Want to lead engineers building software that helps pros get the job done and know exactly how their business is doing?

Then Jobber might be the place for you! We’re looking for a Manager, Software Engineering to be part of our SP (Service Provider) Operations group, focused on helping Service Prov...

Lead a team of engineers to deliver AI amplified solutions for small businesses. Support team members in skill development, set goals, provide feedback, and mentor. Shape the technical direction of the platform, ensuring reliability and performance. Collaborate with stakeholders to find solutions for small businesses.

Want to lead engineers building software that helps pros get the job done and know exactly how their business is doing?

Then Jobber might be the place for you! We’re looking for a Manager, Software Engineering to be part of our SP (Service Provider) Operations group, focused on helping Service Providers run their day-to-day operations efficiently and effectively.

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.

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:

In this role, you will manage the engineering teams behind one of Jobber's most important domains, Jobs Teams, as part of the greater SP Operations Group. The Jobs Team is at the heart of how service businesses operate, and we are constantly improving how service providers orchestrate work from start to finish so they can confidently deliver every job with quality. You will work alongside peers from Product Management, Design, and the rest of the Engineering Leadership team to ensure the tools we build help small businesses run more efficiently and grow with confidence!

The role:

As a leader within the SP Operations group, you will manage the engineering teams to deliver high quality, on time while they get to grow and learn along the way. The SP Operations group's mission is to help Service Providers run their businesses as efficiently as possible. We build the tools that help with day-to-day operations, from scheduling and managing work and crew to ensure every job gets done, to giving business owners the visibility they need to understand their business health and make informed decisions.

Reporting to a Senior Manager of Software Engineering, the Manager of Software Engineering will lead and support their team members in developing their skills and advancing their careers—all while contributing to our mission of empowering small businesses. You'll also play a key role in shaping the technical direction of our platform, ensuring it remains reliable and high-performing as we scale Jobber.

The Manager, Software Engineering will:

Live and breathe performance facilitation. You want to work with your team(s) to help them master their individual crafts, while also collaborating to build extraordinary experiences and systems.

Be committed to the success of your people. You will help them set goals, have regular 1-on-1s, and provide constructive feedback and coaching to ensure your team's success. You’ll work to understand employees’ career direction and work to empower their journey by acting as a mentor and coach.

Develop a world-class team alongside a world-class organization. You’ll participate in recruiting events and the hiring process while also working to level up your internal team while implementing new processes, all to develop a world-class engineering department.

Remove roadblocks and build guardrails. You’ll work with the other leaders to create and maintain an environment where people can rapidly produce top-quality work that ultimately helps our customers be successful.

Collaborate with other stakeholders across the business. Whether it’s our Management teams within Product, or our Business Technology teams, you’re working closely with other Jobberinos to find the best solutions in Jobber for small businesses.

To be successful, you should have:

A track record of success in being an established software engineer, as well as time spent in a leadership position, guiding a team in the delivery of quality software.

Strong full-stack technical background, including design and architectural experience.

A drive to succeed and deliver impactful projects on time. For a high performing team with a solid roadmap that might look like getting out of their way, but for a team whose delivery is in doubt, it means getting in and getting dirty, and working with the team to find a path back to success.

The ability to be agile in an agile environment. You’ll need to be able to lead and teach your team to adapt to change, while also thinking critically and creatively to find answers to problems.

Effective written and oral communication. Being transparent with your team and establishing an open dialogue will be a key to success in supporting your coaching conversations and discussions.

To be a leader and mentor. You’ll bring your shared experience into conversations to influence and provide constructive feedback to direct reports throughout the journey to ensure goals are being met and exceeded.

Familiarity or comfort in AI tools and AI augmented development rhythms.

Highly desired, but not a dealbreaker:

Previous experience with our development stack: ReactJS, Typescript, Ruby on Rails, PostgreSQL, and GraphQL.

Previous experience with building zero to one projects from initial discovery and design, through implementation, and into delivery and measurement.

