Director of Operations

Director, OperationsHelp build Canada’s next global success story.We are hiring for one of Canada’s fastest-growing technology companies, recognized by Deloitte as the #1 Enterprise Software company in the 2025 North American Technology Fast 500 and ranked #5 in Deloitte Canada’s 2024 Technology Fast 50 Companies to Watch.This is a rare opportunity for an accomplished Operations leader to join a high-growth Canadian technology company at a pivotal stage of its journey, with a clear path toward a future VP-level role.We are looking for someone who has been there before, a leader who has helped companies scale, built strong teams and operating infrastructure, navigated complexity, and knows how to evolve an Operations function as a business enters its next chapter.You will work closely with the COO, CEO, and senior leadership in a highly collaborative environment where Operations is a strategic partner to the business.This is an opportunity to help shape what comes next.The MandateAs Director, Operations, you will lead the day-to-day operations function, strengthen the systems and processes that support continued growth, and ensure the business can scale efficiently, reliably, and profitably.You will report to the VP Operations and serve as a key operational leader responsible for translating company priorities into consistent execution. The role offers a clear path toward a broader VP-level mandate as the organization grows.Your responsibilities will include:Manage the full order lifecycle from order intake through fulfillment and delivery.Oversee daily operational performance, ensuring service levels, quality standards, and delivery commitments are consistently met.Manage vendor and partner relationships, including capacity planning, sourcing, integrations, performance reviews, and SLA compliance.Monitor vendor capacity, concentration risk, service issues, and escalation requirements.Support financial operations related to margins, unit economics, monthly billing, reconciliations, and vendor payments.Identify billing discrepancies, cost leakage, margin pressures, and other financial operating risks.Implement and maintain operational controls, governance processes, and compliance procedures, including requirements related to HIPAA and SOC 2.Support day-to-day risk management by identifying issues early, documenting mitigation plans, and escalating material concerns to the VP Operations.Develop and maintain operational reporting and KPIs covering vendor performance, team productivity, fulfillment quality, costs, service levels, and business trends.Partner with Product, Customer Success, Sales, and Marketing to align operational execution with company priorities.Reduce manual dependencies by standardizing workflows, improving documentation, and implementing automation and AI-enabled solutions where appropriate.Lead process-improvement initiatives that improve efficiency, scalability, accuracy, and customer outcomes.Manage and develop operations managers and team leads, creating clear expectations, accountability, and opportunities for growth.Contribute to quarterly planning sessions focused on operational capacity, resource requirements, and business readiness over the next 12–24 months.Provide the VP Operations and leadership team with timely updates, recommendations, and visibility into operational performance.Build a function that can operate effectively without every decision requiring executive involvement.Who You AreYou are an experienced operations leader who has managed complex, high-volume, or distributed fulfillment environments.You have hands-on experience in production and logistics environments comparable to print, mail, transactional communications, postal, or similar distributed operations.You understand how to manage vendor networks, enforce SLAs, monitor capacity, and improve performance among partners who do not report directly to you.You are financially sharp and comfortable with unit economics, margin management, reconciliation, billing integrity, and cost analysis.You understand that compliance must be reflected in daily workflows, access controls, documentation, and vendor practices.You think in systems and processes before adding headcount and have experience moving teams from manual work toward standardized and exception-based operations.You are a strong people leader who has developed managers and team leads into more capable and accountable operators.You bring a collaborative, low-ego approach and are comfortable challenging assumptions constructively.You are adaptable, curious, and able to work effectively in a fast-moving, entrepreneurial environment.You can manage the business across multiple time horizons: resolving today’s operational needs, preparing for the next 12–24 months, and contributing to longer-term planning.You are comfortable working independently while keeping the VP Operations and broader leadership team appropriately informed.You BringSignificant operations leadership experience in a complex, high-volume, or distributed fulfillment model.Experience managing large transaction, piece, order, or unit volumes, or an environment of comparable operational complexity.Strong experience in vendor and partner management, capacity planning, financial operations, billing integrity, and operational compliance.Experience leading and developing managers, supervisors, or team leads.Strong commercial and analytical judgment, including experience with forecasting, trend analysis, cost control, and margin improvement.Comfort with technology, integrations, APIs, automation, and operational systems, even if you are not a technologist.Experience improving processes and reducing manual work through standardization and automation.Existing relationships or credibility within relevant carrier, vendor, production, or logistics networks is an asset.The ability to stay close enough to operational details to identify issues while maintaining a broader view of business priorities.A collaborative leadership style paired with the confidence to make decisions, take ownership, and accept accountability.Experience working successfully in a scaling organization where processes and operating models are still being developed.Why This RoleYou will join at a moment when the operation has real momentum and an even bigger ambition ahead of it.This role is built around a simple standard: if the VP Operations were unavailable for 90 days, the day-to-day operation should continue running effectively. That means real ownership, meaningful trust, and the opportunity to make decisions within your area of responsibility without waiting for unnecessary approvals.You will help strengthen the operating organization, develop the leaders beneath you, and shape how the business scales toward the next level of volume and complexity.For the right leader, this role is more than a Director title. It is an opportunity to become a critical part of the operational backbone of the business, build a strong team, influence how the company scales, and grow into a broader VP-level mandate over time.If you have managed complex operations before and are ready to help build what comes next, this could be the opportunity you have been waiting for.160K - 180K Base CAD per year, plus annual performance bonus and comprehensive benefits.