[All remote jobs](https://jobicy.com/jobs.md)Open role[![Jobber logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/135a74b7-221.jpeg)](https://jobicy.com/company/jobber.md)Remote opportunity at[Jobber](https://jobicy.com/company/jobber.md) # Payments GTM (Go-to-Market) Operations and Strategy Lead Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/jobber.md)Share17 Aug 2026Published43Listing views4Application actions16 Sep 2026Apply before Opportunity details ## About this role. AI SummaryThis principal-level Fintech role establishes Jobber’s Payments GTM Operations function and owns the commercial operating strategy for payments products. The lead will coordinate Marketing, Sales, Account Management, Support, Risk, Operations, Analytics, and Product to improve customer discovery, activation, usage, and payments revenue. Core work includes customer-journey redesign, opportunity sizing, experiment design, performance measurement, and scalable process development. The ideal candidate combines GTM or revenue operations execution with strategic advisory experience, strong analytics, and knowledge of payments or small-business financial services. The position is Canada-wide, with hub-city employees participating in in-office schedules and other Canadian employees working remotely. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a principal-level, greenfield operating role with broad ownership across the commercial side of a payments business. Success requires both strategic judgment and the ability to influence multiple functions without direct authority while delivering measurable growth results. ## Salary analysis Estimated compensation compared with the broader CA market for similar roles. Estimated job medianMarket rateC$177,900CA market rangeC$160k–C$230k0C$253k AI insightThe posting explicitly offers a minimum annual salary of $151,200, a midpoint of $177,900, and a maximum salary of $204,500. Because the role is open anywhere in Canada, the dollar figures are treated as CAD in the extracted compensation fields; the offer midpoint is 177,900 without currency conversion. For comparison, the estimated US-market annual base-salary range for a principal payments GTM operations and strategy leader is USD 160,000–230,000, depending on company stage, payments expertise, and scope; this market comparison is an estimate. ## Core skills Skills and capabilities most closely associated with this opportunity. [Go-to-Market Strategy](https://jobicy.com/jobs?search_keywords=Go-to-Market%20Strategy.md)[Revenue Operations](https://jobicy.com/jobs?search_keywords=Revenue%20Operations.md)[Payments](https://jobicy.com/jobs?search_keywords=Payments.md)[Fintech](https://jobicy.com/jobs?search_keywords=Fintech.md)[Business Operations](https://jobicy.com/jobs?search_keywords=Business%20Operations.md)[Growth Strategy](https://jobicy.com/jobs?search_keywords=Growth%20Strategy.md)[Customer Journey Mapping](https://jobicy.com/jobs?search_keywords=Customer%20Journey%20Mapping.md)[Data Analytics](https://jobicy.com/jobs?search_keywords=Data%20Analytics.md)[Cross-Functional Leadership](https://jobicy.com/jobs?search_keywords=Cross-Functional%20Leadership.md)[Experimentation](https://jobicy.com/jobs?search_keywords=Experimentation.md) Cover letter sampleDear Hiring Team, I am excited to apply for the Payments GTM Operations and Strategy Lead role at Jobber. My experience building data-driven go-to-market programs, aligning cross-functional stakeholders, and improving commercial performance would enable me to help scale adoption of Jobber’s payments products. I bring a structured, experimental approach to ambiguous growth opportunities, combining customer-journey analysis, operational design, and rigorous measurement to turn strategy into measurable outcomes. I am particularly motivated by Jobber’s mission to help small service businesses strengthen their financial operations. I would welcome the opportunity to partner with Payments, Product, Marketing, Sales, Risk, and Analytics teams to establish a scalable GTM operating engine and accelerate sustainable payments growth. Copy Sample interview questionsHow would you design an experiment to increase adoption of a payments feature among existing customers?I would begin by defining the target customer segments, desired activation event, baseline funnel conversion, and key constraints. I would prioritize hypotheses by expected impact, confidence, and implementation effort, run a controlled pilot where feasible, and assess incremental adoption, payment volume, retention, support burden, and unit economics before scaling. Which metrics would you use to manage a payments go-to-market business? I would create a shared payments GTM scorecard with clear metric definitions, owners, targets, and review cadences. Leading indicators would include exposure, enrollment, and activation; lagging indicators would include payment volume, revenue, retention, and customer outcomes. I would use the scorecard to identify funnel drop-offs and convert findings into accountable action plans. Describe your approach to rebuilding a customer journey for a financial product. I would map the end-to-end journey using behavioral data, customer feedback, frontline observations, and operational process documentation. For each stage, I would quantify volume and conversion, identify friction and ownership gaps, then prioritize interventions based on customer impact, revenue potential, and feasibility. How do you gain alignment when Sales, Product, Risk, and Marketing have competing priorities? I would align stakeholders around a common customer and business outcome, make trade-offs explicit with data, and clarify decision rights and milestones. When priorities conflict, I would propose a focused pilot or phased plan that reduces risk while producing evidence for the next decision. What would your first 90 days in this greenfield GTM operations role look like? I would establish an initial operating cadence quickly: a baseline performance dashboard, a cross-functional working group, a prioritized opportunity backlog, and a small set of high-confidence experiments. During the first 90 days, I would focus on learning the payments economics and customer journey, delivering early wins, and building the long-term roadmap and governance model. 