FreshBooks has an ambitious vision. We launched in 2003 but we’re just getting started and there’s a lot left to do. We're a high-performing team working towards a common goal: building an elite online accounting application to help small businesses better handle their finances. Known for extraordinary product and customer service experiences and based in Toronto, Canada, FreshBooks serves paying customers in over 120 countries.

The Opportunity – Director of IT (Billing)

We are seeking for a Director of IT to head the subscription billing development / internal IT departments. You will lead and develop a team of developers & IT professionals and be responsible for the growth, resourcing, maintenance, security and performance of IT and Billing systems at FreshBooks. You will be leading key customer success activities including customer onboarding and engagement and will have experience in developing strategies to mitigate customer churn for a subscription-based business model.

You will be reporting to the CFO and will work closely to support internal teams at FreshBooks. You are a driven individual, with expertise in running corporate operations from an IT stand point. You will be bridging the gap between technical, creative and business needs to confidently distill technical issues and provide solutions to senior leadership and partners.

You will be responsible for:

  • Creating a strategic vision and roadmap for IT infrastructure, billing, and subscription development teams at FreshBooks.
  • Leading and maintaining the implementation of operational efficiencies and continuous improvement in productivity, processes, and communication.
  • Successfully managing multiple departments, work collaboratively across the organization and lead strategic operations.
  • Setting the service standards, procedures, and tools for operational and project management practices to ensure high quality service for our customers and internal partners.
  • Outlining the charging structures for all services (internal and external), matching the actual costs, and ensuring appropriate recovery.
  • Maintaining the overall demand profile, looking for low utilization, more optimal usage patterns, or deployment options.
  • Building, maintaining and optimizing dashboards to get the best analytical view of data for cost, demand, and capacity planning.
  • Managing all demand and billing for our Cloud Platform including AWS and GCP.
  • Establishing clear and consistent reporting and communication methods for all project activities.
  • You will be also presenting reports on usage and optimize of cost.
  • Liaising with Senior Leadership and C-Level executives to design the billing strategy.
  • Automation of billing reports & provide dashboards and insights on billing.

You will have:

  • 7+ years of experience in IT infrastructure, Subscription and Billing where you have demonstrated operational project management expertise.
  • Demonstrated ability to translate strategic priorities into tactical and technical requirements for teams to execute.
  • Experience and knowledge with Agile practices, with the ability to translate principles.
  • Managed end-to-end program management from proposal to solution delivery, business adoption, and post implementation support.
  • You can prioritize multiple projects and meet partner needs in a timely manner.
  • Bachelor's degree in technology, business, management, or related.

Why Join Us

We're a motivated bunch, with our eye’s laser-focused on shipping extraordinary experiences to businesses. You will be surrounded by hardworking team members who share a common vision for what an amazing software company could be and have the opportunity to help build an elite one, right here in downtown Toronto.

Apply Now

Have we got your attention? Submit your application today and a member of our recruitment team will be in touch with you shortly!

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 at phone 416-780-2700 and/or

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