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Apply Digital

Bespoke digital strategy, design, development

Payroll & Rewards Operations Lead

Full-TimeUpdated on 10/23/2026
CA$105k - CA$125k/yr
Senior
Toronto, ON, Canada
HybridHybrid work; preferred candidates are based in the Greater Toronto Area and work hours aligned to Eastern Time.
People & HRHR Operations & Coordination, Compensation & Benefits

About the job

Requirements
  • At least 7 years of progressive experience in Payroll and People Operations, including at least 3 years at a lead level within a fast-growing, global organization.
  • Experience with payroll in Canada and the United States; experience in the United Kingdom and Chile is an asset.
  • A proven track record of managing and supporting finance and payroll audits, ensuring accurate general ledger reconciliations and full audit readiness.
  • Proven experience administering payroll and total rewards across the employee lifecycle for a global employee base, including compliance, benefits, and leave management.
  • Ability to evaluate business opportunities and risks, make sound decisions independently, and communicate with stakeholders.
  • Expert-level administration experience with HiBob, strongly preferred, or a comparable modern global HRIS such as Workday, Rippling, or BambooHR, including building complex workflows and automations.
  • Advanced proficiency with spreadsheets, including VLOOKUPs, Pivot Tables, and Index/Match, and experience translating raw HR data into dashboards and executive insights; Google Sheets is preferred.
  • Experience managing sensitive payroll escalations or complex leave and benefits cases with empathy and discretion.
  • A compliance and audit mindset, with strong attention to detail to identify anomalies and investigate root causes ahead of audit cycles.
Responsibilities
  • Oversee day-to-day payroll administration and processing, advising People & Culture Leads on lifecycle events with complex payroll implications.
  • Take accountability for payroll compliance and accuracy by validating inputs and outputs across Canada, the United States, the United Kingdom, Chile, and employer-of-record arrangements before each payroll cycle.
  • Provide backup payroll processing coverage to ensure uninterrupted, on-time payroll.
  • Monitor and improve data quality and speed when generating new employee profiles to trigger HRIS onboarding processes seamlessly.
  • Partner with Finance on monthly general ledger reconciliations and accurate accruals and cost forecasting for payroll- and benefits-related expenses.
  • Collaborate on month-end close reporting, provide variance analysis, and resolve discrepancies.
  • Serve as a subject matter expert across global benefits programs in Canada, the United States, the United Kingdom, and employer-of-record arrangements; interface with benefits brokers, manage renewal dates, produce regular reporting, and execute reconciliation processes.
  • Manage employee health benefits and retirement plan administration.
  • Collaborate with the People & Culture Director to evaluate benefit plan composition, utilization, and renewal strategies.
  • Own total rewards communication and employee education programs to drive awareness and engagement.
  • Serve as the tier-2 escalation point for employee inquiries, resolving complex or sensitive issues.
  • Collaborate with People & Culture Leads to initiate, manage, and track leaves of absence in line with global policy and compliance requirements.
  • Support recurring pay equity analysis in partnership with the People Operations Lead.
  • Manage the day-to-day relationship with Deel, holding the vendor accountable for product enhancements and support levels.
  • Monitor day-to-day HiBob and Deel administration performed by People Operations Specialists, including regular data-quality audits and ongoing system-integrity monitoring.
  • Design and build HiBob and Deel workflow enhancements, administer complex edge-case scenarios, and use system data to deliver actionable business insights to leadership.
  • Support audit readiness and respond to internal and external audit requests with accurate, timely documentation.
  • Partner with People Operations and cross-functional teams to identify, design, and implement AI-enabled automations, such as using Claude, to streamline payroll, benefits, and HRIS processes, reduce manual effort, and improve data accuracy.
  • Own the development and tracking of key People & Culture metrics, creating dashboards and data models that turn raw HRIS data into strategic analytics and insights for the global team.
Desired Qualifications
  • Experience in the United Kingdom and Chile for payroll.
  • HiBob administration experience is strongly preferred; alternatively, experience with a comparable modern global HRIS such as Workday, Rippling, or BambooHR.
  • Google Sheets experience.
  • Fluency in Spanish.
  • Experience working in a global People & Culture team supporting workers across many countries.
  • Familiarity with employer-of-record models and tools such as Deel, Remote, or Oyster.
  • Exposure to DEI, wellness, or internal communication initiatives.
  • Hands-on experience using generative AI tools such as Claude to build or improve workflows, reporting, or process documentation.

About the company

Apply Digital partners with global brands to plan, design, and build custom digital solutions, offering digital strategy, product design, and development plus ongoing support. It assembles cross-functional teams across multiple offices to guide projects from strategy through execution and maintenance, delivering bespoke digital products tailored to client goals. The company stands out through a culture of inclusion, continuous learning, and experienced leadership, focusing on outcomes-driven, tailored solutions rather than one-size-fits-all tools. Its goal is to help global brands thrive in the digital landscape by delivering practical, user-friendly digital products and experiences that drive client success and business impact.

