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Added 2 mins ago
SH
Housekeeping Aide
Southern Health-Santé Sud
Winkler, MB
- Full-time
Find your rewarding career in a vibrant and diverse community within Southern Health-Santé Sud. Our organization is privileged to provide care for people at every point in their lives.
Added 2 mins ago
PH
Direct Care Nurse, Minimum and Medium Security Units FPS
Provincial Health Services Authority
Port Coquitlam, BC
- Part-time
…direction of the Clinical Nurse Leader or designate, the Direct Care Nurse provides nursing care delivery and care planning for forensic psychiatric patients directly or in conjunction with…
Added 2 mins ago
PH
Patient Care Coordinator, BC Mental Health and Substance Use Services
Provincial Health Services Authority
Vancouver, BC
- Full-time
…interdisciplinary team and within a Trauma Informed model of care and Indigenous Cultural lens coordinates client care activities in a defined area of clinical expertise and provides…
Added 2 mins ago
PH
Direct Care Nurse, Minimum and Medium Security Units FPS
Provincial Health Services Authority
Port Coquitlam, BC
- Part-time
…direction of the Clinical Nurse Leader or designate, the Direct Care Nurse provides nursing care delivery and care planning for forensic psychiatric patients directly or in conjunction with…
Added 2 mins ago
PH
Social Worker
Provincial Health Services Authority
Surrey, BC
- Full-time
The Social Worker reports operationally to the Manager or the Patient Care Coordinator and for discipline/practice reports to the BCMHSUS Practice Consultant Social Work/Professional…
Added 2 mins ago
WC
(CAN) Pharmacy Assistant
Walmart Canada
Mississauga, ON
- Full-time
…to increase the Pharmacist's opportunity to provide patient care. The Pharmacy Assistant is expected to participate in all aspects of Pharmacy Operations required of a team player. They are…
Added 2 mins ago
FB
Assistant Grocery Manager - Overnight
Farm Boy Inc.
Ottawa, ON
- $22 CAD / hour
- Full-time
You’ll work alongside the Department Manager to help deliver standout service and operational excellence that reflect Farm Boy’s commitment to the best fresh shopping experience. Through…
Added 2 mins ago
AI
Account Manager-Retail New Truck Sales
Altruck International Centres
Hamilton, ON
- Full-time
Altruck International Truck Centres is seeking an experienced and motivated Retail Account Manager-Retail New Truck Sales to join our New Truck Sales team at our Hamilton location (2…
Added 2 mins ago
AI
Account Manager-Retail New Truck Sales
Altruck International Centres
Guelph, ON
- Full-time
Altruck International Truck Centres is seeking an experienced and motivated Account Manager-Retail New Truck Sales to join our New Truck Sales team at our Guelph location (405 Laird Road,…
Added 2 mins ago
AI
Account Manager-New Truck Sales
Altruck International Centres
Goderich, ON
- Full-time
Altruck International Truck Centres is seeking an experienced and motivated Account Manager to join our New Truck Sales team at our Goderich location (33910 Airport Road, Goderich, ON).…
Added 17 mins ago
NS
Locum - Family Medicine - Halifax - Duffus Health Centre
Nova Scotia Healthcare System
Halifax, NS
- Full-time
Duffus Health Centre, in collaboration with Nova Scotia Health, is an established collaborative care practice providing comprehensive primary care within a supportive team environment. The…
Added 17 mins ago
UH
TRI Bickle Occupational/Physiotherapist Assistant
University Health Network
Toronto, ON
- Contract
…and international source for discovery, education and patient care. UHN has the largest hospital-based research program in Canada, with major research in neurosciences, cardiology,…
Added 1 hour ago
SH
General Duty Nurse (N2) - Surgery - D2 Orthopedic Trauma/Spine
Shared Health-Soins Communs
Winnipeg, MB
- Full-time
Under the general supervision of the Manager, Health Services, the Registered Nurse (RN) is responsible for providing professional registered nursing services for patients, including those…
Added 1 hour ago
NA
Territory Manager
Newfoundland and Labrador Dairy Co-operative
St. John's, NL
- Full-time
Territory Manager - Avalon Peninsula & Marystown
Added 1 hour ago
SH
Perioperative Nurse (N2) - Adult Operating Room
Shared Health-Soins Communs
Winnipeg, MB
- Full-time
Under the direction of the O.R. Manager, Health Services, the incumbent is responsible for: promotion and compliance with the HSC mission, objectives, goals, policies and procedures for…
