Director, Expansion Marketing at FreshBooks

About The Role

As the Director of Expansion Marketing, you will lead FreshBooks’ strategy and programs that drive revenue growth from our existing customer base. You will be responsible for increasing product usage, improving cross-sell and upsell performance, and reducing churn through targeted, marketing-led lifecycle and engagement initiatives. You will oversee a team of Expansion Marketing Managers who build and execute programs to drive adoption across our product suite—including Payments, Payroll, core product tiers, Financial Services, and partner offerings. This is a highly cross-functional marketing leadership role that collaborates closely with Product, Product Marketing, Customer Success, Revenue Operations, Sales, and Data. It is an ideal role for someone with long-term aspirations toward VP Marketing, GM, or CRO roles.

NOTE: This role can be worked remotely from the above location.

What You'll Do

• Lead and execute FreshBooks’ expansion strategy to grow revenue within the existing customer base by increasing product engagement, enabling tier movement, and driving adoption of add-on offerings.
• Build and scale upsell and cross-sell programs across multiple channels, using clear segmentation, customer insights, and value-based messaging to drive relevant expansion.
• Design and deliver lifecycle journeys that improve product usage and retention through targeted email, in-app messaging, and multi-step campaigns that reinforce the value of the FreshBooks ecosystem.
• Lead, coach, and develop a high-performing team of Expansion Marketing Managers, setting clear priorities, expectations, and accountability for results.
• Partner cross-functionally with Product Marketing, Product, Customer Success, and Partnerships to deliver coordinated, omni-channel expansion programs aligned to customer needs and success motions.
• Own end-to-end execution of expansion initiatives—from planning and creative development through launch, optimization, and iteration—ensuring programs contribute meaningfully to revenue and customer outcomes.
• Own expansion analytics and reporting, using metrics such as attach rate, ARPU growth, adoption, and churn to inform decisions, optimize performance, and guide leadership discussions.
  
  

What You'll Bring

• 8+ years of experience in lifecycle marketing, expansion marketing, CRM, or revenue marketing within a SaaS organization.
• Demonstrated success driving upsell, cross-sell, and retention programs with measurable revenue impact.
• Strong understanding of SaaS metrics including ARPU, churn, expansion rate, adoption, usage funnels, and lifecycle performance indicators.
• Experience managing and developing teams; you have led managers or senior ICs in a fast-paced environment.
• Proven ability to work cross-functionally and influence without authority across Product, Product Marketing, Customer Success, Sales, and Revenue Operations.
• Strong analytical skills and comfort with segmentation, experimentation, cohort analysis, and performance reporting.
• Exceptional execution discipline, with the ability to manage multiple programs simultaneously and deliver strong outcomes.
• Excellent communication and storytelling skills with a customer-focused mindset.
• A high degree of agency; you have a bias for action and strong follow-through.
  
  

You'll Stand Out If You Have

• Experience running your own business or direct experience working with small and micro businesses with a deep understanding of their operational needs.
  
  

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 annual compensation for this role ranges from CA$145,000 to CA$182,000, 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.

Perks & 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. Including a retirement savings program or pension plan matched to your local office, stock options for every full-time employee, generous time off, 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 [email protected].