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 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 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.

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.

Success in this role is measured through outcomes such as save rate, customer retention, and long‑term customer success following retention conversations, with Retention Specialists taking direct ownership of outcomes that impact recurring revenue retention.

Shift
Monday to Friday 11am to 8pm MT (1pm to 10pm ET)

Please note
This role is available only to candidates based in Edmonton, Toronto, Vancouver, or Kitchener‑Waterloo and requires you to attend the office at least 1 day per week according to the department schedule.

The Retention Specialist will:

Engage with customers at risk of cancellation through retention‑focused phone conversations via direct inbound phone line or booked calls, identifying solutions that help them continue to succeed with Jobber.

Conduct proactive outbound retention calls to customers showing signs of churn risk, using available signals such as account health indicators or changes in engagement to help customers address challenges before they lead to cancellation.

Facilitate scheduled value sessions that help customers overcome blockers and unlock the full value of their Jobber subscription through feature adoption, workflow optimization, training, and best practices tailored to their business.

Use a consultative, diagnostic approach to uncover root causes behind churn risk. You’ll ask the right questions, interpret signals such as product usage patterns and account health indicators, and recommend solutions that genuinely address what’s getting in the customer’s way.

Play a direct role in protecting and retaining recurring revenue by influencing customer decisions at critical moments in their lifecycle, guiding at‑risk customers toward solutions that reinforce the long‑term value of their Jobber subscription.

Exercise sound judgment and decision‑making in navigating complex or high‑risk…