Are you the kind of person who knows a great first impression can change the outcome of a conversation?

Then Jobber might be the place for you! We’re looking for a Customer Development Representative to be part of our Success department.

Jobber exists to help people in small businesses be successful. We work with small home service businesses, like your local plumbers, painters, and landscapers, to transform the way service is delivered through technology. With Jobber they can quote, schedule, invoice, and collect payments from their customers while providing an easy and professional customer experience. Running a small business today isn’t like it used to be—the way we consume and deliver service is changing rapidly, technology is evolving, and customers expect more. That’s why we put the power and flexibility in their hands to run their businesses how, where, and when they want!

Our culture of transparency, inclusivity, collaboration, and innovation has been recognized by Great Place to Work, Canada’s Most Admired Corporate Cultures, and more. Jobber has also been named on the Globe and Mail’s Canada’s Top Growing Companies list, and Deloitte Canada’s Technology Fast 50™, Enterprise Fast 15, and Technology Fast 500™ lists. With an Executive team that has over thirty years of industry experience of leading the way, we’ve come a long way from our first customer in 2011—but we’ve just scratched the surface of what we want to accomplish for our customers.

The team:

Our Success team works together with other teams and stakeholders to bring our company values to life for our customers. By being humble, supportive, and truly giving a sh*t, the Success team ensures that our customers are successful in Jobber.

The Customer Development team at Jobber has the mission of connecting the right people with the right resources at the right time. This means ensuring customers are set up with the support they need throughout their journey—whether they’re just getting started with Jobber, entering a new stage of growth, or reaching an important milestone.

Customer Development Representatives guide service providers through their next step via short, impactful outbound conversations, helping customers understand their options and connect with onboarding, training, or other resources that will set them up for success.

In addition to outbound calls, the Customer Development team supports customers by moderating workshops and helping answer questions through live chat. These interactions ensure customers can access critical training resources when it matters most and contribute to a smooth, well-supported onboarding experience.

The role:

Reporting to the Sr. Manager, Customer Growth Programs, the Customer Development Representative is one of the first touchpoints for customers who purchase or upgrade Jobber. Understanding customer needs and quickly triaging them to the right resources is critical, as many of our customers are busy and have limited time for training.

You’ll work within customer constraints to find the best onboarding options while clearly positioning the value of training. Success in this role is measured through a combination of consistent outreach, strong booking and attendance outcomes, and high-quality customer handoffs that set customers up for success. High performers also contribute by identifying opportunities to improve how we reach, engage, and support customers.

You’ll be trusted to use sound judgment in customer conversations and encouraged to suggest improvements to how we engage customers over time. Your insights into customer needs and the post-sale journey will help shape future outreach strategies, identify opportunities to connect at key milestones, and support our mission of providing onboarding opportunities to all customers.

In addition to customer outreach, you’ll support scheduled 1-many training workshops as a moderator—ensuring smooth execution by answering questions via live chat and escalating larger inquiries to the host when appropriate. You’ll also provide post-session insights to product and leadership partners and collaborate with the Customer Onboarding Program Manager to influence the ongoing development of our 1-Many programs.

This role offers exposure to multiple parts of the post-sale customer journey and the opportunity to build skills that support growth into other customer-facing or program-focused roles at Jobber.

The Customer Development Representative will:

• Book calls with Onboarding Specialists for new Jobber customers, clearly positioning the value of onboarding sessions and driving strong attendance rates

• Handle objections by matching customer concerns to Jobber solutions and articulating the value of training to achieve consistent booking results

• Complete a high volume of daily interactions (90+) to reach the maximum number of customers efficiently and effectively

• Support inbound internal inquiries related to bookings, onboarding specialist coordination, or scheduling needs from teams such as Support or Sales

• Support 1-many workshops as a moderator on camera during live, 1-hour sessions (1–5 sessions per week)

• Communicate closely with Onboarding Specialists to ensure a consistent, high-quality customer experience

• Share customer feedback through appropriate channels in a timely manner with relevant teams

• Track accurate and consistent information in existing tools to support smooth onboarding experiences and reliable reporting

• Contribute to team initiatives and projects as capacity allows while prioritizing daily customer outcomes

• Continuously develop skills through feedback from peers and leaders

• Collaborate with leadership and peers to brainstorm, plan, and execute experiments that test new ways of reaching customers and communicating the value of onboarding

• Bring genuine care, energy, and new ideas to continually improve how we support customers at this stage of their journey

To be successful, you should have:

• Previous customer service experience. If you love people and want to create best-in-class experiences, this position is for you.

• The ability to be a self-starter. You will likely dial over 100 calls per day to effectively support the process. You’re energized by a fast pace and high volume.

• Drive and tenacity. Not every customer will say yes. You’re motivated to consistently achieve results and maintain momentum.

• Strong collaboration skills. You can build relationships quickly and work closely with peers, Onboarding Specialists, and leadership to understand what’s working and what isn’t.

• The ability to adapt and pivot. We’re an agile company, and priorities can evolve as we learn.

• Resilience in routine work. You know how to stay focused, set personal milestones, and break down larger targets into manageable pieces.

• Strong communication skills. You actively listen, ask thoughtful questions, and clearly understand customer needs.

• An innovative mindset. You’re motivated to improve existing processes and help shape how we support customers as this role continues to evolve.

Please note: The standard shift for this role is Monday to Friday from 8am to 5pm. There may be flexibility to adjust start and end times by up to one hour to accommodate scheduling preferences, within your local timezone.

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, set at $58,300 CAD.

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!