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](https://www.youtube.com/watch?v=EkfZmHrRLx4&list=PLoktA_D-2UEnxMLfCe93bANKXVXd2bdN8&index=24). 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! Show more [Apply now >](https://jobicy.com/jobs/150910-payments-gtm-go-to-market-operations-and-strategy-lead.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. 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. Next step ## Apply now. Follow the employer’s application method and review Jobicy’s safety guidance before sharing personal information. Keep exploring ## Related remote jobs. Matched by job category10 related opportunities[Product & Operations](https://jobicy.com/categories/management.md) [Browse all jobs](https://jobicy.com/jobs.md) * ![Precision Medicine Group logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/f1277044-221.jpg) Precision Medicine Group Aug 17 ### [Senior Operations Specialist](https://jobicy.com/jobs/150932-senior-operations-specialist.md) Job Summary and Purpose: The Senior Operations Specialist leverages expertise and knowledge to plan and manage initiatives and activities designed to improve the quality, efficiency and effectiveness of the delivery… * ![Clover Health logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/8d4e74b3-221.jpg) Clover Health Aug 17 ### [Buyer](https://jobicy.com/jobs/150921-buyer.md) The Finance team at Clover Health is a group of strategic partners providing financial and operational insights that drive informed decision-making and efficient capital allocation. Guided by our core values… * ![Instructure logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2022/04/430057884baf037dd2aa1e1e017e72b6.jpg) Instructure Aug 17 ### [Director, AI Center of Excellence](https://jobicy.com/jobs/150914-director-ai-center-of-excellence.md) At Instructure, we believe in the power of people to grow and succeed throughout their lives. Our goal is to amplify that power by creating intuitive products that simplify learning… * ![Instructure logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2022/04/430057884baf037dd2aa1e1e017e72b6.jpg) Instructure Aug 17 ### [Sr. Revenue Operations Manager](https://jobicy.com/jobs/150908-sr-revenue-operations-manager.md) At Instructure, we believe in the power of people to grow and succeed throughout their lives. Our goal is to amplify that power by creating intuitive products that simplify learning… * ![Instructure logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2022/04/430057884baf037dd2aa1e1e017e72b6.jpg) Instructure Aug 17 ### [Principal Business Operations Manager – Remote (USA)](https://jobicy.com/jobs/150900-principal-business-operations-manager-remote-usa.md) At Instructure, we believe in the power of people to grow and succeed throughout their lives. Our goal is to amplify that power by creating intuitive products that simplify learning… * ![PolicyMe logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/08/1e29f43a-221.png) PolicyMe Aug 17 ### [Principal Product Manager, Accounts & Automation](https://jobicy.com/jobs/150899-principal-product-manager-accounts-automation.md) Overview of the Role We’re on a mission to modernize insurance – making it simpler, more accessible, and customer-first. The insurance industry is a $1T market that’s remained largely untouched… * ![Instructure logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2022/04/430057884baf037dd2aa1e1e017e72b6.jpg) Instructure Aug 17 ### [Product Specialist: Platform](https://jobicy.com/jobs/150898-product-specialist-platform.md) At Instructure, we believe in the power of people to grow and succeed throughout their lives. Our goal is to amplify that power by creating intuitive products that simplify learning… * ![Nebius logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2026/06/d90c0566-221.webp) Nebius Aug 17 ### [Senior Technical Product Manager, Token Factory](https://jobicy.com/jobs/149361-senior-technical-product-manager-token-factory.md) About Nebius: Nebius is leading a new era in cloud infrastructure for the global AI economy. We are building a full-stack AI cloud platform that supports developers and enterprises from… * ![Gopuff logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2021/05/Jobicy-210510095548-598926.jpg) Gopuff Aug 16 ### [Category Manager – Health & Wellness, Lifestyle](https://jobicy.com/jobs/150833-category-manager-health-wellness-lifestyle.md) The Category Manager for Home Care, Health & Wellness, and Lifestyle will be responsible for managing the P&L, assortment, pricing, and marketing of these departments across Gopuff’s network. We are… * ![NTT DATA logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/09/e2252da5-221.png) NTT DATA Aug 16 ### [Change Management Consultant](https://jobicy.com/jobs/146303-change-management-consultant.md) NTT DATA is a team of more than 190,000 diverse professionals, operating in more than 50 countries throughout the world. The sectors where we have activities include: telecommunications, finance, industry,…