Highstreet
Do you get fired up about using technology to remove friction from people’s workdays? Are you excited by the idea of owning the Microsoft ecosystem, championing smart and efficient tools, and being the go-to partner for creating visual transparent systems? Do you value clear, direct communication and pride yourself on following through? Are you curious about industry trends and always eager to learn more? Are you quick to own your mistakes, adapt quickly and take real satisfaction in achieving results?
If you answered yes to these questions, we have the job for you. Highstreet is seeking an IT Systems Lead to join our head office team in Kelowna, BC.
WHY HIGHSTREET?
Highstreet is the largest developer, builder and operator of net-zero-ready homes in Canada and the only one offering double the standard warranty. We also manage our own growing portfolio of 1,400+ rental apartments with some of the highest customer service scores in any industry.
Our vision is that everyone in Highstreet’s community will want their friends to work with us, live with us and invest with us.
Help us achieve that vision.
CORE VALUES
Known as “Highstreeters” we demonstrate our core values in everything we do:
Humility grants us insight from others
Inquisitive & learning continuously
Guided by always doing what is right
Honest, open and timely communication
Responsible & accountable for our actions and decisions
Determined to persevere, get results and win together
THE OPPORTUNITY
As IT Systems Lead, you will be responsible for managing and advancing the organization’s technology infrastructure, with a focus on Microsoft environments and digital transformation initiatives. This role combines hands-on technical management with strategic implementation of automation, data visualization, and AI-driven solutions to improve efficiency and decision-making across the organization. Additionally, this role has direct responsibility for overseeing the performance and service levels delivered by the external IT service provider, ensuring alignment with business needs and risk management.
Reporting to the VP, Talent & Services, your responsibilities will include:
Administer, maintain, and optimize Microsoft 365, SharePoint, Teams, and Azure services.
Design, build, and deploy PowerApps applications and Power Automate workflows to streamline operations.
Develop and maintain Power BI dashboards, reports, and data models that provide actionable business insights.
Identify and implement emerging technologies and AI tools that enhance productivity and automate manual processes.
Collaborate with department leads to understand business needs and translate them into scalable technology solutions.
Manage IT infrastructure, including network, hardware, and software maintenance and troubleshooting.
Ensure cybersecurity best practices, access management, and data protection compliance.
Provide technical support, training, and documentation to help employees effectively use digital tools.
Partner with external vendors as needed for system upgrades, integrations, and support.
Lead and manage the relationship with the external IT service provider, including monitoring performance, addressing escalated issues, and coordinating projects and incident response.
THE IDEAL CANDIDATE
Highstreet is looking for a highly motivated individual who is willing to learn and grow with a company that values culture and performance. In addition to identifying with Highstreet’s values, the candidate should also have:
Diploma or degree in Information Technology, Computer Science, or a related field.
Certification in Microsoft Power Platform or Azure fundamentals.
3–5 years of experience in IT administration and solution development within a Microsoft ecosystem.
Strong proficiency in PowerApps, Power Automate, Power BI, and SharePoint customization.
Experience with Azure Active Directory, Exchange Online, and Microsoft Endpoint Manager.
Demonstrated ability to identify, pilot, and integrate AI and automation technologies.
Proven experience managing external service providers and vendor relationships.
Excellent analytical, problem-solving, and communication skills.
Strong organizational skills with the ability to balance multiple priorities and projects.
Additional requirements:
Compensation Package:
Annual Salary: $80,000-$105,000 dependent on experience
The posted salary range reflects our target base salary for this role. Most successful candidates are offered salaries near the midpoint of the range, based on their experience and qualifications.
Annual Bonus: Highstreet pays an annual bonus based on company performance. A typical bonus for this position is approximately 14% of annual salary. Determined annually, the bonus could be more or less depending on company performance.
Investment Opportunity: Highstreet encourages all employees to share in our success by offering the opportunity to invest in the projects we build and operate. To encourage employee investment, Highstreet matches employee investment at 50%, up to 20% of annual salary (i.e. for every $1 invested by the employee, Highstreet invests $0.50 on the employee's behalf). The investments are TFSA and RRSP eligible.