Information Technology - Director, Technology Operations & Delivery

Information Technology - Director, Technology Operations & Delivery

Toronto, ON, Canada

Overview

AccertaClaim Servicorp Inc. (ACSI) and its subsidiary Accerta Services Inc. (ASI), both known as Accerta, are social enterprises that manage dental, vision, drug, and healthcare benefits programs exclusively for government and social services agencies in Canada. Our targeted experience and innovative technology provide reliable service, process continuity, cost savings, and accurate data that enables governments to make informed strategic decisions, reducing strain on the healthcare system through streamlined administration.

Accerta is a Certified B Corporation, reflecting the values on which we have built our business: serving customers, caring for employees, and supporting our community and the environment. Being part of the B Corp movement means we are committed to continual improvement and making business a force for good.

JOB TITLE: Director Technology Operations & Delivery

EMPLOYMENT TYPE: Full-time, Permanent, Hybrid

About This Opportunity

The Director, Technology Operations & Delivery is responsible for the operational leadership, coordination, and execution oversight of Accerta’s technology portfolio. This role ensures technology initiatives, operational functions, and cross-functional delivery activities are executed effectively, prioritized appropriately, and aligned to organizational objectives.

The Director acts as the central operational leader across technology delivery functions, ensuring operational accountability, delivery discipline, governance consistency, and execution transparency across infrastructure, software delivery, product operations, data initiatives, vendor engagements, and enterprise technology programs.

This role is accountable for operationalizing delivery processes, coordinating cross-functional execution, managing operational escalations, improving organizational delivery maturity, and ensuring technology teams are operating cohesively and efficiently.

The Director collaborates closely with technology and business leaders to remove operational barriers, coordinate dependencies, improve execution outcomes, and establish scalable operational governance practices across the organization.

The Director helps ensure technology delivery advances not only IT operational effectiveness but also Accerta’s commitment to responsible stewardship, equitable service, and purpose-driven impact.

Primary Accountabilities

Technology Operations & Delivery Leadership

• Provide operational coordination and execution oversight across enterprise technology initiatives, operational programs, and delivery workstreams.
• Ensure initiatives are driven through to completion, including operational readiness, stabilization, and transition into steady-state operations.
• Drive operational accountability and execution discipline across cross-functional technology teams and vendors.
• Coordinate cross-functional operational dependencies and delivery activities across infrastructure, software delivery, product operations, contact center technology, data initiatives, and enterprise platforms.
• Identify operational bottlenecks, delivery risks, resource constraints, and dependency conflicts, and coordinate resolution activities.
• The Director helps ensure technology delivery advances not only IT operational effectiveness but also Accerta’s commitment to responsible stewardship, equitable service, and purpose-driven impact.

Operational Governance & Delivery Management

• Operationalize and maintain delivery governance processes, reporting cadences, execution management practices, and operational coordination frameworks across the technology portfolio
• Leads and enforces prioritization processes across technology functions, ensuring alignment to organizational objectives and capacity constraints
• Facilitate operational review meetings, prioritization discussions, delivery checkpoints, and cross-functional coordination sessions.
• Maintain visibility into initiative health, operational risks, delivery dependencies, and competing priorities.
• Coordinate operational intake and prioritization processes across technology functions.
• Ensure operational processes, governance standards, and delivery practices are consistently applied across teams.
• Maintain enterprise delivery tracking, RAID management, and operational reporting processes.

Cross-Functional Coordination & Execution Oversight

• The role partners closely with business leaders to ensure technology work is sequenced, governed, and executed in a way that supports operational stability, service delivery, and business readiness.
• Owns the escalation framework for technology delivery, including identification thresholds, escalation pathways, executive visibility, and resolution tracking to closure.
• Accountable for ensuring delivery outcomes and execution commitments are achieved by identifying solutions and driving teams to resolution.
• Coordinate cross-functional execution activities involving Infrastructure, Security, Development, Product, Data, Compliance, Operations, and external partners.
• Facilitate alignment between operational technology delivery activities and business requirements.
• Ensure dependencies between teams, systems, vendors, and operational stakeholders are proactively managed.
• Support operational planning and execution management across multiple concurrent initiatives.
• Drive issue resolution and coordination across operational and project delivery functions.
• Manage operational relationships with technology vendors, implementation partners, consultants, and managed service providers.
• Ensure vendors are meeting operational expectations, delivery commitments, service levels, and quality standards.
• Coordinate operational vendor reviews, escalation management, and delivery performance discussions.
• Support procurement activities including Statements of Work (SoWs), renewals, operational evaluations, and implementation coordination.
• Monitor vendor delivery performance, operational risk, and contractual adherence.
• Develop and maintain operational dashboards, delivery reporting, and portfolio visibility across the technology organization.
• Provide leadership teams with visibility into operational performance, initiative health, SLA adherence, delivery risks, and resource constraints.
• Ensure operational documentation, runbooks, governance artifacts, and delivery records are maintained appropriately.
• Support operational readiness activities related to audits, compliance initiatives, disaster recovery exercises, and control validation activities.
• Proactively identify operational risks and coordinate mitigation activities before escalation occurs.

