Payroll Specialist
About the role
The Opportunity Headway Group is conducting a confidential search for a growing Canadian healthcare organization seeking an experienced, bilingual Payroll Specialist. This is not simply a payroll-processing role. The successful candidate will take dependable, end-to-end ownership of payroll within a geographically dispersed organization growing through acquisition. The immediate priority is to ensure employees are paid accurately and on time while strengthening the controls, processes and service standards required to support continued growth. Reporting to the CFO and working closely with Human Resources, this person will manage payroll for several hundred employees across multiple legal entities and Canadian provinces. The role is fully virtual and requires someone who can work autonomously, exercise sound judgment and collaborate effectively without day-to-day in-person oversight.
What You Will Accomplish in the First Year Establish reliable, end-to-end ownership of payroll across multiple entities and provinces .Ensure employees are paid accurately and on time on every scheduled pay cycle .Reduce payroll errors, corrections and avoidable escalations through stronger validation, controls and follow-through .Provide employees, managers, Human Resources and Finance with timely, clear and professional payroll support .Integrate newly acquired operations and employees into payroll accurately, including successful first-payroll processing .Document and improve payroll calendars, procedures, controls and cross-functional handoffs .Support the implementation, testing, data migration and stabilization of a new payroll and HRIS platform .Provide the CFO and Human Resources with early visibility into payroll risks, recurring issues and matters requiring management decisions
. Key Responsibilitie s Manage the complete payroll cycle for hourly and salaried employees on a biweekly schedul e.Compile, verify and process hours worked, absences, leaves, bonuses, commissions, salary changes, deductions and banking informatio n.Ensure payroll complies with applicable tax legislation, employment standards and company policie s.Process source deductions, remittances, records of employment, garnishments, special leaves and employee departure s.Prepare year-end documentation and government filings, including T4s, Releve 1s and applicable provincial reportin g.Administer vacation, statutory holidays, sick leave, parental leave, incentives, allowances and other leave bank s.Validate group insurance, RRSP, pension and other benefit-related invoice s.Prepare payroll accounting entries and support month-end and year-end processe s.Produce payroll reports and analysis for Human Resources, Finance and senior managemen t.Respond to employee payroll questions with clarity, professionalism and sound judgmen t.Recognize when an issue belongs with Human Resources, Finance or Operations and direct it appropriatel y.Identify and implement practical improvements to payroll processes, tools and control
s. What You Bri ng Payroll experience, ideally in a multi-company and multi-province environme nt.Professional fluency in both French and Engli sh.Strong knowledge of Canadian payroll compliance and the ability to research jurisdiction-specific requiremen ts.Experience participating in payroll or HRIS implementation, conversion or process-improvement initiativ es.Advanced Excel skil ls.Experience with payroll platforms such as EmployeurD, Nethris, Dayforce or A DP.Payroll Compliance Professional designation or related payroll education is a strong ass et.A degree or diploma in accounting, administration or a related fie
ld. How You W ork Highly accurate, organized and dependa ble.Comfortable managing confidential employee informat ion.Able to work independently in a fully remote environm ent.Resourceful when information is incomplete or circumstances are chang ing.Professional and service-oriented when responding to employee questi ons.Comfortable recommending solutions while recognizing when a decision belongs with the CFO, Human Resources or another lea der.Motivated by the opportunity to improve an important operational function rather than simply maintain
it. Why Consider This Opportu nity This is an opportunity to take meaningful ownership of payroll in a growing organization where the work is visible and important. The successful candidate will help strengthen a business-critical function, support the integration of newly acquired operations and contribute to a major payroll and HRIS transi
tion. Confidenti ality This search is being conducted confidentially by Headway Group. The identity of the organization will be shared with qualified candidates at the appropriate stage of the process. Candidates may be asked to sign a confidentiality agreement before receiving identifying inform ation.
About Headway Search Group
At Headway Group, we bring structure and evidence to critical hiring decisions.
We work with entrepreneurial and mid-market organizations: founder-led, owner-managed, private equity–backed, and professionally led teams where leadership hires materially affect performance.
Our focus is simple: • Clarify what the business actually needs • Map and engage the relevant talent market • Qualify candidates before they consume executive time • Support a disciplined, defensible hiring decision
If you view hiring as a strategic lever rather than an administrative task, we should connect.
