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GTM Operations Lead

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Remote from
Canada
Salary
CAD 151,200–204,500 / yr
Employment
Full Time
Experience
Director
Published
Apply before
22 Nov 2026
Listing views
34
Application actions
1
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AI Summary

The role, at a glance.

Jobber is hiring a principal-level GTM Operations and Strategy leader to establish the operating model for its payments go-to-market function. The role coordinates Marketing, Sales, Account Management, Support, Risk, Operations, Analytics, and Product to improve discovery, activation, adoption, and ongoing use of payments products. Responsibilities include redesigning the end-to-end payments customer journey, defining core GTM metrics, sizing opportunities, and running measurable growth experiments. This is a strategic, data-led role in an embedded-finance SaaS environment with substantial cross-functional influence and ownership of commercial outcomes.

Role DNA

A quick view of the complexity, pace, ownership and collaboration implied by the job description.

Job Complexity

5/5
EasyHard

Pace & Pressure

5/5
RelaxedFast-paced

Autonomy Level

5/5
GuidedFull ownership

Communication Load

5/5
IndependentCollaborative
AI insightThe role is highly complex because it creates a new cross-functional GTM Operations function while owning growth outcomes for a strategic payments business. Success requires payments-domain knowledge, analytical rigor, executive stakeholder management, and the ability to impose structure on ambiguous, fast-changing problems.

Salary analysis

Estimated compensation compared with the broader CA market for similar roles.

Estimated job median (per year)Market rate
C$177,850
CA market range (per year)C$150k–C$220k
AI insightThe employer explicitly states an annual base-salary range of CAD 151,200 to CAD 204,500, with a CAD 177,900 midpoint. The estimated Canadian market range for a principal-level payments GTM operations and strategy leader is CAD 150,000 to CAD 220,000 annually; actual offers may vary by location, fintech expertise, and scope of commercial ownership.

Core skills

Skills and capabilities most closely associated with this opportunity.

Sample interview questions
How would you identify the highest-impact opportunity to increase payments adoption at Jobber?

I would map the funnel from eligibility and awareness through enrollment, activation, first payment, and repeat usage. I would quantify conversion and drop-off by customer segment, channel, and lifecycle stage, combine this with qualitative feedback, and prioritize opportunities by expected impact, confidence, effort, and risk.

Describe how you would align Sales, Support, Product, and Marketing around a shared payments GTM goal.

I would establish a shared outcome metric, supporting funnel metrics, clear ownership, and a regular operating cadence. Each team would receive role-specific actions and reporting, while a cross-functional forum would review experiment results, resolve blockers, and make prioritization decisions.

What metrics would you use to assess the health of a payments go-to-market motion?

I would track eligible-customer penetration, enrollment conversion, activation rate, time to first transaction, payment volume, repeat usage, retention, revenue contribution, support contacts, and risk or loss indicators. The metric set should connect leading behavioral indicators to durable customer value and financial outcomes.

Tell us about a time you used data to change a commercial or operational strategy.

A strong example would explain the initial hypothesis, the data sources and segmentation used, the insight discovered, and the experiment launched in response. It should conclude with quantified results, stakeholder alignment actions, and how the change was operationalized at scale.

How would you approach experimentation with incentives for payments adoption while protecting unit economics?

I would define a target segment and a clear incremental-behavior hypothesis, then test incentives against a control group. I would measure incremental activation, payment volume, retention, cost per incremental adopter, margin impact, and any risk effects before scaling only the approaches that demonstrate sustainable value.

This analysis is generated from the job description. Salary estimates, role characteristics and sample answers are guidance, not employer-provided facts.
Opportunity details

About this role.

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:

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:

Reporting into the VP & GM, Payments and Fintech you will establish 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.

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, the Payments GTM Operations and Strategy Lead will identify opportunities, design programs, and run experiments to drive adoption and usage of Jobber’s payments products. This will include:

  • Mapping and rebuilding the end-to-end customer journey for payments, from first touch through activation and ongoing usage, working closely with cross-functional partners. This includes identifying where customer-facing teams (sales, post-sales, support) can change their motions to drive better outcomes.

  • Experimenting with a range of actions (e.g. incentives) to drive payments adoption and usage, rapidly iterating based on results.

  • Defining the metrics that matter for payments GTM and holding yourself (and cross-functional partners) accountable to them.

  • Building deep working relationships 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:

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

    • Operating experience: you have experience identifying opportunities, mobilizing teams, and driving measurable results. Could be Revenue Operations, GTM Operations, Strategy & Operations, Product Commercialization, or a GM/Founder role, ideally at a scaling SaaS or Fintech company.

    • Strategy experience (valued): you have been a strategic partner to senior leaders, making data-driven recommendations. Examples could be Management Consulting, VC, or Strategy & Operations.

  • Deep understanding of payments and financial services business models, metrics, and growth strategies is 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.

Location:

We believe great collaboration is intentional, and that means coming together in person to build, brainstorm, and connect from time to time. This role is open to candidates anywhere in Canada. Employees who live in one of our hub cities – Edmonton, Toronto, Vancouver, or Kitchener-Waterloo will participate in their department’s in-office schedule, while employees outside our hub cities will work remotely.

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!

Apply now >

This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content.

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