain focused on reducing biases, with all key hiring decisions  solely made by our team. We continuously review and refine our hiring practices to align with  industry best practices and evolving legal guidelines

AI Usage in Interviews 🤖 The company interview process is designed to help us better understand your professional experiences, as well as your unique perspective and approach to delivery and collaboration. To ensure a fair and accurate assessment, we expect candidates to refrain from using AI-generated content to produce responses to our interview questions during the live interview, as our goal is to evaluate your own knowledge and problem-solving abilities - not those of an AI assistant. If AI-generated responses are identified during the interview, the company reserves the right to disqualify candidates from the interview process.

For specific roles that include a take-home assignment, our AI Interviewee Policy allows the use of AI for initial support; however, the final submission must be a true reflection of your personal insights, skills and decision-making.

The company is an equal opportunity employer that is deeply committed to building equitable workplaces that are diverse and inclusive. We actively encourage candidates from all backgrounds and lifestyles to consider us as a future employer. Please contact a member of our Talent Experience team [link for members] should you require accommodations at any point during our virtual interview processes.