Sales Development Representative

Payworks Inc.; Toronto; Hybrid; CAD 50,000 - 55,000; Full time

Benefits offered by this job

Health Spending Account

Hybrid work model

3 weeks vacation to start

Job summary

Payworks Inc. is hiring a Sales Development Representative in Toronto, ON for a full-time, hybrid role. You will lead outreach to small business prospects, qualify leads, and book meetings for Account Executives, helping guide customers from initial contact to product demonstrations and implementation.

You will work with a collaborative Sales team, maintain CRM records, and engage with partners to expand the pipeline. The position offers comprehensive benefits and flexible scheduling.

Qualifications

• 1–2 years of experience in an inside B2B sales role or equivalent.
• Experience selling or supporting Payroll, HRMS, Workforce Management, or related technology solutions is an asset.
• Proven ability to meet or exceed sales metrics such as lead generation targets, conversion rates and revenue goals.
• Strong communication and interpersonal skills with prospective clients.

Responsibilities

• Conduct proactive outreach via phone, email, and digital channels through the sales funnel.
• Qualify leads and book qualified meetings for Account Executives.
• Maintain CRM accuracy and share feedback with Sales and Marketing to refine messaging.
• Collaborate with external partners to develop relationships and generate shared leads.

Skills

Inside B2B sales

Lead generation

CRM proficiency

Microsoft Office

Strong communication

Ability to meet targets

Tools

CRM systems

MS Office

Job description

Toronto, ON Full-time $50000.00-$55000.00/year

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 proudly Canadian and 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 and nearly 700 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.

DOING RIGHT BY PEOPLE – IT’S WHAT WE DO

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.

WHY YOU SHOULD CHOOSE PAYWORKS

• 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, fun office environment and events, regularly scheduled fitness classes, and more!

PROVIDE AN EXCEPTIONAL CLIENT EXPERIENCE – IT’S WHAT YOU’LL DO

• 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. A key part of your role will be booking qualified meetings for Account Executives, helping to build a strong, active pipeline.
• 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 of Commerce) by keeping them informed on the status of shared leads and helping to maintain strong, trusted relationships. You will also support the development of accountant and referral partner relationships, connecting these partners with the right Account Executives and ensuring smooth handoffs that set the stage for long‑term collaboration.

WHAT YOU’LL NEED TO SUCCEED

• 1–2 years of experience in an inside B2B sales role or an equivalent combination of education and experience.
• Experience selling or supporting Payroll, HRMS, Workforce Management, or related technology solutions is considered an asset.
• Proven ability to meet or exceed sales metrics such as lead generation targets, conversion rates, and revenue goals.
• Strong communication and interpersonal skills, with the ability to build rapport and trust with prospective clients.
• Ability to identify and qualify leads through outreach channels including cold calling, email, social media, and networking.
• Strong understanding of sales processes and the ability to guide prospects through the sales funnel and overcome objections.
• Excellent organizational and time management skills, with the ability to manage multiple opportunities and priorities.
• Self‑motivated and results‑driven, with the ability to work independently and collaborate effectively with cross‑functional teams.
• Demonstrated empathy and active listening skills to understand client challenges and tailor solutions to their needs.
• Proficiency with CRM systems and Microsoft Office tools.
• Adaptability and a willingness to learn new technologies, processes, and approaches in a fast‑paced environment.
• Strong integrity and professionalism in client interactions, maintaining transparency and trust throughout the sales process.
• Ability to uncover client challenges, articulate value, and confidently address objections during sales conversations.

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.

We may use AI‑assisted tools for organization, sorting, and workflow management — however, we pride ourselves on a high‑touch, human‑centered process.

This posting is for an existing vacancy within our team.

Please visit our careers page to see more job opportunities.