Senior Marketing Manager, Expansion

About the Role As a Senior Manager, Expansion, you are the strategic architect of the marketing programs that drive revenue growth and deepen engagement across the FreshBooks customer base. Moving beyond execution, you will own the holistic orchestration of customer communications across Core Subscription, Payroll, Payments, and Financial Services—driving organizational prioritization across workstreams to maximize average revenue per user (ARPU) and long-term retention. You will serve as the primary lead of the customer communication ecosystem, ensuring our contact strategy is expertly balanced between high-conversion performance and a premium user experience. This is a high-impact leadership role requiring a blend of analytical rigor, cross-functional influence, and a deep-rooted understanding of SaaS unit economics. What You'll Do Lifecycle Strategy & Ownership: Own the end-to-end journey for existing customers, including reengagement, and multi-product adoption. Partner with Product and PMM to design journeys and customer success paths that drive long-term retention. Contact Strategy & Governance: Act as the primary lead for the customer communication ecosystem. Define global contact policies and frequency caps to prevent marketing fatigue, ensuring a cohesive, high-value narrative that balances the needs of various business lines. Integrated Calendar Management: Own the master communication calendar for the customer base. Provide cross-functional visibility and lead the prioritization of high-impact expansion initiatives over lower-value noise. Revenue & P&L Impact: Taking accountability for expansion targets by filtering and prioritizing opportunities that offer the strongest P&L impact Advanced Funnel Optimization: Lead the analysis of usage funnels to identify friction points within both marketing channels and the product experience, partnering with Product to drive in-app growth. Cross-Functional Leadership: Serve as a key advisor to Product, Product Marketing and Revenue Ops on pricing, packaging, and GTM plans. Turn high-level business objectives into actionable lifecycle programs that ship and perform. Operational Excellence: Build the expansion marketing playbook, standardizing experimentation frameworks, measurement baselines, and reporting that can be scaled across the organization. Data-Driven Experimentation: Lead an experimentation roadmap tied to core KPIs like multi-product attach and first year retention. Move from reactive reporting to surfacing deep insights that influence future strategy. Other duties may be assigned. What You'll Bring Experience: 7+ years in lifecycle, CRM, or revenue marketing, with at least 3 years focused on post-upgrade expansion within a high-growth SaaS environment. Strategic Governance & Orchestration: Proven track record of managing complex customer contact strategies and global communication calendars. You possess the professional maturity to prioritize high-impact initiatives while protecting the user experience. Advanced Analytical & Financial Rigor: Expert-level ability to interpret complex datasets and build business cases. You are fluent in SaaS unit economics - including cohort retention, ARPU, and expansion rates and can translate these into actionable growth models. Architectural Mindset: Experience building expansion playbooks, including scalable experimentation frameworks, measurement baselines, and standardized reporting structures. Cross-Functional Influence & Storytelling: Proven ability to align cross-functional teams around shared goals. You can distill performance metrics into a compelling narrative that connects business objectives to the customer experience. Execution Discipline & High Agency: A proactive leader with a strong bias for action and the ability to manage multiple high-stakes workstreams from high-level planning through to optimization. Proven Revenue Impact: A demonstrated history of driving measurable revenue growth through sophisticated cross-sell, or retention programs. #LI-SR1 #LI-REMOTE Compensation 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$120,000 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 Benefits We 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. About FreshBooks 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 accessibility@freshbooks.com.