Company Size

51-200

Company Stage

Private

Total Funding

N/A

Headquarters

Vancouver, Canada

Founded

2016

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Simplify's Take

What believers are saying

  • Google named Apply Digital a Cloud Service Partner on September 22, 2026.
  • Kraft Heinz's TasteMaker and a 100-brand CPG deployment validate repeatable ROI.
  • Apply Digital added a sports league, entertainment company, and US airline in March 2026.

What critics are saying

  • Apply Digital still sells services; Salesforce, Accenture, and Publicis compress margins.
  • TORQ AI and ACx face fast imitation from Google Cloud partners by 2027.
  • If clients insource agentic delivery, Apply Digital loses its core advisory and build moat.

What makes Apply Digital unique

  • March 17, 2026 CEO Ali Alkhafaji brings Omnicom AI leadership and enterprise transformation credibility.
  • April 16, 2026 TORQ AI runs on clients' Google Cloud and ships in 30 days.
  • Ragnarok's March 6, 2025 acquisition deepened personalization, MarTech, and omnichannel marketing capabilities.

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Benefits

  • Remote Work Options
  • Hybrid Work Options
  • Home Office Stipend
  • Unlimited Paid Time Off
  • Health Insurance
  • Dental Insurance
  • Professional Development Budget
  • Conference Attendance Budget
  • Parental Leave

Company News

PR Newswire
Sep 16th, 2026
APPLY appoints Adam Steingart as global general manager of entertainment

APPLY has appointed Adam Steingart as Global General Manager, Entertainment. The Vancouver-based Agentic Customer Experience partner, backed by Interlock Equity, brought on the former GameSquare executive to lead its strategy across sports, media, the creator economy and live experiences. Steingart brings over 20 years of experience in content, media and partnerships. Most recently, he served as Head of Commercial Strategy and Business Development at GameSquare Holdings. He previously led revenue and brand partnerships for NBA Take-Two Media and spent nearly two decades at Paramount in senior leadership roles. APPLY works with brands including Kraft Heinz, Coca-Cola, Arc'teryx, Lululemon and Wynn, combining creativity, data and AI to build digital products and platforms.

PR Newswire
Jun 17th, 2026
APPLY appoints Jacquelyn Baker as global GM to lead agentic customer experience practice for consumer brands

APPLY, an agentic customer experience partner backed by Interlock Equity, has appointed Jacquelyn Baker as global general manager of its consumer practice covering CPG and retail. Baker brings over 20 years of experience in commerce marketing, retail media and omnichannel strategy. Most recently founder of her own consultancy, Baker previously served as global CEO of Omnicom Commerce, leading a team of over 700 people. She has also held leadership roles at VML, Rockfish Digital and other agencies, working with major consumer brands. The appointment follows APPLY's recent announcement of its agentic customer experience model, which uses AI systems to deliver adaptive, continuously evolving customer experiences. Baker will guide consumer brands through transitioning from traditional digital transformation to agentic-powered experiences across retail and CPG sectors.

MarTech360
May 21st, 2026
Apply launches ACx agency model to help brands navigate the agentic AI era.