Added 1 hour ago
SH
Clerk III - Health Information
Shared Health-Soins Communs
Brandon, MB
- Internship
Reporting to the Manager, Health Information Services, the Clerk III Health Information is responsible for the accurate and timely registration and associated processing on the admission/…
Added 1 hour ago
NM
Shop Foreperson
Nelson Motors and Equipment
Avonlea, SK
- Full-time
As a working Shop Foreperson, you'll collaborate closely with our Service Manager, Service Writer, and Service Technicians to maintain a high performing, efficient, customer focused service…
Added 1 hour ago
SH
Registered Psychiatric Nurse/ Registered Nurse (N2) - PY2 Psychealth GTU
Shared Health-Soins Communs
Winnipeg, MB
- Full-time
Under the general supervision of the Manager Health Services, the RPN/RN is responsible for providing professional nursing services for patients, including those with complex and…
Added 1 hour ago
WR
Nurse 2 - CIVP
Winnipeg Regional Health Authority (WRHA)
Winnipeg, MB · Greater Winnipeg Metropolitan Area
- Full-time
Reporting to the Manager, Health Services and under the supervision of the Nursing Resource Coordinator, the Registered Nurse Home Care - CIVP provides nursing care to clients in the…
Added 1 hour ago
SH
Unit Clerk - Cardiology Input Unit - 5A/6A/PRU
Shared Health-Soins Communs
Winnipeg, MB
- Full-time
Under the general supervision of the Program Team Manager and a Registered Nurse (RN) or Registered Psychiatric Nurse (RPN), and while demonstrating a commitment to the Mission, Values and…
Added 1 hour ago
SH
Clinical Resource Nurse - Charge Nurse
Shared Health-Soins Communs
Dauphin, MB
- Full-time
Under the general supervision of the Client Care Coordinator and/or Care Team Manager, and while demonstrating a commitment to the vision, mission, values and strategic priorities of…
Added 1 hour ago
SH
Health Care Aide - Cardiology Input Unit -5A/6A/PRU
Shared Health-Soins Communs
Winnipeg, MB
- Full-time
Under the general supervision of the Program Team Manager and a Registered Nurse (RN) or Registered Psychiatric Nurse (RPN), and while demonstrating a commitment to the Mission, Values and…
Added 1 hour ago
SH
Rehabilitation Aide (Rehabilitation Assistant)
Shared Health-Soins Communs
Swan River, MB
- Internship
Completes general group exercise or mobility programs as directed by the therapist, nurse or care team manager.
Added 1 hour ago
TH
Café manager
Tim Hortons Québec
Halifax, NS
- Full-time
Added 1 hour ago
SH
Cook I (Drivers License Required)
Shared Health-Soins Communs
Boissevain, MB
- Full-time
Under the direction of the Nutrition Services Supervisor and/or Manager, the Cook I is responsible for performing the following activities according to related policies and procedures and…

Jobber

Retention Specialist

Kitchener, ON, Canada

This role comes with a fixed compensation structure of $58,300. · Full-time

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Job details

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

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 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, 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 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 of $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 churn insights with cross-functional teams to improve retention and the 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 influencing skills. They should be resilient, accountable, adaptable to changing tools and processes, comfortable using modern software, and interested in using AI tools to improve productivity and insight generation.

Skills

Customer Retention
Consultative Communication
Active Listening
Root Cause Analysis
Problem-Solving
Conflict Resolution
Product Knowledge
Customer Success
Revenue Retention
Outbound Calling
Inbound Call Handling
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
Save Rate
Retention Strategy
Inbound Calls
Outbound Calls
Value Sessions
Feature Adoption
Workflow Optimization
Customer Training
Best Practices
Product Usage Patterns
Account Health Indicators
Consultative Conversations
Root Cause Analysis
Customer Experience
Cross-Functional Collaboration
Product Feedback
Billing
Customer Support
AI Tools
Cloud-Based Software
Software Development

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