Senior Strategy Analyst

FreshBooks•Waterloo, ON

3h•Remote

About The Position

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.

Requirements

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.

Nice To Haves

Experience with third-party data and decisioning platforms (e.g., Plaid, Stripe, etc.)

Responsibilities

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
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
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
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