Vp Software Engineer Jobs in Toronto, ON (NOW HIRING)

About PSD Citywide

Ready to make a real impact on communities across North America?

PSD Citywide isn’t just a software company; we’re transforming how Local, First Nations, and Regional Governments achieve success and build sustainable futures for their communities. As a recognized leader in Enterprise Asset Management, maintenance management, and planning solutions, we provide cutting-edge software and expert advisory services that improve infrastructure and public services.

Why join us? We are a "Fun-clusive" organization! This means we intentionally foster a supportive and engaging culture where your contributions are celebrated, your skills are rewarded, and your career growth is encouraged. 

Ready to influence change? Bring your expertise in technology and data to our team and directly shape how local governments improve service delivery. Apply now!

Job Description 

Our team thrives on collaboration, innovation, and making a difference. As we continue to grow, we’re looking for a VP, Engineering to fill an existing vacancy and join our IT Department in a fully remote role (though occasional travel will be required) based in Canada. If you’re passionate about technology, problem-solving, and helping businesses maximize their potential, we want you to be a part of our team!

PSD Citywide is seeking a VP, Engineering to lead the delivery, performance, and continuous improvement of our integrated SaaS platform serving municipalities and public sector organizations across North America.

Reporting to the Chief Technology Officer (CTO), the VP, Engineering, will translate the Company's technology and product strategy into effective engineering execution. The role leads Software Engineering, Quality Assurance (QA) / Quality Engineering, and Systems Administration / Infrastructure, with day-to-day accountability for engineering operations, software delivery, technical standards, quality, infrastructure, talent, and continuous improvement.

The VP, Engineering will oversee the development, delivery, quality, reliability, and technical operation of PSD Citywide's cloud-based software solutions, including Enterprise Asset Management (EAM), Maintenance, GIS, Budgeting, and Permitting. The role will evolve the engineering operating model as the company scales, with particular focus on AI-enabled software development, quality engineering, automation, organizational effectiveness, and increasing the speed and reliability with which customer value is delivered.

What We Offer

• Competitive Compensation: We offer competitive salaries that recognize your skills and experience.
• Wellness Coverage: Enjoy a comprehensive health and wellness benefits package that keeps you and your family secure and healthy.
• Flexible Working: Work where you thrive! Enjoy remote work flexibility (specific regional options apply) while staying connected to our supportive team.
• Work-Life Balance: Benefit from Flex Hours to manage your personal life and Paid Time Off (PTO) so you can fully recharge.
• Unwind Early: Say hello to summer with our popular Summer Fridays—shorter work weeks to help you kick-start the weekend.
• Culture & Community: Participate in fun social events (both virtual and in-person) and contribute to charity initiatives as part of our community focus.
• Career Growth: Our Career Framework provides clear, structured paths for growth and ongoing learning, ensuring you reach your professional goals.

Job Duties & Responsibilities

• Lead Software Engineering, QA / Quality Engineering, and Systems Administration / Infrastructure, building a high-performing, accountable, and collaborative organization.
• Oversee the design, development, enhancement, maintenance, quality, reliability, and technical operation of PSD Citywide's cloud-based SaaS platform.
• Partner with the CTO, Product Management, Business Analysis, and business leaders to prioritize engineering initiatives, translate product and business priorities into executable engineering plans, and maintain clear accountability between product ownership and engineering delivery.
• Develop and lead the Company's AI-enabled engineering strategy, taking direct ownership of the evaluation, adoption, governance, and effective use of AI tools and practices throughout the software development lifecycle.
• Drive practical adoption of AI and automation across software development, QA / Quality Engineering, and technical operations where appropriate, including design, coding, code review, documentation, debugging, testing, release processes, systems administration, monitoring, and operational workflows.
• Establish, monitor, and communicate meaningful engineering performance metrics, including delivery predictability, development cycle time, team capacity, release frequency, software quality and escaped defects, test automation, platform reliability, operational performance, budget effectiveness, and measurable outcomes from AI-enabled engineering practices.
• Lead the modernization of software quality practices, including increased test automation, AI-assisted test development, improved regression testing, CI/CD practices, release quality controls, and greater engineering ownership of software quality.
• Lead the engineering technology strategy and architectural direction of PSD Citywide's SaaS platform, ensuring architecture, technical debt, scalability, performance, maintainability, and modernization support long-term product and business objectives.
• Establish clear ownership, accountability, and operating rhythms across Engineering teams and technical leaders, including delivery commitments, capacity planning, technical quality, risk identification, performance measurement, and timely escalation of issues affecting product commitments or customer outcomes.
• Provide leadership and oversight for systems administration and infrastructure operations, including cloud environments, deployment infrastructure, platform reliability, monitoring, backup and recovery, operational resiliency, and continuous improvement.
• Partner with Product, Support, Advisory Services, Implementation, and other business functions to manage the upstream and downstream impacts of increased engineering capacity, automation, and delivery velocity and ensure engineering improvements translate into customer and business outcomes.
• Develop and manage departmental budgets, financial plans, resource allocation, vendor relationships, contractor utilization, software licensing, and technology investments to ensure responsible financial stewardship and cost effectiveness.
• Support business case development, effort estimation, and resource planning to ensure technology initiatives are appropriately scoped, prioritized, and budgeted.
• Continuously evaluate and evolve the structure, skills, roles, leadership capacity, and operating model of the Engineering organization as the company scales and technology practices change; lead workforce planning, talent development, succession planning, recruitment, and performance management.
• Ensure security, compliance, resiliency, and risk management are incorporated into engineering operations and software development practices, and establish appropriate AI governance covering customer data protection, source code confidentiality, intellectual property, vendor risk, responsible use, and cost management.
• Other duties as required.

