Senior Director, Engineering - ICM

Jobgether; Canada; On-site; CAD 338,000 - 532,000; Full time

Benefits offered by this job

OTE USD NA

Health insurance

Flexible PTO

401(k) plan

Professional dev stipend

Premium equipment

ERGs

Job summary

Jobgether in Canada is seeking a Senior Director of Engineering for Incentive Compensation Management (ICM). You will lead the engineering organization, define the technical vision, and drive the product toward AI-native capabilities while ensuring reliability and performance.

You will mentor managers, shape team structures, and collaborate with Product, Design, and GTM to translate business opportunities into scalable technology solutions.

Qualifications

• 15+ years software engineering experience with 6+ years leading engineering managers and multi-team organizations.
• Proven track record in building, scaling, and leading high-performing teams in complex tech environments.
• End-to-end product ownership experience from strategy and architecture to deployment and optimization.
• Strong experience scaling enterprise software with focus on reliability, performance, security, and maintainability.
• Hands-on AI/ML-powered product capabilities delivery, ideally with LLMs.
• Experience applying AI to improve engineering productivity or workflows is a plus.
• Excellent communication and collaboration with product, design, and leadership teams.

Responsibilities

• Define and own the engineering strategy and roadmap for the ICM product.
• Lead evolution toward AI-native capabilities and AI-powered features.
• Establish QA, testing, and evaluation frameworks for trustworthy AI outcomes.
• Oversee scalable enterprise systems with high accuracy and performance requirements.
• Guide architectural decisions balancing speed, scalability, and maintainability.
• Mentor engineering managers and develop senior technical leaders.
• Shape team structures, ownership models, and processes as the product evolves.
• Foster accountability, technical excellence, and delivery velocity across teams.
• Identify architectural risks and ensure high engineering standards.
• Collaborate with executive leadership to translate tech strategy into business impact.
• Improve productivity through AI-powered development tools and modern practices.

Skills

Leadership

Software architecture

AI/ML

Enterprise SaaS

Stakeholder management

Cross-functional collaboration

Strategic thinking

People management

Job description

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Senior Director, Engineering – ICM based in the Canada.

As Senior Director of Engineering for Incentive Compensation Management (ICM), you will lead the engineering organization responsible for developing and scaling a mission-critical enterprise software platform. You will define the technical vision and engineering strategy for a flagship product, driving its evolution toward AI-powered capabilities while maintaining the highest standards of accuracy, reliability, and performance. Leading multiple engineering teams and managers, you will foster a culture of innovation, accountability, and continuous improvement. Working closely with Product, Design, Go-to-Market, and executive leadership, you will translate complex business opportunities into scalable technology solutions. You will also play a central role in developing future engineering leaders, optimizing organizational structures, and strengthening technical excellence. This is a high-impact leadership opportunity within a fast-growing SaaS environment where technology, AI, and enterprise performance management intersect.

Accountabilities

• Define and own the engineering strategy and technical roadmap for the Incentive Compensation Management (ICM) product, ensuring alignment with business priorities, customer requirements, and long-term platform objectives.
• Lead the evolution of the product toward AI-native capabilities, identifying opportunities to integrate artificial intelligence into compensation plan design, calculations, payout workflows, and other customer-facing processes.
• Establish robust quality assurance, testing, and evaluation frameworks to ensure AI-powered features deliver reliable, accurate, and trustworthy customer outcomes.
• Oversee the development and scaling of complex enterprise systems where calculation accuracy, data integrity, performance, and reliability are critical.
• Guide architectural decisions and technical investments, balancing development speed with scalability, maintainability, infrastructure resilience, and long-term product quality.
• Recruit, develop, mentor, and inspire engineering managers and senior technical leaders, building a high-performing organization capable of delivering ambitious product and technology objectives.
• Design and evolve engineering team structures, responsibilities, ownership models, and operating processes as the product and organization mature.
• Foster a strong engineering culture centered on accountability, technical excellence, innovation, delivery velocity, and continuous improvement.
• Maintain sufficient technical involvement to identify architectural risks, challenge assumptions, guide critical decisions, and ensure engineering standards remain consistently high.
• Establish clear priorities and alignment across Engineering, Product, Design, and Go-to-Market teams to ensure coordinated execution and successful product delivery.
• Make strategic trade-offs and remove organizational or technical obstacles, enabling teams to move efficiently while maintaining high-quality standards.
• Build strong partnerships with executive leadership and cross-functional stakeholders, translating technical strategy into business impact.
• Identify opportunities to improve engineering productivity through AI-powered development tools, automation, and modern engineering practices.
• Oversee operational reliability and participate in the escalation and support framework for critical production issues, including the required after-hours on-call rotation.

