Director, Product Management - Fintech

300K+ users on Platform // 40B+ invoiced using Jobber // Profitable - Not VC-pressure dependent

THE PROBLEM YOU'D OWN

A plumber wraps up a job and sends an invoice. The work is done. The customer is happy. But two weeks later, he's still waiting to get paid. He's got another job to start, a supplier to pay, and no visibility into whether the money is coming tomorrow or next month. He's not a banker. He's a tradesperson trying to run a business.

This is the financial reality for most businesses on Jobber. They do great work. They just don't have the tools to get paid efficiently, access capital when they need it, or understand whether their business is actually healthy. The ones who try cobbling together solutions waste time on disconnected tools that weren't built for how they operate.

That's the gap. And Jobber is the right company to close it.

Embedded finance is the future of how small businesses will manage money—and Jobber is positioned to be the financial hub for the home service industry. The decisions you make here won't just define one product. They'll define what financial empowerment looks like for 100,000+ small businesses.

That's the problem you'd own.

THE CUSTOMER

You're building for the person who is already running on empty.

The landscaper who invoices at the kitchen table after a 10-hour day and doesn't know why cash feels tight even when jobs are coming in. The painting company owner who turned down a big contract because she wasn't sure she could cover payroll while waiting on outstanding invoices. The HVAC technician who wants to offer financing to his customers but has no idea where to start.

Money is not abstract for these people. It is the difference between taking on the next job and turning it down. Between growing a business and selling it. They are not looking for a finance course or a dashboard full of ratios. They want to get paid, stay solvent, and grow—without adding more to their plate.

The Senior Director who succeeds in this role will understand that instinctively. They'll do discovery with actual business owners, not just analysts. They'll feel the difference between a fintech feature that checks a box and one that genuinely changes how a business operates financially.

WHAT YOU'D OWN

Full ownership of Jobber's Fintech product portfolio, from vision to execution.

This is not a feature team. You'd own the product end to end: what it does, how it works, and what it means to build financial products that small businesses actually trust and rely on.

Product scope Invoicing, payments (cards, pay by bank, consumer financing), capital, financial insights, and the next generation of embedded financial services

Cross-functional partners Engineering, Design, Analytics, Risk, Operations, GTM, and customer-facing teams

What 'good' looks like More businesses getting paid faster. Higher adoption of payments and capital products. Transaction volume and customer LTV growing together. Financial products that earn trust because they deliver real outcomes.

The opportunity Embedded finance is still early. More and more, small businesses will turn to their vertical SaaS platform—not just to run operations, but to manage their financial lives. You'd be defining what that looks like for an industry with no dominant financial player.

Team structure You'd lead a team of PMs across an established portfolio and new bets, reporting to the SVP of Product, with close partnership across Engineering, Design, and GTM leadership.

The person we're looking for will have genuine convictions about where embedded finance is going, the credibility to align a cross-functional team around a bold direction, and the judgment to build financial products that work for businesses operating on thin margins and tight schedules.

WHAT WE'RE LOOKING FOR

• You've built and shipped financial products where trust is central to the value. You understand what it means to get payments, capital, or financial data right when real money is on the line.

• You have direct experience with SMB merchant acquiring and understand the complexity of moving money on behalf of small businesses.

• You understand SMB customers—not just their workflows, but their financial constraints. What "getting paid faster" actually means when you're managing a crew and reconciling at midnight.

• You can take incomplete data, emerging market signals, and undefined baselines and turn them into clear product decisions. You're honest about uncertainty and direct about your reasoning.

• You have strong commercial judgment. You can connect fintech product strategy to transaction volume, revenue, and customer LTV—and you've owned metrics that mattered.

• You've led and developed teams of Product Managers. You know how to build a strong product culture, not just manage a roadmap.

• You have proven experience in senior-level product management focused on financial services, ideally within vertical SaaS serving service-based businesses.

WHY JOBBER, WHY NOW

Stable company. Genuine fintech bet. These don't usually come together.

Most senior product leaders are choosing between stability and interesting work. Jobber is something rarer: a company that found product-market fit, is profitable, has 300,000 customers on platform, and is making aggressive bets on embedded finance right now. Not because it has to. Because the opportunity is real and the foundation is there to take it.

We've been building for over 15 years. The Globe and Mail named us a Top Growing Company. Deloitte put us on the Fast 500. We have real tenure in the leadership team and a culture where decisions get made and stuck to.

Payments and capital products are already live and growing. The next chapter is building a full financial ecosystem for the home service industry—and this role owns that chapter.

The $400 billion home services market has no dominant financial player embedded in its software stack. That's the opportunity in front of you.

How we work: This is a remote-first role open to candidates in Canada or the United States.

THE PROCESS

We run a structured, respectful process. No surprise homework. No trick questions. We're evaluating whether you can do the job, and you should be evaluating whether this is the right place to do it.

• TA screen: 30–40 minutes. Focused on your background, how you work, and what you're looking for.

• HM screen: 60 minutes with the Chief Product Officer. Focused on how you think about fintech product problems: discovery, prioritization, and strategy.

• Leadership interview: A conversation with members of our executive team.

• Functional panel: Structured interviews with the broader product team. We'll be specific about what we're evaluating and why.

• Reference and background checks: We do these. We'll ask about the things that matter for this role specifically.

• Offer: If we're aligned, we move fast.

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.