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Added 11 mins ago
Guest Service Agent Lead 3rd Shift
River Cree Resort & Casino
Spruce Grove, AB
Full-time
Leads all areas of the Front Office in the absence of the Guest Services Manager or Guest Services Supervisor.
Added 41 mins ago
Merchandising Supervisor
Bloomstar Bouquet
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Full-time
Responsible for hiring, training, administering and managing a team of regional Merchandisers.
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Project Manager - PL#60915
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Full-time
Peter Lucas Project Management invests in people and community to provide gold standard project delivery. We are currently looking for a Project Manager to join our team.
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Senior Project Manager
AgileGrid Solutions
Canada
Full-time
We are seeking an experienced Senior Project Manager with a strong background in mining to lead multidisciplinary engineering teams in delivering capital mining and mineral processing…
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Assistant Manager - Stock Yards Village
Old Navy
Toronto, ON
Full-time
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Added 2 hours ago
Management Trainee
Enterprise
Yarmouth Indian Reserve No. 33, NS · Yarmouth, NS
Full-time
Whether you see yourself in sales, business development, customer service, retail management, or operations, as a manager in training, you can count on a career path with a clear beginning…
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Management Trainee
Enterprise
Sydney Indian Reserve No. 28A, NS · Sydney, NS
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Whether you see yourself in sales, business development, customer service, retail management, or operations, as a manager in training, you can count on a career path with a clear beginning…
Added 3 hours ago
Front End - Manager Front End
Sobeys Capital Incorporated or a Franchise/Affiliate / ou une franchise/société affiliée
Stoney Creek, NB
The Front-End Manager is responsible for coaching, motivating, and developing department staff to foster customer loyalty, fulfil customer needs and actively contribute to an environment of…
Added 3 hours ago
Guest Service Agent Lead 3rd Shift
River Cree Resort & Casino
Enoch, AB
Full-time
Leads all areas of the Front Office in the absence of the Guest Services Manager or Guest Services Supervisor.
Added 4 hours ago
Banking Advisor
National Bank of Canada
Red Deer, AB
Full-time
…depending on team availability. This position reports to the Branch Manager. On a day-to-day basis, you’ll work with a team of experts specializing in investment, mortgage financing, and…
Added 4 hours ago
Banking Advisor
National Bank of Canada
Courtenay, BC
Full-time
…depending on team availability. This position reports to the Branch Manager. On a day-to-day basis, you’ll work with a team of experts specializing in investment, mortgage financing, and…
Added 4 hours ago
Banking Advisor
National Bank of Canada
Montreal, QC
Full-time
…availability. This position reports to the Customer service Branch Manager or the Branch Manager. Every day, you will work with a team of a experts specialized in investment, credit,…
Added 4 hours ago
Technical Advisor
National Bank of Canada
Montreal, QC
Full-time
Within the compliance group, you are part of a team of seven colleagues and report to the Manager, Registration Department. Our team stands out for its expertise in regulatory…
Added 4 hours ago
Personal Banking Advisor
National Bank of Canada
Montreal, QC
Full-time
You’ll report to the Mortgage Retention Manager and routinely work with a team of a hundred experts specializing in credit, mortgage financing and other areas.
Added 4 hours ago
Retention Specialist
Jobber
Remote, Canada
Full-time · Remote
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…
Added 4 hours ago
Assistant Manager - BOSS Outlet, McArthur Glen
HUGO BOSS Canada, Inc.
Vancouver, BC
Other
Utilize effective communication skills in training and developing staff, delivering exceptional service to customers, driving business with the merchant group and general problem solving.
Added 4 hours ago
Assistant Manager - BOSS Store, St. Foy
HUGO BOSS Canada, Inc.
Ste.-Foy, QC
Other
Utilize effective communication skills in training and developing staff, delivering exceptional service to customers, driving business with the merchant group and general problem solving.
Added 4 hours ago
Assistant Manager - HUGO Outlet, Mirabel
HUGO BOSS Canada, Inc.
Mirabel, QC
Other
Utilize effective communication skills in training and developing staff, delivering exceptional service to customers, driving business with the merchant group and general problem solving.
Added 4 hours ago
Assistant Manager - BOSS Store, St. Foy
HUGO BOSS Canada, Inc.
Ste.-Foy, QC
Other
Utilize effective communication skills in training and developing staff, delivering exceptional service to customers, driving business with the merchant group and general problem solving.
Added 4 hours ago
Regional Manager, Canada West
HUGO BOSS Canada, Inc.
Vancouver, BC
Other
The Regional Manager is charged with achieving success relating to the sales goals, loss control, P&L planning, and achievement of UPT goals in all of the Directly Operated Stores and Shops…
Added 4 hours ago
Assistant Store Manager - BOSS Store, Oakridge
HUGO BOSS Canada, Inc.
Vancouver, BC
Other
Utilize effective communication skills in training and developing staff, delivering exceptional service to customers, driving business with the merchant group and general problem solving.
Added 4 hours ago
Store Manager - BOSS Store, Vaughan Mills
HUGO BOSS Canada, Inc.
Vaughan, ON
Other
Utilize effective communication skills in training and developing staff, delivering exceptional service to customers, driving business with the merchant group and general problem solving.
Added 4 hours ago
Regional Manager, Canada West
HUGO BOSS Fashions, Inc.
Vancouver, BC
Other
The Regional Manager – Canada West is charged with achieving success relating to the sales goals, loss control, P&L planning, and achievement of sales and customer centric KPI’s in all the…
Added 4 hours ago
Assistant Manager - BOSS Store, St. Bruno
HUGO BOSS Canada, Inc.
Saint-Bruno-de-Montarville, QC
Other
Utilize effective communication skills in training and developing staff, delivering exceptional service to customers, driving business with the merchant group and general problem solving.
Added 5 hours ago
Banquet Server
Grey Eagle Resort & Casino
Calgary, AB
Full-time
Handle guest questions, concerns and complaints professionally and notify a manager as required

Jobber

Retention Specialist

Remote, Canada

Pay: This role comes with a fixed compensation structure of $58,300.
Job type: Full-time
Workplace: Remote
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 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

The Retention Specialist manages at-risk customer accounts through inbound and outbound calls to identify churn drivers and provide tailored solutions. They collaborate with cross-functional teams to share insights and improve the overall customer experience and retention strategy.

Requirements

Candidates should have a proven track record in high-volume, customer-facing roles with strong problem-solving and communication skills. Proficiency in navigating modern software tools and a consultative approach to customer success are essential for this position.

Skills

Customer retention
Consultative selling
Problem solving
Communication
Product knowledge
Relationship management
Data analysis
Conflict resolution
Account management
Customer success
Time management
Adaptability
Active listening
Technical proficiency

Benefits

Extended health benefits
Stock options
Retirement savings matching
Annual stipends for health and wellness
Career coaching
Leadership programs

Visa sponsorship

Not detected in the job text

Keywords

Retention Specialist
Customer Success
Churn Prevention
Recurring Revenue
Consultative Sales
Account Health
Feature Adoption
Workflow Optimization
Customer Experience
SaaS
Cloud-based software
AI tools
Problem Solving
Relationship Building
Data-driven
Customer Retention
Inbound Sales
Outbound Sales
Product Knowledge
Cross-functional Collaboration

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