About FreshBooks

FreshBooks is a leading cloud-based SaaS accounting software designed with one goal: to help small business owners grow. We reached unicorn status after raising our valuation to more than $1 billion and continue to scale our business to serve business owners, their clients, and accountants in more than 160 countries worldwide. FreshBookers are found all over the globe, and we know that different folks thrive in different working environments: Remote, onsite, and everything in between, you’ll find it with us.

The Opportunity - Senior Systems Administrator

The FreshBooks Global IT Services team is responsible for the availability, integrity, confidentiality, and performance of the internal systems used by FreshBookers to provide outstanding support to our amazing customers, support the development and delivery of our leading SaaS accounting application, and enable the company to scale and grow. These systems include; collaboration and communication (voice, video, chat), email, identity and access management, networking, desktop, and mobile devices, as well as many SaaS services that cross a broad spectrum of uses.

As a Senior Systems Administrator, we expect you to lead initiatives that improve the services and IT infrastructure that we deliver to our internal customers, promote standardized methodologies and industry best practices, all while providing mentorship to other members of our Global IT Services Team. 

What you'll do as a Senior Systems Administrator

  • Ensure that existing IT services are fit for use and fit for purpose
  • Implement new IT services & infrastructure as per IT roadmap and transition to IT Operations for Day to Day support
  • Provide documentation and technical specifications to IT staff related to the planning and implement new, or upgrades to, IT infrastructure (eg. Change Management)
  • Maintain and configure existing services and infrastructure to availability standards and SLAs
  • Implement appropriate processes for data protection, disaster recovery, and failover procedures
  • Provide recommendations to IT Leadership on IT procedures, strategy, and roadmap
  • Provide 3rd level support to IT Operations team as needed

What You'll Bring to the Role

  • You’ve done this before – you’ve had at least five years of experience dealing with IT systems in a dynamic SaaS-based environment with an understanding of best practices and security principles
  • You have planned and implemented key core infrastructure systems (eg. Servers, Phone Systems, Directory Services, Networking, etc)
  • You have a deep curiosity that motivates you to keep on top of technology trends and informs your ability to suggest tools and approaches to interesting problems.
  • You have a strong understanding of the process and system flow mapping in complex systems, with an emphasis on data flow and system interdependence.
  • You have a passion for customer service and the ability to empathize with and communicate clearly to all parts of the business to establish strong partnerships
  • You have excellent documentation skills and an ability to mentor junior staff
  • You have a strong understanding of IT Service Delivery methodologies.
  • You are able to participate in an on-call rotation providing after-hours support
  • You have a knack for finding the perfect answer to a problem you've never seen before
  • An understanding of most of the technologies we use, including deep familiarity implementing and managing several of the following areas:
    • Cloud Infrastructure (VMware, Google Cloud Platform, Amazon Web Services)
    • Identity & Access Management (Okta, Active Directory, Azure)
    • Collaboration & Communication (VoIP, Zoom, Avaya IP Office, Slack)
    • Productivity & Workflow (Google Workspace, Microsoft 365, Confluence, Jira)
    • Operating systems (macOS, Windows, Linux/*nix)
    • Device Management (Mosyle, Intune, Workspace One)
    • Code & Version Management (Git)
    • Management & Monitoring
    • Networking & Security (TCP/IP, DNS, SSL/TLS, SSL/TLS, Public Key Infrastructure, Anti-malware, WiFi, Cisco)
    • Experience with the Cisco Meraki platform would be considered an asset 
    • Experience with IT ticketing systems (eg. Jira, ServiceNow, ZenDesk, etc)
    • Scripting & programming skills – shell (bash, sh) and at least one other relevant language (Python, Powershell, Terraform), with an emphasis on Infrastructure as Code (IaC) and RESTful APIs

Our Commitments to You

At FreshBooks each person knows their opinion is valued, and can see their impact on the lives of over 10 million small business owners around the world. Accelerate your career, work on projects you're passionate about, and work as a part of a collaborative team without ego! Here are some of the ways FreshBooks recognises and rewards our employees:

  • 🩺 Comprehensive Compensation and Wellness Benefits. Including Pension Plan matched to your local office, stock options for every full time employee, generous time off, annual healthy living credit, 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 locale.
  • 🌱Working Environments to Help You Thrive. Beautiful office spaces welcome you in Germany, Croatia, and Netherlands, and remote FreshBookers receive a home office credit to set up your home office.
  • 🤗 Supportive Peer Group, Mentors, and Leaders. We care about each other across the organisation and have programs to support this so everyone feels a strong sense of belonging, and believes in collective impact.
  • 🚀 Accelerated growth. 3 week dedicated company onboarding, career development through continuous coaching, training, and learning on the job, and a bi-annual review process.


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 at phone 416-780-2700 and/or accessibility@freshbooks.com.


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