Sales Development Representative, Account Expansion (Remote - US and Canada)

Salary: $55,000 - $60,000 per year base (US), plus up to $30,000 per year on-target commission. A software company serving landscaping and tree care businesses in North America is hiring a sales development representative to grow revenue from its existing customer base. You will phone customers who already use the platform, find features and payment tools they have not adopted, and book expansion meetings for the Customer Success team. The role is a launchpad for a sales career, and you will help shape the outreach playbook as the first person in the position.

What you'll do

• Call existing customers to qualify upsell and cross-sell opportunities, with a focus on the invoicing and payments product
• Run conversations with clients who have not yet turned on key features and guide them toward adoption
• Qualify and book expansion meetings for Customer Success from the current book of business
• Maintain high-volume, phone-first outreach with email and sequences supporting the calls
• Coordinate warm handoffs with the Payments and Customer Success teams when expansion signals appear
• Log activity, pipeline and outcomes accurately in Salesforce and share what messaging and objections you hear

What you need

• Prior sales, customer success or account management experience; upsell or expansion conversations are a plus
• Strong phone presence and the ability to move from small talk to a business conversation naturally
• Goal-oriented, organized and disciplined with daily activity
• Comfortable learning a software product quickly and handling common objections
• Able to work well in a fast-paced, collaborative team and accept feedback
• Work authorization in the US or Canada without sponsorship

Applicants must be based in: United States, Canada.

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