Senior Workday Analyst, Payroll

Jackalope Digital LLC; Toronto; On-site; CAD 110,000 - 150,000; Full time

Job summary

Stripe is seeking a Senior Workday Analyst, Payroll, to serve as the technical anchor for Workday payroll across our Canadian and global teams. You will drive automation, support new country onboarding, and partner with Payroll, Compliance, and IT to ensure secure, scalable payroll operations.

You will own the health of the Workday Payroll environments, balance KLTO work with strategic projects, and translate business needs into scalable solutions while ensuring data integrity and user

Qualifications

• Five+ years in HRIS/People Systems with Workday payroll configuration.
• Experience handling confidential information and critical operations.
• Ability to lead cross-functional projects with ambiguity and tight timelines.
• Canada/US payroll knowledge is a plus.

Responsibilities

• Own the technical health of Workday Payroll environments and KLTO operations.
• Lead technical configuration for Workday Payroll changes end to end, from requirements to deployment.
• Support onboarding of new payroll countries, including configuration and testing.
• Collaborate with Payroll, Compliance, Legal, and Internal Audit to ensure payroll controls and data integrity.

Skills

Workday HCM

Payroll

HRIS

Stakeholder management

Automation

AI features in HR tech

Education

Bachelor’s degree or equivalent practical experience

Tools

Workday Studio

EIBs/Integrations

Core Connectors

Job description

Who we are

About Stripe

Stripe is a financial infrastructure platform for businesses. Millions of companies - from the world’s largest enterprises to the most ambitious startups - use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career.

About the team

Stripe’s People Systems Team sits at the intersection of technology and human experience. We are internal consultants who turn ambiguity into scale. Part of the People Solutions org, we partner with Corporate Technology, Finance, Payroll, the wider People team including Total Rewards & Benefits teams to build a world-class employee experience. We are a "strategy-first, quality- execution-always" team that values technical rigor, nimble problem-solving, and a deep empathy for the Stripes we serve.

What you’ll do

As a Senior Workday Analyst, Payroll, you'll be a technical anchor for our Workday ecosystem and a driver of what's next for it. This role goes beyond keeping the lights on: you'll bring new Workday feature knowledge into the team, help automate manual payroll processes, and shape how we use emerging Workday capabilities (including AI-driven and agent-based tools) to modernize our payroll operations.

You’ll own the technical health of our Workday Payroll environments for Workday in-house payrolls, balancing critical keep-the-lights-on (KLTO) operations with high-impact strategic projects. You’ll also act as a bridge to our broader tech stack, supporting HRIS tools built on top of Workday and partnering with Payroll and other internal and external stakeholders for smooth data flow and a unified user experience.

Payroll partnership and delivery

• Partner with Payroll: Act as the primary technical partner for the Payroll team, translating business needs into scalable Workday solutions and setting clear expectations on delivery.
• Deliver payroll changes: Lead technical configuration for Workday Payroll changes end to end, from requirements through implementation, testing, and deployment.
• Support new country onboarding: Lead implementation to onboard new payroll countries as Stripe expands, covering configuration, testing, and knowledge transfer so the team can support new geographies independently.

Innovation and automation

• Bring new capability into the team: Stay current on new Workday Payroll features and functionality, and assess and pilot them for Stripe's environment.
• Automate and modernize: Identify manual, repetitive payroll processes and redesign them using Workday automation, integrations, or agent-based tools, reducing manual effort and error rates.
• Drive strategic roadmapping: Work alongside People Solutions to lead product-led strategic projects from discovery to deployment, so our Workday footprint evolves ahead of Stripe's growth.
• Influence best practices: Ability to influence stakeholders on workday and HRIS best practices to apply, to deliver solutions and projects that are scalable and supportable.

HCM operations support

• Resolve open tickets: Provide operations support on the Workday HCM & Payroll side to resolve and close Stripe's open Workday tickets.
• Handle integration-specific tasks: This includes issue resolution, data access requests, report writing, and managing integration errors and warnings.
• Serve as Tier 3 expert: Act as the escalation point for complex HCM, Payroll, and security issues that other tiers can't resolve.
• Day to Day Project work: Project work may include developing Workday configurations, creating Workday dashboards, and producing custom Workday reports.

Governance and collaboration

• Maintain compliance: Partner with Payroll, Compliance, Legal, and Internal Audit to manage payroll compliance controls (SOX ITGCs, segregation of duties, ACA reporting, multi-state tax nexus, FLSA rules, provincial obligations, and leave laws), annual access certifications, EEO-1/VETS-4212 filings, and T4/ROE year-end processes.
• Share knowledge: Contribute to a supportive team culture by sharing knowledge and helping peers, and use good judgment to elevate risks and roadblocks early.

Who you are

We're looking for someone who meets the minimum requirements to be considered for the role. If you meet these requirements, you are encouraged to apply. The preferred qualifications are a bonus, not a requirement.

Minimum requirements

• 5+ years in HRIS/People Systems, with at least 3+ years of deep configuration experience in the Workday HCM, Reporting, Time and Absence and Payroll modules.
• Proven experience working with highly confidential informationand supporting critical business operations and processes.
• Strong interpersonal skills with the ability to set clear expectations with senior stakeholders and the confidence to
• Ability to lead cross-functional projects, navigating ambiguity and high-pressure timelines with a sense of urgency.
• Deep understanding of payroll processing, payroll calculations, costing, retro payroll, reconciliations, payroll auditing, and payroll security.
• Bachelor’s degree or equivalent practical experience.

Preferred qualifications

• Workday certifications in Payroll for US and Canada.
• Understanding of EIBs, Studio, or Core Connectors to support data flow between Workday and third-party vendors.
• Hands-on experience with Workday automation tools, AI-driven features, or agent-based capabilities (for example, Workday Illuminate or Extend), and an interest in applying them to payroll operations.
• Prior experience supporting Workday Payroll implementations in new countries.
• You’re a "low-ego, high-talent" person who likes bringing order to complexity.