About OBRYN GUARD

OBRYN GUARD is building a browser-based cyber risk and compliance platform designed to help hotels and multi-location organizations identify operational risks, strengthen internal controls, manage evidence and prepare for compliance, insurance and audit requirements.

The platform supports organizations working toward frameworks such as PCI DSS, SOC 2, ISO 27001 and NIST CSF 2.0.

We are building an execution-focused leadership team capable of taking the company from an early-stage operation into a scalable enterprise SaaS organization. The Role OBRYN GUARD is seeking a highly organized and execution-driven Head of Operations to oversee company-wide coordination, accountability and operational performance.

This individual will work directly with the Founder and CEO to ensure that sales, marketing, product, engineering, compliance and client-facing functions remain aligned and execute against clear priorities.

This is not an administrative role.

The Head of Operations will act as the operational leader of the company—turning strategy into measurable execution, identifying breakdowns, holding department leaders accountable and ensuring that critical work is completed on time.

The successful candidate must be capable of operating in an early-stage environment where systems are still being built, priorities move quickly and leadership requires direct ownership.

Key Responsibilities Company-Wide Execution

Translate the CEO’s strategic direction into clear operational priorities, timelines and deliverables.

Build and maintain company-wide execution plans across sales, marketing, product, engineering, compliance and client operations.

Ensure department leaders understand their responsibilities, deadlines and expected outcomes.

Identify stalled work, unclear ownership and operational bottlenecks before they affect company performance.

Drive projects through completion rather than simply tracking activity. Leadership and Accountability Run structured weekly leadership and operational review meetings.

Establish clear agendas, action items, owners and deadlines.

Hold department heads accountable for agreed commitments and performance standards.

Follow up on incomplete work and escalate significant execution issues directly to the CEO.

Improve communication between departments and prevent teams from operating in isolation.

Provide the CEO with a explicit view of company progress, risks and required decisions. Sales and Marketing Operations Coordinate sales and marketing activity around shared pipeline and revenue objectives.

Ensure lead-generation campaigns, outreach activities, sales follow-ups and reporting systems are operating effectively.

Track core sales metrics, including outreach volume, qualified meetings, pipeline value, proposals, closed contracts and conversion rates.

Track marketing performance, campaign delivery, lead sources, content production and brand initiatives.





Ensure responsibilities between sales and marketing are clearly defined.

Support the implementation and enforcement of CRM standards and pipeline-management processes. Product and Engineering Coordination Work with product and engineering leadership to maintain transparent priorities, milestones and delivery schedules.

Ensure business requirements are translated into actionable product and development tasks.

Track product progress, quality assurance, testing, documentation and release readiness.

Coordinate communication between technical and non-technical teams.

Prevent uncontrolled scope expansion and ensure development remains aligned with customer and business priorities.

Ensure operational, compliance and client requirements are considered during product development. Compliance and Service Delivery Coordinate the operational delivery of cyber risk reviews, compliance support, onboarding and client-facing services.

Ensure responsibilities between the platform, internal team members and external specialists are clearly defined.

Maintain consistent procedures for client onboarding, evidence collection, reporting and ongoing account support.

Help establish quality-control standards for customer deliverables.

Ensure the company does not make unsupported compliance, certification or security claims.

Coordinate complex client requirements with qualified compliance and technical personnel. Systems and Process Development Build repeatable operating procedures across all major company functions.

Create clear workflows for hiring, onboarding, reporting, approvals, project management and client delivery.

Maintain company operating dashboards, performance scorecards and accountability systems.

Document responsibilities, decision rights and escalation procedures.

Introduce systems that improve efficiency without creating unnecessary bureaucracy.

Prepare the company’s operating structure for revenue growth, additional hires and enterprise clients. Team and Resource Management Support the CEO in evaluating team capacity, performance and hiring requirements.

Help define role expectations, performance metrics and reporting structures.

Coordinate onboarding for new employees, contractors and advisors.

Identify underperformance early and recommend corrective action.

Ensure company resources are allocated toward the highest-priority commercial and product objectives.

Support compensation, contractor and performance-review processes when required.

Required Qualifications Demonstrated experience in operations, business management, program management, consulting or cross-functional leadership.





Experience coordinating multiple departments or business functions.

Robust understanding of B2B sales, marketing, SaaS product development and service delivery.

Proven ability to build operational systems within an early-stage or rapidly growing organization.

Strong project-management, documentation and performance-tracking capabilities.

Ability to hold experienced professionals accountable while maintaining productive working relationships.

Excellent written and verbal communication skills.

Strong judgment, discretion and problem-solving ability.

Comfortable working directly with a founder in a fast-moving environment.

Able to operate independently without waiting for constant direction.

Preferred Qualifications Experience in B2B SaaS, cybersecurity, governance, risk, compliance or hospitality technology.

Experience supporting a founder-led or pre-revenue company.

Familiarity with CRM systems, project-management tools, KPI dashboards and operating-review processes.

Experience working with remote and internationally distributed teams.

Understanding of enterprise software implementation, customer onboarding or compliance operations.

Previous experience as a Head of Operations, Director of Operations, Chief of Staff, Program Director or Business Operations Lead.

What Success Looks Like

Within the first 90 days, the Head of Operations should:

Establish a clear company-wide operating rhythm.

Implement structured weekly leadership and departmental reviews.

Define ownership, deadlines and KPIs across every major function.

Create visibility into sales, marketing, product and engineering performance.

Identify and resolve major operational bottlenecks.

Improve communication and accountability between department leaders.

Give the CEO a reliable operating system for managing the company.

Long-term success means the CEO is no longer required to chase every department, remind team members about deadlines or personally coordinate routine execution.

Ideal

Candidate The ideal candidate is highly structured, commercially aware and comfortable creating order inside an early-stage company.

They do not confuse meetings with progress.

They are willing to challenge weak execution, ask difficult questions and hold people accountable regardless of title. They understand that strategy has no value unless it produces completed work, stronger systems, satisfied clients and revenue.

This person must be capable of becoming a trusted operational partner to the Founder and CEO while maintaining the authority and discipline required to manage company-wide execution. Why Join OBRYN GUARD

Work directly with the Founder and CEO.

Influence company strategy, team development and product execution.

Build systems that can support long-term enterprise growth.

Opportunity to grow into a broader executive leadership position based on company performance and demonstrated results.

Thanks,

Leadership Team

OBRYN GUARD Inc.

📌 Head of Operations | August 5, 2026 (Toronto)
🏢 OBRYN GUARD
📍 Toronto