Director, Delivery & Implementation

Job Description: 

The role is accountable for implementation delivery from initial planning through to configuration, integration, testing, launch, hyper care, and transition. By establishing clear standards, governance, and operating practices, the Director will ensure complex programs are delivered with appropriate visibility, control, and focus on client business outcomes.

The ideal candidate brings enterprise SaaS implementation leadership, strong client-facing experience, and an understanding of loyalty, eCommerce, grocery, or retail operations. They will serve as a trusted advisor to client executives, a senior escalation point for strategic engagements, and a key partner to Product, Engineering, Sales, Customer Success, Support, and Partnerships leadership.

This leader will build and develop a high-performing delivery team while advancing CORA Loyalty's implementation methodology, automation capabilities, and use of AI-enabled tools. The role will strengthen delivery consistency, improve operational efficiency, accelerate time to value, and create a more scalable implementation model.
 

Key Performance Indicators: Success in this role will be measured against the following:

• Implementation Cycle Time
• Scope Control
• Milestone Performance and On-Time Go-Live %
• Client Adoption
• First-Time Right Implementation
• Customer Health After Hypercare
• Utilization
• Delivery Margin

Key Responsibilities

Strategic Leadership & Delivery Excellence

• Set and uphold the strategic direction for CORA Loyalty's Delivery and Implementation function.
• Build and scale the program delivery capability required to support complex and strategically significant engagements.
• Own the Client Implementation Methodology including delivery playbooks, governance, templates, reusable assets, onboarding standards, launch readiness, and transition to Customer Success.
• Establish measurable delivery standards and KPIs focused on quality, client adoption, operational efficiency, financial performance, and team development.
• Advance the use of AI to improve implementation planning, project delivery, documentation, testing, client enablement, and operational reporting while maintaining appropriate governance and quality standards.
• Develop and maintain reusable implementation assets—including templates, automation, AI-assisted tooling, integration patterns, configuration libraries, and delivery playbooks—to improve implementation quality, consistency, and time-to-value.
• Drive continuous improvement across implementation processes, governance, and operating practices.

Client Leadership & Program Delivery

• Serve as senior sponsor and escalation point for strategic and high-risk client implementations.
• Build trusted relationships with client sponsors, operational leaders, technology stakeholders, and executive teams.
• Ensure client objectives, adoption goals, business outcomes, and success measures are clearly defined and managed throughout each engagement.
• Provide executive oversight of complex deployments and personally lead or support the most strategically significant programs.
• Lead risk identification, mitigation planning, issue resolution, and executive communication across the implementation portfolio.
• Partner with Customer Success and Support to ensure effective transition from implementation to ongoing adoption and value realization.
• Collaborate with Sales and Solution Consulting to align client expectations, implementation strategy, scope, and success criteria from project inception.

Implementation Governance & Quality

• Establish and enforce implementation standards across planning, discovery, solution design, configuration, integration, testing, training, launch, and hypercare.
• Implement governance models that strengthen visibility, accountability, decision-making, risk management, and delivery quality.
• Maintain executive oversight of program health and ensure delivery gaps are addressed with appropriate speed and rigor.
• Capture lessons learned and use them to improve frameworks, operating processes, and team capability.

Solution Delivery & Technical Enablement

• Maintain a strong working knowledge of CORA Loyalty platform capabilities, configuration models, integration patterns, and implementation best practices.
• Provide implementation leadership and coordinate with Product and Engineering on solution architecture, data migration, system configuration, integration strategy, and technical deployment approaches.
• Coordinate delivery of complex integrations in partnership with Product, Engineering, client technical teams, and third-party vendors.
• Build organizational capability across implementation tooling, integration patterns, configuration approaches, deployment practices, and client enablement.

Operational & Commercial Leadership

• Establish operational rhythms including portfolio reviews, delivery forecasting, utilization management, implementation analytics, and continuous improvement initiatives.
• Monitor implementation portfolio health through delivery, financial, operational, and client outcome metrics.
• Oversee implementation forecasting, staffing, utilization, capacity planning, and resource allocation.
• Support Statements of Work, implementation estimates, change requests, and delivery commitments.
• Partner with PMO leadership to strengthen governance, forecasting, resource planning, and project execution.
• Provide executive reporting on implementation performance, client health, delivery risks, capacity, and emerging trends.

Team Leadership & Talent Development

• Lead, mentor, and develop a high-performing team of Implementation Managers, Program Delivery Leads, Senior Consultants, and Implementation Consultants.
• Establish clear roles, performance expectations, decision rights, and accountability across the team.
• Attract, develop, and retain talent with strong delivery, technical, commercial, and client leadership capabilities.
• Build team capability through structured coaching, training, mentorship, and knowledge-sharing.
• Partner with leadership on workforce planning, hiring, onboarding, succession planning, and organizational development.
• Foster a culture of accountability, collaboration, continuous learning, innovation, and strong client focus.

Required Experience and Capabilities

• Bachelor's degree in Business, Information Systems, Computer Science, Supply Chain, Retail Operations, or a related field; equivalent practical experience may be considered.
• 5+ years of progressive experience leading enterprise software, SaaS, or technology implementations.
• 3+ years of people-leadership experience managing implementation, consulting, delivery, or professional services teams.
• Proven experience leading client-facing delivery for complex enterprise customers and managing multiple concurrent implementations.
• Strong knowledge of SaaS implementation methodologies, program governance, and enterprise software deployment practices.
• Demonstrated ability to manage delivery risk, scope, timelines, budgets, resource requirements, and client expectations.
• Strong analytical, problem-solving, decision-making, and executive presentation capabilities.
• Strong understanding of data architecture, system integrations, APIs, EDI, and enterprise application ecosystems.
• Loyalty platform experience strongly preferred; familiarity with grocery, retail, or eCommerce operations is an asset.

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More About Jonas Software:

Jonas Software is a leading provider of enterprise management software solutions, serving a wide range of vertical markets including hospitality, healthcare, construction, education, personal care, fitness, leisure, moving and legal services, to name a few. Within these markets, Jonas is comprised of over 65 distinct brands, each a respected leader in its domain.

Jonas’ vision is to be the branded global leader across these verticals and to be recognized by customers and industry stakeholders as the trusted provider of “Software for Life.” We are committed to technology, product innovation, quality, and exceptional customer service.

Jonas Software supports over 60,000 customers in more than 30 countries. We employ over 6,000 skilled professionals, including industry experts and technology specialists. Across our broader network, we support a global workforce of more than 30,000 employees.

Headquartered in Canada, Jonas Software has a global footprint with offices around the world. We’re a 100% owned subsidiary of Constellation Software Inc., based in Toronto, publicly listed on the TSX (CSU.TO), and a member of the S&P/TSX 60 Index.