Requirements

• At least 15 years of professional software engineering experience, including 6 or more years leading engineering managers and multi-team engineering organizations.
• Proven track record of building, scaling, and leading high-performing engineering teams within complex technology environments.
• Demonstrated experience owning software products end to end, from technical strategy and architecture through development, deployment, and ongoing optimization.
• Strong experience scaling enterprise software systems while maintaining high standards of reliability, performance, security, and maintainability.
• Hands-on experience delivering AI- and machine learning-powered product capabilities, ideally involving Large Language Models (LLMs).
• Understanding of AI product evaluation, quality measurement, monitoring, and continuous improvement to ensure trustworthy customer-facing functionality.
• Experience applying AI to improve engineering productivity, development workflows, or organizational efficiency is an advantage.
• Strong technical expertise across software architecture, infrastructure, system reliability, scalability, and developer experience.
• Ability to provide strategic technical direction while maintaining sufficient technical depth to engage effectively with engineers and challenge complex architectural decisions.
• Proven ability to collaborate closely with Product and Design teams, prioritizing customer outcomes and business value beyond purely technical objectives.
• Strong organizational leadership skills, including experience developing managers, establishing clear ownership, and adapting team structures to evolving business requirements.
• Ability to create clarity, establish priorities, and drive execution in fast-moving environments characterized by complexity and ambiguity.
• Excellent communication, interpersonal, and stakeholder management skills, including experience influencing and collaborating with executive leadership.
• Strong strategic thinking, decision-making, and problem-solving capabilities.

Additional advantages:

• Experience within enterprise B2B SaaS organizations.
• Background in financial technology, incentive compensation management, sales performance management, or other domains where calculation accuracy, transparency, and auditability are essential.
• Experience leading engineering organizations through significant product transformations or the introduction of AI-native capabilities.

Benefits

• Competitive compensation: Annual On-Target Earnings (OTE) ranging from $237,440 to $373,630 USD across North America. For candidates based in Toronto, Canada, the disclosed range is $237,440 to $317,094 USD. Actual compensation depends on location, experience, individual capabilities, and anticipated performance.
• Comprehensive healthcare: 100% employer coverage for employee medical, dental, and vision insurance, with approximately 75% coverage for eligible dependents.
• Flexible time off: Flexible vacation policy and quarterly mental health days to support personal well-being and work-life balance.
• Annual stipends: Dedicated financial support for professional development and caregiving needs.
• Work anniversary bonuses: Annual bonuses recognizing professional milestones and contributions, increasing with tenure.
• Retirement savings: Access to a 401(k) retirement savings plan for eligible employees in the United States.
• Premium equipment: Latest Apple hardware and technology tools to support productivity and collaboration.
• Inclusive community: Employee Resource Groups (ERGs) that encourage connection, celebrate diverse identities, and promote inclusion and belonging.
• Leadership opportunities: Significant ownership and influence over engineering strategy, product direction, and organizational development.
• Professional growth: Opportunity to work alongside experienced engineering, product, and design leaders in a high-growth technology environment.
• Innovation-driven culture: Direct involvement in shaping next-generation AI-powered enterprise software and advancing the future of incentive compensation management.

We appreciate your interest and wish you the best!

How Jobgether works:

We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.

Data Privacy Notice:

By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.