Head of Operations & Business Management
Trick Dog Technology
Director Of OperationsWe are seeking a visionary, results-driven Director of Operations to lead and scale the delivery organization of a growing IT services company. This individual will assume comprehensive ownership of service delivery, project execution, operational performance, and divisional profit and loss (P&L) while providing strategic direction to an already thriving and rapidly expanding business ecosystem.The Director of Operations will oversee the full spectrum of client delivery, including long- and short-term IT projects, ongoing managed services, and daily break-fix support. The ideal candidate has a proven track record of managing operations within an IT services provider, developing project management teams, optimizing service delivery, and translating business objectives into scalable processes and measurable results.The successful candidate will serve as the operational leader of the division, empowering teams, strengthening accountability, identifying growth opportunities, and building the infrastructure necessary to support continued expansion.Operational Leadership & Strategic DirectionOwn the overall operational direction, performance, and execution of the division across all service delivery functions.Develop and implement a forward-looking operational strategy that supports continued growth, scalability, and long-term business objectives.Serve as a visionary leader who identifies opportunities to improve service delivery, expand capabilities, and strengthen the division's competitive position.Establish clear operational standards, performance expectations, accountability structures, and measurable objectives across teams.Build repeatable, scalable processes that support increasing client volume, project complexity, and service demand.Identify operational risks, capacity constraints, and opportunities for innovation before they impact business performance.Service Delivery & Client SuccessOversee the entirety of service delivery, including project-based engagements, recurring IT services, and daily break-fix support.Ensure work is delivered on time, within scope, within budget, and in accordance with established quality standards and client expectations.Maintain visibility into service performance, ticket backlogs, response and resolution times, project milestones, resource utilization, and client satisfaction.Establish and refine service delivery workflows, escalation procedures, quality controls, and communication standards.Ensure effective coordination between service desk personnel, technical teams, project managers, and other operational stakeholders.Drive continuous improvement in service quality, responsiveness, efficiency, and consistency.Project Management & ExecutionDirect and develop the project management function, ensuring consistent execution across short-term engagements and complex, long-term projects.Manage, mentor, and hold project managers accountable for delivery timelines, budgets, scope, resource planning, risk management, and client communication.Establish standardized project management methodologies, reporting structures, and governance practices.Monitor project health, identify delivery risks, and implement corrective action when projects deviate from established objectives.Ensure appropriate coordination between project managers, technical resources, clients, and leadership.Improve project forecasting, resource allocation, scheduling, utilization, and delivery predictability.Drive consistency in project documentation, change management, closeout procedures, and post-project reviews.Divisional P&L & Financial PerformanceOwn divisional financial performance, including revenue, gross margin, operating expenses, and profitability in accordance with the company's financial reporting structure.Develop and manage operational budgets, financial forecasts, staffing plans, and resource allocation strategies.Monitor key financial and operational indicators to identify margin erosion, inefficiencies, underutilization, and opportunities for improvement.Ensure projects and service engagements are appropriately scoped, resourced, priced, and executed to meet financial objectives.Partner with finance and executive leadership to maintain accurate forecasting, financial visibility, and performance reporting.Establish accountability for financial outcomes across project management and service delivery leadership.Drive sustainable profitability without compromising service quality, employee development, or client satisfaction.Team Leadership & DevelopmentLead, mentor, and develop project managers and other operational leaders, building a culture of ownership, accountability, collaboration, and continuous improvement.Set clear expectations for individual and team performance, providing coaching and constructive feedback to support professional growth.Assess organizational structure, leadership capabilities, staffing levels, and resource needs as the division scales.Develop future leaders and build a sustainable management structure that reduces operational dependency on any single individual.Systems, Processes & Continuous ImprovementOptimize operational workflows, policies, procedures, and reporting systems to improve visibility, efficiency, and consistency.Leverage professional services automation (PSA) and related business systems to improve ticket management, project tracking, resource utilization, financial reporting, and operational decision-making.Establish and maintain meaningful key performance indicators (KPIs) and management dashboards.Identify opportunities to automate manual processes, reduce administrative overhead, and eliminate recurring delivery bottlenecks.Promote data-driven decision-making and continuous operational improvement.Ensure operational systems and processes support both current business demands and future growth.Qualifications & ExperienceRequired Qualifications5+ years of management experience within an IT services company, managed service provider (MSP), or comparable technology services organization.Demonstrated experience leading service delivery, technical operations, project execution, or a combination of these functions.Proven ability to manage and develop project managers, team leads, or other operational personnel.Experience overseeing multiple concurrent projects, ongoing client support operations, and competing resource demands.Demonstrated understanding of divisional financial performance, budgeting, forecasting, cost management, and profitability.Strong knowledge of IT service delivery models, ticketing and escalation workflows, client service expectations, and operational performance metrics.Experience building processes, improving operational efficiency, and supporting organizational growth.Ability to operate at both the strategic and tactical levels, moving comfortably between executive planning and day-to-day operational challenges.Preferred QualificationsAutotask experience is a significant advantage, particularly in PSA administration, service delivery workflows, project management, reporting, time entry, resource utilization, and financial visibility.Experience working within an MSP or IT services provider delivering a combination of managed services, project work, and break-fix support.Experience overseeing both recurring service revenue and project-based revenue streams.Familiarity with service desk operations, SLA management, escalation management, and technician utilization.Experience implementing operational dashboards, standardized project methodologies, and performance management frameworks.Familiarity with ITIL principles, service management best practices, and relevant project management methodologies.Project management or IT service management certifications are beneficial but not required.Leadership ProfileThe ideal candidate is an established IT services leader who combines operational rigor, financial acumen, strategic vision, and strong people leadership.Able to see where the business needs to go and build a practical roadmap to get there.
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