The Senior Strategy Analyst leads strategic programs, builds analytical models, presents insights to leadership, and supports operational decision-making aligned with business goals.
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 / programs that contribute towards the development and refinement of FreshBooks’ enterprise-level strategy across domains. Provide leadership and ownership of "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 that we understand the impact, recommend solutions and help execute 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. Assess unusual patterns and use data to identify root causes
- Lead the development of dashboards and KPIs to monitor portfolio performance and margin. Devise solutions for data visualization based on limited information or precedent
- Present findings and recommendations to senior leadership with clarity and influence, translating complex datasets into visual narratives accessible to non-technical audiences, enabling the business to select the right course of action
- 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, stress-test performance. Use interpretation 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 the 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
Other duties as may be assigned
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 suggests variations in analytical approach to get better results.
You'll Stand Out If You Have
Experience with third-party data and decisioning platforms (e.g., Plaid, Stripe, etc.)
#LI-SR1 #LI-REMOTE
At FreshBooks, we approach each individual's compensation with a promise of fair market value and internal equity commensurate with experience and specific skill set.
The total compensation for this role ranges from CA$102,000 - CA$127,000 per year, which may include participation in our incentive programs. Additionally, this position offers an equity grant and immediate enrollment in FreshBooks' comprehensive benefits program, detailed below.
NOTE: This posting is reflective of an existing vacancy at FreshBooks.
Perks and BenefitsWe understand that you'll weigh many factors when deciding if FreshBooks is the right next step in your career. Here are some of our offerings for our employees (we call ourselves ✨ FreshBookers✨) to support their growth:
- 🩺 Comprehensive health and wellness benefits. Generous time off including a flexible vacation plan, a 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 dependent on your region, and more.
- 📚 Perks that matter. Including a Peer Recognition Program, an Employee Assistance Program, headphone credit, meaningful in-person gatherings to bring onsite and remote employees together, and more perks matched to your local cluster.
- 🌱 Working environments to help you thrive. Beautiful office spaces welcome you in Toronto, Amsterdam, and San Luis Potosi. If you don't have access to a FreshBooks office, you receive a home office credit to set up your home office.
- 🤗 Supportive peer group, mentors, and leaders. We care about each other across the organization and have programs to support this so everyone feels a strong sense of belonging, and believes in collective impact.
- 🚀 Accelerated growth. Comprehensive company onboarding, career development through continuous coaching, training, and learning on the job.
You've probably learned a bit about FreshBooks before making it to this point, but let us take a moment to introduce ourselves: At FreshBooks, we believe that small business owners are the backbone of the economy, yet they are often the most underserved when it comes to technology. For over 20 years, we’ve been on a mission to support owners, from the scrappy solopreneur with a big dream to the growing business with employees to manage.
Our leading platform is more than just business software; it’s an all-in-one financial toolkit that automates invoicing, expenses, payments and payroll, allowing our customers to spend less time on paperwork and more time doing the work they love.
We believe in human-centric connections that empower teams to do their best work. Headquartered in Toronto, Canada, our team operates in clusters across North America and Europe using a variety of working environments - remote, hybrid, and in-office - all based on what’s best for the team, collaboration, and mental well-being. We are committed to creating a supportive and flexible workplace where everyone can thrive, grow, and make an impact on the lives of small business owners worldwide.
Even if your experience doesn't meet every bullet on the above lists, we'd love to learn more about you and why you think FreshBooks is the next step in your career. FreshBooks is an equal-opportunity employer. We do not discriminate based on gender, religion, race, mental disability, sexual orientation, age, or any other status. All applicants are considered based on their qualifications and merits. At FreshBooks, we inspire an environment of mutual respect and we believe diversity and inclusion are crucial to our success. FreshBooks provides employment accommodation during the recruitment process. Should you require any accommodation, please indicate this on your application and we will work with you to meet your accessibility needs. For any questions, suggestions or required documents regarding accessibility in a different format, please contact us by phone at 1-416-780-2700 and/or email at [email protected].
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