ABOUT OBRYN GUARDOBRYN GUARD Inc. is a Canadian cybersecurity and continuous compliance company building a cloud-based platform for organizations that need greater visibility, accountability, and readiness across security and compliance requirements.

Our platform is designed to help organizations continuously manage controls, evidence, remediation, access risk, vendor risk, and compliance readiness across frameworks including PCI DSS, SOC 2, and ISO 27001.

As the company continues to scale, we are seeking a highly capable Head of Operations to establish and lead the operational infrastructure required to support our teams, customers, and long-term growth.

THE ROLEThe Head of Operations will work directly with the Founder & CEO and leadership team to ensure the company operates efficiently across all departments.

This person will serve as a central operational leader across Sales, Engineering, Security & Compliance, Quality Assurance, Customer Success, Solutions, Marketing, Partnerships, and corporate operations.

The role requires someone who can translate company strategy into clear execution, establish accountability, improve cross-functional communication, identify operational risks, and build scalable systems across the organization.

The successful candidate will have strong experience operating within a growing technology company and will be comfortable working across multiple business functions simultaneously.

KEY RESPONSIBILITIESCompany Operations

- Build and manage the company's overall operating structure.
- Translate executive priorities into clear objectives, owners, timelines, and measurable outcomes.
- Establish weekly, monthly, and quarterly operating rhythms across leadership and departments.
- Maintain visibility across major company initiatives and ensure commitments are completed.
- Identify operational bottlenecks, dependencies, risks, and inefficiencies before they affect customers or company performance.
- Develop scalable internal systems as the organization grows.
- Support leadership with strategic planning, execution, and organizational priorities.

Cross-Functional Execution
- Coordinate execution across Sales, Engineering, Security & Compliance, QA, Customer Success, Solutions, Marketing, and Partnerships.
- Ensure responsibilities and departmental ownership remain clearly defined.
- Establish effective handoffs between teams.
- Prevent critical projects from becoming delayed or lost between departments.
- Lead cross-functional initiatives requiring coordination between multiple areas of the company.
- Create escalation processes for operational, customer, product, and internal issues.

Performance & Accountability
- Establish company and departmental KPIs.
- Build executive dashboards and operational scorecards.
- Track priorities, deadlines, commitments, risks, and performance.
- Ensure department leaders maintain accountability for agreed deliverables.
- Provide the CEO and leadership team with concise visibility into company performance.
- Identify underperformance, operational gaps, and resource constraints early.

Customer Operations
- Develop and continuously improve the operational process from signed customer through onboarding, implementation, go-live, and ongoing service.
- Ensure Sales, Solutions, Security, Engineering, QA, and Customer Success remain aligned throughout the customer lifecycle.
- Establish onboarding standards, timelines, responsibilities, and escalation procedures.
- Support the development of a consistent and skilled enterprise customer experience.




- Help ensure customer commitments accurately reflect product and operational capabilities.

Product, Engineering & QA Coordination
- Maintain operational visibility into product priorities, delivery timelines, dependencies, and release readiness.
- Coordinate business requirements between leadership, Engineering, QA, Security, and customer-facing teams.
- Support structured release, testing, and escalation processes.
- Ensure business-critical issues have defined owners and resolution timelines.
- Help leadership identify resource or execution risks affecting product delivery.

The Head of Operations will not replace technical leadership but will ensure technical and business teams remain operationally aligned. Security & Compliance Operations
- Coordinate operational activities supporting PCI DSS, SOC 2, ISO 27001, and internal security initiatives.
- Work closely with Security & Compliance leadership to ensure responsibilities, documentation, customer requirements, and timelines remain organized.
- Support evidence management, internal policy implementation, vendor processes, and compliance-related operational workflows.
- Ensure commercial commitments remain aligned with approved security and compliance capabilities.

Technical compliance decisions remain under Security & Compliance leadership.

Sales &

• Revenue Operations
- Strengthen processes across prospecting, pipeline management, closing, contracting, customer handoff, and implementation.
- Support consistent CRM usage, reporting, forecasting, and pipeline visibility.
- Help establish clear responsibility between SDRs, Account Executives, leadership, and implementation teams.
- Improve the operational connection between revenue generation and customer delivery.
- Identify inefficiencies affecting sales velocity or customer conversion.

