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Doing business to business, person to person.Payworks is a leading workforce management solutions provider and multi-year winner of the Canada’s Best Managed Companies program. We are proud to be Canadian owned and operated as well as committed to developing world-class products and providing a progressive workplace culture where Doing Right by People is our purpose.

With clients of all sizes from coast to coast and more than 600 employees, we currently have an exciting opportunity on our Sales team for the right candidate. Because when it comes to great people, there’s always room for one more.

Reporting to the Account Executive & Team Lead, as a Sales Development Representative with Payworks your main focus will be engaging with prospective small business clients. You will be a key player in our sales pipeline—generating leads, qualifying prospects and helping guide them toward tailored workforce management solutions. This includes everything from initial outreach to product demos and supporting their transition into Implementation. You will be the first voice many clients hear from Payworks, so your ability to listen, build rapport and spark interest is critical. Along the way, you will collaborate closely with Account Executives to create seamless, positive client experiences that set the stage for long-term success.

• Comprehensive employer paid benefits, including a Health Spending Account, for you and your family and excellent pension plan with employer contributions.
• Plenty of professional development opportunities.
• Community-minded culture – Receive two paid days per year to volunteer and lots of opportunity to “Pay it Forward”.
• Time and flexibility to meet your needs – Hybrid work model with flexible work options, plus 3 weeks vacation to start, flex time and parental leave benefits.
• Cool perks – Annual Lifestyle Spending Account, Costco membership, fun office environment and events, and more!

• Conduct proactive outreach – You will follow up on inbound leads and engage new prospects through phone, email and digital channels. From the first touchpoint to product demos and pricing discussions, you will help prospects understand our solutions and feel confident in their decision to partner with us. You will also work toward clear sales targets and KPIs related to lead generation, outreach volume, conversion rates and revenue—taking pride in consistent, results-driven execution.
• Work collaboratively with the Sales team – You will support a seamless sales process by qualifying leads, sharing insights, maintaining clear handoffs and providing first-level backup coverage for Account Executives during absences.
• Maintain CRM accuracy and share feedback – You will keep detailed records of all prospect interactions in our CRM, ensuring smooth transitions to Implementation. You will also share insights with Sales and Marketing to help refine messaging, strategy and product alignment.
• Engage with partners – You will collaborate with external partners (like CFIB and local Chambers) by keeping them informed on the status of shared leads and helping to maintain strong, trusted relationships.

• Excellent communication and interpersonal skills, with the ability to build rapport quickly and engage prospects in meaningful conversations.
• A client-first mindset—you are empathetic, solutions-oriented and focused on understanding and addressing client needs.
• Strong organizational and time management skills, with the ability to prioritize tasks, manage multiple opportunities and maintain attention to detail in a fast-paced environment.
• Self-motivated and goal-oriented, with a demonstrated ability to work independently while contributing to team success.
• High level of integrity and professionalism, with a commitment to ethical sales practices and transparent communication.
• Adaptability and eagerness to learn new technologies, sales strategies and market trends.
• A track record of meeting or exceeding sales or customer satisfaction metrics such as revenue goals, conversion rates or client retention.
• Proficiency with CRM software and the Microsoft Office suite.
• Access to reliable transportation (in any format - the Payworks office in Etobicoke has free parking and is accessible by the TTC!).

• Recent experience in B2B inside sales or an equivalent combination of education & experience is an asset.
• A background in Payroll, HRMS, or Workforce Management solutions is an asset.
• Proven experience identifying and qualifying leads through cold calling, email outreach, social media and networking and moving prospects through the sales funnel is an asset.

We are proud to support a Flexible Work Plan that recognizes the diverse needs and lifestyles of our people. The Sales Development Representative has the option to work fully from a Payworks office or on a hybrid work model, working in the office at least three (3) days a week.

Payworks is committed to providing an inclusive, accessible environment, and collaborating with employees, clients and guests to identify and effectively remove barriers, in a manner that respects the principles of independence, dignity, integration, reasonable accommodation and equal opportunity. Payworks welcomes and encourages applications from all persons. Individuals applying for employment with Payworks may request accommodations at all stages of recruitment and employment from Human Resources.

Employees at Payworks’ come from different backgrounds, and we celebrate those differences. We are looking for the best candidate for this opportunity, but do not expect applicants to meet every qualification in order to be considered.