Fintech Operations Lead

DOES STANDING UP OPERATIONS FOR BRAND NEW FINANCIAL SERVICES EXCITE YOU? Then Jobber might be the place for you! We're looking for a Fintech Operations Lead to be part of our Fintech Operations team. About Jobber: 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 https://www.youtube.com/watch?v=EkfZmHrRLx4&list=PLoktA_D-2UEnxMLfCe93bANKXVXd2bdN8&index=24. The Team: 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. You'll report to the Senior Director of Fintech Risk & Operations and work as a peer to our Senior Fintech Operations Manager, collaborating closely with senior leadership including the VP of Fintech and the Senior Director, Fintech New Bets. Flexibility and the ability to thrive in ambiguity are key—the fintech space is constantly changing, and we're looking for someone who can lead through that change while keeping a team grounded and high-performing. The Role: Jobber is looking for a dynamic and experienced Fintech Operations Lead to own two critical pillars of our fintech business: bookkeeping operations and capital operations. This role is central to how Jobber scales its fintech business responsibly, and the person who takes it on will shape not just the processes but help build the business. This is a rare opportunity to build from the ground up in a high-growth fintech environment. We're looking for a self-starter who sets the standard through their own work, cultivates relationships, and is genuinely energized by turning complex operational problems into clean, repeatable systems. You have a bias toward action, data and automation, you're comfortable with AI tools, you know how to hold multiple workstreams without anything slipping through the cracks. You can work cross functionally. The Fintech Operations Lead will own: - Bookkeeping Operations: Build and lead the operational foundation for Jobber's bookkeeping product. This means standing up the function from scratch, one that supports Jobber customers day-to-day through customer support, issue escalation, and vendor support , while also designing the processes and systems that allow the operation to scale. You won't just be running this function; you'll be influential in shaping its strategy and direction, working closely with Product and leadership to define what great looks like for this part of the business. - Capital Operations: Run the operational backbone of Jobber's lending products. This covers the end-to-end lifecycle of merchant loan activity. As the product grows, you'll ensure the operational infrastructure scales with it. This requires working closely with our lending partners and their compliance / regulatory teams. - Data, Reporting and AI-Assisted Operations: Build and own the reporting that gives leadership real-time visibility into capital performance, and bookkeeping health. You're comfortable working with data directly, writing queries, interpreting results, and surfacing what matters. You actively use AI tools to cut down on manual work and improve output quality, and you build that same orientation into your team's day-to-day. - Policy and Process Development: Design and document the policies, controls, and standard operating procedures that underpin your areas of ownership. You see process documentation as a strategic asset, something that reduces key-person risk, enables scale, and holds up to regulatory scrutiny. You build things that outlast any single person. - Cross-Functional Partnership: Partner closely with Support, Legal, Finance, Product, Analytics and Engineering to ensure compliance and operational requirements get embedded early, not as an afterthought. You communicate clearly across functions and can translate complex regulatory or operational constraints into practical guidance for people who don't live in your world. To be successful, you should have: - Strong working knowledge of compliance operations including KYC/KYB, AML/ATF, and PCI DSS, ideally across both Canada and the US. - Hands-on experience with bookkeeping or financial operations, including reconciliation and close collaboration with Finance on ledger accuracy. - Familiarity with lending or capital products and how loan disbursement, repayment, and delinquency workflows operate in practice. - A data-first mindset with practical SQL/Python or analytics skills and comfort building and interpreting operational dashboards. - Familiarity with credit risk management, being comfortable with concepts such as credit exposure, probability of default, loss at default etc. - A genuine track record of using AI tools to improve output and operational efficiency, and enthusiasm for pushing this further. - Demonstrated ability to build policy, process, and controls from scratch in a fast-moving environment. - Strong project management skills with the ability to manage multiple workstreams simultaneously. - Familiarity with operational tooling such as Jira, Asana, Salesforce etc. - A willingness to possibly lead people in the future as the business grows. - Bachelor's degree in a relevant field (Business, Finance or similar) is required. Advanced certifications or degrees add bonus points. 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 $121,000, a midpoint of $142,200, and a maximum salary of $163,600, 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!