People & • Organizational Operations
- Support organizational planning as the company grows.
- Develop structured onboarding processes for employees and contractors.
- Maintain clear responsibilities, reporting relationships, and departmental ownership.
- Assist leadership with workforce planning, performance processes, and resource allocation.
- Ensure company documentation and operational knowledge remain centralized and accessible.
- Support the continued development of a high-accountability operating culture.

Process & • Documentation
- Develop and maintain company SOPs, playbooks, workflows, responsibility matrices, and internal operating standards.
- Create reliable documentation for recurring operational processes.
- Establish a clear internal source of truth for company procedures and responsibilities.
- Continuously evaluate processes for opportunities to simplify, automate, or improve them.

Vendors & • Business Infrastructure
- Oversee operational relationships with key technology and service vendors.
- Maintain visibility into company software, systems, subscriptions, and operational tools.
- Support vendor evaluation, purchasing decisions, and contract administration.
- Help ensure business infrastructure remains appropriate for the company's stage and growth requirements.





REQUIRED EXPERIENCE
- 5+ years of experience in operations, business operations, SaaS operations, program management, strategy and operations, Chief of Staff, Director of Operations, or a related leadership role.
- Experience operating within a B2B SaaS, cybersecurity, enterprise technology, fintech, healthtech, compliance, or similarly complex technology environment.
- Demonstrated experience building operational systems and processes within a growing organization.
- Strong cross-functional leadership experience.
- Experience establishing and managing KPIs, dashboards, reporting structures, and operating cadences.
- Strong project and program management capability.
- Experience working directly with founders, executives, or senior leadership.
- Strong understanding of SaaS business operations and customer lifecycle management.
- Excellent written and verbal communication.
- Strong organizational judgment and ability to manage multiple priorities simultaneously.
- Demonstrated ability to operate independently in fast-moving environments.

PREFERRED EXPERIENCE
- Previous experience within an early-stage or scaling SaaS company.
- Cybersecurity or compliance industry experience.
- Experience supporting enterprise B2B customers.
- Familiarity with PCI DSS, SOC 2, ISO 27001, or related compliance environments.
- Experience supporting customer onboarding and implementation.
- Revenue operations or sales operations experience.
- Experience coordinating Product, Engineering, QA, Security, and commercial teams.
- Experience with CRM, project management, documentation, analytics, and SaaS business systems.
- Experience working within distributed or remote organizations.

CORE COMPETENCIESOperational Leadership

Ability to establish structure, discipline, and accountability across the organization.

Execution

Ability to convert strategic priorities into completed initiatives.

Systems Thinking

Ability to understand how departments, processes, technology, customers, and business objectives interact.

Cross-Functional Leadership

Ability to coordinate senior professionals across multiple departments without creating unnecessary bureaucracy.

Prioritization

Ability to identify what materially affects company performance and focus resources accordingly.

Problem Solving

Ability to identify root causes and implement practical, sustainable solutions.

Communication

Ability to provide concise, accurate executive-level information and maintain alignment across teams.

Process Design

Ability to build scalable operating systems suitable for a growing technology company.

Data & Performance Management

Ability to use metrics and operational data to improve decision-making and performance.

Ownership

Ability to take responsibility for outcomes and drive initiatives from identification through completion.

SUCCESS IN THE ROLESuccess will be measured by the company's ability to operate with greater clarity, accountability, predictability, and efficiency.

Key outcomes will include

- Clear ownership across major company priorities.
- Reliable visibility into departmental performance.
- Stronger coordination between leadership and functional teams.
- Faster identification and resolution of business risks.
- Reduced operational dependency on the Founder & CEO.
- Scalable internal systems capable of supporting continued customer and organizational growth.
- And more.

OBRYN GUARD Inc. Automated Cyber Assurance. Built for hospitality.

obrynguard.com

📌 Head of Operations | Oct 6, 2026 (Toronto)
🏢 OBRYN GUARD
📍 Toronto