Principal Strategic Finance Manager

"Shape the financial strategy that will define the future of Jobber and the small businesses we serve!"

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:

The Finance team is the engine that ensures we grow sustainably and strategically. From financial planning to operational excellence, this team turns insights into action, enabling Jobber to scale while staying laser-focused on our mission to help small businesses be successful. Whether it’s forecasting growth, optimizing efficiency, or shaping the story we share with investors and our board, Finance is where strategy meets execution.

• We're a small team: Senior people sometimes do junior work—report updates, data dumps, and process optimization—if parts of the job are too small for you, then so is our team.
• We are all executors: Everyone on our team can be thought of as a player / coach—whether that is within our team or across others. Managing this dual responsibility is hard. 
• Change is constant: Just when we think things are stable, we release a new product, hire a new leader, open up a new revenue stream, or face some kind of challenge that forces a model or process rebuild.
• We have high standards: Quality, rigour and professionalism in your work is key - this stuff takes time, focus and curiosity.
• Many on our team are remote: Even though we have two offices (Toronto and Edmonton), our team is distributed across Canada—so you have to be accountable to your work and be highly self-motivated.

The Role:

The Principal Strategic Finance Manager is one of the most senior individual contributors in our finance organization. They will tackle the company's most complex strategic questions—capital allocation, long-term planning, pricing and packaging, and big-bet investments. This role is for a finance leader who can blend deep analytical rigor with strong strategic instincts and influence at the C-suite level.

The Principal Strategic Finance Manager will:

• Own enterprise-level strategic analyses: Lead modeling and scenario planning for long-range growth, acquisitions, and market expansions.
• Be a trusted advisor: Partner directly with the CFO, CEO, CRO, and CPO to pressure-test strategies and resource allocation.
• Shape the narrative: Build executive-ready materials that influence board decisions and investor confidence.
  Drive cross-functional alignment: Partner with GTM, Product, Fintech, and Operations leaders to link business strategy to financial outcomes.
• Mentor and elevate: Coach Senior and Finance Managers on strategic thinking, ensuring best practices permeate the org.
• Innovate processes: Introduce advanced forecasting techniques, valuation frameworks, and capital efficiency metrics.

To be successful, you should have:

• 8+ years in strategic finance, FP&A leadership, investment banking, PE/VC, or management consulting.
• Demonstrated track record of influencing C-level decisions and driving outcomes in high-growth SaaS or fintech environments.
• Exceptional modeling skills—capable of building from scratch and challenging assumptions.
• Strong executive presence and communication: can distill complexity into a clear, compelling story
• Bias toward action, comfort with ambiguity, and passion for helping small businesses win.

It would be really great (but not a deal-breaker) if you had:

• CFA / CPA / MBA designation.
• Experience with SQL, PowerBI, PowerPivot, Tableau, Python or other advanced analytics techniques.
• Additional academic achievements (research, awards).

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 $181,400, a midpoint of $213,500, and a maximum salary of $245,400, 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, retirement savings plan matching, 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.
• Support for all your breaks: from vacation to rest and recharge, your birthday off to celebrate, health days to support your physical and mental health, and parental leave top-ups to support your growing family.
• 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!