Jobber
Success
RetentionSpecialist
Neural analysis suggests this role is
optimal for Mid+ candidates.
“Retention Specialist at Jobber. Skills: Customer Retention, Customer Success, Consultative Selling, Problem Solving, Relationship Building. Engage with customers at risk of cancellation through retention-focused phone conversations. Conduct proactive outbound retention calls to customers showing signs of churn risk”
What You'll Achieve.
Save rate; Customer retention; Long-term customer success following retention conversations; Protecting and retaining recurring revenue; Driving the best possible retention result; Influencing cross-functional improvements to product, onboarding, and customer experience
Industry & Context.
Solving meaningful problems; Understand what’s getting in the way; Connect them to the Jobber features and workflows that solve their specific problems; Understand the underlying causes behind cancellation requests or disengagement; Identify barriers to success; Guide customers toward solutions that strengthen their experience; Ask the right questions before offering solutions; Translate Jobber’s capabilities into practical, meaningful solutions; Leverage your expertise to showcase how Jobber’s features solve meaningful problems; Assess situations critically, identify root causes, and propose creative, practical solutions with confidence.
Attend the office at least 1 day per week according to the department schedule
What They're Looking For.
Must Have
A track record of thriving in high-volume, customer-facing environments where you consistently deliver 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., 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., 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.
Nice to Have
Interest or experience in leveraging AI tools to enhance productivity and insight generation.
What You'll Do.
Engage with customers at risk of cancellation through retention-focused phone conversations
Conduct proactive outbound retention calls to customers showing signs of churn risk
Facilitate scheduled value sessions that help customers overcome blockers and unlock the full value of their Jobber subscription
diagnostic approach to uncover root causes behind churn risk
Play a direct role in protecting and retaining recurring revenue by influencing customer decisions
Exercise sound judgment and decision-making in navigating complex or high-risk customer situations
Partner with cross-functional teams to share insights from retention conversations
Contribute to improving long-term retention strategy by identifying patterns in churn drivers
Adapt quickly to evolving processes
How You'll Work.
Team & Collaboration
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.; 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.
Communication Scope
Verbal communication skills; Customer-first mindset; Build rapport quickly; Navigate challenging conversations with empathy and clarity
Full Job Description
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. 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, pro
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