Sales Development Representative, Account Expansion (Existing Customers)

Accountabilities: Proactively contact existing customers to identify, develop, and qualify account expansion opportunities, focusing on upselling and cross-selling invoicing and payment solutions. Drive product adoption by engaging customers who have not yet activated key platform features and demonstrating the value of additional solutions. Generate qualified expansion opportunities and schedule meetings for the Customer Success team, contributing to revenue growth across the existing customer portfolio. Execute high-volume, phone-first outreach campaigns, supported by email sequences and other communication channels, while maintaining consistent activity levels. Collaborate with Customer Success, Payments, and Onboarding teams to identify customer needs, recognize expansion signals, and coordinate effective handoffs. Maintain accurate records of sales activities, pipeline development, and outcomes within Salesforce. Develop strong product knowledge, particularly around invoicing and payment solutions, to confidently communicate benefits and address common customer objections. Share customer feedback, successful messaging strategies, and recurring objections to help continuously improve the account expansion playbook. Requirements: Previous experience in sales, customer success, or account management, ideally involving upselling, cross-selling, or account expansion. Strong interpersonal and communication skills, with the ability to build rapport, engage customers naturally, and turn conversations into meaningful business opportunities. A customer-oriented mindset, with excellent listening and questioning skills to understand customer challenges and recommend relevant solutions. A results-driven attitude, with strong motivation to achieve sales targets and contribute to revenue growth. Excellent organizational skills and the ability to manage high-volume outreach while maintaining consistency, accuracy, and follow-through. Adaptability and the ability to thrive in a fast-paced, collaborative environment, with openness to feedback and continuous improvement. Strong learning agility, with the ability to quickly understand software products and communicate their value confidently. A genuine interest in developing a long-term career in sales, particularly within the B2B SaaS industry. Previous experience selling payment solutions to small and medium-sized businesses, B2B SaaS sales, or serving customers in the landscaping, arboriculture, tree care, or snow and ice management industries would be considered a strong advantage. Must be legally authorized to work in Canada without requiring employer-sponsored work authorization. Ability to travel across Canada and the United States at least once per quarter. Benefits: Competitive compensation: Annual base salary of CAD $65,000–$70,000, plus CAD $20,000 in on-target commission. Flexible healthcare coverage: Employer-funded Health Spending Account (HSA)-based benefits plan in Canada, including prescription drug, dental, and mental health coverage. Retirement savings: RRSP matching program to support long-term financial well-being. Work-life balance: Unlimited paid time off, paid company holidays, and a company-wide winter break from December 24 to January 1. Career development: Personalized career development discussions and access to tools, courses, and resources to support professional growth. Collaborative culture: A supportive, innovative, and people-focused environment that encourages teamwork, accountability, transparency, and continuous improvement. Meaningful impact: The opportunity to contribute to an evolving industry while helping customers improve their operations and grow their businesses. Remote work: Flexibility to work remotely from Canada.