Location:

We believe great collaboration is intentional, and sometimes that means coming together in person to build, brainstorm, and connect. To support this, the role is open to candidates based in one of our hub cities: Edmonton, Toronto, Vancouver, or Kitchener-Waterloo.

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 $169,200 CAD, a midpoint of $199,100 CAD, and a maximum salary of $228,900 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.

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!

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!

Massachusetts

Previous experience with ReactJS, Typescript, Ruby on Rails, PostgreSQL, and GraphQL

Familiarity with maintaining reliability within systems outside your own team

Experience working with high-risk data and high-criticality features

A track record of success in being an established software engineer

Experience in a leadership position guiding a team in the delivery of quality software

Strong full-stack technical background, including design and architectural experience

Deep knowledge and experience in Ruby On Rails or ReactJS

Daily hands-on experience building with agentic AI tools

Experience leading a team's AI adoption

Ruby On Rails

ReactJS

AI tools

Communication

Leadership

Typescript

PostgreSQL

GraphQL

Manager, Software Engineering, Operations

Lead a team of engineers to deliver AI amplified solutions for small businesses. Support team members in skill development and career advancement, shape the technical direction of the platform, and collaborate with stakeholders across the business.

Want to lead engineers building software that helps pros get the job done and know exactly how their business is doing?

Then Jobber might be the place for you! We’re looking for a Manager, Software Engineering to be part of our SP (Service Provider) Operations group, focused on helping Service Providers run their day-to-day operations efficiently and effectively.

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.

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:

In this role, you will manage the engineering teams behind one of Jobber's most important domains, Jobs Teams, as part of the greater SP Operations Group. The Jobs Team is at the heart of how service businesses operate, and we are constantly improving how service providers orchestrate work from start to finish so they can confidently deliver every job with quality. You will work alongside peers from Product Management, Design, and the rest of the Engineering Leadership team to ensure the tools we build help small businesses run more efficiently and grow with confidence!

The role:

As a leader within the SP Operations group, you will manage the engineering teams to deliver high quality, on time while they get to grow and learn along the way. The SP Operations group's mission is to help Service Providers run their businesses as efficiently as possible. We build the tools that help with day-to-day operations, from scheduling and managing work and crew to ensure every job gets done, to giving business owners the visibility they need to understand their business health and make informed decisions.

Reporting to a Senior Manager of Software Engineering, the Manager of Software Engineering will lead and support their team members in developing their skills and advancing their careers—all while contributing to our mission of empowering small businesses. You'll also play a key role in shaping the technical direction of our platform, ensuring it remains reliable and high-performing as we scale Jobber.

The Manager, Software Engineering will:

Live and breathe performance facilitation. You want to work with your team(s) to help them master their individual crafts, while also collaborating to build extraordinary experiences and systems.

Be committed to the success of your people. You will help them set goals, have regular 1-on-1s, and provide constructive feedback and coaching to ensure your team's success. You’ll work to understand employees’ career direction and work to empower their journey by acting as a mentor and coach.

Develop a world-class team alongside a world-class organization. You’ll participate in recruiting events and the hiring process while also working to level up your internal team while implementing new processes, all to develop a world-class engineering department.

Remove roadblocks and build guardrails. You’ll work with the other leaders to create and maintain an environment where people can rapidly produce top-quality work that ultimately helps our customers be successful.

Collaborate with other stakeholders across the business. Whether it’s our Management teams within Product, or our Business Technology teams, you’re working closely with other Jobberinos to find the best solutions in Jobber for small businesses.

To be successful, you should have:

A track record of success in being an established software engineer, as well as time spent in a leadership position, guiding a team in the delivery of quality software.

Strong full-stack technical background, including design and architectural experience.

A drive to succeed and deliver impactful projects on time. For a high performing team with a solid roadmap that might look like getting out of their way, but for a team whose delivery is in doubt, it means getting in and getting dirty, and working with the team to find a path back to success.

The ability to be agile in an agile environment. You’ll need to be able to lead and teach your team to adapt to change, while also thinking critically and creatively to find answers to problems.

