Web Development Director Jobs in Toronto, ON (NOW HIRING)

The Opportunity

We are looking for a Manager of Web Operations to take ownership of a large-scale, multi-site web ecosystem. Our digital portfolio includes hundreds of web properties that serve millions of users, and we need a technical leader who can architect for scale, drive operational excellence, and continuously improve how our sites perform and evolve.

This is a hands-on leadership role that blends deep technical work with team and vendor management. You'll own the architecture and operational health of our web platform, partner with an external agency on ongoing development, and manage a small internal team of 1-2 direct reports. You should be equally comfortable designing system architecture and reviewing code as you are running sprint planning and communicating with senior stakeholders.

Who You Are

You are a pragmatic, hands-on technical leader who thrives in complexity and takes real ownership of outcomes.

• Equally comfortable in code and in a meeting room-you move fluidly between deep technical work and stakeholder communication
• A pragmatic problem-solver who finds the right solution, not just the most sophisticated one
• A collaborative leader who sets clear expectations, mentors others, and holds partners accountable
• Comfortable with ambiguity and motivated by building systems that scale

The Impact You'll Have

This role sits at the heart of Dentalcorp's digital presence, directly shaping the platforms that millions of users interact with.

• Directly influences the performance and scalability of hundreds of web properties serving millions of users
• Drives tangible business outcomes: faster updates releases, higher conversion rates, and a more resilient digital platform
• Leads the development and deployment of dynamic web components
• Acts as the primary point of contact with our external agency partner-owning the relationship, sprint cadence, and delivery accountability

In This Role, You Will

• Influence the technical architecture of a large, multi-site web ecosystem-ensuring it's scalable, performant, secure, and well-documented
• Influence platform patterns that combine CMS-driven content with API-driven front-end experiences
• Define, build, and deploy reusable component libraries, integration patterns, and content modeling strategies across a broad portfolio of sites
• Lead web operations: release management, deployments, etc.
• Establish QA processes, and governance standards for operating sites at scale
• Drive the development and rollout of interactive, conversion-focused features: booking flows, dynamic forms, calculators, and more
• Manage the external agency relationship-coordinating sprints, prioritizing the backlog, and holding partners accountable to quality and timelines
• Serve as the organization's technical authority on complex web ecosystems: APIs, CDNs, caching layers, and third-party integrations
• Manage, mentor, and develop 1-2 direct reports, supporting their growth and setting clear expectations

What You'll Bring

Required qualifications:

• 7+ years in web development, platform engineering, or web operations; 2+ years in a senior technical or team leadership role
• Proven experience operating multi-site web platforms at scale
• Proficiency in React (Next.js or Gatsby) and modern JavaScript/TypeScript
• Strong understanding of modern web architecture: headless CMS, RESTful and GraphQL APIs, SSR, static generation, and edge caching
• Experience with enterprise CMS platforms and managed hosting environments
• Hands-on multi-site WordPress experience including custom plugin/theme development and Gutenberg block architecture; WordPress VIP familiarity is a strong asset
• Proven ability to manage small teams and collaborate effectively with external agency partners
• Excellent communication skills-able to translate technical complexity into clear business recommendations

Nice to have:

• Hands-on experience operating a portfolio of 20+ web properties with shared infrastructure and governance
• PHP proficiency
• Familiarity with web performance optimization: Core Web Vitals, Lighthouse, and real-user monitoring
• Experience building transactional digital experiences: booking engines, payment flows, or multi-step forms
• Background in enterprise healthcare or financial organizations with a broad digital footprint

About Dentalcorp

Dentalcorp is Canada's largest and fastest growing network of dental practices, committed to advancing the overall well-being of Canadians by delivering the best clinical outcomes and unforgettable experiences. Dentalcorp acquires leading dental practices, uniting its network in a common goal: to be Canada's most trusted healthcare network. Leveraging its industry-leading technology, know-how and scale, Dentalcorp offers professionals the unique opportunity to retain their clinical autonomy while unlocking their potential for future growth.

Candidates must be legally eligible to work in Canada. At Dentalcorp, we recognize that inclusivity and diversity strengthen our culture and make us better. We are committed to ensuring that the talent we hire is reflective of the diverse communities and patients we serve. To ensure equal opportunity for all candidates, we strongly encourage applicants requiring an accommodation to let their recruiter know during the recruitment/selection process. We appreciate all applicants for taking the time to apply, however, only those selected for an interview will be contacted.

The salary range for this position is $100,000 CAD to $130,000 CAD annually (plus a bonus of up to 15% and competitive total rewards and benefits package). Offers within this range are determined based on relevant experience, skills, and qualifications, as well as internal equity considerations.

This role requires working in the Toronto Support Centre office four days per week.

This job posting is for an existing vacancy.