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Added 13 mins ago
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Manager, Marketing Operations, Campaigns & Emails
Caseware
Toronto, ON
- $110,000 to $125,000 CAD / year
- Full-time
…ensure that the tools and systems used by the global Marketing team run smoothly and contribute to efficient, data-driven marketing operations. Your priorities include maintaining database…
Added 13 mins ago
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Overnight Lead Department Manager
Walmart
Regina, SK
- Full-time
Working as an Overnight Lead Department Manager at Walmart Canada is a great opportunity to build leadership experience in a fast‑paced retail environment. In this role, you lead and…
Added 13 mins ago
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Senior Internal Auditor
Stantec
Calgary, AB
- Full-time
Stantec’s Internal Audit team is evolving and growing to meet the company’s assurance needs. Internal Audit team members can make a difference in improving Stantec’s business and financial…
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Sr. Developer - Application Development JAVA N 4B
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Montreal, QC
- Full-time
At Genpact, we don’t just adapt to change, we lead it. AI and digital innovation are transforming the way businesses work, and we’re at the forefront of it. Genpact’s AI Gigafactory, our…
Added 13 mins ago
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Class 1 Pickup & Delivery Driver
J.D. Irving, Limited
Saint John, NB
- Full-time
…Ontario, Newfoundland and Labrador), as well as in USA. We are a team of 20,000 dedicated employees. At J.D. Irving, Limited, you are part of a dynamic team of professionals who lead with…
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Montreal, QC
- Full-time
Lead major pursuit strategies, partnerships, and business development initiatives.
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Senior Relationship Manager, Commercial Financial Services
RBC
Halifax, NS
- Full-time
…individual needs. You are a key member of a Client Relationship Team and your deeply collaborative and client-centric nature allow you to coordinate with multiple partners resulting in an…
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Inside Sales Representative
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Parksville, BC
- Full-time
· In office 5 days a week 8-5 working with sales team
Added 13 mins ago
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Student Intern - Talent Acquisition - Winter Term
TMX Group
Montreal, QC
- Full-time
…organizations enhancing capital markets. United as a global team, we’re connecting cross-functionally, traversing industries and geographies, moving opportunity into action, advancing…
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Vice President, ETF Distribution, Eastern Canada
TD
Montreal, QC
- Full-time
…Canada, who will be an integral member of our Distribution team supporting efforts to drive sales and increase market share for TD…
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HR
Manager, Loss Prevention
Holt Renfrew
Toronto, ON
- Full-time
Lead, motivate, and retain a team of high performing employees that is capable of delivering results
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Assistant Manager, Market Development
Desjardins
Alma, QC · Baie-Saint-Paul, QC · Dolbeau-Mistassini, QC · Roberval, QC · Saguenay, QC
- Full-time
Put in place management and communication practices that promote talent acquisition and management, team synergy and change management, in keeping with Desjardins’s values. Lead, coach and…
Added 13 mins ago
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Accounts Manager
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Collingwood, ON
- Full-time
At Battlefield Equipment Rentals, we don’t just rent out top-tier construction equipment, we empower our team to grow, thrive, and make a real impact in local communities every day. As part…
Added 13 mins ago
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Associate Investment Advisor- Bilingual
CIBC
Laval, QC · Montreal, QC
- Full-time
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Low Latency Java Developer, Vice President
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Mississauga, ON
- Full-time
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Added 13 mins ago
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Inventory Coordinator
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Mount Pearl, NL · Canada-Mount Pearl
- Full-time
…records. Identifies and reports variances to Customer Care team and ensures that customers are shipped variances promptly, and documents all variances and issues in line with…
Added 27 mins ago
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LPN - Emergency-Urgences- Repost
Southern Health-Santé Sud
St-Pierre-Jolys, MB
- Full-time
Be part of the Southern Health-Santé Sud team, who is rooted in what matters most. Joina region that offers a lifestyle like no other – a safe, peaceful, beautiful, fulfilling life for you…
Added 27 mins ago
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Bilingual Facility Services Manager (EN/FR)
BGIS
Montreal, QC
- Full-time
…learn and grow into various roles. Success in the role offers Team Members the opportunity to explore various roles – some…
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Spécialiste en Architecture PDP / PDP Architecture Specialist
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Mirabel, QC · Montreal, QC
- Full-time
Added 27 mins ago
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Manager, Financial Accounting & Reporting
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- Full-time
Fantastic Opportunity to Be Part of a Great Team!
Added 27 mins ago
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Human Capital Data Advisor
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AB · Calgary, AB
- Full-time
Make an impact with our Human Capital team as a Human Capital Data Advisor. This diverse team of professionals are dedicated to cultivating and fostering our firm’s unique culture and…
Added 27 mins ago
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Buyer, Senior
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- Full-time
Monitor commodity and material market conditions, cost drivers, lead times, industry trends, and capacity constraints that may impact purchasing decisions.
Added 27 mins ago
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Winter Sidewalks Crew Leader
BROGAN LANDSCAPING
Hamilton, ON
- $27 to $30 CAD / hour
- Temporary
…and the potential for a rewarding long-term career. We value team members who enjoy working collaboratively, take pride in quality workmanship, and contribute to a positive experience for…
Added 27 mins ago
Manager, Commercial Asset Management
Trans Mountain
Calgary, AB
Trans Mountain is seeking a collaborative, motivated, and values driven individual to join our dynamic team as a Manager, Commercial Asset Management. In this position, you will play a key…
Added 28 mins ago
SP
Influencer Lead
StellarMettle Placements
Canada
- Full-time
The Influencer Marketing Lead will own the strategy and execution of influencer programs across a portfolio of consumer and DTC brands. This person will manage creator partnerships, develop…

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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