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Staff Strategy Analyst

Canada, Toronto Employment contract 120000.00 - 140000.00 CAD / Year · Job Posted May 29, 2026
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Job Description

As a Staff Strategy Analyst for our Strategic Initiatives portfolio at FreshBooks, you will partner cross-functionally to build the frameworks, models, and policies that guide operational decisions. Serving as a key architect, you will shape FreshBooks' enterprise-level strategy and influence critical business decisions, ensuring long-term business growth in creative and effective ways. While specific deliverables will change periodically based on the needs of the business, you will consistently be responsible for a key strategic priority for FreshBooks.

Job Responsibility

  • Lead the development and refinement of company-wide strategy, providing oversight for special or cross-functional projects
  • Translate high-level business goals into actionable frameworks and operational reality by partnering with functional teams like Marketing, Sales, and Product
  • Diagnose and resolve cross-functional friction and structural issues, acting as the primary link between departments to improve operating rhythms
  • Proactively extract, validate, and synthesize data from disparate sources using tools like SQL to build models and trackers for early performance visibility
  • Develop robust ROI models to evaluate new opportunities, prioritize the strategic roadmap, and present complex findings as clear, executive-level narratives
  • Oversee the execution and optimization of strategic frameworks and delivery models, managing interlocks and dependencies to ensure high-priority initiatives are delivered at scale
  • Drive organizational adoption of new frameworks and governance, ensuring transformations are permanent, measurable, and yield intended business results while proactively exploring AI tools for innovation

Requirements

  • 8+ years of experience in strategy, business operations, or marketing analytics
  • Strong data analytics and business casing skills, with the ability to pull your own data and navigate databases independently in Google Sheets/Excel, Slide Decks/PowerPoint or similar
  • General technical aptitude and the ability to think of creative tech-powered solutions to solving challenges
  • A proven track record of influencing executive-level strategy and driving initiatives that have a measurable impact on company performance
  • Experience leading cross-functional transformation initiatives, including the introduction of new policies, programs, tools, or systems at scale
  • Proven ability to influence without authority and drive alignment across stakeholders at all levels within a matrixed environment
  • Strong understanding of SaaS/Fintech operational drivers and how GTM decisions impact profitability and long-term growth
  • Exceptional communication skills, including the ability to create structure, clarity, and momentum within ambiguous or fast-moving environments

Nice to have

Experience with SQL, Python, Mode, Looker, Tableau, or similar

What we offer

  • Comprehensive health and wellness benefits
  • Generous time off including a flexible vacation plan
  • Retirement savings program or pension plan matched to your local office
  • Stock options for every full-time employee
  • Parental leave and new parent support
  • Annual healthy living credit
  • Comprehensive medical and dental benefits
  • Fertility and gender-affirming benefits
  • Peer Recognition Program
  • Employee Assistance Program
  • Headphone credit
  • Meaningful in-person gatherings
  • Home office credit
  • Equity grant
  • Immediate enrollment in FreshBooks' comprehensive benefits program

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