Lead Senior Specialist, Payroll in Winnipeg

Please note that the work location can be anywhere in Canada (remote working out of your home office).

At ConnectCPA, we’re not your traditional accounting firm. We are an online/virtual firm, paperless, and tech-savvy. We are growing rapidly and searching for a team member who meshes with our unique firm culture. We are a Licensed, Chartered Professional Accounting (CPA) firm that operates with a startup mentality: we experiment, we collaborate, we embrace new technologies, we automate, and we actually like Mondays (most of the time). We’re big believers in working smart, not just hard.

We wear hoodies, not suits. We talk on Slack more than email. And we’re constantly on the lookout for new tools and better ways of doing things. We’ve made growth and innovation a part of our DNA.

We’re building a workplace where people can grow, feel heard, and actually enjoy their work. Here’s what that looks like:

• Fully Remote. You will be working from your home office.
• Room to Grow. Opportunities for career development and annual performance increase.
• Fully paid for health, dental, and vision benefits. Plus access to virtual healthcare.
• Fridays off in July & August (paid).
• Paid December holiday shutdown.
• Equipment Provided. A brand-new laptop and all the gear you need to hit the ground running.
• Your voice matters. From improving workflows to shaping our culture, everyone has a seat at the table.
• Supportive, inclusive, and low-ego environment. We value respect, collaboration, and open communication, without unnecessary corporate politics.
• Comfortable, casual, and professional. We don’t require formalwear; wear what helps you do your best work.

What is the role? We're looking for a payroll professional who enjoys solving complex challenges, working directly with clients, and continuously expanding their expertise. Unlike traditional in-house payroll roles, you'll support a diverse portfolio of growing Canadian businesses across multiple industries and provinces. Every week brings new challenges, opportunities to advise clients, and exposure to situations that will accelerate your professional growth.

You’ll use online payroll software and apps and work closely with our clients to ensure their payroll is delivered seamlessly. You'll become one of the most technically well-rounded payroll professionals in Canada with exposure to the following responsibilities:

• Running payroll on time, making changes to payroll (adding/removing employees, adding/removing deductions, etc.), handling the T4 process, and submitting ROE forms.
• Answering often complex inquiries from clients related to payroll, providing recommendations and problem-solving, and analyzing data, all while maintaining compliance, accuracy, and efficiency.
• Processing end-to-end payroll for multiple clients with different pay frequencies.
• EHT, WCB filings for multiple provinces.
• Reviewing CRA accounts and responding to notices.
• Correspondence with clients and the bookkeeping team to ensure timely service and a hands-off experience.
• Champion process improvements and contribute to the development of departmental best practices.
• Act as a technical resource for the team, supporting knowledge sharing and complex payroll inquiries.

Required Experience:

• PCP certified.
• At least 12 years of payroll experience in a fast-paced environment for a large company or companies with multi-jurisdictional payroll exposure.
• Experience with complex payroll scenarios and escalations, including advanced data analysis, reporting, and implementing continuous improvement initiatives.
• Advanced understanding of the Canadian payroll process, including withholding taxes, source deductions, other deductions, benefits, ROE forms, T4 slips, and more.
• Experience processing payroll in multiple provinces (QC is an asset).

What you bring to the table:

• Great communicator. You’re confident, clear, and professional in both writing and conversation.
• Organized & efficient. You can juggle multiple clients and tasks without dropping a beat.
• Self-starter energy. You’re proactive, motivated, and comfortable working independently in a remote setting.
• Tech-savvy. You learn new software quickly and maybe even geek over automations and workflow hacks.
• Payroll know-how. Payroll processing, T4, multi-province experience, benefits, and more.
• Proven Success. You are recognized for your analytical skills, attention to detail, and commitment to compliance and process improvements.
• Strong internet. At least 6Mbps up/down to keep Zoom running smoothly and work flowing freely.

ConnectCPA is an equal opportunity employer. We are committed to a work environment that supports, inspires, and respects all individuals without discrimination on the basis of race, colour, religion, sex, sexual orientation, gender identity, marital status, age, disability, national or ethnic origin, veteran status or any other protected class.