Customer Retention Specialist

Jobber; Toronto; On-site; CAD 50,000 - 70,000; Full time

Job summary

Jobber is looking for a Customer Retention Specialist in Toronto, Ontario. In this role, you will engage with customers who may be at risk of canceling their service and work to understand their challenges, guiding them toward effective solutions. Your success will be measured through key outcomes such as customer retention and satisfaction.

The ideal candidate will possess strong communication and problem-solving skills, the ability to adapt in a dynamic environment, and a genuine interest in customer success. Experience in high-volume customer service roles is a plus.

Qualifications

• Experience in customer-facing environments with a focus on results and customer experience.
• Ability to influence outcomes through consultative conversations.
• Interest or experience in leveraging AI tools for productivity.

Responsibilities

• Engage with customers to identify and solve issues related to cancellation.
• Lead consultative conversations to enhance customer experience with Jobber.
• Develop product knowledge to act as a trusted advisor.

Skills

Strong verbal communication skills

Problem-solving ability

Adaptability

Reliability and accountability

Confidence with modern software tools

Resilience under pressure

Curiosity about customer challenges

Job description

Requirements

• A track record of thriving in high-volume, customer-facing environments where you consistently deliver strong results while maintaining a high-quality customer experience
• A genuine curiosity about what’s driving customer challenges. You ask great questions, listen closely, and understand the problem before proposing a solution
• The ability to translate product knowledge into customer solutions. You don’t just know what Jobber does – you can connect its features to the specific needs of each customer’s business in a way that resonates
• The ability to influence outcomes through consultative conversations, confidently guiding customers through complex situations such as cancellation decisions, product challenges, or pricing concerns
• Strong verbal communication skills and a customer-first mindset, allowing you to build rapport quickly and navigate challenging conversations with empathy and clarity
• A results-driven mindset that motivates you to take ownership of customer outcomes and work toward solutions that support long-term customer success
• Resilience and composure. You stay calm under pressure, handle rejection professionally, and learn quickly from difficult conversations
• Strong problem-solving ability. You assess situations critically, identify root causes, and propose creative, practical solutions with confidence
• Adaptability in a growth environment. You’re energized by change and comfortable learning new tools, systems, and workflows
• Reliability and accountability. You show up for your team and customers, follow through on commitments, and take responsibility for results
• Confidence working with modern software tools and navigating multiple systems in a fast-paced, cloud-based environment
• Interest or experience in leveraging AI tools to enhance productivity and insight generation

What the job involves

• 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
• 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
• The Customer Retention Specialist (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 customer situations, balancing customer needs with business outcomes to drive the best possible retention result
• Partner with cross-functional teams to share insights from retention conversations, helping identify churn trends, surface product gaps, and contribute to improvements across the customer experience
• Contribute to improving long-term retention strategy by identifying patterns in churn drivers and influencing cross-functional improvements to product, onboarding, and customer experience
• Adapt quickly to evolving processes, tools, and product updates in a growing environment where customer needs and solutions continue to evolve
• Become an ambassador of our culture by being humble, supportive – and someone who truly gives a shit!