Group Lead, Technical Product Management - Systems

ARE YOU AN ACCOMPLISHED LEADER WITH A TECHNICAL EDGE, READY TO INSPIRE AND ELEVATE A TEAM OF TPMS?

Then Jobber might be the place for you! We’re looking for a Group Lead, Technical Program Management, to be a part of our Systems group! 

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 role: 

Reporting to the Director of Technical Program Management, the Group Lead, Technical Program Management will drive clarity and alignment between company strategy, technical execution, and measurable outcomes for the Systems group. You’ll coach and develop TPMs to own their metrics, build quality roadmaps, and deliver meaningful impact in their domains while ensuring cross-team dependencies and long-term technical strategy are connected. This role requires a leader who can balance mentorship with accountability, foster collaboration across Jobber, and translate between business priorities and technical realities to keep work moving at scale.

The team:

The systems group works with the fundamental technology pieces that make up Jobber, Production Engineering (AWS cloud infrastructure), Backend Foundations, Comms Systems and other core technology teams. We are always looking for ways to drive impact in how Jobber’s technology operates and how we can continue to help Jobber scale sustainably.   We work closely with the Product teams to ensure that changes are in the best interest of the customers we serve, and are always looking for ways to improve their experience.  Performance, quality, uptime, and speed to deliver quality code are some of the key pillars with which we look at our work.  We sometimes work across teams and across business silos within Jobber, and we look for solutions that will drive success across the whole organization, not just within our teams.

The Group Lead, Technical Program Management will:

• Oversee and guide team metrics and goals.  Work with the TPMs who set the goals to ensure strong leading and lagging indicators, and hold them accountable to their impact in their area of responsibility.
• Discovering and understanding the connections between Jobber’s day-to-day work, the overall product vision, technical strategy and scaling, and customers’ (internal and/or external) needs.  With those inputs, you can prioritize building what matters in order to achieve product and company goals and initiatives.  You build relationships across the organization in order to keep work moving and help unblock your people when needed.
• Balance coaching, feedback, and mentorship of your team to help them get better at their craft and achieve their career ambitions. 
• Hold your TPMs accountable to a quality roadmap that is delivered in a timely manner.  Help them connect the product, cross-team internal roadmaps and the long-term technical strategy of Jobber.
• Foster collaboration. Partner and collaborate with the respective leadership teams and stakeholders in the focus areas your TPMs cover. 
• Help drive large-scale initiatives.
• Have a close relationship to technology. You’re able to communicate business requirements to a technical audience and understand the implications of the solutions proposed by the engineering members.

To be successful, you should have: 

• Dedicated management and leadership experience, managing a team of TPMs (Program, Project or Product) or equivalent in an always-changing and often quick growth environment. Ability to provide feedback, advise and/or steer TPMs in the right direction based on business and user goals.
• Demonstrated experience as a Technical Program Manager or Technical Product Manager or Technical Project Manager for internal engineering team(s). 
• A strong technical background that has allowed you to support interactions with engineering teams. 
• Experience specialized in one or more of the following is an asset:  AWS infrastructure teams, Developer Acceleration teams, Core stack (Ruby/Rails ideal), Data and streaming technologies (postgres/data streaming/event-driven architectures). 
• It’s an asset if you were a software developer and/or infrastructure/sysadmin earlier in your career.
• Experience in SAAS businesses and an understanding of the basic SAAS metrics that lead to business success.
• Next level communication skills. Your written and verbal communication skills help articulate the voice of the customer and the needs of the business. 
• A data mindset. You look to data to define a problem and you also look to data to demonstrate impact. You are energized by the ability to contextualize your work through various tools, systems and processes.
• A desire to collaborate. To deliver high-quality features as quickly as possible, you’ll need to partner with many different people and departments.
• Execution excellence. Creating insights is one thing – leading and driving execution is another. You are motivated by getting things across the finish line and have a solid track record of managing projects and multiple priorities at any given time.
• A knack for the details, with an understanding of the big picture. In your role, the details matter and help drive your team forward with a sense of direction and clarity. 
• Ownership. You are driven to do the right things for your work and are accountable for the outcomes of the Technical Program Managers that you lead.

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 $145,900, a midpoint of $171,600, and a maximum salary of $197,400, designed to show the progression from learning the ropes to truly excelling.

We design our compensation to reflect each new hire’s skills, experience, and 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!

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!