Senior Manager, Procurement & Procurement Operations

Caseware is seeking a Senior Manager, Procurement & Procurement Operations to own, lead, and continue building our global procurement function and operating model. Reporting to the General Counsel, this role will own the development, execution, and continuous improvement of Caseware’s procurement strategy, infrastructure, governance, technology, and supplier management practices. This is a hands-on leadership role for an experienced procurement professional who can both build the function and lead complex, strategic procurement initiatives.

The Senior Manager will establish scalable procurement capabilities across the organization, including the contract and vendor repository, renewal management, software license and seat management, procurement analytics and reporting, Delegation of Authority (DOA) frameworks, purchasing workflows, and procurement policies and controls. A key mandate will be to modernize and automate procurement operations, including identifying opportunities to leverage AI, workflow automation, data, and procurement technology to improve visibility, decision-making, efficiency, compliance, and the employee experience.

The successful candidate will bring strong commercial judgment, experience negotiating complex technology and professional services agreements, and demonstrated experience building procurement processes and infrastructure within a growing global technology or SaaS organization.

❗This is a full-time, permanent position.  

❗This is a new role.

📍 Location:  This is a hybrid role, requiring the successful candidate to work 3 days a week in our Toronto office located at 351 King Street East, Toronto, Ontario 

What you will be doing:

Procurement Strategy & Strategic Sourcing 

• Own and evolve Caseware’s procurement strategy, operating model, and roadmap, ensuring procurement capabilities scale with the organization. 
• Lead complex, high-value and strategically important sourcing initiatives from business requirements and market analysis through vendor selection, negotiation, contracting, implementation, and ongoing supplier management. 
• Develop category and sourcing strategies that balance commercial value, service quality, operational requirements, risk, scalability, and business objectives. 
• Lead competitive sourcing processes, including RFIs, RFPs, negotiations, vendor evaluations, and commercial assessments. 
• Partner with senior business leaders to challenge requirements, evaluate alternatives, and develop procurement strategies aligned with organizational priorities. 
• Identify and execute opportunities to consolidate vendors, rationalize technology and services, standardize purchasing practices, and reduce total cost of ownership. 
• Develop strategic supplier management practices for Caseware’s most critical and highest-spend vendors. 

Procurement Infrastructure, Technology & AI 

• Own the design and build-out of Caseware’s centralized contract and vendor repository, creating a reliable source of truth for vendor, contract, commercial, renewal, licensing, and ownership information. 
• Establish the data standards, controls, processes, and accountabilities required to maintain accurate and complete procurement and contract information. 
• Build scalable processes and technology for contract intake, approvals, purchasing, renewals, amendments, terminations, and vendor lifecycle management. 
• Evaluate, implement, and optimize procurement, contract lifecycle management (CLM), spend management, and related technologies. 
• Develop and execute a procurement automation and AI roadmap, identifying opportunities to use AI and automation to streamline contract and vendor data capture, sourcing activities, renewal management, spend classification, analytics, reporting, and procurement workflows. 
• Partner with Legal, IT, Information Security, Finance, and other stakeholders to integrate procurement processes and technology into broader enterprise workflows and systems. 
• Continuously evaluate emerging procurement technologies and AI capabilities and develop business cases for investments that improve efficiency, controls, insight, and scalability. 

Renewal, License & Vendor Lifecycle Management 

• Build and own a centralized renewal management program providing forward-looking visibility into upcoming renewals, commercial commitments, notice periods, pricing changes, and business decisions. 
• Establish proactive renewal planning processes that enable sufficient time for negotiation, competitive sourcing, consolidation, or termination. 
• Develop visibility and governance over SaaS licenses, subscriptions, and seat counts, partnering with IT, Finance, and business owners to identify unused or underutilized licenses and optimize subscription costs. 
• Establish processes to compare contracted licenses and entitlements against actual utilization and business requirements. 
• Develop mechanisms to identify duplicate technology, overlapping functionality, unnecessary subscriptions, and opportunities for vendor consolidation. 
• Establish vendor lifecycle processes spanning onboarding, due diligence, contracting, performance management, renewal, and offboarding. 
• Build vendor scorecards and performance management frameworks for strategic suppliers. 

Procurement Analytics & Spend Intelligence 

• Build the procurement analytics capability, creating visibility into organizational spend, supplier concentration, contract commitments, renewals, savings, license utilization, procurement activity, and supplier performance. 
• Develop procurement dashboards, KPIs, and executive reporting that provide leadership with actionable insight into spend, risk, opportunities, and procurement performance. 
• Establish spend categorization and data standards to enable reliable enterprise-wide procurement analysis. 
• Develop reporting that tracks realized and forecast savings, cost avoidance, supplier consolidation, renewal outcomes, and procurement pipeline. 
• Use procurement and financial data to identify sourcing opportunities, demand management opportunities, and areas of commercial or operational risk. 
• Provide data-driven recommendations to senior leadership to support budgeting, forecasting, vendor strategy, and investment decisions. 

