OverviewAre 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 TeamThe 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.ResponsibilitiesReporting 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.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.



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.ShiftMonday to Friday 11am to 8pm MT (1pm to 10pm ET)QualificationsA 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.Solid 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.Solid problem‑solving ability. You assess situations critically, identify root causes, and propose creative, practical solutions with confidence.Adaptability in a growth setting. 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.Compensation & BenefitsBase salary: $58,300. Includes equity rewards, annual stipends for health and wellness, retirement savings matching, and an extended health package with fully paid premiums.Additional benefits: dedicated talent development program with career coaching, learning and leadership programs; extended health benefits package with fully paid premiums for both body and mind; matching in RRSP,TFSA or FHSA; stock options.Equal Opportunity StatementWe believe that diverse teams perform better and that fostering an inclusive work environment is a key part of growing a successful team. We welcome people of diverse backgrounds, experiences, and perspectives. We are an equal‑opportunity employer, and we are committed to working with applicants requesting accommodation at any stage of the hiring process.#J-18808-Ljbffr

📌 Retention Specialist (Kitchener) - C$58,300 A Year (Winnipeg)
🏢 Jobber
📍 Winnipeg