Work In Tech

Director, IT Operations and Information Security

📍 Remote (Canada) | Hybrid Available – Kitchener, ON
🧑‍💼 Reports to: CTO

🏢 About Encircle

Encircle is leading the $1.6 trillion property insurance industry out of the dark ages of pen and paper, into the digital age of transparency and empowerment. Our easy-to-use software platform enables thousands of restoration contractors and insurance professionals across North America to process claims faster and with greater accuracy.

We’re a remote-first company with a collaboration hub in downtown Kitchener—and we’re growing.

📌 About the Role

As the Director of IT Operations and Information Security, you have a passion for delivering exceptional service, optimizing processes, and supporting technology that drives the business forward. Encircle is looking for an energetic, technically strong, purpose-driven IT leader to play a critical role in ensuring the efficiency, effectiveness, and scalability of our daily IT operations, security and compliance, and supporting resilience and continuous IT service delivery.

As the leader of IT Operations and Information Security you’ll be setting the IT & Security direction for the company as well as being a hands-on contributor to executing the daily IT needs of the business, solving problems, and providing stellar service delivery in a remote first organization. This role is responsible for the strategic IT planning, implementation, execution and maintenance of IT operations as well as working on Encircle’s cybersecurity program, maintaining SOC 2 Type II compliance and adhering to other industry standards. The Director will identify and address current gaps in IT operations, security, governance, and vendor relationship management to evolve Encircle’s IT and Security functions as we move from Start Up to Scale Up.

🔧 Key Responsibilities

♟️ Strategic and Leadership

• IT Strategy Development: Collaborate with the leadership team to define and execute IT strategies that align with business goals.
• Technology Roadmap Planning: Develop and maintain a technology roadmap to meet future organizational needs and technological advancements.
• Budget Management: Oversee IT budgets, ensuring cost-effective investments in technology, tools, and resources.
• Collaboration with Stakeholders: Act as a liaison between IT and other business units to ensure alignment and seamless communication.
  

💼 Day-to-Day Operations

• Service Desk Management: Oversee IT support services, ensuring timely resolution of user issues and continuous service improvement.
• Onboarding and Offboarding: Execute the activities required to onboard new employees into Encircle as well as the offboarding tasks.
• Capacity Planning: plan for scalability and resource allocation to accommodate organizational growth and changing technology needs.
• Vendor Management: develop a vendor due diligence process which documents the assessing, selecting, managing, and overseeing third-party vendors providing IT products and services. Key functions include vendor selection, contract negotiation, vendor performance evaluation, risk management, user access configuration, and relationship management.
• Asset Purchasing and Management: responsible for overseeing the purchasing and management of the organization's IT assets. This includes the procurement of hardware (laptops, phones) and software solutions. Keeping track of all hardware and software, ensuring everything is properly licensed, and managing asset life cycles.

🛡️ Security and Compliance

• Cybersecurity Oversight: Implement and manage robust cybersecurity policies, tools, and practices to protect organizational data and systems.
• Disaster Recovery and Business Continuity: Develop and maintain disaster recovery and business continuity plans to minimize downtime during incidents.
• Data Privacy: Participate in designing, developing, implementing, enforcing and monitoring of Encircle’s posture for data privacy
• Regulatory Compliance: Ensure IT operations comply with industry regulations (e.g., GDPR, SOC 2) and internal policies.

💡 Innovation and Optimization

• Performance Optimization: Identify opportunities to enhance IT performance, reduce costs, and improve user experience.
• Emerging Technologies Exploration: Stay updated on industry trends and emerging technologies to drive innovation and maintain competitive advantage.

✅ What You Bring

• Minimum of 10 years of experience in IT Operations and Information Security , internal help desk support with relevant experience in a SaaS scale up
• Bachelor's degree in Computer Science, Information Systems, or a related field or equivalent work experience.
• Strong IT Operations, Vendor, and Asset Management experience (Vanta, BambooHR, or similar tools)
• Demonstrated experience with Information Security Risk Management and Data Privacy Programs, specifically helping to define risks and threats to the organization. Previous experience managing a successful SOC 2 Type II audit
• Experience with key cloud providers (Azure, Google) and their respective IAM security products/solutions
• Strong work ethic and ability to multitask, manage stress during periods of intense activity and handle a wide variety of projects and tasks
• Experience with leading discussions, establishing outcomes, and negotiating paths forward with stakeholders.
• Excellent analytical and problem-solving skills with attention to detail
• Ability to effectively communicate technical requirements to non-technical professionals in a simple manner
• Must be available as needed for on-call support during critical incidents and business continuity events.
• Ability to work in the Eastern timezone

🌱 What You’ll Gain at Encircle

• Ownership and impact on the technology and tools that will continue to drive the business forward.
• A fast-moving, thoughtful culture where you can learn and grow in your career.
• The flexibility of a remote-first company with a strong culture of trust and transparency.
  
  

🤝 Why Encircle?

We VALUE our people:

• Balance: Flexible hours, self-managed vacation, and trust to manage your time
  
• Remote-first: Work where you’re most productive—with access to our collaboration hub in Kitchener
  
• Growth-oriented: We support your learning and career development
  
• Well-being: We care about the full human—inside and outside of work
  
  

Encircle is an equal opportunity employer committed to building a diverse and inclusive team. We encourage all qualified candidates to apply and will work with applicants to accommodate accessibility needs throughout the hiring process.