Director, Software Engineering (AI Workflows & Ecosystem) at Jobber

ARE YOU DRIVEN TO BRING PEOPLE, TECHNOLOGY, AND STRATEGY TOGETHER TO BUILD IMPACTFUL SOFTWARE? Then Jobber might be the place for you! We’re looking for a Director, Software Engineering to provide technical leadership to our AI Workflow & Ecosystem groups. If you’re passionate about leveraging technology to drive organizational impact, we want to hear from you! 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 [Upgrade to PRO to see link] We help employees grow professionally; we have a ton of onboarding resources, tutorials, hackathons and buddies to support learnings and provide opportunities to innovate. We have a range of experience levels on teams, which allows for mentor/mentee opportunities. Leaders at Jobber work with empathy and support employees to build healthy work-life harmony. Bring your dedication and passion to this job to fulfill your goals. THE TEAM: At Jobber, we don’t just build a product – we work on real problems that help people in small businesses to become successful. We are inspired by our company values: be humble, be supportive and give a sh*t, which is not just said but lived. We work in a collaborative environment where teams make decisions with autonomy and contribute directly to shaping the company’s future. We release early and often while dedicating time to addressing technical debt. We believe in getting instant feedback from our customers and leveraging that to make their lives easier. We help employees grow professionally; we have a ton of onboarding resources, tutorials, hackathons, and buddies to support learning and provide opportunities to innovate. We have a range of experience levels on teams, which allows for mentor/mentee opportunities. Leaders at Jobber work with empathy and support employees to build healthy work-life harmony. Bring your dedication and passion to this job to fulfill your goals. THE ROLE: Reporting to our VP, Software Engineering, the Director, Software Engineering will be a critical part of Jobber’s continued success. As a seasoned engineering leader, you will be accountable for delivering high-quality software that meets our customers' needs. With your extensive experience in people management, agile software development, and business strategy, you’ll provide strategic direction and technical leadership for our AI Workflow and Ecosystem groups. These 2 groups are comprised of the following teams: - Platform Experience/Marketplace - Supply - Automations - Copilot - AI Foundations AS DIRECTOR OF ENGINEERING, YOU WILL: - Develop and execute a forward-thinking product strategy that aligns with Jobber’s long-term business goals - Manage a team of Engineering Managers and Senior Engineering Managers, supporting them in leading the growth and continuous improvement of a team of 30+ Software Engineers - Drive product quality, stability, and performance as the team scales, while protecting agility and maximizing impact through each stage of growth. Amplify engineering excellence through high-quality software development best practices, mentorship, and a culture of continuous improvement - Partner with peers on the Leadership Team to drive company strategy and advance critical company objectives. - Utilize AI tools to enhance development practice. At Jobber, we use AI tools to complement human skills and augment productivity, not to replace human creativity, critical thinking and decision-making. TO BE SUCCESSFUL, YOU SHOULD HAVE: - Proven experience as an organizational leader at the Director-level or higher. - A strong track record of managing and developing people managers across multiple teams and disciplines. - Hands-on experience running agile organizations at scale, with a sense of urgency to deliver high-quality solutions to customer problems. - Experience developing and executing a strategy that balances feature development, infrastructure improvement, and ongoing software maintenance. - A demonstrated ability to balance customer value with business impact while managing a multi-million dollar budget. - A mindset that embraces AI and emerging technologies as opportunities to accelerate innovation and elevate team capabilities. - Experience building diverse, high-performing teams. - A passion for AI technology and agentic systems. IT WOULD BE REALLY GREAT IF YOU HAD: - Familiarity with our tech stack: Ruby on Rails, TypeScript, and/or React (React Native for mobile is a plus) in a production environment - Experience working with GraphQL, API Layer, and performance optimization - Foundational knowledge of AWS (e.g., Lambda, ECS, EC2) - Proven experience leading 5+ engineering teams, including managing other managers - Experience building software via leading LLM providers - Experience building agentic systems COMPENSATION: At Jobber, we also believe that compensation should be transparent, fair, and supportive of your experience and growth. This role has a minimum annual salary of $221,800 CAD, a midpoint of $261,000 CAD, and a maximum salary of $300,100 CAD, designed to reflect the progression from learning the ropes to truly excelling. We design our compensation to reflect each new hire’s skills, experience, and 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. 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! 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!