HEAD OF OPERATIONS

OBRYN GUARD Inc.

ABOUT OBRYN GUARD

OBRYN GUARD Inc. is a Canadian cybersecurity and continuous compliance company building a cloud-based platform designed to help organizations strengthen security visibility, accountability, evidence management, remediation, and compliance readiness.

Our platform supports continuous readiness across frameworks including PCI DSS, SOC 2, and ISO 27001 .

As OBRYN GUARD continues to scale, we are seeking an experienced Head of Operations to establish and lead the operational infrastructure required to support our leadership team, customers, and long-term growth.

THE ROLE The Head of Operations will work directly with the Founder & CEO and functional leadership to ensure efficient execution across the company.

This individual will serve as the central operational accountability layer across Sales, Engineering, Security & Compliance, Quality Assurance, Customer Success, Solutions, Marketing, Partnerships, and corporate operations .

The Head of Operations is not expected to replace departmental leadership or act as the subject-matter expert within each function. Department leads remain responsible for their teams and functional decisions.

The Head of Operations is responsible for ensuring those leaders execute against agreed priorities, KPIs, deadlines, and company objectives.

KEY RESPONSIBILITIES

Operational Leadership

- Translate CEO and leadership priorities into clear objectives, owners, deadlines, and measurable outcomes.
- Establish weekly, monthly, and quarterly operating rhythms.
- Maintain visibility across major company initiatives.
- Identify operational bottlenecks, dependencies, risks, and missed commitments.
- Drive issues through resolution and escalate material risks when required.
- Build scalable operating systems as the company grows.

Departmental Accountability

- Maintain regular operating reviews with functional leaders.
- Ensure each department has clearly defined KPIs, priorities, deliverables, and timelines.
- Hold department leads accountable for the performance and execution of their teams.
- Identify repeated underperformance and establish corrective actions.
- Ensure accountability without unnecessarily interfering with functional leadership.
- Provide the Founder & CEO with concise visibility into company-wide execution.

Cross-Functional Execution

- Coordinate work across Sales, Engineering, Security & Compliance, QA, Customer Success, Solutions, Marketing, and Partnerships.
- Establish clear handoffs between departments.
- Prevent important projects from becoming delayed or lost between teams.
- Resolve conflicting priorities and cross-functional dependencies.
- Establish escalation paths for operational, customer, product, and internal issues.

Performance & Reporting

- Establish company and departmental KPI frameworks.
- Build executive dashboards and operational scorecards.
- Track commitments, deadlines, risks, performance, and corrective actions.
- Produce concise leadership reporting showing what is on track, at risk, delayed, and requiring executive intervention.





Customer & Revenue Operations

- Strengthen the process from prospect and signed customer through onboarding, implementation, go-live, and ongoing service.
- Ensure effective handoffs between Sales, Solutions, Security, Engineering, QA, and Customer Success.
- Support CRM discipline, forecasting, pipeline visibility, contracting, and customer onboarding.
- Ensure commercial commitments remain aligned with operational and technical capabilities.

Product, Engineering & QA Coordination

- Maintain operational visibility into product priorities, technical milestones, dependencies, QA readiness, and release timelines.
- Support structured release, testing, escalation, and issue-management processes.
- Ensure critical technical issues have transparent owners and resolution timelines.
- Work with technical leadership without replacing their technical authority.

Security & Compliance Operations

- Coordinate operational activities supporting PCI DSS, SOC 2, ISO 27001, and internal security initiatives.
- Ensure responsibilities, documentation, customer requirements, timelines, and dependencies remain organized.
- Support evidence management, policy implementation, vendor processes, and compliance-related workflows.
- Technical compliance decisions remain under Security & Compliance leadership.

People & Organizational Operations

- Support workforce and resource planning.
- Establish structured onboarding for employees and contractors.
- Maintain role clarity, reporting structures, and departmental ownership.
- Support performance management and leadership accountability.
- Ensure critical operational knowledge is properly documented and centralized.

Process & Documentation

- Develop and maintain SOPs, playbooks, workflows, responsibility matrices, and operating standards.
- Build a reliable internal source of truth for company processes.
- Continuously identify opportunities to simplify, automate, and improve operations.

Vendors & Business Infrastructure

- Maintain visibility into operational vendors, software, subscriptions, systems, and tools.
- Support vendor evaluation, contract administration, purchasing decisions, and operational performance.

REQUIRED EXPERIENCE
- 5+ years in operations, business operations, SaaS operations, strategy and operations, Chief of Staff, Director of Operations, Head of Operations, or a related leadership role.
- Experience within B2B SaaS, cybersecurity, enterprise technology, compliance, fintech, healthtech, or another complex technology environment preferred.
- Demonstrated experience building operational systems and processes.
- Strong cross-functional leadership experience.
- Experience establishing KPIs, dashboards, reporting structures, and recurring operating cadence.




- Experience working directly with founders, executives, or senior leadership.
- Strong project and program management capability.
- Strong organizational judgment and ability to manage competing priorities.
- Ability to operate independently in a fast-moving environment.

PREFERRED EXPERIENCE
- Early-stage or scaling SaaS experience.
- Cybersecurity, compliance, or enterprise technology experience.
- Enterprise customer exposure.
- Familiarity with PCI DSS, SOC 2, ISO 27001, or similar compliance environments.
- Customer onboarding and implementation experience.
- Revenue or Sales Operations exposure.
- Experience coordinating Product, Engineering, QA, Security, and commercial teams.
- Experience with CRM, project management, documentation, analytics, and SaaS business systems.
- Experience managing distributed or remote teams.

CORE COMPETENCIES Operational Leadership — Establish structure, discipline, visibility, and accountability.

Execution — Convert company priorities into completed outcomes.

Systems Thinking — Understand how departments, processes, technology, customers, and business objectives interact.

Cross-Functional Leadership — Coordinate experienced leaders without unnecessarily undermining their authority.

Accountability — Ensure commitments have clear owners, deadlines, corrective actions, and follow-through.

Prioritization — Focus leadership attention on what materially affects company performance.

Problem Solving — Identify root causes and drive practical solutions.

Executive Communication — Deliver concise, accurate information to the Founder & CEO.

Data & Performance Management — Use KPIs and operating data to improve decisions and execution.

SUCCESS IN THE ROLE

Success will be measured by OBRYN GUARD operating with greater clarity, accountability, predictability, and efficiency .

Key outcomes include

- Clear ownership across every major company priority.
- Department leaders accountable for their teams and objectives.
- Reliable visibility into company and departmental performance.
- Faster identification and resolution of blockers.
- Stronger coordination between Sales, Engineering, Security, QA, Marketing, Solutions, and Customer Success.
- Consistent execution against company objectives.
- Structured and repeatable customer onboarding.
- Strong operational documentation.
- Reduced operational dependency on the Founder & CEO.
- Scalable internal systems capable of supporting continued growth.

OPPORTUNITIES As OBRYN GUARD grows, the Head of Operations may have opportunities to:
- Represent OBRYN GUARD at hospitality, cybersecurity, technology, and compliance events .
- Participate in industry conferences, webinars, panels, and partner presentations .
- Support strategic customer and partnership meetings.
- Contribute directly to international expansion and operational scaling.
- Help shape the long-term organizational structure and operating model of the company.

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

obrynguard.com

📌 Head of Operations | Oct 9, 2026 (Toronto)
🏢 OBRYN GUARD
📍 Toronto