Director, Customer Onboarding

Does your definition of success mean empowering others? Then Jobber might be the place for you We’re looking for a Director, Customer Onboarding to join 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. This team thrives on meaningful and impactful communication with one another and with our customers, and plays a significant role in the lives of entrepreneurs and business owners that utilize Jobber. The role: Reporting to the VP, Customer Success, the Director, Customer Onboarding will lead the strategy, execution, and evolution of one of the most critical customer-facing functions. You will be accountable for delivering a world-class onboarding experience that accelerates time-to-value and drives activation, retention, and revenue growth for new customers. You will oversee a growing team of onboarding specialists and managers, with responsibility for outcomes including activation, net revenue retention, and customer engagement. This role works cross-functionally with Product, Sales, Revenue Operations, Enablement, and Support to deliver a seamless and scalable customer journey. The Director, Customer Onboarding will: Team Leadership & Development Lead, coach, and scale a high-performing Customer Onboarding team. Establish clear roles, development paths, and performance frameworks for ICs and managers. Foster a culture of ownership, accountability, and continuous improvement. Partner with Enablement to drive training, learning, and QA initiatives. Promote cross-functional collaboration to align with broader Success, Sales, and Product strategies. Customer Experience & Operational Strategy Own the end-to-end onboarding journey from implementation to early success. Evolve and scale onboarding processes across 1:1, 1:many, and tech-touch delivery models. Leverage data and insights to optimize onboarding timelines and accelerate time-to-value. Identify and implement best practices that increase adoption, engagement, and retention. Performance, Tooling, and Measurement Set and manage onboarding performance targets (activation rates, payments adoption, NRR, customer retention, CSAT). Build dashboards and reporting frameworks in collaboration with RevOps. Identify opportunities to automate workflows and streamline customer interactions. Ensure systems (Salesforce, ChiliPiper, Revenue.io, etc.) are optimized for scale and insight. Partner with VOC teams to close feedback loops between Onboarding, Product, and Marketing. To be successful, you should have: Extensive experience leading Customer Onboarding, Customer Success, or implementation teams in a B2B SaaS environment. Proven ability to develop and scale high-performing teams, including both managers and ICs. Demonstrated success in improving onboarding outcomes and increasing customer retention. Strong operational background with experience in tools like Salesforce or similar platforms. Excellent communication and stakeholder management skills, with the ability to influence peers and executives. Passion for customer outcomes, continuous improvement, and building world-class customer-facing teams. Compensation : At Jobber, we believe that compensation should be transparent, fair, and reflective of your experience and growth. This role has a minimum annual salary of $162,000, a midpoint of $190,600, and a maximum salary of $219,100, designed to show the progression from learning the ropes to truly excelling. We design our compensation to reflect each new hire’s skills, experience against the complexity of the role, ensuring a fair and competitive salary. Our range is intentionally broad to support growth and long-term impact, with fully established hires typically starting around the midpoint. The higher end of the range is reserved for those who have demonstrated deep expertise and lasting contributions, while offers below the midpoint reflect strong potential with room to develop. This approach ensures that compensation aligns with both an individual’s current capabilities and their opportunity for future growth. 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. We believe in transparency and open conversations about compensation. If you have any questions about our approach, we’re happy to discuss them throughout the hiring process Where you can expect to work: Our product provides entrepreneurs the flexibility of working in their office or the field and we offer that same opportunity to our employees. You will have the choice to work in either our Edmonton or Toronto offices or remotely anywhere within Canada. We’re committed to ensuring the best experience for all Jobberinos to do impactful work. 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, retirement savings plan matching, 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. Support for all your breaks: from vacation to rest and recharge, your birthday off to celebrate, health days to support your physical and mental health, and parental leave top-ups to support your growing family. 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 #J-18808-Ljbffr