Vice President of Operations / Chief Operating Officer - Canada, GreyOwl

Job Description:

GreyOwl is seeking a Vice President, Operations or COO for its Canadian operations to take overall leadership of the company's day-to-day operations and help lead its next stage of growth.

This is not simply an operational-maintenance position. The VP, Operations will assess how GreyOwl operates today, identify opportunities to improve structure and efficiency, build scalable processes and accountability, strengthen service delivery, and create the operational foundation required for continued growth across North America.

The successful candidate will bring a combination of operational leadership, business acumen, technology orientation and execution discipline. They will be equally comfortable developing strategy with senior leadership, reviewing performance and financial metrics, improving processes, leading managers and teams, solving client-service issues, and getting directly involved when an operational challenge needs to be resolved.

The mandate is clear: help GreyOwl operate better, scale intelligently and grow without losing the responsiveness, innovation and ownership mentality that built the company.

What You Will Do

Lead the Operation

• Provide overall leadership and direction for GreyOwl's operational functions, ensuring teams, resources and processes are aligned with company priorities.
• Oversee day-to-day service delivery and operational performance across the business.
• Establish clear operating structures, responsibilities, decision-making authority and accountability across teams.
• Build a disciplined operating rhythm around priorities, KPIs, service levels, reporting, meetings and follow-through.
• Ensure operational issues are identified early, properly owned and driven through to resolution.
• Create consistency and scalability while maintaining the responsiveness and flexibility that clients expect from GreyOwl.

Build a More Efficient and Scalable Organization

• Assess existing workflows, systems, organizational structure and operating practices to identify opportunities for improvement.
• Design and implement processes that improve productivity, service quality, communication and accountability.
• Identify operational bottlenecks, duplication, unnecessary complexity and areas where resources can be deployed more effectively.
• Develop scalable systems and processes capable of supporting continued geographic, client and service-line growth.
• Establish meaningful operational metrics and dashboards that provide leadership with visibility into performance.
• Continuously evaluate whether GreyOwl has the right people, processes, technology and organizational structure to support its growth.

Drive Technology and Innovation

• Champion the use of technology, automation and AI to improve how GreyOwl operates internally and serves its clients.
• Identify opportunities to automate repetitive work, improve workflows and provide teams with better operational information.
• Work closely with technical leadership to ensure GreyOwl continues evolving its managed-services capabilities and technology platform.
• Encourage experimentation and practical innovation while ensuring new technology produces measurable business and client value.
• Help translate emerging technologies into scalable services and operational advantages.

Strengthen Service Delivery

• Maintain a relentless focus on client experience, responsiveness and accountability.
• Ensure Help Desk, managed services, field support and other operational functions deliver consistent service standards.
• Develop processes for escalation, problem resolution and communication when service issues occur.
• Ensure teams take ownership of client problems rather than allowing issues to move between departments without resolution.
• Work with leadership to continually improve service offerings based on client needs, operational data and changes in technology.

Help Grow the Business

• Partner with ownership and senior leadership to develop and execute GreyOwl's growth strategy.
• Translate growth objectives into operational plans, staffing requirements, systems and execution priorities.
• Help evaluate new markets, services, partnerships and business opportunities from an operational and commercial perspective.
• Ensure new clients and portfolios can be onboarded effectively without compromising service quality.
• Support major client relationships, proposals and strategic business-development opportunities where senior operational leadership is required.
• Help build the infrastructure necessary to expand GreyOwl's footprint across North America.

Lead People and Performance

• Lead, coach and develop operational leaders and teams.
• Establish clear expectations, measurable objectives and accountability throughout the organization.
• Evaluate organizational capacity and recommend changes to structure, roles and staffing as the company grows.
• Recruit and develop strong leaders capable of operating independently and taking ownership of results.
• Build a culture of urgency, collaboration, continuous improvement and accountability.
• Create an environment where people are encouraged to solve problems rather than simply identify them.

Financial and Business Management

• Partner with senior leadership on annual operating plans, budgets, forecasts and business priorities.
• Monitor operational costs, resource utilization, productivity and overall business performance.
• Identify opportunities to improve margins and operating leverage without compromising client service.
• Evaluate investments in people, systems and technology based on expected operational and financial returns.
• Use financial and operational data to support decision-making and resource allocation.
• Provide leadership with clear reporting on operational performance, risks, priorities and opportunities.

What You Bring

• Significant progressive leadership experience overseeing operations within a technology, Managed Services, IT services or similarly complex service organization.
• Experience leading multiple operational functions, teams and managers with responsibility for overall business performance.
• Demonstrated ability to structure, professionalize and scale an organization while preserving entrepreneurial speed and client responsiveness.
• Strong understanding of Managed Services and recurring service-delivery environments.
• Experience with technology-enabled operations, process automation and modern business systems.
• Genuine interest in emerging technology, including practical applications of AI and automation.
• Strong financial and commercial acumen, including budgeting, forecasting, operational metrics, margins and resource planning.
• Demonstrated experience improving processes, productivity, accountability and service quality.
• Experience supporting organizational growth, new client onboarding and expansion into new markets or service offerings.
• Strong leadership and people-development capability.
• Excellent judgment and the ability to make decisions in a fast-moving environment where not every problem comes with an established process.
• Exceptional communication skills with the ability to work effectively with ownership, senior executives, technical professionals, operational teams, clients and external partners.
• Highly proactive, solutions-oriented and comfortable taking ownership of difficult or ambiguous problems.
• A strong bias toward execution - someone who moves from identifying an issue to determining the solution and ensuring it gets done.

Experience within commercial real estate, property technology, building technology, smart buildings, security systems or technology supporting multi-site property portfolios would be highly valuable.

The Leadership Profile

GreyOwl is looking for an operator who sees both what the company is today and what it can become.

The right person will walk into an operation and naturally ask:

How can we organize this better? Where are we losing time? What should we automate? Where do we need stronger accountability? What will break when we double in size? How do we improve the client experience? What technology can make us better? What should we build now so we are ready for where the company is going?

This individual should be strategic enough to help shape the future of the business but operational enough to get involved and make things happen.

Salary Range:

$175,000 - $250,000

AI Use:

This role may involve the use of artificial intelligence (AI) tools to support research, analysis, content development, design, reporting, or operational efficiency. Employees are expected to use AI responsibly and in compliance with company policies, data privacy requirements, confidentiality obligations, and applicable laws.

All AI-generated or AI-assisted outputs must be reviewed for accuracy, quality, and appropriateness before use. Employees are also expected to disclose when AI tools have been used in the creation of work and must not present AI-generated content as solely their own original work.

How To Apply:

Please apply through the link on the job posting and attach your resume and any other required documents.

We thank all applicants for your interest in the Onni Group. Note that only those applicants under consideration will be contacted.