Customer Retention Specialist

ARE YOU PASSIONATE ABOUT HELPING CUSTOMERS SUCCEED, SOLVING MEANINGFUL PROBLEMS, AND MAKING A REAL IMPACT ON THE BUSINESSES YOU SUPPORT EVERY DAY?

We’re looking for a Customer Retention Specialist (Retention Specialist) to join our Customer Success team and play a key role in helping customers overcome challenges, rediscover the value of Jobber, and continue growing their businesses with confidence.

The Team

The Retention team plays a critical role in protecting recurring revenue and strengthening long-term customer relationships, supporting customers at pivotal moments when they are deciding whether to continue their Jobber subscription.

Through both inbound and outbound retention conversations, our team connects with customers who may be experiencing challenges, exploring alternatives, or not yet seeing the full value of the platform. We take the time to understand what’s getting in the way, and then connect them to the Jobber features and workflows that solve their specific problems and help their businesses grow.

We partner closely with Customer Success, Support, Product, and Billing to surface churn risks, share insights from customer conversations, and continuously improve the overall customer experience.

The Role

Reporting to the Manager, Customer Retention, the Customer Retention Specialist (Retention Specialist) works directly with customers who may be at risk of cancelling or disengaging from Jobber. Your job is to understand what’s standing in their way, and connect them to solutions that help them succeed.

You’ll lead meaningful, consultative conversations to understand the underlying causes behind cancellation requests or disengagement, identify barriers to success, and guide customers toward solutions that strengthen their experience with Jobber and make a real difference for their business. You’ll ask the right questions before offering solutions, and you’ll treat every conversation as an opportunity to genuinely improve someone’s experience.

Retention Specialists engage with customers through inbound calls, proactive retention outreach, and scheduled value sessions, translating Jobber’s capabilities into practical, meaningful solutions tailored to each customer’s unique situation.

You’ll develop deep product knowledge and act as a trusted advisor to customers, confidently navigating complex conversations and leveraging your expertise to showcase how Jobber’s features solve meaningful problems for businesses, helping customers make informed decisions that drive their long-term success.