Senior Director - Engineering - Remote - Contract to hire

Sr. Director, Engineer – Toronto Development Center

Position Summary

The Sr. Director, Engineer – Toronto Development Center is a senior technology leader responsible for building, scaling, and leading the technology organization in Toronto Development Center (TDC). This role is accountable for delivering high quality software and platform capabilities that align with technology strategy, while developing local leadership, establishing strong technology practices, and fostering a high‑ performance, people‑ first‑ culture.

Reporting to the Chief Technology Officer, this leader partners closely with Application Development, System Engineering, Enterprise Architecture, Technical Product Management, Information Security, and HR to ensure TDC is an integrated, strategic extension of company's global technology organization

Essential Job Functions

Strategic leadership & site vision

• Define and execute the multi‑year strategy for the Toronto Development Center, including scale, capabilities, and operating model.
• Translate enterprise technology roadmap into a clear engineering agenda for TDC across application development, quality engineering, DevOps/SRE, and technical product management support.
• Represent TDC in technology leadership forums and ensure alignment with global standards for architecture, security, and delivery.

Engineering delivery & execution

• Own delivery outcomes for engineering teams based in TDC, including scope, schedule, quality, and reliability of assigned products, platforms, and services.
• Establish and continuously improve engineering practices (code quality, testing, CI/CD, observability, documentation) to meet or exceed global benchmarks.
• Ensure TDC teams support key enterprise programs (e.g., policy admin, rating, data, AI/ML, platform modernization) with predictable, high‑quality execution.
• Provide technical leadership on the responsible use and integration of AI and AI platforms (e.g., OpenAI, Claude, and related tooling) into engineering workflows, products, and internal platforms, in partnership with Architecture, Security, and Data/AI teams.

Organization build‑out & talent management

• Design and evolve the TDC organizational structure (teams, leadership layers, capabilities) to support current and future business needs.
• Hire, develop, and retain top engineering and quality talent in Toronto, including managers and technical leaders (e.g., Staff/Principal Engineers, DevOps, SRE, Staff QE).
• Lead performance management, calibration, and compensation recommendations for TDC engineering, in partnership with HR and Total Rewards.

Culture, engagement, and inclusion

• Build and sustain a strong, inclusive culture in TDC that reflects core values and emphasizes collaboration, accountability, psychological safety, and continuous learning.
• Sponsor site‑level engagement activities, communication rhythms, and recognition programs that connect TDC team members to company's mission and the broader MTS organization.

Partnership & stakeholder management

• Serve as the primary technology point of contact for TDC with executive stakeholders (CTO, CIO/COO, EDS leadership, Product leaders) for roadmap, staffing, and site strategy.
• Partner with HR Business Partners, Finance, and Operational Effectiveness on headcount planning, budgeting, workforce analytics, and AI‑driven productivity initiatives.
• Collaborate with Enterprise Infrastructure, Security, and Compliance to ensure TDC environments, tools, and practices align with corporate standards and AI/InfoSec controls.

Operational excellence & risk management

• Ensure robust operational processes for TDC (change management, incident/problem management, on‑call rotations, environment management).
• Monitor and manage key performance indicators (delivery throughput, quality/defect rates, uptime/SLAs, utilization, budget adherence) and drive corrective actions as needed.
• Own TDC engineering operating and capital budgets for people, tools, and infrastructure; partner with Finance to forecast, track, and optimize spend across initiatives and fiscal years.
• Identify and mitigate risks related to talent, delivery, architecture, security, and regulatory/compliance requirements, including cross‑border considerations between Canada and the U.S.

Leadership development & coaching

• Coach and develop direct reports (e.g., associate directors, senior managers, staff engineers) to build a strong local leadership bench.
• Promote a data‑driven, experimentation‑oriented mindset, including responsible use of AI tools in engineering to improve productivity and quality.

Education and Experience

• Education
• Bachelor’s degree in Computer Science, Software Engineering, Information Systems, or related technical field required.
• Master’s degree in a technical field or business (e.g., M.S. in Computer Science, MBA) preferred.
• Experience
• Typically 12+ years of progressive experience in software engineering, systems engineering, or platform engineering, including:
• Significant experience leading multiple engineering teams or sites.
• Proven track record delivering complex, mission‑critical systems in a 24x7 environment.
• 5+ years in a senior leadership role (e.g., Director/Sr. Director) responsible for people leadership, budgeting, and strategic planning.
• Experience building or scaling an offshore/nearshore or regional development center or distributed engineering organization strongly preferred.
• Insurance, financial services, or other highly regulated industry experience a plus.

Knowledge and Skills

• Strong command of modern software engineering practices (cloud‑native architectures, microservices, CI/CD, automated testing, observability).
• Deep understanding of organizational design, engineering leadership, and how to build high‑performing teams in a matrixed, global environment.
• Demonstrated ability to formulate and execute strategy, translate business objectives into technology roadmaps, and manage trade‑offs between speed, quality, and risk.
• Excellent people leadership skills: coaching managers and senior ICs, leading through influence, and communicating clearly across cultures and time zones.
• Strong financial and analytical skills: headcount and budget planning, productivity and utilization analysis, compensation/bonus input, and data‑driven decision making.
• Deep technical understanding of AI/ML concepts and modern AI platforms (e.g., OpenAI, Claude, and related tooling), with experience guiding teams on practical, responsible adoption in products and internal engineering workflows.
• Ability to navigate and implement security, compliance, privacy, and AI governance standards within engineering teams, including alignment with Canadian and U.S. regulatory expectations as applicable.
• Strong familiarity with the Toronto and broader Canadian technology and engineering talent market, including hiring channels, competitive landscape, and compensation trends.
• Working knowledge of Canadian employment standards and labour requirements (federal and provincial), with the ability to partner effectively with HR and Legal on complex matters.
• Knowledge of property & casualty insurance (e.g., rating, underwriting, claims workflows, or regulatory context) is a strong asset but not required.
• Fluent English; French language skills an asset for broader Canadian stakeholder engagement.

Reporting Structure and Classification

• Reports to: VP, Chief Technology Officer (MTS).
• Direct reports: Combination of managers, staff/lead engineers, and senior individual contributors across application development, quality, DevOps/SRE, and associated functions in TDC.
• Employment classification: Exempt (leadership role not eligible for overtime under internal wage/hour guidelines).
• Job Code: TBD – Sr. Director, Engineer – Toronto Development Center (to be assigned during job architecture setup).