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Payroll Specialist
About the role
The Opportunity Headway Group is conducting a confidential search for a growing Canadian healthcare organization seeking an experienced, bilingual Payroll Specialist. This is not simply a payroll-processing role. The successful candidate will take dependable, end-to-end ownership of payroll within a geographically dispersed organization growing through acquisition. The immediate priority is to ensure employees are paid accurately and on time while strengthening the controls, processes and service standards required to support continued growth. Reporting to the CFO and working closely with Human Resources, this person will manage payroll for several hundred employees across multiple legal entities and Canadian provinces. The role is fully virtual and requires someone who can work autonomously, exercise sound judgment and collaborate effectively without day-to-day in-person oversight.
What You Will Accomplish in the First Year Establish reliable, end-to-end ownership of payroll across multiple entities and provinces .Ensure employees are paid accurately and on time on every scheduled pay cycle .Reduce payroll errors, corrections and avoidable escalations through stronger validation, controls and follow-through .Provide employees, managers, Human Resources and Finance with timely, clear and professional payroll support .Integrate newly acquired operations and employees into payroll accurately, including successful first-payroll processing .Document and improve payroll calendars, procedures, controls and cross-functional handoffs .Support the implementation, testing, data migration and stabilization of a new payroll and HRIS platform .Provide the CFO and Human Resources with early visibility into payroll risks, recurring issues and matters requiring management decisions
. Key Responsibilitie s Manage the complete payroll cycle for hourly and salaried employees on a biweekly schedul e.Compile, verify and process hours worked, absences, leaves, bonuses, commissions, salary changes, deductions and banking informatio n.Ensure payroll complies with applicable tax legislation, employment standards and company policie s.Process source deductions, remittances, records of employment, garnishments, special leaves and employee departure s.Prepare year-end documentation and government filings, including T4s, Releve 1s and applicable provincial reportin g.Administer vacation, statutory holidays, sick leave, parental leave, incentives, allowances and other leave bank s.Validate group insurance, RRSP, pension and other benefit-related invoice s.Prepare payroll accounting entries and support month-end and year-end processe s.Produce payroll reports and analysis for Human Resources, Finance and senior managemen t.Respond to employee payroll questions with clarity, professionalism and sound judgmen t.Recognize when an issue belongs with Human Resources, Finance or Operations and direct it appropriatel y.Identify and implement practical improvements to payroll processes, tools and control
s. What You Bri ng Payroll experience, ideally in a multi-company and multi-province environme nt.Professional fluency in both French and Engli sh.Strong knowledge of Canadian payroll compliance and the ability to research jurisdiction-specific requiremen ts.Experience participating in payroll or HRIS implementation, conversion or process-improvement initiativ es.Advanced Excel skil ls.Experience with payroll platforms such as EmployeurD, Nethris, Dayforce or A DP.Payroll Compliance Professional designation or related payroll education is a strong ass et.A degree or diploma in accounting, administration or a related fie
ld. How You W ork Highly accurate, organized and dependa ble.Comfortable managing confidential employee informat ion.Able to work independently in a fully remote environm ent.Resourceful when information is incomplete or circumstances are chang ing.Professional and service-oriented when responding to employee questi ons.Comfortable recommending solutions while recognizing when a decision belongs with the CFO, Human Resources or another lea der.Motivated by the opportunity to improve an important operational function rather than simply maintain
it. Why Consider This Opportu nity This is an opportunity to take meaningful ownership of payroll in a growing organization where the work is visible and important. The successful candidate will help strengthen a business-critical function, support the integration of newly acquired operations and contribute to a major payroll and HRIS transi
tion. Confidenti ality This search is being conducted confidentially by Headway Group. The identity of the organization will be shared with qualified candidates at the appropriate stage of the process. Candidates may be asked to sign a confidentiality agreement before receiving identifying inform ation.
About Headway Search Group
At Headway Group, we bring structure and evidence to critical hiring decisions.
We work with entrepreneurial and mid-market organizations: founder-led, owner-managed, private equity–backed, and professionally led teams where leadership hires materially affect performance.
Our focus is simple: • Clarify what the business actually needs • Map and engage the relevant talent market • Qualify candidates before they consume executive time • Support a disciplined, defensible hiring decision
If you view hiring as a strategic lever rather than an administrative task, we should connect.