Organizational Leadership & Continuous Improvement

• Lead and develop operational delivery, governance, coordination, or project management resources assigned to the function.
• Foster a culture of accountability, collaboration, operational excellence, and continuous improvement.
• Identify opportunities to improve delivery consistency, operational maturity, governance effectiveness, and organizational scalability.
• Establish operational management standards, reporting rhythms, and execution frameworks across the technology organization.
• Support organizational change initiatives and operational transformation efforts related to technology delivery and execution.

Required Skills & Qualifications

Knowledge and Experience

10+ years of progressive experience in Information Technology, operational leadership, enterprise delivery management, or technology operations roles.

• Minimum 4 years of leadership experience managing cross-functional technology teams, operational functions, or enterprise delivery initiatives.
• Strong experience leading operational delivery management and cross-functional execution activities within enterprise technology environments.
• Demonstrated experience coordinating complex technology initiatives involving multiple teams, stakeholders, vendors, and operational dependencies.
• Experience working within regulated or compliance-driven environments such as healthcare, insurance, financial services, or public sector organizations.
• Strong understanding of enterprise IT operations, software delivery practices, operational governance, and service delivery management.
• Experience managing vendor relationships, operational delivery expectations, and implementation coordination activities.
• Familiarity with Agile delivery methodologies, operational governance practices, and enterprise technology environments.
• Experience supporting operational readiness activities related to SOC 2, ISO 27001, disaster recovery, or operational compliance initiatives is considered an asset.
• Familiarity with Microsoft technologies including Microsoft 365, Azure, Entra ID, and enterprise collaboration platforms is considered an asset.

Education

• Bachelor’s degree in Information Technology, Computer Science, Business Technology Management, or related field, or equivalent practical experience.
• PMP, ITIL, Agile, Lean, or equivalent governance/delivery certifications are considered strong assets.

Non-Technical Skills & Abilities

• Strong operational leadership skills with the ability to coordinate and drive accountability across cross-functional teams.
• Excellent organizational, prioritization, and execution management capabilities.
• Strong communication and stakeholder management skills, including the ability to communicate effectively with technical and business audiences.
• Proven ability to manage multiple concurrent operational priorities within fast-paced environments.
• Strong analytical, problem-solving, and operational decision-making abilities.
• Ability to navigate organizational complexity and facilitate cross-functional collaboration effectively.
• Results-oriented with a strong ownership mindset and focus on execution outcomes.
• Demonstrated ability to improve operational maturity, delivery discipline, and organizational coordination.

Annual Salary: $110,000 – 165,000

Performance Bonus: Up to 10% of annual salary

What We Offer

• Group Benefits : Coverage begins on the employee's first day and includes a Health Care Spending Account and Personal Spending Account (depending on allocation).
• Pension Plan : Eligibility starts on the employee's first day, and a 5% employee contribution is matched by a 5% employer contribution.
• Performance-based incentive programs : Opportunities to increase your earnings.
• Growth Opportunities : in a company that promotes from within.
• Volunteering : Time off to volunteer within our community
• Hybrid Work Environment : working environment with a laptop and two monitors.
• Home Office Stipend : A one-time payment of $750 included in the employee's first paycheck.
• Mental Health Support : Access to Mental Health on Demand for employees and their dependents.
• Member Assistance Program : Includes Employee Assistance Program services.
• Community Volunteering : Up to 8 hours of paid time off annually to volunteer in your community.
• Financial Wellness : Opportunities to contribute to non-matching GRRSPs, TFSAs, and FHSAs, along with financial information sessions.
• Education Reimbursement : Tuition reimbursement for post-graduate courses, upon prior approval.
• Employee Referral Reward : Employees can earn a $1,500 reward for successful referrals of other employees.

Flexible Work Arrangement

Employees are expected to work on-site at least once per month at our Toronto office (4 New Street., Toronto, ON), with additional in-office days as required based on business needs. Hybrid schedules are determined collaboratively between employees, managers, and teams.

How to Apply

We accept applications submitted via our Dayforce Portal - Click this link to apply. Please note that we use AI tools to support and enhance our recruitment process, including scribing tools during interviews. Artificial intelligence (AI), however, is not used to screen candidates.

Rest assured that your application will be reviewed thoroughly by our hiring team.

Inclusion and Equal Opportunity Employment

Accerta is an equal opportunity employer and committed to fostering diversity and inclusion in the workplace. We are committed to fair employment practices, and all qualified applicants will receive consideration for employment. We offer accommodation for applicants with disabilities, as required throughout the recruitment process. Reasonable accommodation is also available on request for candidates taking part in all aspects of the selection process.

We appreciate your interest in working with us; however, only those applicants selected for interviews will be contacted.

Final candidates for this position may be required to undergo a security screening, including criminal records check, judicial matters check, vulnerable sector screening and employment reference check.