Senior Director, Engineering - ICM

CaptivateIQ; Canada; On-site; CAD 335,000 - 527,000; Full time

Benefits offered by this job

Healthcare coverage

Flexible time off

Professional stipends

Annual bonuses

401(k) plan

Apple hardware

ERGs

Job summary

CaptivateIQ seeks a Senior Director of Engineering for Incentive Compensation Management (ICM) to lead the engineering org behind our flagship product, ensuring accurate payouts and AI-native enhancements at enterprise scale. You will partner with Product, Design, GTM, and executives to turn ambiguity into scalable solutions.

You’ll build and guide managers across multiple teams, shaping culture and structure, while balancing speed, reliability, and data integrity in a critical system used by

Qualifications

• 15+ years of software engineering experience, incl 6+ years leading managers.
• Proven track record building and scaling high-performing teams.
• Experience owning products end to end and scaling systems.
• Hands-on AI/ML features shipping, ideally LLM-based.
• Strong technical instincts across product architecture, infra, reliability.
• Close partnership with Product and Design, focused on customer outcomes.

Responsibilities

• Set engineering strategy aligned with company priorities and product direction.
• Lead the organization of managers and senior technical leaders.
• Design team structures and processes that evolve with product maturity.
• Guide architecture decisions balancing speed, reliability, and maintainability.
• Drive cross-functional alignment across Engineering, Product, Design, and GTM.

Skills

Leading managers

AI/ML features

Product ownership

System architecture

Executive communication

Cross-functional collab

Reliability

Scalability

Stakeholder management

Customer outcomes

Job description

About CaptivateIQ

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

We’re building a category-defining platform at the intersection of finance, sales, operations, and AI. We’re looking for ambitious builders to help shape what comes next.

About the Role

As Senior Director of Engineering for Incentive Compensation Management (ICM), you’ll lead the engineering organization behind our flagship product that customers rely on to pay their teams accurately and motivate performance. You’ll lead managers across multiple teams and set the technical direction for making ICM AI-native without compromising the accuracy and trust our customers depend on.

This role combines product thinking, technical leadership, and organization building. You’ll partner closely with Product, Design, GTM, and executive leadership to turn ambiguous opportunities into scalable products, and you’ll shape the engineering culture and structure that delivers them.

The Problems You’ll Solve

• Making ICM AI-native. Decide where AI creates real customer value in plan design, calculation, and payout workflows, and build the quality and evaluation practices that make those features trustworthy.
• Scaling a system where correctness is non-negotiable. Customers pay real people based on our calculations. You’ll balance speed of delivery with reliability, performance, and data integrity at enterprise scale.
• Evolving the organization with the product. You’ll develop managers, clarify ownership, and adapt structure and process as the product matures.

What You'll Do

Set the strategy

• Own the engineering strategy for ICM, aligned with company priorities, customer needs, and long-term platform direction
• Identify new opportunities and guide product evolution, including the thoughtful application of AI to create differentiated customer workflows

Lead the organization

• Recruit, grow, and inspire engineering managers and senior technical leaders
• Build a culture of ownership, velocity, and continuous improvement
• Design team structures and processes that evolve with product maturity

Raise the technical bar

• Guide architecture decisions that balance speed, scalability, reliability, and maintainability
• Stay close enough to the work to spot risks, challenge assumptions, and raise quality across the organization. You don’t need to write production code, but you do need to earn the respect of the engineers who do.

Drive execution

• Create alignment and clear priorities across Engineering, Product, Design, and GTM
• Make thoughtful tradeoffs and help teams move quickly while holding a high quality bar

What You'll Bring

• 15+ years of software engineering experience, including 6+ years leading managers and multi-team engineering organizations
• A track record of building and scaling high-performing teams
• Experience owning products end to end and scaling existing systems
• Hands-on experience shipping AI/ML-powered product features, ideally LLM-based, including how you measure and maintain their quality. Experience applying AI to improve how engineering teams work is a plus.
• Strong technical instincts across product architecture, infrastructure, reliability, and developer experience
• A close partnership with Product and Design, and a focus on customer outcomes beyond engineering
• The ability to create clarity for teams in fast-moving, ambiguous environments
• Strong communication and stakeholder management skills, including experience working with executive leadership

Nice to have: Experience in enterprise B2B SaaS, finance or compensation systems, or other domains where calculation accuracy and auditability matter.

Why You'll Love This Role

• You’ll own a flagship product in a category CaptivateIQ helped define and drive the next generation of AI-native capabilities

• 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

Benefits

• 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.
• Annual Stipends: Dedicated funds for your professional development and caretaking needs.
• 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.
• Premium Tools: The latest Apple hardware to empower you to do your best work.
• Inclusive Community: Active Employee Resource Groups (ERGs) that celebrate shared identities and support our DEI goals by fostering an environment where diverse talent thrives.

$237,440 - $373,630 a year

The OTE range in USD represents the minimum and maximum for this position across North America. For candidates in Toronto, Canada the range is $237,440 - $317,094. The OTE offered for this position will depend on numerous factors, including individual proficiency, anticipated performance, and the location of the selected candidate. Our OTE is just one component of CaptivateIQ's competitive total rewards package.

CaptivateIQ participates in E-Verify, web-based system that allows enrolled employers to confirm the eligibility of their employees to work in the United States