Director, Technology Delivery and Enablement

This is a hybrid position, with four days per week in the office and one day remote.

Office Location: 1 Presidents Choice Cir, Brampton, ON L6Y 5S5 (near Hwy. 407 and Mississauga Rd)

Lifemark Health Group (LHG) is a market leader in customized healthcare solutions. With over 20 years of service excellence, LHG is one of the largest, most trusted, and most comprehensive providers in Canada. As a national healthcare company, LHG employs over 5,000 highly trained clinicians, medical experts, and team members in almost 400 locations coast-to-coast and continues to grow both organically as well as through acquisitions. With that growth is a vision to be the most innovative healthcare provider in community rehabilitation, workplace health and wellness, and medical assessment services. Lifemark was acquired by Loblaw Companies on May 10, 2022.

Role Overview:

Lifemark Health Group is hiring a Director, Technology Delivery and Enablement to lead our Application Development Team and advance the modernization of our enterprise application landscape. Reporting to the VP of Applications and Security Services, you will oversee the development, implementation, modernization, and ongoing reliability of critical business applications supporting Lifemark’s national operations.

In this hands-on technology leadership role, you will lead teams of developers, DevOps engineers, and QA specialists to deliver secure, scalable, and resilient solutions while evolving our engineering practices and technology platforms. You will champion modern approaches including cloud-native architecture, DevSecOps, platform engineering, intelligent automation, and AI-assisted software development, while improving application observability, engineering productivity, and delivery effectiveness.

Working closely with business and technology leaders, you will help shape Lifemark’s application modernization and technology strategy, including the responsible adoption of generative AI and emerging technologies, reduction of technical debt, modernization of legacy platforms, and continued evolution of our Azure ecosystem. You will also collaborate across departments, security and infrastructure teams, architecture, data and analytics, and external technology partners to ensure technology investments deliver measurable business value.

About You:

You are an experienced technology leader with a strong background in software and application development and a track record of leading high-performing technical teams. You combine hands-on technical depth with strong people leadership, delivery discipline, and the ability to translate business needs into secure, scalable technology solutions.

You are comfortable managing multiple concurrent initiatives, guiding application architecture and development practices, building strong cross-functional and vendor relationships, and continuously improving release management, DevOps, monitoring, quality, and reliability. You communicate clearly, develop talent, and stay current with emerging technologies and industry best practices.

Key Responsibilities:

Strategic Leadership and Team Management

• Manage the development and maintenance of Lifemark websites and enterprise applications, providing technical leadership, oversight, and execution.
• Plan, organize, prioritize, and delegate work assignments; oversee team results for quality, timely delivery, and adherence to policies and procedures.
• Attract, mentor, develop, and retain top talent while supporting career development and succession planning.

Architecture, Development and Reliability

• Provide guidance on application architecture, UI/UX, database design, and integration with back-end applications.
• Maintain high stability, uptime, and reliability of enterprise applications through robust monitoring and QA practices.
• Experience leading modern DevSecOps and platform engineering practices, including CI/CD, infrastructure as code, automated testing and security, observability, cloud-native architecture, and AI-assisted software development.

Project Execution and Release Management

• Lead and support concurrent initiatives, ensuring alignment with business goals, schedules, and quality standards.
• Plan, coordinate, and execute successful software releases using disciplined release management practices.

Vendor and Cross-Functional Collaboration

• Manage relationships with third-party agencies and technology vendors to deliver robust and scalable solutions.
• Build strong relationships across departments to align technology solutions with business objectives and improve operational efficiency.

Continuous Improvement and Innovation

• Research and evaluate emerging technologies to meet business needs and continuously enhance development practices and tools.
• Identify opportunities to leverage AI technologies, including machine learning and cognitive services, for automation solutions where appropriate.

What we’re looking for:

• Post-secondary education in Computer Science or equivalent experience.
• 10+ years of software/application development experience, including 3+ years in leadership roles.
• Strong understanding of application lifecycle management, system architecture, and development methodologies.
• Proficiency in .NET development, relational databases, and cloud platforms; Azure experience is preferred.
• Experience managing parallel projects, with strong time-management and organizational skills.
• Excellent verbal and written communication skills.
• Exceptional project and account management abilities, with a demonstrated ability to establish and meet schedules.
• Current knowledge of industry trends and development best practices.
• Collaborative mindset with proven team leadership experience.
• Strong release management experience, including planning, coordinating, and executing software releases.
• Demonstrated success attracting, mentoring, and retaining top talent and supporting career development and succession planning.
• Proven record of maintaining high stability, uptime, and reliability of enterprise applications through robust monitoring and QA practices.
• Expertise implementing DevOps best practices, including automated pipelines, CI/CD, and infrastructure as code.
• Experience evaluating and applying generative AI, large language models, AI agents, machine learning, and intelligent automation to improve business processes, engineering productivity, and customer or employee experiences. Familiarity with responsible AI, security, privacy, and governance considerations is an asset.

What Success Looks like:

• Enterprise applications and Lifemark websites are delivered and maintained with strong technical leadership, quality, stability, and reliability.
• Development, DevOps, and QA teams are effectively organized, supported, and developed to deliver high-quality outcomes on schedule.
• Application architecture, development practices, monitoring, QA, and release management continue to mature and support secure, scalable solutions.
• Concurrent initiatives are delivered in alignment with business goals, schedules, and quality standards.
• Vendor and cross-functional partnerships effectively support business objectives and operational efficiency.
• Emerging technologies and improved development practices are evaluated and adopted where they provide clear business value.

Our Perks:

You will be issued a company laptop, headset and a home office monitor, keyboard, and mouse. After your successful probation period, you will:

• Eligibility to earn a STIP (Short-Term Incentive Plan)
• Have access to a yearly education re-imbursement fund
• Receive 30% discount from Shopper Drug Mart purchases
• Contribute to an Employee Stock Ownership Plan (ESOP) with employer matching percentage
• Have paid vacation days as well as wellness days
• Have a choice to enroll in our Health & Dental Flex Life Benefits (or in lieu contribute to your RRSPs)
• Access to employee assistance program
• On-site gym, Basketball & Volleyball courts, Ice Rink, Groceries delivered to work via PC Express, Dry-Cleaning services (1 Presidents Choice Circle Office)

Inclusion

We are committed to creating an inclusive environment where people from all backgrounds can thrive. Improving inclusion and equity is a collective responsibility. Lifemark promotes equal employment opportunities for all job applicants, including but not limited to those self-identifying as a member of the employment equity groups: Indigenous peoples, Newcomers to Canada, Women, and Visible minorities.

Accommodation

Accommodations are available on request for all candidates taking part in any aspect of the recruitment and selection process. Email us at Talentatlifemark

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