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Added 15 mins ago
Store Manager | Richmond Centre
lululemon
BC · British Columbia, Canada
Full-time
As the ultimate leader of their store, a Store Manager is accountable for every aspect of the retail store performance, ensuring that all areas of the store are engaged, achieving key…
Added 2 hours ago
Senior Manager, Digital Delivery Enablement
Royal Bank of Canada
Toronto, ON
Full-time
In this role you will manage the development and execution of digital product strategies and projects of moderate complexity, ensuring alignment with business objectives and delivering…
Added 3 hours ago
Principal Product Manager - Technical AI Solutions
Royal Bank of Canada
Toronto, ON
Full-time
We are seeking a seasoned Principal Product Manager (individual contributor) to lead RBC's AI-powered conversational banking experience. In this role, you will be responsible for leading…
Added 3 hours ago
Part Time Bridal Sales
David's Bridal
Winnipeg, MB
$16 to $22.32 CAD / hour
Part-time
…presentation and operations of the store. S/he reports to the Store Manager in partnership with the Sales Manager. Bridal Stylists are brand ambassadors and demonstrate the values and…
Added 4 hours ago
RISE Mechanical Engineer at Intuitive
UCI-OC Alliance
Engineer, BC
Full-time
…across various functions and business units to complete a 2-year program. The program provides accelerated learning and development experience along with acquisition of product knowledge,…
Added 5 hours ago
Software Developer Co-op - Cloud Provisioning Service (Winter Term - January - April 2027)
Ross Video
Ottawa, ON · Nepean, ON
Full-time
Reporting to the Software Manager, the successful candidate will be part of a dynamic and collaborative team. You will gain exposure and relevant experience in the IT industry as a Software…
Added 6 hours ago
Senior Product Manager, Wealth Management
Royal Bank of Canada
Toronto, ON
Full-time
Wealth Technology Group is seeking an exceptional Senior Product Manager to drive transformational innovation and accelerate our digital evolution. This is a pivotal role where you'll serve…
Added 6 hours ago
The Shoe Co. - Sales Associate
DSW Designer Shoe Warehouse
Saskatoon, SK
Part-time
As a (Part-time) Sales Associate, you will report to the Store Manager and assist in fostering inclusivity and diverse customer connections. In this role, you will be responsible for…
Added 7 hours ago
Senior Manager, Organic Growth
Mistplay
Toronto, ON
$120,000 to $165,000 CAD / year
Full-time
Mistplay is seeking a strategic and hands-on Senior Manager of Organic Growth to help build and scale the organic acquisition engine for our fast-growing rewarded gaming platform. This…
Added 8 hours ago
Assistant Manager, Operations | Masonville Place
lululemon
London, ON
Full-time
…connecting, and being well. We owe our success to our innovative product, emphasis on stores, commitment to our people, and the incredible connections we make in every community we're in.…
Added 8 hours ago
Global Fulfillment Strategy Manager
lululemon
Vancouver, BC
Full-time
Develop financial and cost-benefit modeling to support business case development for new and continuing Global Fulfillment strategic initiatives.
Added 8 hours ago
Assistant Manager, Guest Experience | Masonville Place
lululemon
London, ON
Full-time
…connecting, and being well. We owe our success to our innovative product, emphasis on stores, commitment to our people, and the incredible connections we make in every community we're in.…
Added 8 hours ago
Development, Winter 2027 - Vancouver (Co-op/Internship) - 4 Months
QuadReal Property Group
Vancouver, BC
Full-time
Based in Vancouver, the Co-op/Intern, Development, will report to the Manager, Development Analysis, and support QuadReal’s Development, Western Canada team. The in-house development team…
Added 9 hours ago
The Shoe Co. - Sales Associate
The Shoe Co.
Saskatoon, SK
As a (Part-time) Sales Associate, you will report to the Store Manager and assist in fostering inclusivity and diverse customer connections. In this role, you will be responsible for…
Added 9 hours ago
Quality Assurance Manager
Redpath Sugar Ltd
Belleville, ON
Full-time
Work with the Plant Team and Sales on new product development including supporting plant trials.
Added 9 hours ago
Recruiter-Digital Engagement and Communications
Lethbridge Polytechnic
Lethbridge, AB
Full-time
Create written reports for dissemination to internal stakeholders such as the manager, program chairs, associate deans, and Polytechnic leadership
Added 10 hours ago
Security Remediation & Resilience Lead, BWI
TD
Toronto, ON
Full-time
…opportunities to all colleagues. Growth opportunities and skill development are defining features of the colleague experience at TD. Our compensation policies and practices have been…
Added 10 hours ago
Team Lead, Software Development
Croesus
Montreal, QC
Full-time
Estimate workloads and plan activities in collaboration with the Product Manager.
Added 10 hours ago
Team Lead, Software Development
Croesus
Laval, QC
Full-time
Estimate workloads and plan activities in collaboration with the Product Manager.
Added 10 hours ago
District Sales Representative
Gordon Food Service - Canada
Delta, BC
Full-time
Constantly seeking opportunities for growth and development for new and existing customers.
Added 10 hours ago
Customer Success Manager
MissionPerform
Mississauga, ON
$75,000 to $110,000 CAD / year
MissionPerform is seeking a Customer Success Manager to serve as the primary business point of contact for our customers and to own the full lifecycle of customer engagement - from proposal…
Added 11 hours ago
Senior Personal Banker Trainee - Investing | Dorval
TD
Montreal, QC
Full-time
…opportunities to all colleagues. Growth opportunities and skill development are defining features of the colleague experience at TD. Our compensation policies and practices have been…
Added 11 hours ago
Sales Manager (Planet Ford)
Performance Auto Group
Brampton, ON
Assist the General Manager in the planning and forecasting of goals and objectives for the department and strive to meet them, as well as the development and implementation of new and…
Added 11 hours ago
Senior Manager, HR Digital Solutions Design
Royal Bank of Canada
Toronto, ON
Full-time
The Workday Solutions Senior Manager is the technical backbone and people leader for RBC's Workday platform, accountable for its architectural integrity - configuration, integrations, data…
Added 11 hours ago
Line Supervisor (Westbrook)
Boston Pizza
Calgary, AB
Full-time
…organized, safe, and efficient kitchen. You’ll support the Kitchen Manager and management team while providing direction, coaching, and hands-on leadership to the line…

Jobber

Customer Retention Specialist

Toronto, 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

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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 diagnose challenges, recommend tailored solutions, and help customers realize the value of their subscription. Protect recurring revenue, make sound decisions in complex retention situations, and share churn insights with cross-functional teams to improve the customer experience and long-term retention strategy.

Requirements

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

Skills

Customer Retention
Consultative Selling
Customer Success
Churn Prevention
Active Listening
Verbal Communication
Problem-Solving
Product Knowledge
Conflict Resolution
Decision-Making
Resilience
Adaptability
Accountability
Software Proficiency
AI Tools

Benefits

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

Visa sponsorship

Not detected in the job text

Keywords

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

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