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Added 1 min ago
CTO | VC-backed AI | Relocate to Barcelona | €120–150k + equity
Ink
Toronto, ON
Full-time
He spent nearly a decade at Dell, including as Director of Software Engineering in software incubation and architecture. His work included an AI/ML incubation lab and architecture and…
Added 1 min ago
Project Manager, Capture and Optimization of Research Data (CORD) Platform
RI-MUHC | Research Institute of the MUHC | #rimuhc
Montreal, QC
Full-time
…to join the Capture and Optimization of Research Data (CORD) platform of the Centre for Outcomes Research and Evaluation (CORE). CORD provides researchers with expert support, technical…
Added 1 min ago
Digital Architect (GOAPRDJP00000987) – 5 Resources
Amyantek
Canada
Contract
A Digital Architect provides architectural expertise and strategic guidance and is responsible for overseeing the software architecture of digital services, the alignment of services to a…
Added 1 min ago
Technical Architect- AI
Mphasis
Toronto, ON
Full-time
We are seeking a highly experienced AI Architect to lead the design, architecture, and implementation of enterprise-scale Generative AI solutions on Google Cloud Platform (GCP). The ideal…
Added 1 min ago
Senior Data Engineer - Toronto
Trisura Guarantee Insurance Company
Toronto, ON
…growth and our entrepreneurial style, niche market position and development opportunities ensure that our people see the results of their commitment reflected in the company’s…
Added 1 min ago
Product Owner
Redwood Software
ON
Redwood Software is the leader in full stack automation for mission-critical business processes. With the first SaaS-based composable automation platform specifically built for ERP, we…
Added 16 mins ago
People Technology Integrations Manager - Team Lead (All Genders)
HelloFresh
Toronto, ON
…its remit will expand across workflow automation, low-code development, AI-enabled solutions and modern engineering capabilities. You will act as the engineering architect and design…
Added 30 mins ago
Senior Product Manager (Maple Ridge BC)
Orica
Maple Ridge, BC
Full-time
We are seeking a strategic and execution-oriented Product Director / Senior Product Director to lead the evolution of an integrated portfolio of hardware, software, and services for the…
Added 30 mins ago
Regional Sales Director (Mississauga)
BoomerangFX
Mississauga, ON
Full-time
…dental offices, vision clinics, and more with an all-in-one SaaS platform. Our solutions streamline practice management, EMR, scheduling, lead generation, and digital marketing, helping…
Added 31 mins ago
Senior Software Engineer, Platform & Integration - EN 362
Export Development Canada | Exportation et développement Canada
Remote, Canada
Full-time · Remote
Position: Senior Software Engineer (Level 18) – Platform & Integration
Added 31 mins ago
Senior Software Engineer, Platform & Integration - EN 362
Export Development Canada | Exportation et développement Canada
Remote, Canada
Full-time · Remote
Position: Senior Software Engineer (Level 18) – Platform & Integration
Added 31 mins ago
Senior Software Engineer, Platform & Integration - EN 362
Export Development Canada | Exportation et développement Canada
Remote, Canada
Full-time · Remote
Position: Senior Software Engineer (Level 18) – Platform & Integration
Added 31 mins ago
Senior Software Engineer, Platform & Integration - EN 362
Export Development Canada | Exportation et développement Canada
Remote, Canada
Full-time · Remote
Position: Senior Software Engineer (Level 18) – Platform & Integration
Added 31 mins ago
Senior Software Engineer, Platform & Integration - EN 362
Export Development Canada | Exportation et développement Canada
Remote, Canada
Full-time · Remote
Position: Senior Software Engineer (Level 18) – Platform & Integration
Added 31 mins ago
Senior Software Engineer, Platform & Integration - EN 362
Export Development Canada | Exportation et développement Canada
Remote, Canada
Full-time · Remote
Position: Senior Software Engineer (Level 18) – Platform & Integration
Added 35 mins ago
Senior Engineering Manager
Optum
Canada
Full-time
Lead multiple software engineering teams responsible for the Stratus Imaging Archive platform
Added 35 mins ago
Senior Software Engineer, Platform & Integration - EN 362
Export Development Canada | Exportation et développement Canada
Laval, QC
$96,557 to $128,743 CAD / year
Full-time
Position: Senior Software Engineer (Level 18) - Platform & Integration
Added 35 mins ago
Senior/Lead Azure Cloud Data Engineer
Nityo Infotech
Toronto, ON
Contract
We are seeking a highly skilled Senior/Lead Azure Cloud Data Engineer to design, develop, and optimize large-scale cloud-based data solutions on Microsoft Azure. The ideal candidate will…
Added 35 mins ago
Director AI Center of Excellence
Future Electronics
Kirkland, QC
Full-time
Build, lead, and grow a team of AI specialists / automation engineers.
Added 35 mins ago
Sr. Firmware Developer
AEM
Victoria, BC
$85,000 to $110,000 USD / year
Full-time
The ideal candidate combines strong embedded software fundamentals with hands-on hardware integration, system debugging, verification, and technical leadership. This is a hands-on product…
Added 47 mins ago
Director, Quality Assurance
Assent
Ottawa, ON
$150,000 to $170,000 CAD / year
Full-time
…Security and other stakeholders to embed quality throughout the software development lifecycle. The Director provides clear, risk-based insight into release readiness and champions shared…
Added 1 hour ago
Senior Frontend Engineer
Arkion Identity Systems
Toronto, ON · Greater Toronto Area, Canada
Full-time
4+ years of frontend development experience with at least 2 years in a senior or lead role.
Added 1 hour ago
Senior Salesforce Developer
Hire DigITalent Inc.
Toronto, ON · Greater Toronto Area, Canada
Full-time
One of our financial services clients is seeking a highly skilled and experienced Senior Salesforce Developer to lead the technical design, development, and secure implementation of…
Added 1 hour ago
Senior Software Engineer, Platform & Integration - EN 362
Export Development Canada | Exportation et développement Canada
Ottawa, ON
$96,557 to $128,743 CAD / year
Full-time
Position: Senior Software Engineer (Level 18) - Platform & Integration
Added 1 hour ago
Senior Software Engineer, Platform & Integration - EN 362
Export Development Canada | Exportation et développement Canada
Brossard, QC
$96,557 to $128,743 CAD / year
Full-time
Position: Senior Software Engineer (Level 18) - Platform & Integration

