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Salary: CAD 58,300 - 0 / annual
Jobber is seeking a Customer Retention Specialist to join the Customer Success team. This role focuses on protecting recurring revenue and strengthening long-term customer relationships by engaging with customers at pivotal moments when they are deciding whether to continue their Jobber subscription.
The Retention team works with customers who may be experiencing challenges, exploring alternatives, or not yet seeing the full value of Jobber's platform. The team partners closely with Customer Success, Support, Product, and Billing to surface churn risks, share customer insights, and continuously improve the overall customer experience.
In this role, you will report to the Manager of Customer Retention and work directly with at-risk customers. You'll lead consultative conversations to understand underlying causes behind cancellation requests or disengagement, identify barriers to success, and guide customers toward solutions that strengthen their experience with Jobber.
Key responsibilities include:
- Engaging with customers at risk of cancellation through retention-focused phone conversations via inbound calls or booked appointments
- Conducting proactive outbound retention calls to customers showing signs of churn risk, using account health indicators and engagement signals
- Facilitating scheduled value sessions to help customers overcome blockers and unlock full value through feature adoption, workflow optimization, and tailored training
- Using a consultative, diagnostic approach to uncover root causes behind churn risk and recommend genuine 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 across product, onboarding, and customer experience
- Adapting quickly to evolving processes, tools, and product updates in a growing environment
The role operates Monday to Friday, 11am to 8pm MT (1pm to 10pm ET). This position requires attendance at the office at least 1 day per week according to department schedule.
Jobber is a B2B SaaS platform that helps service businesses (lawn care, cleaning, plumbing, painting, etc.) connect with customers, save time, invoice faster, and get paid. The company is transforming how service is delivered across a $400-billion industry.
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; connecting features to specific customer business needs in a resonant way
- Ability to influence outcomes through consultative conversations, confidently guiding 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 with 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 fast-paced, cloud-based environments
- Interest or experience leveraging AI tools to enhance productivity and insight generation
