Senior Manager - Fintech Bets

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.

Why Fintech at Jobber:

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 looking for a Senior Manager - Fintech New Bets to own some of Jobber’s most critical Fintech bets - taking them from idea, to business case, to live product with real customers and real revenue ultimately driving growth of these businesses.

You’ll join the Fintech team - a small, scrappy, high-performing group building financial tools that power small business success.

Today, a limited number of people - primarily our VP and Director-level leaders - are carrying a wide range of critical initiatives, from pricing to partnerships to piloting new products. This role exists to fill that execution gap: a versatile operator who can lead projects from idea through implementation, run their own analytics, and move between pricing, GTM, product, and risk.

The Role:

As the Senior Manager - Fintech New Bets , you’ll be a high-impact business athlete - equally comfortable shaping strategy and executing it. This is not a traditional strategy or advisory role. You’ll actively drive and own outcomes.

• Drive key strategic projects:
  • Taking loosely defined opportunities and turning them into shipped products
  • Materially improving the unit economics of an existing Fintech offering
  • Leading complex cross-team initiatives that directly impact revenue, margin, or risk
• Scope new businesses:
  • Identify new Fintech product lines and opportunities
  • Work cross-functionally and with external partners to build and, in some cases, execute business cases
  • Evaluate unit economics, risk, and scalability to inform go/no-go decisions
• Build partnerships:
  • Engage and negotiate with external partners unlock new economics, capabilities, or risk structures through partnerships
• Unlock revenue and efficiency:
  • Analyze Fintech business performance to identify margin and revenue opportunities
  • Lead initiatives such as defining the business strategy for Instant Payouts, including pricing, risk tradeoffs, product requirements, and GTM approach
• Support GTM and product expansion:
  • Act as connective tissue between Fintech, Product, Risk, Compliance, Finance, and GTM teams
  • Accelerate Fintech product launches and drive customer adoption

To be successful, you should have:

• Extensive experience in strategy, operations, growth, or related roles (e.g., consulting, finance, payments, or a fast-scaling tech company)
• A proven track record of actively driving and owning projects end-to-end with measurable business outcomes
• Strong financial and business acumen , including experience building and pressure-testing unit economics, pricing models, and business cases
• Exp…