Jobber

Customer Retention Specialist

Kitchener, ON, Canada

Pay: This role comes with a fixed compensation structure, starting at $58,300.
Job type: Full-time
Apply by: Oct 23, 2026
Posting language: English
Posted: Sep 23, 2026

Apply About employer

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Original 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 Customer Retention Specialist (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 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.

Shift: Monday to Friday 11am to 8pm MT (1pm to 10pm ET)

Please note: This role is available only to candidates based in Edmonton, Toronto, Vancouver, or Kitchener-Waterloo and requires you to attend the office at least 1 day per week according to the department schedule

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!

To be successful, you should have:

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.

Compensation:

At Jobber, we believe that compensation should be transparent, fair, and supportive of your experience and growth. This role comes with a fixed compensation structure, starting at $58,300.

Base salary is just one part of a total compensation package that will include equity rewards, annual stipends for health and wellness, retirement savings matching, and an extended health package with fully paid premiums for body and mind. Your professional growth matters to us too! You’ll have access to a dedicated talent development program that includes career coaching and opportunities for career development.

If you have any questions about our compensation approach, we encourage open conversations throughout the hiring process!

What you can expect from Jobber:

A total compensation package that includes an extended health benefits package with fully paid premiums for both body and mind, matching in RRSP, TFSA or FHSA, and stock options.
A dedicated Talent Development team and access to coaching, learning, and leadership programs to help you grow your career, reach your goals, and unlock your full potential.
A unique opportunity to build, grow, and leave your impact on a $400-billion industry that has no dominant player...yet.
To work with a group of people who are humble, supportive, and give a sh*t about our customers.

We 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.

A bit more about us:

Job by job, we’re transforming the way service is delivered. Your lawn care provider, home cleaning service, plumber or painter could use Jobber to better connect with their customers, save time in the office, invoice faster, and get paid! We’re bringing tens of thousands of people together with technology to deliver billions of dollars a year in services to happy customers. Jobber exists to help make these small businesses successful, and when they’re successful we all win!

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More about this job

Responsibilities

Engage at-risk customers through inbound and outbound calls and scheduled value sessions to identify the causes of churn risk and recommend tailored solutions that help them succeed with Jobber. Protect recurring revenue, guide customers through complex decisions, and share customer insights with cross-functional teams to improve retention and the overall customer experience.

Requirements

Candidates should have a track record of delivering strong results in high-volume customer-facing work, with excellent communication, listening, problem-solving, and consultative influence skills. They should be resilient, accountable, adaptable to changing tools and processes, comfortable using modern software systems, and interested in using AI tools to improve productivity and insight generation.

Skills

Customer Retention
Consultative Selling
Customer Success
Churn Prevention
Product Knowledge
Verbal Communication
Active Listening
Problem-Solving
Conflict Resolution
Customer Empathy
Revenue Retention
Account Health Analysis
Adaptability
Resilience
AI Tool Proficiency

Benefits

Equity Rewards
Health And Wellness Stipends
Retirement Savings Matching
Extended Health Benefits
Fully Paid Health Premiums
Stock Options
Career Coaching
Learning And Leadership Programs

Visa sponsorship

Not detected in the job text

Keywords

Customer Retention
Customer Success
Churn Risk
Recurring Revenue
Retention Rate
Save Rate
Inbound Calls
Outbound Calls
Value Sessions
Feature Adoption
Workflow Optimization
Customer Training
Product Usage Patterns
Account Health Indicators
Consultative Conversations
Root Cause Analysis
Customer Experience
Cross-Functional Collaboration
Product Feedback
Billing
Customer Support
Software Development
Cloud-Based Systems
AI Tools
Jobber

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