The Staff Strategy Analyst will develop frameworks and models for operational decisions, influence enterprise-level strategy, and lead cross-functional projects to drive business growth at FreshBooks.
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.
This role is hybrid, meaning that the team comes together in our Downtown Toronto office up to twice per month.
What You'll Do
- 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.
What You'll Bring
- 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.
You'll Stand Out If You Have
- Experience with SQL, Python, Mode, Looker, Tableau, or similar.
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$120,000 - CA$140,000 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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