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.