Director of Engineering Operations

About Kooltra 

Kooltra is a Canadian fintech company building FX infrastructure and cross-border payment technology for banks and financial institutions. With over a decade in market, long term established customers, and a growing footprint in North America, we are now accelerating our US expansion and undertaking a fundamental shift toward an AI-first development and delivery model. 

To fuel that shift, we need to free our CTO to focus entirely on transforming how we build. That's where you come in. 

The Opportunity 

As Director of Engineering Operations, you will absorb everything that sits between our CTO and his ability to think, build, and lead. You will own the operational, compliance, and people machinery of the engineering organization — running it with precision so our technical leadership can stay focused on what matters most: shipping great product and reinventing how we develop it. 

This is not a coding role. This is the role that makes everything else possible. 

What You'll Own 

Compliance & Audit 

• Lead annual SR&ED (Scientific Research & Experimental Development) credit process — owning documentation, working with external consultants, and ensuring maximum eligible claim 

• Own SOC 2 audit readiness and coordination — managing auditor relationships, evidence collection, and remediation tracking 

• Project manage annual penetration testing cycles — coordinating with vendors, prioritizing findings, and tracking remediation to closure 

• Maintain a compliance calendar and ensure engineering never misses a deadline 

People Operations 

• Own the engineering performance review cycle end-to-end — scheduling, tooling, calibration, and documentation 

• Support managers with performance improvement processes and documentation 

• Partner with HR on headcount planning, onboarding coordination, and team communications 

• Track team health and flag issues to leadership proactively 

Delivery & Project Management 

• Own cross-team project management — tracking dependencies, risks, and delivery milestones across engineering squads 

• Run or optimize sprint ceremonies where needed to improve delivery predictability 

• Maintain engineering roadmap visibility for executive and board reporting 

• Identify and eliminate operational friction slowing engineering output 

Vendor & Tool Management 

• Own relationships with key engineering vendors and tooling providers 

• Track contracts, renewals, and cost optimization opportunities 

• Support evaluation of new tools, particularly in the AI development toolchain 

What Success Looks Like 

In your first 90 days, our CTO has measurably more time for technical leadership. Within six months, our SR&ED claim is filed cleanly, our SOC 2 posture is documented and audit-ready, and our engineering delivery is more predictable. Within a year, you have built a quietly excellent operational backbone that the team depends on — and nobody has to think about. 

What You Bring 

• 5+ years in engineering operations, technical program management, or a Chief of Staff / engineering leadership support role 

• Experience owning or coordinating SR&ED claims — you know how to document eligible work and work with external consultants 

• Familiarity with SOC 2 audit processes — you have been through at least one cycle and know what auditors want 

• Strong project management instincts — you close loops, track risks, and communicate status without being asked 

• Comfortable leading performance review processes and having direct conversations with managers about people outcomes 

• Able to earn credibility with engineers without writing code — you speak the language without needing to be a developer 

• Experience in a SaaS or fintech environment is a strong plus 

• Based in or willing to work aligned with EST / CST time zones 

What We Offer 

• Competitive base salary depending on location and experience 

• Meaningful equity participation in a growing fintech 

• Remote-first with flexibility — we care about output, not hours 

• A CTO who is eager to hand this work to someone great 

• Front-row seat to an AI-first engineering transformation at a company with real customers and real revenue 

To apply or learn more, contact us at careers@kooltra.com