Director of Technical Operations

Development · Victoria, British Columbia
Department Development
Employment Type Full time
Minimum Experience Senior Manager/Supervisor

About us


Join the adventure and innovate with a talented team that’s pushing the capabilities of experience management! Empower thousands of tour and activity operators.

One of Canada’s top SaaS growth companies located on beautiful Vancouver Island. As the industry's leading independent booking software, we have customers who run businesses in fascinating destinations all over the world. We have over 5,000 businesses using our platform and have processed over $10B in bookings to date, operating in 136 countries and 36 languages.

About the Job


We are looking for someone who has the technical capability to drive excellence in technical operations and a cost management mindset to manage & optimize our Cloud costs. Checkfront is growing and we’re looking for passionate leaders to deliver product features, improve our development processes and help achieve our business goals.  We ship code every day and we're proud of our deployment and agile process and are looking for someone with experience with release management.

Please note the preference for this role is located remotely from anywhere in Canada, or in our beautiful head office in Victoria, BC.

Team Structure

This role will support DevOps, Security & Compliance and Data teams and is expected to expand over time with additional responsibilities.  This role reports to the VP of Technology.

Your Responsibilities

You are a collaborative, empowering, and humble teammate ready to lead your team to success. You strive to support, direct and encourage your team members to enable them to thrive and grow.

  • A Leader
    • The Director Technical Operations first and foremost is a high-level departmental leader who develops and maintains the department’s operational roadmap, ensuring that technology capabilities continually support the overall business goals and objectives.  
    • This role is a key member of the technology leadership team and Checkfront’s senior leadership team.
  • Collaboration and Support
    •  The role of the Director is a collaborative one and, as such, they build a collaborative culture within the department and partners with various departments within the organization. 
    •  The Director will also work closely with the VP of Technology & VP of Product in the planning process to develop the Technology Operations roadmap. 
    • They additionally work closely with the customer support team in gathering consumer feedback and developing insights that will lead to the improvement of operational technology services.
  • Budget & Cloud Cost Management
    • The Director plays an analytical role where they constantly assess the effectiveness of development tools, as well as  Checkfront applications & data.
    •  The Director will collaborate with the financial department in managing our SaaS & Cloud costs - both budget and forecast.
  • Performance Management
    •  The Director will collaborate, set objectives (OKRs) and determine measurement KPI’s for each team.
  • Project Management
    • The role of the Director is to ensure the overall management and timely delivery of [virtual] infrastructure-related projects.  The Director will be responsible for the Technology Operations roadmap and work with all relevant stakeholders to gain buy-in. 
  • On-Call, Incident Management and Point of Escalation
    • The Technology Operations team is the point team responsible for all incident management. The Director is responsible for refining and communicating the incident management process to the organization and is the primary escalation point for the team.  
    • The Director is responsible for managing the on-call Scheduling across all technology teams.
  • Security, Compliance and Privacy
    • A critical component of Technology Operations is our Security, Compliance and Privacy team.  This team is responsible for all cyber-security initiatives and compliance programs (eg. PCI), as well as supporting technical auditing activities as required.
  • Knowledge Enabler
    • The Director plays a lead role in ensuring the maintenance of knowledge within the Technology Operations department, coordinating the implementation of best practices and the adoption of suitable trends. 


Ideally, you should have

  • 5+ years of experience in a technical leadership position, or 7+ years experience building scalable SaaS solutions
  • A passion for mentorship, project management, and process improvement
  • The empathy to understand the needs of the developers, the platform, and the customer
  • Passion for people, building excellence through coaching, feedback, and career development of team members
  • The desire to empower team members, hold them accountable, measure productivity and motivate them to do great work
  • Possess a growth mindset, open to learning from diverse perspectives and experiences from both your peers and from you team
  • Experience with e-commerce, bookings, and the tourism and activity industry

If you don’t meet all of our requirements exactly or have some gaps in your resume know that we would still love to hear from you! Use your cover letter to tell us about your unique experience - we understand that talent comes from many places and that skills are transferable.

Life at Checkfront 

At Checkfront, people empower others by providing opportunities for growth and learning, fostering teamwork and encouraging ideas. We support the well-being of our employees and dedicate our overall efforts toward a positive employee experience. 

We value psychological safety and transparency across all levels of the organization, and as a result, there is a tremendous sense of camaraderie and support felt throughout the company. Everyone is caring about their teammates and is passionate about their work. 

We are committed to upholding the values of diversity, equity, and inclusion. In pursuit of this, we actively seek new members who will work respectfully and constructively with our team, propelling our company and the community forward.

There are also fun events throughout the year; skiing, cabin getaways, fireside chats, holiday parties, and more! Do you prefer a flexible work location? That’s great! Whether you are at home or in-office, we aim to provide an inclusive environment. 

As a company, we are committed to upholding the values of diversity, inclusion, and equity. In pursuit of this, we actively seek new members who will work respectfully and constructively with our team, and challenge the status quo, propelling our company and the community forward.

Perks and Benefits

  • A company that values work-life balance
  • Half-day Fridays 
  • Vacation, personal days, health days, paid volunteer day 
  • Extended health benefits and EAP program 
  • Parental benefits 
  • Professional development allowance 
  • Mentorship program 
  • A renovated “tourism themed” office space in downtown Victoria (unless you’re remote)

Checkfront acknowledges and respects that we work, learn, and innovate on the unceded Coast Salish Territory of the Lekwungen & WSÁNEĆ nations.

Thank You

Your application was submitted successfully.

  • Location
    Victoria, British Columbia
  • Department
  • Employment Type
    Full time
  • Minimum Experience
    Senior Manager/Supervisor