Payroll and Benefits Lead

Our mission is to increase the success rate of small businesses. Traditional banking has been a growth limiter rather than a growth enabler for business owners, and we’re changing that. Relay is the all-in-one, collaborative money management platform. We’re building for employer SMBs and their finance function, internal and external, and are focused on delivering a human-centric customer experience. Ultimately, we help SMBs be ‘on the money'.

As we grow our team and our office hubs, we recognize the critical need for a dedicated Payroll and Benefits Lead. This role is responsible for ensuring accurate and timely payroll processing, compliance with local regulations, and delivering a personable and seamless employee experience. The ideal candidate will have a keen eye for detail, a passion for improving processes, and the ability to manage both operational tasks and strategic initiatives. Your role will be pivotal in maintaining team member satisfaction, financial accuracy, and legal compliance. You’ll also be empowered to strategize and think ahead to Relay’s future payroll and benefits needs, thinking about scalability and efficiencies.

If you are looking for a challenging and rewarding opportunity to lead payroll and benefits operations in a dynamic North American environment, we would love to hear from you!

What You'll Be Doing:

• Overseeing and executing payroll processing for both Canadian and US employees, including handling expense reimbursement and taxable benefits
• Maintain accurate employee records and manage payroll audits
• Engaging with Gusto (our US payroll provider) and various State tax offices to set up payroll and payroll tax accounts as we continue to open new entities across the US
• Ensuring accurate and timely payment of wages, taxes, and deductions while adhering to federal, state/provincial, and local regulations
• Serving as the main point of contact for our benefits advisor and insurance carriers, managing benefits administration, and coordinating open enrolment activities
• Collaborating with Finance and People Ops teams to ensure taxable benefits, expenses, when applicable make it onto the payroll
• Utilizing payroll and benefits software platforms (e.g. Gusto for the USA, Rippling for Canada) to streamline processes, maintain data accuracy, and generate reports for analysis
• Staying current with employment tax laws, regulatory changes, and industry best practices to ensure compliance and mitigate risk
• Strategizing and future planning for payroll and benefits, and making recommendations for process improvements
• Serving as a good steward to answer team inquiries and ensure they understand all payroll and benefits items, which means acting as the primary point of contact for employee inquiries related to payroll and benefits
• Conduct onboarding and general team sessions to explain payroll and benefits programs
• Identify and implement improvements to payroll and benefits processes to enhance efficiency and employee experience

Who You Are:

• You have 4-8 years of progressive experience in payroll and benefits administration, preferably in a multi-state/province or multinational environment
• You are detail-oriented, with a focus on accuracy, confidentiality, and data integrity
• You are proficient in using payroll and HRIS software, with experience in platforms like Gusto (USA) and Rippling (Canada) being a plus
• In-depth knowledge of payroll systems (e.g., ADP, Workday, or similar)
• Strong understanding of tax laws, labor regulations, and benefits administration
• Advanced proficiency in Google Sheets, Excel or other data analysis tools
• Exceptional attention to detail and organizational skills
• Excellent communication and interpersonal skills. Helping your team members with important questions related to their payroll or benefits fills your cup
• Ability to manage multiple priorities in a fast-paced environment
• You possess expertise in employment tax nuances and regulations in both Canada and the US, with a strong ability to calculate and process payroll accurately
• You have experience in setting up payroll and business entities set up in new US States
• You are skilled with analyzing data to identify trends & concerns, and initiate strategic discussions around process improvement
• You are experienced in owning projects / programs & tracking their effectiveness
• You have excellent communication skills, both written and verbal, with the ability to effectively interact with team members, vendors, and external stakeholders
• You are a proactive problem solver with a customer-centric approach to resolving payroll and benefits-related issues
• You are a collaborative team player who can work independently and manage priorities effectively in a fast-paced environment
• You are familiar with creating and updating internal collateral related to payroll and benefits for employee education and reference

Research shows that women-identifying and other marginalized individuals tend to only apply when they meet 100% of the qualifications; if you don't have all the listed qualifications, we encourage you to apply anyway!

Our Commitment To You:

• Competitive salary and meaningful equity: Relay employees are Relay owners, complete with equity and a competitive salary.
• Comprehensive health benefits: enjoy full health benefits from day one. We offer flexible Health or Wellness Spending Accounts and medical, dental, and vision coverage for you and your dependents.
• Flexible vacation and time off: every team member starts with 15 vacation days and 5 flex days to use as needed, plus an extra week of office closure during the end-of-year holidays so you can take time off to recharge and come back better for our customers.
• Parental leave with top-up: we offer 12 weeks off with a 100% salary top-up for all full-time employees, regardless of location, and accessible for all parents: birthing, non-birthing, and adoptive.
• Hybrid work environment: we value meaningful collaboration and connection at our Toronto office twice a week, with lunch, snacks, and beverages on us.
• Dog-friendly space: can dogs really make you happy and healthy? We don’t know for sure, but since we don’t want to chance it, our office is 100% floof-friendly.
• Personal and professional growth: through ongoing feedback, mentorship, and coaching, work with peers and leaders who are invested in your growth and success.
• Top-tier equipment: as a Mac-first company, our Toronto offices have everything you need to produce your best work comfortably, from multiple screens to ergonomic seating.
• Social connection: we believe in celebrating our wins with two annual company-wide get-togethers, quarterly team events, happy hours, and special events and networking opportunities with industry leaders.

We’re driving real change for small business owners, powered by truly remarkable people. At Relay, you’ll find the confidence to take changes, trust to take initiative, and the support you need to build a career you love. Here, we make sure every team member feels empowered to make big decisions, encourage to ask tough questions, and challenged to take risks that result in work we’re all proud of. We give you the baton–you run the Relay.

The Interview Process:

• Stage 1: A 30-minute Google Meets video call with a member of the Talent team
• Stage 2: A 45-minute Google Meets video call with the VP People & Customer Experience
• Stage 3: A take-home case study + writing sample, followed by a 60-minute presentation of your solution to our People and Finance team
• Stage 4: A 30-minute Google Meets video call with a member of the Leadership team

What’s Important to Us:
At Relay, we believe that diversity is key to building high-performing teams, and creating an inclusive work environment is our priority. We are an equal-opportunity employer and we welcome people of diverse backgrounds, perspectives, and skills.

We will work with applicants to provide accommodations at any stage of the hiring process. If you require accommodations during the interview process, please email your People Team contact, and we will work with you to meet your needs.