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Salary: CAD 58,300 - 58,300 / annual
Jobber is seeking a Retention Specialist to join the Customer Success team and help at-risk customers rediscover value in the platform and continue growing their businesses.
The Retention team protects recurring revenue and strengthens long-term customer relationships by engaging with customers at pivotal moments when they are deciding whether to continue their subscription. Through inbound and outbound retention conversations, the team connects with customers experiencing challenges, exploring alternatives, or not yet seeing full platform value. The team partners closely with Customer Success, Support, Product, and Billing to surface churn risks and improve the overall customer experience.
Reporting to the Manager of Customer Retention, the Retention Specialist works directly with customers at risk of cancellation or disengagement. The role involves understanding what's standing in their way and connecting them to solutions that strengthen their experience with Jobber.
Key responsibilities include:
- Engaging with at-risk customers through inbound calls, proactive outreach, and scheduled value sessions
- Conducting consultative, diagnostic conversations to uncover root causes behind churn risk
- Facilitating value sessions that help customers overcome blockers and unlock full platform value through feature adoption, workflow optimization, and training
- Using product usage patterns and account health indicators to recommend tailored solutions
- Playing a direct role in protecting recurring revenue by influencing customer decisions at critical lifecycle moments
- Exercising sound judgment in navigating complex or high-risk customer situations
- Partnering with cross-functional teams to share insights, identify churn trends, and surface product gaps
- Contributing to long-term retention strategy by identifying churn patterns and influencing improvements
- Adapting quickly to evolving processes, tools, and product updates
Shift: Monday to Friday, 11am to 8pm MT (1pm to 10pm ET). This role requires attendance at the office at least 1 day per week according to department schedule. Available only to candidates based in Edmonton, Toronto, Vancouver, or Kitchener-Waterloo.
Requirements:
- Track record of thriving in high-volume, customer-facing environments with strong results and high-quality customer experience
- Genuine curiosity about customer challenges; ability to ask great questions, listen closely, and understand problems before proposing solutions
- Ability to translate product knowledge into customer solutions and connect features to specific business needs
- Ability to influence outcomes through consultative conversations and confidently guide customers through complex situations (cancellations, product challenges, pricing concerns)
- Strong verbal communication skills and customer-first mindset; ability to build rapport quickly and navigate challenging conversations with empathy and clarity
- Results-driven mindset with ownership of customer outcomes and commitment to long-term customer success
- Resilience and composure under pressure; ability to handle rejection professionally and learn from difficult conversations
- Strong problem-solving ability; capacity to assess situations critically, identify root causes, and propose creative, practical solutions
- Adaptability in growth environments; comfort learning new tools, systems, and workflows
- Reliability and accountability; follow-through on commitments and responsibility for results
- Confidence working with modern software tools and navigating multiple systems in cloud-based environments
- Interest or experience leveraging AI tools to enhance productivity and insight generation
