Head of Technology

Olive is entering an exciting phase of our journey as we look to build on our early customer success and to scale rapidly. This opportunity will have a meaningful impact on an industry and an organization directly affecting the lives of millions around the world.

As the Head of Technology you will be defining the way Olive delivers new products while establishing the foundations for a world-class product team. This opportunity is perfect for an experienced software engineer who loves to dig into the code to build great products while developing their customer and executive facing experience.



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In the first 90 days you’ll be:

  • Taking a deep dive into the Olive platform refactoring v1.0 on route to v2.0.
  • Establishing a high-functioning, scalable product team and the processes to support rapid growth and evolution of the Olive platform.
  • Setting product team priorities in support of strategic, sales and customer needs.
  • Collaborating with Olive executive team, customers and partners to identify and articulate product roadmap and backlog.

In addition, and ongoing, you will be:

  • Architecting and coding new features.
  • Providing technical leadership to the team through coaching and mentorship.
  • Maintaining high standards of software quality within the product team.
  • Collaborating with both software developers and business stakeholders to plan, design, develop, test, and maintain web- and mobile-based business applications built on Microsoft technologies.
  • Assisting in the collection and documentation of user's requirements, development of user stories, estimates and work plans.
  • Preparing reports, manuals and other documentation on the status, operation and maintenance of software.
  • Designing, developing, and unit testing in accordance with established standards.
  • Packaging and supporting deployment of releases.
  • Analyzing and resolving technical and platform problems.
  • Assessing opportunities for technology and process improvement, and sharing those with team members.
  • Providing third-level support to business users.
  • Several years of experience working in roles as a full stack developer.
  • Passion for collaborating with internal and external customers to build features that solve problems.
  • Enthusiasm for working in small, fast moving teams.
  • Detailed understanding of the current and emerging trends in application development, platforms as a service, and payment technologies.
  • Pride in your abilities to deliver solid code, to scale technology platforms and to build and grow effective product teams.
  • College or University degree in Computer Science or a related discipline.
  • Proficient with Microsoft .NET and .NET Core development using C#.
  • In depth knowledge and experience with core Microsoft .Net technologies including: LINQ and EF.
  • Extensive experience designing and developing enterprise grade software.
  • Experience with source control management systems and continuous integration/ deployment environments.
  • Experience with automated testing.
  • Experience with agile development methodologies including Kanban and Scrum.
  • Experience with multi-threading and concurrency.
  • Experience with debugging, performance profiling and optimization.
  • Comprehensive understanding of object-oriented and service-oriented application development techniques and theories.
  • Experience mentoring other developers and/or managing a team of developers.
  • Strong communication skills with both internal team members and external business stakeholders.
  • Strong initiative to find ways to improve solutions, systems, and processes.

It would also be nice (but not a deal-breaker!) if you had:

  • Prior experience in a technical leadership position.
  • Experience with multiple front-end languages and libraries (e.g. HTML/ CSS, JavaScript, XML, jQuery).
  • Experience with React, Node.js and SQL Server.
  • Experience with Microsoft Azure, Docker and Kubernetes.
  • Experience with DevOps methods such as CI/CD pipelines.
  • Olive is a hybrid workplace environment - we recognize the advantages of working flexibly. We have two hub locations, meaning that employees live and work within a 100 KM radius of Waterloo (within Ontario) or Montreal (within Quebec). 
  • Olive’s headquarters are located in Waterloo, and we have co-working space in Montreal. Employees have the option to work in the office (when it’s safe to do so) or from home.
  • As part of the Product Team you’ll collaborate with your team in the office during core hours. Otherwise, you have the flexibility to work remotely or in the office on your deliverables. 
  • Experience a unique opportunity to build, grow, and leave your impact on a new, growing industry and the millions of people around the world we will help.
  • Work alongside an executive team that supports your development by providing ongoing feedback and regular 1-on-1s.
  • Tons of autonomy and responsibility: this role provides an opportunity to try new things and push creative boundaries.
  • You’ll be set up with a MacBook laptop and internet allowance.
  • Receive a total compensation package that includes a competitive health benefits package and stock options.
  • Support for your breaks to rest and recharge including three weeks vacation, paid sick days, and the additional flexibility to take pre-approved workcation weeks that let you work from any internet-connected location you’ve always wanted to visit.
  • Join us in quarterly company celebrations and company-wide annual retreat to celebrate the big wins and milestones as one team.