The OpportunityWHC is looking for a strategic, pragmatic, and capable Director of Technology to lead our next chapter of technical growth. This is not a vision-only role. We need a builder-operator who can set a clear technical direction, improve execution, modernize our platforms, and ensure our products and infrastructure are secure, reliable, scalable, and aligned with business needs.
As Director of Technology, you will lead WHC's technical roadmap across engineering, infrastructure, DevOps, architecture, and security. Working closely with the CEO and leadership team, you will turn business goals into clear technical outcomes and help shape our approach to emerging technologies, including applied AI, in a practical and focused way.
What You'll Do- Own WHC's technology vision, strategy, and roadmap in alignment with company goals.
- Lead and unify software engineering, infrastructure/platform, DevOps, product engineering, and security under one clear technical direction.
- Ensure our hosting, domain, email, and website platforms are resilient, scalable, secure, and deliver an excellent customer experience.
- Improve release quality, observability, incident response, and operational maturity.
- Modernize systems, tooling, and development practices pragmatically, avoiding unnecessary complexity.
- Own technical governance, including architecture standards, security posture, business continuity, and key technology decisions.
- Lead build vs. buy decisions, technology partnerships, vendor relationships, and technical due diligence.
- Drive pragmatic adoption of emerging technologies, including applied AI, across product, customer experience, and internal operations.
- Build and coach a high-performing technology team.
- Translate complex technical topics into clear, actionable insights for leadership and business stakeholders.
- Own the technology budget, ensuring disciplined investment and strong ROI.
- Support R&D initiatives and partner with Finance on funding opportunities such as SR&ED.
What You Bring- Proven success in senior technology leadership roles such as Director of Technology, Director of Engineering, VP Engineering, CTO, or equivalent.
- Experience leading multi-disciplinary technical functions, including software development, infrastructure/platform, DevOps/SRE, and security.
- Strong technical judgment across architecture, scalability, reliability, security, and engineering operations.
- Track record of improving execution, maturing teams, and driving results in fast-moving environments.
- Background in SaaS, hosting, internet infrastructure, subscription businesses, or similarly complex, always-on environments.
- Comfortable operating in a growth-stage, owner-led business that requires both strategic range and hands-on realism.
- Strong communication skills with the ability to influence senior leaders and align technical and non-technical stakeholders.
- Calm, pragmatic, solutions-oriented approach to incidents, ambiguity, and change.
Nice to Have- Experience in web hosting, domains, email infrastructure, WordPress, cloud platforms, or adjacent internet services.
- Exposure to cybersecurity, compliance, and risk management in a customer-facing technology business.
- Experience helping modernize legacy systems or inherited technical environments.
- Familiarity with M&A-related technical diligence and post-acquisition integration.
- Experience contributing to or supporting R&D funding programs (e.g., SR&ED).
- Bilingualism in English and French.
Why Join WHC?- A true leadership seat at the table, with meaningful influence on the future of the business.
- A collaborative leadership team where your voice matters and your impact is visible.
- The opportunity to shape technology at a respected Canadian company with a clear market identity and loyal customer base.
- Competitive compensation, bonus opportunity, and benefits.
- A flexible hybrid work model that supports strong leadership and real-life balance.
- The chance to build, improve, and leave a lasting mark on a business with ambition and heart.
- Frequent social events, a vibrant team culture, and a renovated office in Little Italy.
- Certified a Great Place to Work® for multiple years running-because we believe work should be fun, fulfilling, and rewarding.
Ready to Make an Impact?If you're a thoughtful, high-ownership technology leader who knows how to turn strategy into execution, build trust across teams, and create the conditions for great technical work, we want to hear from you.
Apply today and help shape the future of WHC as we continue helping Canadians succeed online.
