Director of Services

Job Title: Director of Services

Location: Mississauga, Ontario (Hybrid)

Type: Full-Time

Department:
Professional Services

Reports to:
Chief Executive Officer

Director Of Services

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 have a deep, practical, and comprehensive understanding of the technologies that power the modern internet, with a security-first mindset. You should be able to explain not just what these are, but how they interact and how to secure them from the client to the origin.

Position Overview:

We are looking for a hands-on, highly technical, and strategic leader to head our Professional Services, Managed Services, and Project Management Office (PMO). You will play a pivotal part in defining and delivering successful implementation projects, ensuring the ongoing success of our managed service offerings, and aligning execution with client objectives and cybersecurity best practices.

Key Responsibilities

Technical Acumen

• DNS: A thorough understanding of DNS resolution, record types (A, AAAA, CNAME, MX, TXT, NS), anycast routing, and security extensions like DNSSEC.
  
• IP Routing & Networking: Strong knowledge of the TCP/IP suite. You should be able to discuss topics like packet routing and network topology with authority.
  

• TLS/SSL: Expertise in the TLS handshake, certificate management (issuance, chains of trust, revocation), and cipher suites. You understand what enables the lock icon in a browser.
  

• Load Balancers: In-depth knowledge of Layer 4 vs. Layer 7 load balancing, various algorithms (e.g., Round Robin, Least Connections), and concepts like session persistence ("sticky sessions").

• Web & Proxy Servers: Hands-on experience or deep architectural knowledge of servers like Nginx or Apache, and the critical role of reverse proxies in security, caching, and request routing.

• Cloud & CDN: Proven experience with major cloud provider networking (AWS, GCP, Azure) and a firm grasp of how Content Delivery Networks (CDNs) work to accelerate content globally.

• Storage Technologies: Solid understanding of cloud storage architectures, including the trade-offs between object storage (like S3), block storage (like EBS), and file storage (like EFS/NFS).

• Automation & Scripting: Experience with Infrastructure as Code (IaC) principles and tools like Terraform or Ansible. Proficiency in a scripting language such as Python or Bash for automating operational tasks.

• Security Expertise: Deep knowledge of web security principles. You can confidently discuss the OWASP Top 10, DDoS mitigation strategies, Web Application Firewall (WAF) configurations, bot management, and API security. Familiarity with compliance frameworks like SOC 2 or PCI-DSS is a major asset.
  

Professional Services Delivery & Management

• Own end-to-end delivery of implementation, integration, and advisory projects for DataStealth solutions. Ensuring projects are completed on time, within budget, and to the highest quality standards.

• Develop and refine service offerings, methodologies, processes, and best practices to enhance efficiency and client satisfaction.

• Own the P&L for the Professional Services business line; drive service revenue through delivery excellence and scalable service offerings.
  
• Track and report on KPIs including billable hours, revenue, backlog, delivery timelines, and Net Promoter Score (NPS).

• Lead the buildout and operation of the Managed Services division including onboarding, monitoring, performance optimization, SLAs, and incident response.

• Ensure service delivery is aligned with cybersecurity best practices and compliance standards (e.g., SOC 2, ISO 27001, NIST).
  

Qualifications

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

• 10+ years of progressive experience in IT Professional Services, Technical Consulting, or Solutions Architecture, with at least 5 years in a leadership or Senior Technical Lead role.

• Strong knowledge of hosting, cloud (AWS, Azure), networking, and secure operations. Proven experience working for a Managed Services Provider (MSP) or Managed Hosting Provider is highly desirable.

• Multiple relevant industry certifications (e.g., AWS Certified Solutions Architect - Professional, Azure Solutions Architect Expert, VMware Certified Advanced Professional, Kubernetes CKA/CKAD).

• Exceptional analytical, and problem-solving abilities. Strong communication, presentation, and interpersonal skills, with the ability to articulate complex technical concepts to both technical and non-technical audiences.

• Deep technical knowledge of cybersecurity concepts, data protection, threat intelligence, encryption, access control, and compliance.
• Hands-on experience with infrastructure architecture, DevOps practices, and secure system integration.

• Strong project management acumen with demonstrated success in managing complex, multi-stakeholder projects.

• Excellent communication skills with the ability to engage C-level clients, internal teams, and technical stakeholders.
  

Preferred:

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

PMP, CISSP, or other relevant certifications.

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

We look forward to reviewing your application!

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