CaptivateIQ is transforming the way companies plan, manage, and optimize sales performance. We started by revolutionizing incentive compensation management, and now we're expanding our platform to solve broader enterprise performance challenges. Recognized by industry analysts like Forrester and G2 and backed by top-tier investors, including Sequoia, ICONIQ, Accel, and Sapphire Ventures, we empower high-growth companies like Netflix, Figma, and Stripe with the flexibility and insights needed to drive revenue performance.

We’re building a category-defining platform at the intersection of finance, sales, operations, and AI, reimagining how revenue organizations plan, operate, and make decisions. We’re looking for ambitious builders to help shape what comes next. We’re looking for an Engineering Director to lead our flagship Incentive Compensation Management product with a focus on building innovative, customer‑centric, AI‑first capabilities that transform the world of incentives.

This role is equal parts product thinking, technical leadership, and organizational building. You’ll partner closely with Product, Design, GTM, and executive leadership to identify opportunities, shape strategy, and deliver meaningful customer and business impact. You’ll lead multiple engineering teams and managers through ambiguity to turn new ideas into scalable products and platforms.

Develop and execute the engineering strategy for a portfolio of initiatives, ensuring alignment with company priorities, customer needs, and long‑term platform direction. Help identify new opportunities, shape technical direction, and guide product evolution at scale,



including the thoughtful application of AI to create differentiated customer experiences and workflows. Recruit, grow, and inspire high‑performing engineering organizations.

Develop engineering managers and senior technical leaders while fostering a culture centered around ownership, velocity, innovation, and continuous improvement. Design organizational structures and engineering processes that evolve with product maturity. Guide architectural and organizational decisions that balance speed, scalability, reliability, and long‑term maintainability.

Stay close enough to the work to identify risks, challenge assumptions, and raise the quality bar across the organization. Drive alignment, prioritization, and execution across Engineering, Product, Design, and GTM teams. Create clarity in ambiguous environments, make thoughtful tradeoffs, and help teams move quickly while maintaining a high quality bar.

Participate in an on‑call rotation to provide after‑hours support, ensuring timely resolution of critical issues and maintaining system uptime. 10+ years of software engineering experience, including 4+ years leading managers and multi‑team engineering organizations. Proven track record of building and scaling high‑performing engineering teams.





Experience building AI/ML‑enabled products — or robust interest and aptitude in leveraging AI to create differentiated product experiences. Strong technical instincts across product architecture, infrastructure, reliability, and developer experience. you think beyond engineering and care deeply about customer outcomes. You’ll own a market leading product and shape the next step function evolution in capabilities and company impact.

You’ll operate with significant ownership and influence across product and engineering strategy. You’ll work alongside deeply collaborative product, design, and engineering leaders. You’ll join a high‑growth company with strong product‑market fit and ambitious expansion plans.

You’ll have the opportunity to shape not only products, but the engineering culture and organization that builds them.

Comprehensive Healthcare: 100% coverage for medical, dental, and vision for all FTEs, with roughly 75% coverage for dependents.

Flexible Time Off: Flexible vacation days plus quarterly mental health days to ensure you have the space to recharge.

Work Anniversary Bonuses: Annual bonuses to celebrate your milestones and contributions to the CaptivateIQ team that grow as your tenure does.

Retirement

Savings (US‑Only): A 401(k) plan to help you invest in and secure your future.

Inclusive Community: Compensation is location‑dependent and includes equity, comprehensive health benefits, and other perks and benefits. CaptivateIQ participates in E‑Verify, a web‑based system that allows enrolled employers to confirm the eligibility of their employees to work in the United States. #

📌 Director of Engineering, ICM (Winnipeg)
🏢 CaptivateIQ
📍 Winnipeg