Senior Director, Controllership & Operations Transformation

Leadout Capital; Toronto; Hybrid; CAD 190,000 - 270,000; Full time

Job summary

Leadout Capital is seeking a Senior Director to own our finance system architecture and AI-driven automation strategy within the Controllership group. You will bridge accounting requirements with technical execution, guiding Workday Cloud ERP evolution and subledger automation at scale.

You will lead global R2R initiatives, drive system improvements, and partner with IT to minimize disruptions while shaping the future of digital finance. Strong leadership and communications are essential.

Qualifications

• 12+ years of progressive experience in accounting, financial systems, or finance transformation, with strong R2R background.
• Technical acumen in enterprise ERP systems and accounting data architecture.
• Experience with Workday Cloud ERP and AI-driven finance automation.

Responsibilities

• Direct and oversee complex R2R initiatives across revenue and non-revenue functions.
• Own the accounting ERP system, define system architecture, data integrity, and scalability.
• Partner with IT to manage ERP production issues and drive automation roadmaps.
• Lead initiatives to integrate AI-driven solutions to modernize accounting workflows.
• Influence senior stakeholders across Accounting, Finance, Engineering, and Operations.
• Align controllership initiatives with Global Process Owners and technology teams.
• Support executive decision-making with clear, data-driven storytelling.

Skills

R2R leadership

ERP systems

AI & automation

Executive communication

Stakeholder management

Education

BA/BS in Accounting/Finance/IS

Tools

Workday

ERP reporting

Job description

The Experience

As the Senior Director within the Salesforce Controllership group, you will be the strategic owner of our Finance system architecture, data flow, and enhancement roadmap. It is a critical leadership position requiring you to bridge the gap between complex accounting requirements and technical execution. You will oversee initiatives, drive the evolution of our Workday Cloud ERP ecosystem, and ensure AI is at the forefront of our financial automation strategy. With Agentforce woven into every layer of our platform, our team builds intelligent systems that automate repetitive subledger flows, elevate strategic accounting tasks, and power better financial decision-making at scale.

What You'll Actually Be Doing

• Strategic Record to Report (R2R) Leadership:Direct and oversee comprehensive R2R initiatives involving complex data streams across both revenue and non-revenue business functions.

  • Systems:Act as the business sponsor for the finance technology stack, deploying ERP enhancements, automation, and reporting infrastructure to reduce manual touchpoints.

  • Processes: Redesign end-to-end R2R cycles (close, consolidation, statutory reporting) to drive operational efficiency and shorten time-to-insight.

  • People:Serve as the primary change agent, guiding cross-functional teams through transition periods, breaking down silos between technical and accounting teams, and transforming workforce capabilities to support a modern digital finance organization.

• ERP System Ownership:Serve as the primary business owner for the accounting ERP system. Define the strategic vision for system architecture, data integrity, and operational scale.

• IT Partnership & Issue Resolution:Partner directly with IT to manage, prioritize, and resolve critical ERP production issues, ensuring minimal disruption to accounting operations.

• AI & Automation Roadmap:Champion and lead initiatives to continuously automate and enhance the ERP system, actively identifying and integrating AI-driven solutions to modernize accounting workflows.

• Cross-Functional Influence:Act as a central strategic partner. Drive alignment, influence decision-making, and secure buy-in from senior stakeholders across Accounting, Finance, Engineering, and Operations.

• AI & Automation Enablement: Identify and deploy with finance transformations high-impact AI/agent use cases to scale automated, data-driven operations across Controllership.

• Lead Global Controllership Alignment:Serve as a central integration point to ensure that as we scale, our initiatives are aligned across our Global Process Owners (GPOs), cross-functional partners, and technology teams.

• Drive Holistic Stakeholders Engagement: Facilitate alignment across diverse groups (Tax, Treasury, Legal, M&A) to ensure that Controllership initiatives consider the full financial picture and regulatory landscape.

• Strategic Decision Support:Lead key strategic projects within the Global Accounting organization, specifically identifying decision bottlenecks and presenting clear facts to the appropriate stakeholders to facilitate resolution.

• Technology & Business Liaison:Serve as a key bridge between the Accounting function and the Digital Enterprise Transformation (DET) team. You will help articulate clear business facts, define requirements, and support critical design decisions to ensure our systems support our accounting needs.

• Executive Communication & Storytelling:Transform complex project updates and accounting data into clear, compelling narratives. You will act as the content creator for executive presentation

You're Our Person If...

• 12+ years of progressive experience in accounting, financial systems, or finance transformation, with a strong background in R2R processes.

• Technical Acumen - Deep expertise in enterprise-level ERP systems and accounting data architecture.

• Strategic Execution - Proven ability to act as a strategic driver rather than a task manager, with a track record of translating complex financial needs into scalable system solutions.

• Stakeholder Influence - Exceptional executive communication skills with the ability to influence cross-functional technical and non-technical stakeholders without direct reporting authority.

• Forward-Thinking - Demonstrated passion for exploring and implementing emerging technologies, specifically AI and machine learning, within the finance and accounting domain.

• Demonstrated track record of successfully designing and implementing process improvements that reduced manual effort and improved accuracy

• BA/BS degree is required in Accounting, Finance, Business Administration, Information Systems, or related subject area or equivalent relevant experience required. Experience will be evaluated based on the Core Competencies for the role (e.g. extracurricular leadership roles, military experience, volunteer roles, work experience, etc.

• Expertise in US GAAP, IFRS and local statutory requirements; Robust experience with SOX audit framework

• You bring exceptional problem-solving skills using structured frameworks to dissect complex operational failures and present technical roadmaps to finance leadership.

Even Better If...

• You have a combination of prior experience in management or technology consulting focused on transformation and have hands-on Finance Operations experience.

• System experience - Workday experience preferred

• You have first-hand experience driving AI transformation initiatives, specifically implementing agentic automation and intelligent workflows within Finance.

This role is hybrid and goes into the office 3 days per week.