Senior Strategy Analyst

About The Role

We’re looking for a strategic Senior Strategy Analyst who will support our Strategic Initiatives portfolio. This role will partner cross-functionally to build the frameworks, models, and policies that guide operational decisions. You will apply a complete understanding of analytical principles to assess performance, identify trends, and resolve complex issues in creative ways. Working independently, you will act as a key collaborator across Product, Engineering, and Operations to ensure our strategic projects are measurable and aligned with departmental goals, enterprise-level decisions, and support long-term business resilience.

What You\'ll Do

Leadership of Strategic Programs / Projects: Provide independent leadership of strategic projects and programs that contribute towards the development and refinement of FreshBooks’ enterprise-level strategy across domains. Lead and own \\"Special Projects\\" that don\'t have a natural home.

Translate business goals into actionable frameworks and partner with Product, Engineering, and Operations teams to operationalize them.

Identify and diagnose areas of cross-functional friction. Use evaluation and judgment to recommend solutions and support execution to improve organizational flow.

Act as a connective tissue, ensuring an understanding of impact, recommending solutions, and helping with execution when required.

Serve as a subject matter expert, providing professional advice to stakeholders related to modelling and forecasting that inform executive decision-making and shape future company objectives.

Analytics and Insights: Build and manage sophisticated models to assess and analyze performance and new opportunities using internal and third-party data. Identify root causes from unusual patterns.

Lead the development of dashboards and KPIs to monitor portfolio performance and margin. Design data visualizations based on limited information or precedent.

Present findings and recommendations to senior leadership with clarity, translating complex datasets into visual narratives accessible to non-technical audiences.

Partner with Data teams to ensure data accuracy, integrity, and pipeline reliability underpinning reporting and models.

Forecasting and Reporting: Build forward-looking models to estimate expected losses and stress-test performance. Use interpretations to guide departmental strategy based on these results.

Own the delivery of monthly reporting for senior leadership and cross-functional stakeholders.

Execution and Optimization: Support the implementation and refinement of decisioning systems. Move beyond individual project management to contribute toward the methodology of change at FreshBooks. Establish governance and KPIs that ensure transformation is sustainable and measurable.

Collaborate with Data Teams to validate and calibrate operational models, including scorecards.

Proactively identify opportunities and risks and recommend mitigations.

What You\'ll Bring

4+ years of experience in analytics or strategy in a fintech, payments, lending, or financial services company.

Strong understanding of financial and operational drivers in a SaaS or fintech business, and how decisions impact profitability and long-term growth.

Proven track record of influencing executive-level strategy and driving initiatives that have a measurable impact on company performance.

Experience leading transformation initiatives, including the introduction of new policies, tools, or systems at scale.

Aptitude and curiosity for AI, leveraging groundbreaking technology and methods to achieve financial outcomes.

Strong SQL skills and general technical aptitude / ability to think of creative tech-powered solutions to solving challenges.

Demonstrated expertise in designing and implementing frameworks that balance growth, compliance, and customer experience.

Proven ability to lead cross-functional, greenfield projects of diverse scope.

A passion for building systems that scale and make life better for small businesses.

Proficiency in data visualization and BI tools (e.g., Looker, Tableau, Mode, Python, or equivalent).

Experience translating complex datasets into clear visual narratives.

Ability to build productive working relationships to resolve problems and conflicts.

Ability to resolve a wide range of issues in creative ways and adapt analytical approaches to achieve better results.

You\'ll Stand Out If You Have Experience with third-party data and decisioning platforms (e.g., Plaid, Stripe, etc.).

Compensation The total compensation for this role ranges from CA$102,000 - CA$127,000 per year, which may include participation in our incentive programs. This position offers an equity grant and immediate enrollment in FreshBooks\' comprehensive benefits program.

Perks And Benefits

Comprehensive health and wellness benefits, generous time off, retirement savings or pension plan, matched stock options for full-time employees, parental leave and new parent support, and other benefits.

Peer Recognition Program, Employee Assistance Program, and work-life balance perks.

Supportive offices and home office support where applicable.

Opportunities for growth through onboarding, career development, coaching, and learning on the job.

About FreshBooks At FreshBooks, we believe that small business owners are the backbone of the economy, yet they are often underserved by technology. For over 20 years, we\'ve been on a mission to support owners, from solopreneurs to growing businesses. Our platform is an all-in-one financial toolkit for invoicing, expenses, payments and payroll, helping customers focus on their work.

Headquartered in Toronto, Canada, we operate in clusters across North America and Europe with remote, hybrid, and in-office options. We are committed to a supportive, flexible workplace where everyone can thrive, grow, and make an impact on small business owners worldwide.

Note: This posting is reflective of an existing vacancy at FreshBooks. FreshBooks is an equal-opportunity employer. We do not discriminate on the basis of gender, religion, race, disability, sexual orientation, age, or any other status. We provide employment accommodation during the recruitment process. If you require any accommodation, please indicate this on your application. For accessibility in a different format, contact us at accessibility@freshbooks.com.

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