Sr. Director, Customer Experience and Strategic Execution

CanadaRemoteFull-timesenior

Customer SuccessCustomer Experience

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Requirements Summary

Typically 7–12+ years of progressive leadership experience in a relevant professional discipline, with a proven record of building high-performing teams and delivering measurable business results.

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Customer SuccessCustomer Experience

The Sr. Director, Customer Experience and Strategic Execution will lead a multidisciplinary organization focused on elevating customer experience, resolving complex escalations, and delivering strategic business initiatives. This executive role brings together customer journey management, enterprise program governance, continuous improvement, and proactive customer recovery. Leading a team of approximately 20 professionals, the successful candidate will collaborate across Product, Technology, Support, Sales, Customer Success, Finance, and other functions to improve retention, onboarding outcomes, and service quality. The role combines strategic planning and financial accountability with hands-on operational leadership, data-driven decision-making, and organizational change. It also offers the opportunity to scale AI-enabled productivity initiatives, strengthen cross-functional execution, and establish sustainable processes that deliver measurable business impact.

Lead, develop, and coach a multidisciplinary organization of approximately 20 team members, building a culture of accountability, collaboration, and continuous improvement.
Design and manage an enterprise-wide escalation framework covering executive, strategic-account, and Tier-3 issues, including severity classifications, service-level expectations, customer communications, and post-incident reviews.
Take senior-level ownership of critical customer escalations, develop recovery plans, and communicate directly with customer executives to restore trust and drive resolution.
Establish recurring root-cause analysis processes that identify underlying issues, assign accountable owners, and implement preventive measures in partnership with Product and Engineering.
Own the end-to-end customer journey and Voice of Customer program, identifying friction across sales, onboarding, go-live, and ongoing product use.
Lead HyperCare initiatives during the first 120 days following go-live for cloud-based products, accelerating adoption and time to customer value while addressing early churn risks.
Define and operationalize leading indicators for customer experience, uptime, delivery quality, and customer effort, collaborating with Data & Analytics to identify at-risk customers and trigger proactive interventions.
Direct the enterprise Project Management Office (PMO), overseeing portfolio governance, cross-functional dependencies, and strategic initiatives such as data conversions, migrations, automated provisioning, and churn reduction.
Establish a consistent operating cadence through daily stand-ups, weekly performance reviews, monthly business reviews, and executive scorecards that communicate results, trends, root causes, and corrective actions.
Identify and scale AI-enabled internal processes that improve team productivity and reduce support demand in collaboration with Support, IT, and Data & Analytics.
Develop the function’s annual strategy, objectives, budget, and workforce plan, ensuring alignment with enterprise priorities and reporting progress to executive leadership and, when needed, the Board of Directors.
Recruit, mentor, and develop managers and senior professionals, strengthen succession planning, and promote data-informed decisions and sustained operational excellence.

Requirements

~2 min read

Typically 7–12+ years of progressive leadership experience in a relevant professional discipline, with a proven record of building high-performing teams and delivering measurable business results.
Bachelor’s degree or equivalent international qualification in a related field; a master’s degree or equivalent is an advantage.
Experience in project management, with relevant certifications such as CAPM, PMP, Project+, or equivalent preferred.
Demonstrated AI literacy, including familiarity with large language models (LLMs), data structures, and AI-enabled business applications.
Extensive experience managing executive-level customer escalations, leading customer recovery efforts, and driving sustainable root-cause resolution.
Strong executive presence, commercial awareness, emotional intelligence, and the judgment to challenge decisions constructively while maintaining trusted relationships.
Experience in strategic planning, budgeting, forecasting, workforce planning, and resource management.
Proven success designing and scaling customer-facing programs and experiences in B2B and small-to-medium-sized business (SMB) environments.
Exceptional written, verbal, presentation, storytelling, and documentation skills, including the ability to translate complex data into clear and actionable insights.
Strong customer orientation, conflict-resolution capabilities, and confidence navigating sensitive conversations and high-pressure situations.
Demonstrated ability to build cross-functional partnerships, influence stakeholders, align diverse teams, and lead organizational change.
Advanced analytical, problem-solving, and decision-making skills, with the ability to balance strategic priorities and operational details in a fast-paced environment.
Strong understanding of industry best practices, business processes, operational systems, and procedures.
Advanced experience with cloud-based SaaS platforms, client/server technologies, and enterprise software environments.
Knowledge of regulatory compliance requirements and advanced technical understanding of enterprise infrastructure and applications, including networking, WANs, Citrix, virtual servers, SQL Server, hosted solutions, and third-party integrations.
Advanced proficiency with Microsoft Office, CRM platforms, SaaS applications, and related business technologies.
Demonstrated ability to communicate and present effectively at the executive level.
Experience with practice management software and related services is an advantage.