Director of Delivery

2 days ago


Mississauga, Ontario, Canada DataStealth Full time $120,000 - $200,000 per year

About DataStealth:

DataStealth is a single, unified data security platform (DSP) that discovers, classifies, and protects sensitive data across your entire environment, from on-premise to legacy cloud to cloud; wherever your data lives or flows, we protect it. We do this without requiring complex integrations or changes to your existing applications, ensuring security that enables, rather than hinders, your business. By seamlessly applying data protection strategies, such as tokenization, we ensure that even if your perimeter is breached, your data remains unusable if it falls into the wrong hands.

Recognized for the fifth consecutive year as a Great Place to Work, we are one of the world's leading and fastest growing cybersecurity software companies. Our team is the best in the business. Our patented technology provides our large enterprise customers with the ability to solve complex data security problems with a paradigm shifting technology that can actually solve problems.

About You:

You are an accomplished delivery leader who thrives at the intersection of technology, execution, and client success. With a proven track record of steering complex enterprise projects from inception to completion, you excel at building delivery organizations that consistently meet and exceed performance targets. You combine deep technical acumen with strong operational discipline, transforming business requirements into secure, scalable, and impactful outcomes.

Position Overview:

The Director of Delivery is a hands-on and strategic leader responsible for the end-to-end delivery of client projects — ensuring every implementation, integration, and engagement is executed efficiently, securely, and with measurable business impact. This role requires deep technical expertise and a passion for delivery excellence, translating complex customer requirements into successful, scalable outcomes.

You will oversee all phases of project execution, from planning to deployment, and build a high-performing delivery organization that consistently meets scope, timeline, and quality expectations.

Key Responsibilities

  • Own and oversee the end-to-end delivery of all DataStealth solution implementations, integrations, and advisory engagements.

  • Ensure on-time, on-budget, and high-quality delivery of projects, while maintaining customer satisfaction and retention.

  • Define, standardize, and continuously improve delivery methodologies, frameworks, and best practices for repeatability and scalability.

  • Collaborate with cross-functional teams (Product, Engineering, Sales, Security) to ensure delivery alignment with product capabilities and client goals.

  • Drive delivery KPIs including billable utilization, revenue recognition, backlog reduction, delivery timelines, and Net Promoter Score (NPS).

  • Establish governance processes to ensure consistent delivery performance, risk management, and client reporting.

Operational Excellence

  • Develop and optimize delivery processes and tools that enable project visibility, risk mitigation, and execution efficiency.

  • Implement automation and standardization across delivery operations, configuration management, and deployment pipelines.

  • Ensure delivery practices comply with cybersecurity frameworks and data protection standards (PCI-DSS, SOC 2, ISO 27001, NIST).

  • Partner with PMO leadership to track delivery milestones, manage dependencies, and resolve execution challenges proactively.

  • Client Success & Stakeholder Management

  • Serve as the executive sponsor for key client deliveries, ensuring strategic alignment and continuous value realization.

  • Foster a delivery culture focused on transparency, accountability, and customer trust.

  • Provide regular executive-level reporting on delivery performance, risks, and forecasts.

  • Collaborate with sales and pre-sales teams to ensure accurate delivery scoping and client onboarding readiness.

Team Development

  • Build, mentor, and lead a high-performing delivery organization comprising technical project managers, implementation engineers, and solution architects.

  • Establish a culture of delivery ownership, technical excellence, and continuous learning.

  • Define and track team performance metrics tied to delivery success and client satisfaction.

Qualifications

  • Bachelor's degree in Computer Science, Information Technology, or a related field; Master's preferred.

  • 10+ years of experience in delivery management, professional services, or technical project execution within enterprise software, cloud, or cybersecurity environments.

  • 5+ years in a leadership capacity, managing multi-disciplinary delivery teams.

  • Proven success in leading complex technical delivery for enterprise clients, including cloud, networking, and secure infrastructure solutions.

  • Expertise in project governance, stakeholder communication, and cross-functional execution.

  • Strong understanding of secure system integration, data protection, and compliance standards (PCI-DSS, SOC 2, ISO

  • Demonstrated experience with cloud environments (AWS, Azure, GCP) and automation tools (Terraform, SaltStack, Ansible, Python, or Bash).

  • Excellent communication and presentation skills, capable of engaging both C-level executives and technical teams.

Preferred

  • Experience working in a high-growth B2B SaaS or cybersecurity company.

  • Certifications such as PMP, ITIL, CISSP, AWS/Azure Architect, or Scrum Master.

  • Familiarity with tokenization, data masking, or secure data integration technologies.

Why Join Us

At DataStealth, you'll lead the delivery of transformative projects that safeguard critical data and strengthen enterprise resilience. You'll be part of a high-performing team that values innovation, collaboration, and excellence in execution.

We look forward to reviewing your application

DataStealth is an equal opportunity employer. We encourage applications from candidates of all backgrounds and experiences.



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