Senior Director, Engineering - ICM

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.

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