Director, Software Engineering

📍 Toronto, Canada

Jobber

Job Description

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Director, Software Engineering

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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 Foundation and Production Engineering teams. Jobber exists to help people in small businesses be successful. As featured in the Globe and Mail, we work with home and field service companies to help them better quote, schedule, invoice and collect customer payments. Having been named the #2 fastest-growing software company in Canada and one of Fast Company’s Most Innovative Companies in 2020, it’s clear we have 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. Our product provides entrepreneurs the flexibility of working in their office or the field and we offer that same opportunity to our employees. You can 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. 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. 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 Production Engineering and Foundation Software Engineering teams. These 2 groups are comprised of the following teams: Design System Mobile Platform Web Platform Infrastructure (Compute and Database) Queueing/Streaming Trust/Auth Developer Acceleration 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 50+ Software Engineers Drive product quality, stability, and performance as the team scales, while protecting agility and maximising impact through each stage of growth. Partner with peers on the Leadership Team to drive company strategy and advance critical company objectives. Requirements

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. Nice to Have

It would be really great if you had: Familiarity using 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 What We Offer

Our Software Engineering team is central to Jobber’s success – focused on creating software that delivers value to tens of thousands of users around the world. At Jobber we never stop growing and learning, and you shouldn’t either. Through frequent 1:1’s, ongoing feedback, support from your manager, our Learning and Development team, and your own sense of curiosity, your skills will develop to a higher level. 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.

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Job Details

Posted Date: October 9, 2025
Job Type:
Location: Toronto, Canada
Company: Jobber

Ready to Apply?

Don't miss this opportunity! Apply now and join our team.