CMS Operations & Web Development Manager Job Toronto area,Ontario Canada,Software Development

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 ( or Gatsby) and modern JavaScript/Type Script

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 Word Press experience including custom plugin/theme development and Gutenberg block architecture;
Word Press 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…