Effective written and oral communication. Being transparent with your team and establishing an open dialogue will be a key to success in supporting your coaching conversations and discussions.

To be a leader and mentor. You’ll bring your shared experience into conversations to influence and provide constructive feedback to direct reports throughout the journey to ensure goals are being met and exceeded.

Familiarity or comfort in AI tools and AI augmented development rhythms.

Highly desired, but not a dealbreaker:

Previous experience with our development stack: ReactJS, Typescript, Ruby on Rails, PostgreSQL, and GraphQL.

Previous experience with building zero to one projects from initial discovery and design, through implementation, and into delivery and measurement.

Location:

We believe great collaboration is intentional, and sometimes that means coming together in person to build, brainstorm, and connect. To support this, the role is open to candidates based in one of our hub cities: Edmonton, Toronto, Vancouver, or Kitchener-Waterloo.

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 $169,200 CAD, a midpoint of $199,100 CAD, and a maximum salary of $228,900 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.

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!

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!

United States

Previous experience with our development stack: ReactJS, Typescript, Ruby on Rails, PostgreSQL, and GraphQL

Experience working with high-risk data, high-criticality features

Deep knowledge and experience in either Ruby On Rails environments or ReactJS

Are you driven to bring people, technology, and strategy together to build impactful software?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 thr...

Own the end-to-end AI system layer at Jobber, ensuring intelligence flows across the entire product. Responsible for decision-making processes, context movement across workflows, and action triggers. Evaluate AI performance and reliability, and oversee agentic workflows and cross-product context.