Apply launches ACx agency model to help brands navigate the agentic AI era. Apply's digital consulting business, Apply, has launched its ACx offering, which is an innovative approach that has been specially created for what Apply terms as the "agentic era." This refers to the current time when AI applications are not simply becoming helpers but rather agents that can take decisions and perform workflows by adapting the customer experience at any point in real time. As per the information provided, ACx is designed to enable brands to move beyond traditional digital experiences to those which have the capability to learn from changing customer behavior. As mentioned by Apply, the model would assist in various consulting, transformation, and experience design initiatives in retail, sports, entertainment, enterprise, and consumer domains. The firm explains that ACx is an approach whereby organizations can be enabled to develop "continuously adaptive customer experiences" through the use of AI agents as opposed to depending on marketing campaigns only. The approach is not focused on treating the customer's interaction as a single event but seeks to design a system that can adapt and optimize itself. The release comes at a time when there are many changes taking place in the advertising and marketing industry. In the past ten years, companies have spent significant resources on technologies such as automation, customer data platforms, personalized engines, and predictive analysis. But now, the introduction of agentic AI means that Martech360 will have an entirely new layer of operations. Agentic AI is being characterized by industry experts not only by their ability to respond to prompts but also by the capability to achieve set objectives autonomously using reason, planning, tool utilization, and action. Such AI applications incorporate memory, decision-making, and workflow management functions, enabling them to function independently from other AI assistants. In terms of advertising and marketing, the launch of ACx by Apply shows the increasing relevance of the development of an organization that is built for an ecosystem where artificial intelligence will play the role of connecting with customers. Traditionally, digital marketing has been about winning customer attention, which has involved media buying, content creation, and channel optimization. With the advent of the agentic age, this might change. Such a change would radically alter the way agencies function. Traditionally, agencies have focused on the creation of campaigns, creative processes, media strategies, and customer acquisition efforts. As automation starts to handle many operations-related functions, it is likely that agencies will transform into masters of intelligent customer systems that can constantly adapt to changing user attitudes and behaviors. The ACx paradigm represents this shift through the creation of customer experience not as a static design process but as an ever-evolving, AI-driven infrastructure layer. Companies today have begun looking for solutions that can help them personalize the experience, engage customers, and provide contextually relevant interactions at all stages of their journey. Marketers need to be aware that the future of customer engagement will likely become much more autonomous and predictive. In fact, AI-powered agents might eventually handle all these processes in an automated manner without any human involvement at all. There are significant ramifications of this for companies that function within the realms of advertising, martech, and customer experience. Such firms will find themselves needing to reassess their technology platforms and business processes in light of having to support AI-native interaction paradigms. Organizations that have been set up in the context of fragmented marketing technologies will find themselves at a disadvantage. The new launch also underscores the increasing convergence between consulting organizations, creative agencies, and AI platform providers. The distinctions between strategic planning, technological implementation, and action planning are rapidly diminishing with the widespread adoption of AI in nearly every facet of digital engagement. Creatives who are able to combine their creative talents with AI orchestration will be at an advantage going forward. There is another equally critical consequence to the changing nature of how human creativity interacts with marketing businesses. Although agency-based AI could help in optimizing workflows and executing tasks, humans may still be key in defining the vision for a brand, telling stories, ethics, governance, and empathy with customers. In other words, there might be more cases of hybrid operations in the marketing industry whereby humans set goals and AI executes them. The emergence of agentic AI will also likely speed up the need for governance structures and measures. Academicians and executives alike have raised concerns that highly autonomous AI systems necessitate proper mechanisms for control, observability, and even human interventions. For companies that embrace customer experience technologies that are based on agentic principles, governance can become equally crucial as innovation. There needs to be a boundary around the use of artificial intelligence for decisions, customer data, personalization, and automation. The announcement also reflects the way in which customer experience is becoming more of a competitive advantage for organizations. Consumers have started expecting business organizations to offer an interaction experience that is personalized, adaptive, and contextually aware. The concept of agentic AI can be used by firms to fulfill consumer demands. At the same time, the rapid rise of agentic systems may create pressure across the broader martech landscape. Software vendors are increasingly racing to incorporate AI agents, autonomous workflows, and intelligent orchestration into their platforms. Businesses may soon evaluate marketing technology not just by analytics or automation capabilities, but by how effectively systems can operate independently and create measurable business outcomes. Ultimately, Apply's introduction of ACx represents more than a new consulting framework. It reflects a larger transition taking place across the advertising and marketing industry as AI evolves from a productivity tool into an operational intelligence layer capable of shaping customer engagement autonomously. As businesses prepare for this agentic future, organizations that successfully combine human creativity with adaptive AI systems may define the next generation of digital customer experience.

PR Newswire
Apr 16th, 2026
Apply Digital launches TORQ AI on Google Cloud to achieve content personalisation at scale in 30 days

Apply Digital has launched TORQ AI, an agentic accelerator built on Google Cloud designed to help CPG, retail, sports and media enterprises deploy working AI systems within 30 days. The platform addresses enterprise AI adoption challenges, as a 2025 MIT study found 95% of enterprise AI initiatives fail to deliver ROI. TORQ AI enables organisations to scale content creation, orchestration and delivery for personalised customer experiences. The platform runs on clients' own Google Cloud environments with full compliance. Apply Digital partnered with a major CPG company to deploy the system across 100-plus brands, reducing an eight-week process to eight hours and achieving three times ROI within five months with 70% team adoption. The solution combines Apply Digital's delivery expertise with Google Cloud AI technologies and Gemini models.

PR Newswire
Apr 16th, 2026
Apply Digital launches TORQ AI on Google Cloud, cutting CPG content creation from eight weeks to eight hours

Apply Digital has launched TORQ AI, an agentic accelerator built on Google Cloud designed to help CPG, retail, sports and media enterprises deploy working AI systems within 30 days. The announcement comes as a 2025 MIT study found 95% of enterprise AI initiatives fail to deliver ROI. TORQ AI is a production-grade solution that scales content creation, orchestration and delivery for personalised customer experiences. In a deployment with a major CPG company, the system reduced an eight-week process to eight hours, achieving 70% team adoption and 3x ROI within five months across 100-plus brands. The platform runs on clients' own Google Cloud environments, ensuring data compliance whilst integrating with existing services. Apply Digital positions TORQ AI as a solution to bridge the gap between AI investment and measurable business impact.