Procurement Governance & Operating Model 

• Own the design, implementation, and ongoing evolution of Caseware’s procurement governance framework and processes. 
• Partner with Finance and Legal to develop and maintain the Delegation of Authority (DOA) framework as it relates to purchasing, contracting, financial commitments, and vendor approvals. 
• Define clear procurement thresholds, approval requirements, decision rights, escalation paths, and accountabilities. 
• Build and maintain procurement policies, standard operating procedures, workflows, playbooks, templates, and controls. 
• Establish clear intake and purchasing processes that provide employees with an efficient and consistent experience when engaging vendors. 
• Ensure procurement activities comply with internal policies, financial controls, legal requirements, privacy standards, security requirements, and applicable regulatory obligations. 
• Partner with Information Security, Privacy, Legal, Finance, IT, and business stakeholders to establish coordinated vendor due diligence and risk-management processes. 
• Monitor adherence to procurement policies and identify opportunities to strengthen controls without unnecessarily slowing the business. 

Commercial & Vendor Management 

• Lead sophisticated commercial negotiations across technology, SaaS, cloud services, professional services, consulting, and corporate services agreements. 
• Develop negotiation strategies for strategically important and high-value suppliers, including pricing, commercial structures, renewal protections, usage commitments, and other key business terms. 
• Serve as a senior commercial advisor to business leaders evaluating significant vendor investments. 
• Establish and manage relationships with strategic suppliers and develop executive-level vendor governance where appropriate. 
• Partner with Legal on contractual negotiations and with Finance on commercial modelling, budgeting, and financial commitments. 
• Identify commercial, operational, concentration, and supplier risks and develop appropriate mitigation strategies. 

Financial & Business Partnership 

• Partner with Finance and business leaders to develop enterprise-wide visibility into third-party spend and contractual commitments. 
• Support annual budgeting, forecasting, and strategic planning through supplier, renewal, licensing, and spend analysis. 
• Develop procurement savings targets and methodologies for measuring realized savings, cost avoidance, and other procurement value. 
• Advise senior leaders on sourcing strategies, commercial structures, supplier decisions, and procurement risk. 
• Build strong relationships across Caseware and position Procurement as a strategic business partner rather than solely a transactional function. 

Transformation & Continuous Improvement 

• Lead procurement transformation initiatives that improve scalability, efficiency, governance, data quality, commercial outcomes, and employee experience. 
• Develop a multi-year roadmap for the maturity of Caseware’s procurement function, including people, processes, technology, data, governance, and automation. 
• Establish procurement performance measures and use them to identify and prioritize improvement opportunities. 
• Stay current on procurement, SaaS commercial models, AI, automation, supplier management, and procurement technology trends. 
• Lead cross-functional initiatives supporting operational excellence and broader organizational priorities. 

What you will bring:

• 8-10 years of progressive experience in procurement, strategic sourcing, procurement operations, vendor management, or related disciplines, preferably within a global SaaS, technology, or professional services organization. 
• Demonstrated experience building or significantly transforming procurement capabilities, processes, governance, or operating models, rather than solely operating within established processes. 
• Significant experience leading complex, high-value commercial negotiations and strategic sourcing initiatives. 
• Deep understanding of technology procurement, SaaS licensing, software subscriptions, cloud services, professional services, and related commercial models. 
• Experience developing contract repositories, renewal management programs, procurement workflows, supplier management processes, or CLM/procurement technology. 
• Strong understanding of Delegation of Authority, procurement governance, financial controls, contract lifecycle management, and vendor risk management. 
• Demonstrated ability to analyze spend, contractual commitments, licensing data, and supplier information and translate data into actionable business recommendations. 
• Experience developing procurement KPIs, dashboards, executive reporting, and spend analytics. 
• Strong commercial judgment with the ability to identify opportunities beyond negotiated price, including demand management, license optimization, vendor consolidation, and total cost of ownership. 
• Demonstrated ability to influence and advise senior leaders and navigate competing priorities across Legal, Finance, IT, Information Security, and business functions. 
• Strong project and change management capabilities with demonstrated success leading cross-functional transformation initiatives. 
• Advanced analytical and financial modelling skills. 

Preferred 

• Experience implementing or optimizing procurement, spend management, vendor management, or contract lifecycle management platforms. 
• Experience applying AI, automation, or advanced analytics to procurement or contract management processes. 
• Experience developing SaaS license and seat optimization programs. 
• Experience establishing procurement operations in a growing or transforming organization. 
• Experience supporting global procurement across multiple jurisdictions and business units. 
• Professional procurement certification such as SCMP, CPSM, CIPS, or equivalent is considered an asset. 

Success in This Role

• A centralized and reliable source of truth for contracts and vendors. 
• Proactive visibility and management of renewals and contractual commitments. 
• Improved visibility and optimization of SaaS licenses, subscriptions, and seat utilization. 
• Meaningful procurement analytics and executive-level spend intelligence. 
• Clear procurement governance, approval authorities, and purchasing processes. 
• Increased automation and effective application of AI across procurement workflows. 
• Stronger strategic supplier management and commercial outcomes. 
• Measurable savings, cost avoidance, and improved control of third-party spend. 
• A simpler, more consistent procurement experience for stakeholders across the organization. 

Salary Range