Senior Manager - Fintech New Bets

Please note the internal job title is: Principal Fintech New Bets Manager

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:

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: Lead high-priority cross-functional projects that aren’t being tackled today or are progressing too slowly. Example projects could include:

  • 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

• Experience negotiating with external partners or vendors where economics, risk, or compliance were on the line

• High agency and comfort navigating ambiguity without waiting for perfect clarity

• Excellent stakeholder management and communication skills, with the ability to explain complex topics simply

It would be nice, but not a deal-breaker if you have:

• Experience with vertical SaaS and/or embedded fintech products

• Comfort working with large datasets and analytics tools (e.g., Tableau, Looker); ability to write SQL or build self-serve dashboards is a plus

• Genuine interest in small businesses, particularly in home and field services

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 $204,00, 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!