Sales Development Representative, Account Expansion (Existing Customers)

In this role, you will focus on developing existing customer relationships and unlocking new revenue opportunities within an established client base. You will identify opportunities to introduce additional products and services, with a particular focus on invoicing and payment solutions. Through proactive, high-volume outreach, you will help customers maximize the value of the platform while generating qualified expansion opportunities. Working closely with Customer Success, Payments, and Onboarding teams, you will contribute to stronger customer adoption and long-term growth. As the first representative dedicated to this function, you will also play an important role in shaping the account expansion strategy, refining outreach approaches, and building scalable processes. This is an exciting opportunity for a motivated sales professional looking to grow within a collaborative, fast-paced B2B SaaS environment.

• 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.