Director of Delivery & Operations (Hybrid)

Toronto, ON, Canada

Full Time

Executive

Company Overview:
iTmethods is a 20+ year-old firm specializing in managed services, enterprise AI, DevOps, and cloud integration. As an AWS MSP and SOC 2 Type II certified company, we're radically transforming from pre-AI capabilities to post-AI dominance through our iTmethodsONE platform—a central hub for AI/ML, DevOps, Cloud, Compliance, Security, and FinOps. Key offerings include:

AI-Assisted Development (enterprise-grade coding assistants, MLOps integration for productivity boosts),
Agentic AI Automation (autonomous agents for workflows, powered by partnerships for any enterprise use case—expertly managed by iTmethods),
Modular DevOps & AI Ops (LEGO-like secure CI/CD workflows, flexible automation, scalable pipelines with MLOps integration),
Self-Hosted ISV and Open Source Tools Platform (expertly managed by iTmethods for regulated industries, with hybrid/on-premise patterns),
Secure Deployments & Optimization (24/7 monitoring, DevSecOps, FinOps for up to 50% cost reduction, GDPR-aligned protection),
FinOps Capabilities (resource optimization, CapEx-to-OpEx conversion with up to 50% cost reduction, real-time visibility for ruthless efficiency).

With 50+ integrations (e.g., Coder, Sonar, GitHub, CI/CD, JFrog, AWS, Azure), we deliver up to 67% development cycle reductions and drive results for enterprises across the US, Canada, and Europe. Profitable and founder-led, we operate with warrior mindset—urgency, speed, and purpose—to seize $85.2B+ opportunities in self-hosted/Agentic AI and FinOps via strategic partnerships. Our customer-obsessed culture is shifting to a post-AI era of ruthless efficiency, elite performance, and extraordinary value creation, with no spectators—only warriors.

Role Summary:
As Director of Delivery and Operations, you will join our Executive Leadership Team (ELT) to oversee all Professional Services (PS), Engineering, and Operations delivery with warrior-speed execution. This hands-on role requires driving AI transformation—embedding Agentic AI for 5x productivity via partnerships—while optimizing synergies and hitting PE metrics like up to 50% cost reductions and up to 67% faster cycles. You'll thrive with zero-excuses urgency, delivering via iTmethodsONE and evolving our elite culture for market dominance.

Key Responsibilities:

Lead end-to-end delivery of PS, Engineering, and Ops, ensuring seamless integration of AI/ML, DevOps, cloud deployments, security/compliance, and FinOps via iTmethodsONE.
Drive hands-on execution: Optimize workflows for up to 67% development cycle reductions and up to 50% cost savings, leveraging internal assets, partner ecosystems, and 3rd-party synergies; maintain super-organized sprint planning and resource coordination across multiple customers in 12-week frameworks/war rooms.
Manage people and teams: Lead direct and cross-functional teams, overseeing groups to foster talent development, AI adoption, and high-performance warrior culture for customer success in a post-AI landscape.
Champion AI transformation: Embed/resell Agentic AI solutions (e.g., for automation in regulated sectors) into services/ops, enabling rapid iteration and productivity.
Ensure mature metrics and delivery: Track KPIs (e.g., utilization, revenue growth, compliance adherence) aligned with PE expectations; scale operations using modular tools and hyperscaler integrations for 3x speed.
Manage Forward Deployed Engineers embedded within platform offerings to drive fixed-price business outcomes and accelerate customer success.
Build partnerships: Leverage 3rd-party delivery partners (e.g., for AI agents) while maintaining SOC 2 standards and enterprise-grade outcomes.
Collaborate with ELT: Align on strategic goals, mitigate risks, and support growth in Toronto's tech ecosystem, emphasizing urgency and purpose in marketplace wins.

Qualifications:

10+ years in technical leadership roles, with proven success in PS, Engineering, and Ops delivery within tech/AI/DevOps firms.
Track record in PE-backed companies: Experience scaling with mature metrics (e.g., cost optimization, delivery efficiency) in agile environments.
Hands-on expertise: Deep knowledge of AI/ML integration (including Agentic AI), cloud platforms (AWS, Azure), DevOps tools (CI/CD, GitHub, Sonar), security/compliance (DevSecOps, GDPR), and FinOps.
People management skills: Managed direct and cross-functional teams with emphasis on collaboration, agility, and results in resource-constrained settings, while cultivating a customer-obsessed, warrior culture.
Super-organized execution: Demonstrated ability in sprint planning, coordinating resources for multiple customers, and driving synergies without bureaucracy, with purpose and urgency to excel in competitive markets.
Bachelor's/Master's in Computer Science, Engineering, or related; Hyperscaler (AWS/Azure/GCP) certifications a plus.
Based in or willing to relocate to Toronto, ON.

What We Offer:

Competitive salary + long-term compensation incentives, bonuses tied to PE metrics.
Hybrid work in Toronto, professional development (e.g., AI certifications), and impact in a transforming firm via our elite performer path—fast-track growth, signature projects, and direct leadership access.
Inclusive culture focused on innovation, customer obsession, and work-life balance—but with warrior mentality for extraordinary value.

iTmethods is an equal opportunity employer. Apply with resume and cover letter highlighting PE-backed achievements.

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Do you have at least 10 years of experience in technical leadership roles, including proven success in Professional Services (PS), Engineering, and Operations delivery within tech, AI, DevOps, or cloud-focused firms?*

If "yes" to the previous question, briefly describe one key achievement in scaling operations in a PE-backed or agile environment (e.g., cost optimization or cycle time reductions).

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Have you managed direct and cross-functional teams (e.g., 10+ people) in resource-constrained settings, with a focus on fostering collaboration, AI adoption, and a customer-obsessed culture?*

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Do you have demonstrated experience in super-organized execution, such as sprint planning, resource coordination across multiple customers, and driving synergies with partners/3rd-party providers without bureaucracy?*

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