Payments GTM (Go-to-Market) Operations and Strategy Lead

Please note the internal job title is: Principal Payments GTM Operations and Strategy

Want to build the go-to-market engine for a fast growing payments business?

Then Jobber might be the place for you! We’re looking for a Payments GTM Operations and Strategy Lead to be part of our Fintech 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:

Fintech is one of the fastest-growing parts of Jobber’s business and a core strategic priority for the company. With financial tools embedded directly into our platform, we help small business owners get paid faster, access capital, and invest in growth. As the business scales, we’re focused on expanding our financial products beyond payments into new, high-impact Fintech offerings.

We’re building the financial backbone for field service businesses. Our Fintech team is one of the most strategically important and fastest growing parts of Jobber. We help businesses get paid, access capital, understand their financial health, and ultimately stay in business longer.

The future of financial services is embedded, and we’re still early. Small businesses increasingly rely on vertical SaaS platforms like Jobber not just to run their operations, but to manage their money. Payments is the foundation of everything we do in Fintech, and how we go to market with our Get Paid products (invoicing, payments, instant payouts, etc) is the single biggest lever we have to grow the business.

This role will own how Jobber’s payments business grows. Think of this as running the commercial side of a payments business inside a SaaS company.

The role:

This role establishes Payments GTM Operations as a new function at Jobber. You will bring together every team that touches payments go-to-market (Marketing, Sales, Account Management, Customer Support, Risk, Operations, Analytics, Product Development) and build the programs, processes, and measurement that turn these teams into a coordinated growth engine. There is no playbook. You will build it. If you want to own the commercial outcome of a payments business and have the direct ear of the VP & GM, Payments and Fintech, keep reading.

The job has two objectives: help more customers discover and get value from Jobber’s payments products, and accelerate revenue growth for the business. Day to day, you will identify opportunities, design programs, and run experiments to drive adoption and usage of Jobber’s payments products.

The Payments GTM Operations and Strategy Lead will:

• Operating and strategy experience, ideally a mix of both:

• Operating experience (primary): You have identified opportunities, mobilized teams, and driven measurable results in Revenue Operations, GTM Operations, Strategy & Operations, Product Commercialization or GM/Founder role at a scaling SaaS or Fintech company

• Strategy experience (valued): you have been a strategic partner to senior leaders, making data-driven recommendations in management consulting or strategy & operations

• Diagnose where payments adoption breaks down - by segment, by channel, by motion - and rebuild the customer journey from first touch through activation. This includes identifying where customer-facing teams (sales, post-sales, support) can change their motions to drive better outcomes.

• Run structured experiments (incentives, messaging, changes, sales motion shifts and iterate fast based on results.

• Define metrics that matter. Then hold yourself and cross functional partners to them without any direct authority over any of them.

• Build a deep working relationship across GTM teams, Product, RevOps, Analytics, etc. You are the connective tissue between these teams on payments GTM.

• Using data and qualitative insights to find opportunities, size them, run experiments, and measure results.

• Staying close to what other vertical SaaS and embedded payments players are doing. Knowing where Jobber can differentiate.

To be successful, you should have:

• Deep understanding of payments and financial services business models, metrics, and growth strategies is highly desirable, particularly financial services for small businesses.

• Strong data instincts. You use analytics to measure impact, make decisions, and optimize performance. You are not just comfortable with data, you reach for it first.

• Experience using languages such as SQL to manipulate large data sets is a plus, but not required.

• Exceptional communication and stakeholder management skills with the ability to work across GTM teams, Product, Executive Leadership, etc. You translate data into stories and strategies into action plans.

• Demonstrated ability to design and implement scalable operational processes that enhance efficiency and ultimately drive growth.

• Passion for helping small businesses succeed through innovative financial solutions.

• A curious mind and a growth mindset. You are a scrappy learner who can quickly become an expert and build new capabilities.

• A proactive drive to solve problems. You are capable of bringing structure to ambiguous problems, corralling resources, and delivering results.

• A preference for working in an ambiguous and fast-paced environment. We’re growing fast and things are changing every day.

• You have worked horizontally; influencing Sales, Marketing, and Product without owning any of them, and you have the receipts to prove it worked

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 who are either based in one of our hub cities: Edmonton, Toronto, Vancouver, or Kitchener-Waterloo or who are remotely based in Canada.

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 $151,200 a midpoint of $177,900 and a maximum salary of $204,500 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!

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!