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GTM Operations and Strategy

Job in Regina, Saskatchewan, S4M, Canada
Listing for: Jobber
Full Time position
Listed on 2026-10-20
Job specializations:
  • Business
    Data Analyst, Business Development
Salary/Wage Range or Industry Benchmark: 120000 - 160000 CAD Yearly CAD 120000.00 160000.00 YEAR
Job Description & How to Apply Below
Position: Payments GTM Operations and Strategy
  • 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
  • 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
  • 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, Rev Ops, 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

Operating and strategy experience, ideally a mix of both:

Operating experience: you have experience identifying opportunities, mobilizing teams, and driving measurable resultsA preference for working in an ambiguous and fast-paced environment. We’re growing fast and things are changing every day Strategy experience (valued): you have been a strategic partner to senior leaders, making data-driven recommendations. Examples could be Management Consulting, VC, or Strategy & OperationsA proactive drive to solve problems.

You are capable of bringing structure to ambiguous problems, corralling resources, and delivering results

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

Could be Revenue Operations, GTM Operations, Strategy & Operations, Product Commercialization, or a GM/Founder role, ideally at a scaling SaaS or Fintech company

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

Passion for helping small businesses succeed through innovative financial solutions

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

Experience using languages such as SQL to manipulate large data sets is a plus, but not requiredA curious mind and a growth mindset. You are a scrappy learner who can quickly become an expert and build new capabilities

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

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