Qualifications

• 10+ years of progressive experience in software engineering, technology operations, or software delivery leadership, including 5+ years leading engineering managers, technical leads, or multidisciplinary software development teams.
• Demonstrated experience leading and scaling a multidisciplinary engineering organization of comparable size and complexity, including developing technical leaders, establishing effective management structures, and evolving processes as the organization grows.
• Demonstrated experience successfully leading an engineering organization through the adoption of AI-enabled software development practices, with direct leadership involvement in strategy, implementation, adoption, and measurement of results.
• Demonstrated ability to measure and communicate the impact of AI-enabled engineering practices, including improvements in developer productivity, development cycle time, product delivery velocity, software quality, testing efficiency, release frequency, or organizational capacity.
• Strong working knowledge and practical experience with contemporary AI-assisted software engineering tools and techniques, including the ability to evaluate their capabilities, limitations, security implications, and appropriate use across development and quality engineering workflows.
• Demonstrated experience leading or overseeing QA / Quality Engineering functions, including test automation, regression testing, release quality, and integration of quality practices throughout the software development lifecycle.
• Experience managing significant departmental budgets, financial planning, resource allocation, vendor relationships, contractor utilization, and technology investments.
• Experience operating in a private-equity-backed or similarly metrics-driven environment, including supporting executive and Board-level reporting, performance reviews, and presentations.
• Bachelor's degree in Computer Science, Engineering, Information Technology, or a related field, or an equivalent combination of education and relevant professional experience.
• Strong understanding of SaaS application development, cloud platforms, software architecture, APIs, and modern software delivery practices.
• Experience leading the modernization and evolution of established SaaS platforms, including managing technical debt, architectural improvement, scalability, maintainability, and modernization alongside ongoing customer and product delivery commitments.
• Demonstrated experience establishing and continuously improving modern software delivery practices, including iterative planning, capacity management, CI/CD, release management, engineering metrics, and appropriate use of Agile or Lean methodologies.
• Demonstrated ability to balance technical priorities with business objectives, budget considerations, and customer requirements.
• Demonstrated ability to build and lead high-performing, accountable engineering organizations, including developing managers and technical leaders, coaching and performance management, succession planning, talent development, and attracting and retaining strong technical talent.
• Exceptional executive communication and stakeholder management skills, with the ability to translate complex technical issues, risks, investment decisions, and trade-offs into clear business terms for executive, Board, and non-technical audiences.
• Demonstrated experience successfully leading distributed or remote technical teams, including maintaining strong communication, accountability, collaboration, and team culture across locations.
• Experience in GovTech, municipal technology, enterprise SaaS, asset management, ERP, or public sector software is considered an asset.

What Success Looks Like

• A high-performing, accountable Engineering organization with strong technical and people leadership.
• Improved delivery predictability, software quality, platform reliability, and release efficiency.
• Material progress in test automation and modern QA / Quality Engineering practices.
• Measurable, responsible adoption of AI that improves engineering productivity, product velocity, quality, and organizational capacity.
• An engineering operating model, leadership structure, and skill base capable of supporting PSD Citywide's continued growth.

The Candidate Journey

Resume Review: Once you apply, an actual person will review your resume and we are committed to getting back to you with a response.

Phone Interview: PSD’s People and Culture team will connect with you to learn about your experience and discuss the role further. They’ll also give you an understanding of what the interview process involves, along with an estimated timeline.

Virtual Interview: Depending on the position, there will be one or two interviews with the Hiring Team that will include questions related to your skills, work experience, values and goals. We provide the opportunity to meet with a wide range of staff members so you can learn more about life at PSD Citywide.

Offer/Feedback: The Hiring Team will debrief and make a decision within a few days of your final interview. If successful, your Recruiter will present you with a verbal offer, followed by a formal offer letter via email. If the timing was not right for this particular opportunity, we will connect with you and provide feedback.

PSD Citywide is committed to ensuring equal access and participation for people with disabilities. We believe in integration, and we are committed to meeting the needs of people with disabilities in a timely manner. We will do so by removing and preventing barriers to accessibility.

We are committed to accommodating people with disabilities. Accommodations are available upon request for candidates taking part in all aspects of the recruitment and selection process. Should you require any accommodation, please indicate this when you apply, and we will work with you to meet your accessibility needs.

PSD Citywide may use Google Gemini to assist with recruitment note taking during the hiring process. While we incorporate select AI features to enhance process efficiency, we remain committed to human-led decision making. All AI-generated outputs are subject to human review to ensure accuracy and fairness.