<h2>Are you driven to bring people, technology, and strategy together to build impactful software?</h2>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!<h3></h3><h2>THE PROBLEM YOU’D OWN</h2>Jobber has AI in production, but not yet at its full potential.We already have AI answering calls, drafting responses, and powering parts of our product. But today, those systems are still fragmented. Some teams are ahead. Others aren’t. Some workflows are intelligent. Others are still manual. And most importantly, the system doesn’t yet think across the product.A service pro still has to:<ul style="min-height:1.5em"><li>Manually follow up on jobs</li><li>Piece together context across workflows</li><li>Decide what to do next</li></ul>The platform doesn’t proactively help them run their business. That’s the gap.The opportunity is to evolve Jobber from: AI-powered features → AI-powered workflows → AI-powered business operationsThis role owns that shift. Not a team. Not a feature. The system.<h2>THE CUSTOMER</h2>You’re building for people who don’t have time to think about software.<ul style="min-height:1.5em"><li>A plumber finishing their last job at 6 pm</li><li>A cleaner managing 30 clients and 5 employees</li><li>A landscaper juggling scheduling, payments, and follow-ups</li></ul>They’re not asking for “AI.” They’re asking:<ul style="min-height:1.5em"><li>“What should I do next?”</li><li>“Why didn’t this job convert?”</li><li>“Who should I follow up with today?”</li></ul>And eventually:<ul style="min-height:1.5em"><li>They shouldn’t have to ask at all.</li></ul>The Director who succeeds here will understand: This isn’t about building clever systems; it’s about building systems that remove thinking from already overwhelmed people.<h2>WHAT YOU’D OWN</h2>End-to-end ownership of Jobber’s AI system layer. You’re not owning a single team. You’re owning how intelligence flows across the entire product.<h3>Product + Platform Scope</h3><ul style="min-height:1.5em"><li>AI Foundations (models, orchestration, evals, guardrails)</li><li>Copilot (user-facing intelligence layer)</li><li>Automations (workflow execution layer)</li><li>Platform Experience / Marketplace (integration + ecosystem surface)</li><li>Emerging surfaces (voice, messaging, cross-product intelligence)</li></ul><h3>What this actually means</h3>You are responsible for:<ul style="min-height:1.5em"><li>How decisions get made inside the system</li><li>How context moves across workflows</li><li>How actions get triggered (and when they shouldn’t)</li><li>How we evaluate whether AI is actually working</li></ul>This includes:<ul style="min-height:1.5em"><li>Agentic workflows (reason → decide → act → evaluate)</li><li>Cross-product context (jobs, customers, payments, communication)</li><li>Reliability, safety, and failure modes</li><li>Developer experience for building on top of AI systems</li></ul><h3>Team Structure</h3><ul style="min-height:1.5em"><li>~30 engineers across 4–6 teams</li><li>4–6 EMs / Sr EMs reporting into you</li><li>Close partnership with Product, Design, Data</li></ul><h2>WHAT “GOOD” LOOKS LIKE</h2>Not “we shipped AI features.”Instead:<ul style="min-height:1.5em"><li>The system proactively recommends and takes actions</li><li>Teams build on shared AI primitives, not reinventing them</li><li>AI output is reliable, measurable, and improving over time</li><li>Engineers trust the system, and move faster because of it</li><li>Customers feel like the product is working for them, not just responding</li></ul><h2>THE AI BAR (THIS ROLE IS DIFFERENT)</h2>We are not looking for:<ul style="min-height:1.5em"><li>Someone who rolled out Copilot internally</li><li>Someone who used LLM APIs for features</li><li>Someone adjacent to AI</li></ul>We are looking for someone who has:Built real systems where AI makes decisions and takes actions in production.That means experience with:<ul style="min-height:1.5em"><li>Agent orchestration (not just prompts)</li><li>Tool use and workflow execution</li><li>Evaluation (offline + online)</li><li>Observability and failure handling</li><li>Guardrails and safety in real systems</li><li>Tradeoffs between autonomy vs. control</li></ul>You don’t need to code daily, but you must be able to reason at the system level.<h2>WHAT YOU’LL ACTUALLY DO</h2><ul style="min-height:1.5em"><li>Define how AI should work across Jobber, not just within a team</li><li>Build and evolve a multi-team org to execute on that vision</li><li>Make tradeoffs between speed, quality, and safety</li><li>Push teams beyond feature thinking into system thinking</li><li>Challenge assumptions, including leadership’s</li><li>Drive adoption across engineering, product, and the company</li></ul><h2>WHAT WE’RE LOOKING FOR</h2><h3>Leadership</h3>You’ve led orgs through complexity, not just growth.<ul style="min-height:1.5em"><li>Managed managers across multiple teams</li><li>Built organizations that scale (not just teams that ship)</li><li>Driven cross-org alignment in ambiguous spaces</li></ul><h3>Product + Systems Thinking</h3>You think in systems, not features.<ul style="min-height:1.5em"><li>You understand how user workflows connect end-to-end</li><li>You’ve partnered deeply with Product and Design</li><li>You care about customer outcomes, not just technical output</li></ul><h3>AI Depth (non-negotiable)</h3>You’ve built or led production LLM/agentic systems.<ul style="min-height:1.5em"><li>You understand what actually works (and what doesn’t)</li><li>You’ve seen systems fail and improved them</li><li>You have opinions about evaluation, reliability, and safety</li></ul><h3>Execution</h3>You can move fast without breaking everything.<ul style="min-height:1.5em"><li>You’ve balanced shipping vs infrastructure vs tech debt</li><li>You know when to iterate and when to redesign</li></ul><h2>WHY JOBBER · WHY NOW?</h2>This is not “AI theatre.”We already have:<ul style="min-height:1.5em"><li>AI Receptionist (live, handling real customer calls)</li><li>AI features embedded across the product</li><li>250,000+ businesses using the platform</li></ul>What we don’t have yet is: A unified, intelligent system across the product.That’s what this role builds.<h2>TLDR:</h2>Most Director roles optimize delivery. This one defines: How an entire product becomes intelligent.What you can expect from Jobber:<ul style="min-height:1.5em"><li>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.</li><li>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.</li><li>A unique opportunity to build, grow, and leave your impact on a $400-billion industry that has no dominant player...yet.</li><li>To work with a group of people who are humble, supportive, and give a sh*t about our customers.</li></ul>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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