HEAD OF OPERATIONS OBRYN GUARD Inc.

Cybersecurity | Continuous Compliance | B2B SaaS

Remote

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 build and lead the operational infrastructure required to support our teams, customers, and long-term growth.

THE ROLE The Head of Operations will work directly with the Founder & CEO and leadership team to ensure effective execution across the organization.

This individual 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 a strong operator who can translate company strategy into execution, establish accountability, improve cross-functional coordination, identify operational risks, and build scalable systems as the company grows.

KEY RESPONSIBILITIES

Operational Leadership

- Build and manage the company's operating structure and execution cadence.
- Translate executive priorities into clear objectives, owners, timelines, and measurable outcomes.
- Establish weekly, monthly, and quarterly operating rhythms.
- Maintain visibility across major company initiatives, dependencies, risks, and deadlines.
- Identify operational bottlenecks and drive issues through resolution.
- Build scalable systems, processes, and internal standards.
- Support executive leadership with strategic planning, resource allocation, and company-wide execution.

Cross-Functional Execution

- Coordinate execution across Sales, Engineering, Security & Compliance, QA, Customer Success, Solutions, Marketing, and Partnerships.
- Establish clear ownership and accountability across departments.
- Develop effective handoffs between teams.
- Lead cross-functional initiatives involving multiple departments.
- Create escalation processes for customer, product, operational, and internal issues.
- Ensure high-priority initiatives maintain clear ownership and completion timelines.

Performance & Accountability

- Establish company and departmental KPIs.
- Build executive dashboards and operational scorecards.
- Track priorities, deadlines, performance, risks, and commitments.
- Maintain accountability across departmental leadership.
- Provide the Founder & CEO with concise visibility into company performance.
- Identify operational gaps, underperformance, and resource constraints early.

Customer & Revenue Operations

- Develop and optimize the process from signed customer through onboarding, implementation, go-live, and ongoing service.
- Strengthen coordination between Sales, Solutions, Security, Engineering, QA, and Customer Success.
- Establish onboarding standards, timelines, responsibilities, and escalation procedures.
- Support CRM discipline, forecasting, pipeline visibility, contracting, and customer handoffs.




- Ensure commercial commitments remain aligned with operational and product capabilities.
- Improve the connection between revenue generation and successful customer delivery.

Product, Engineering & QA Coordination

- Maintain operational visibility into product priorities, timelines, dependencies, and release readiness.
- Coordinate business requirements between leadership, Engineering, QA, Security, and customer-facing teams.
- Support structured testing, release, issue-management, and escalation processes.
- Ensure business-critical issues have defined owners and resolution timelines.
- Identify execution risks affecting product or customer 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 initiatives supporting PCI DSS, SOC 2, ISO 27001, and internal security programs.
- Work closely with Security & Compliance leadership on documentation, responsibilities, customer requirements, and timelines.
- Support evidence management, policy implementation, vendor processes, and compliance-related workflows.
- Ensure commercial and operational activities remain aligned with approved compliance capabilities.

Technical compliance decisions remain under Security & Compliance leadership.

People, Process & Business Infrastructure

- Support organizational planning, workforce requirements, and resource allocation.
- Develop structured onboarding processes for employees and contractors.
- Maintain clear responsibilities, reporting relationships, and departmental ownership.
- Develop and maintain SOPs, playbooks, workflows, responsibility matrices, and operating standards.
- Establish a centralized source of truth for company processes and documentation.
- Continuously identify opportunities to simplify, automate, and improve operations.
- Oversee key operational vendors, software systems, subscriptions, and business tools.
- Support vendor evaluation and contract administration.

REQUIRED EXPERIENCE

- 5 years of experience in operations, business operations, SaaS operations, strategy and operations, program management, Chief of Staff, Director of Operations, or a related leadership role.
- Experience within B2B SaaS, cybersecurity, enterprise technology, compliance, fintech, healthtech, or another complex technology environment.
- Demonstrated experience building operational systems and processes within a growing organization.
- Strong cross-functional leadership and project management experience.
- Experience establishing KPIs, dashboards, reporting structures, and operating cadences.
- 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 competing priorities.
- Ability to operate independently in a fast-moving environment.

PREFERRED EXPERIENCE

- Experience within an early-stage or scaling SaaS company.
- Cybersecurity, compliance, or enterprise software experience.
- Experience supporting enterprise B2B customers.
- Familiarity with PCI DSS, SOC 2, ISO 27001, or related compliance environments.
- Customer onboarding and implementation experience.
- 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 operating within distributed or remote organizations.

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

Execution — Convert strategic priorities into measurable outcomes.

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

Cross-Functional Leadership — Coordinate senior professionals across multiple departments.

Prioritization — Identify what materially affects company performance and allocate attention accordingly.

Problem Solving — Identify root causes and implement practical, scalable solutions.

Executive Communication — Deliver concise, accurate information to leadership while maintaining alignment across teams.

Data & Performance Management — Use metrics and operational data to improve execution and decision-making.

Ownership — Drive initiatives from identification through completion.

SUCCESS IN THE ROLE Success will be measured by OBRYN GUARD's ability to operate with greater clarity, accountability, predictability, and efficiency.

Key outcomes include

- Clear ownership across company priorities.
- Reliable visibility into departmental performance.
- Stronger coordination between leadership and functional teams.
- Consistent execution against company objectives.
- Efficient handoffs between Sales, implementation, Security, Engineering, QA, and Customer Success.
- A structured and repeatable customer onboarding process.
- Strong internal documentation and operational continuity.
- 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. Pasted markdown

WORKING ENVIRONMENT OBRYN GUARD operates as a distributed technology company with professionals working across multiple business and technical functions.

The Head of Operations should be comfortable operating with autonomy, strong judgment, direct communication, rapid problem solving, and significant ownership.

This is a high-impact leadership position with direct exposure to company strategy, product development, customers, operational execution, and organizational growth.

OBRYN GUARD Inc.

Automated Cyber Assurance. Built for hospitality.

obrynguard.com

📌 Head of Operations (Toronto)
🏢 OBRYN GUARD
📍 Toronto