--- title: 'Legal Operations Manager at Caseware' canonical: 'https://feeny.ai/job/legal-operations-manager-caseware-toronto-6xdkwfan1bey' type: 'job' last_seen: '2026-10-17' --- # Legal Operations Manager at Caseware - **Company:** Caseware - **Location:** Toronto, Canada - **Employment:** full-time - **Work type:** hybrid - **Posted:** 2026-10-14 - **Last confirmed live:** 2026-10-17 - **Apply:** https://jobs.lever.co/caseware/63bb7bd5-420e-42cb-9d8e-23adcffcf7de ## Job description Caseware is one of Canada's original Fintech companies, having led the global audit and accounting software industry for over 30 years, with more than 500,000 users across 130 countries and available in 16 different languages. While you might not have heard of us (yet) over 36,000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles! Caseware is looking for a Legal Operations Manager to help scale our in-house legal function. This is a unique opportunity for an operationally minded individual to join a 4-lawyer in-house team supporting a global company. Reporting directly to the General Counsel, you will be the operational backbone of the department, bringing structure, efficiency, and scalable processes to how the team works at a fast-paced SaaS company. You will own the systems, processes, vendor relationships, and metrics that allow the lawyers to focus on legal judgment. You will have a wide range of responsibilities, with a focus on legal technology and systems, process design, and outside counsel and vendor management. As the first dedicated Legal Operations hire at Caseware, you will have the opportunity to shape and own legal operations processes from an early stage, with direct exposure and access to the General Counsel and senior leadership. This is a hands-on, generalist role suited to someone with strong technology and AI skills who is motivated to help others succeed. ❗This is an existing vacancy. ❗This is a full-time, permanent position. 📍This is a hybrid role, requiring the successful candidate to work three days a week at our Toronto office  (351 King St E, Toronto, ON). ## What you will be doing - Administer and continuously improve the contract lifecycle management (CLM) platform, e-signature tools and matter management systems, driving adoption across the business. - Design, document, and maintain repeatable workflows for contract intake, review routing, approvals, and escalations so the legal team can scale with the business. - Manage relationships and budgets with outside counsel and legal vendors, including negotiating rates, tracking spend against budget, and reviewing invoices. - Maintain the legal department budget, prepare spend and matter-volume reports, and build dashboards and metrics that demonstrate the legal team’s impact to the business. - Support the end-to-end contract process, including templates, playbooks, clause libraries, and self-serve tools for the Sales and Procurement teams. - Maintain corporate records for all legal entities, handle all statutory and annual filings, ensure corporate compliance in all jurisdictions, and respond to UBO and KYC requests independently. - Design and maintain the department’s internal knowledge base, training materials, and onboarding resources for new hires and business stakeholders. - Identify gaps and design process improvements, and where appropriate, take the lead in legal technology implementations and use of AI to achieve objectives. - Keep legal documents and records accurate, organized, and easy to access; provide support to lawyers and other stakeholders. ## What you will bring - Bachelor’s degree in business, legal studies, or a related field; a paralegal diploma or equivalent experience is an asset. A law degree is not required for this role. - 3–7 years of experience in legal operations, paralegal work, or a similar operational role; an in-house legal team or law firm operations background is strongly preferred. - Hands-on experience implementing and using CLM and e-signature tools and other legal technology, including AI. - Strong project management skills, with the ability to independently prioritize across multiple concurrent initiatives in a lean team. - Experience managing budgets, vendor relationships, and outside counsel spend and invoicing. - Excellent written and verbal communication skills, with the ability to work directly with lawyers and business stakeholders at all levels. - A high degree of discretion and judgment when handling confidential and sensitive information. - Experience building a legal operations function from the ground up in a small legal department is an asset. - Exposure to data analytics or BI tools (e.g., Power BI, Tableau) for legal reporting is an asset. - Strong AI aptitude, with experience applying AI tools to drive operational efficiency and process improvement. Salary Range: The annual base salary for this position is between $100,000 CAD and $120,000 CAD per year. This role is also eligible for discretionary bonus and/or commission, as well as other benefits. Actual pay within the listed range will be determined based on factors such as transferable skills, relevant experience, market conditions, and primary work location. The posted range is subject to change and may be updated periodically. What's in it for you: ▪️Innovation is at our core. We work with cutting-edge technology in accounting and financial reporting, constantly pushing the boundaries to create impactful software solutions. ▪️We are committed to a collaborative culture, where your ideas are valued, and knowledge sharing is encouraged within a supportive, inclusive team. ▪️Work-life balance is important to us. We offer flexible work options, remote opportunities, and generous time-off policies to ensure a healthy work-life balance. ▪️We offer competitive compensation, including a competitive salary and comprehensive benefits such as health insurance and retirement plans. ▪️We are driven by impactful work. Your contributions directly affect how our clients manage financial processes and drive their success. ▪️Recognition and rewards matter to us. We celebrate hard work through recognition programs, performance bonuses, and opportunities for career growth. ▪️We embrace global opportunities. Work on international projects and collaborate with a diverse, global team. About Caseware: Caseware's cutting-edge software products are meticulously designed for accounting firms, corporations, and governments. Our teams are continually collaborating, innovating, and building upon our existing suite of products. With a customer-focused mindset, we are building technology that is shaping what the future of audits, financial reporting, and financial data analytics will look like. With a recent strategic investment from Hg Capital in 2020, Caseware is now in its next major growth phase as we double down on the people and products that have made Caseware so successful to date. One of Caseware's core values is Many Voices, One Team and with that in mind, we're dedicated to building teams as diverse as our customers in an equitable and inclusive way. We welcome and encourage candidates of all backgrounds to apply. Should you require accommodations or have any questions at any point during the application or interview process, please e-mail our People Operations team at talent@caseware.com. AI Usage: The recruitment process may use AI assisted tools but not for candidate screening or assessment. All final hiring decisions are made by humans to ensure fairness, transparency, and oversight. Background Check: Any candidates successful in obtaining an offer for a position will need to successfully complete a background check through Certn.co which typically includes an Identity Verification and Criminal Record Check. Executives and Senior Managers will undergo a Soft Credit Check as well. Candidates residing in the Netherlands and Germany are excluded from undergoing background checks via Certn.co Security and Fraud: Caseware takes the security of candidates seriously. All legitimate communication from us will come from email addresses ending in @caseware.com and our open positions are always listed on reputable job boards and on our website https://jobs.lever.co/caseware. We will NEVER ask for payment or financial information from you. If you receive an unsolicited job offer, proceed with extreme caution. ## About Caseware ## Company Overview - **One-liner**: Caseware provides a cloud-enabled, AI-powered platform purpose-built for audit and financial reporting, helping accounting firms and organizations deliver high-quality, defensible engagements. - **Entity Type**: Private (backed by a leading private equity technology investor; funding stage not publicly disclosed) - **Headquarters**: Toronto, Ontario, Canada - **Founded**: 1988 - **Founders**: Not publicly disclosed ## Core Business - **Primary industry/industries**: Audit & Accounting Software, Financial Reporting, Data Analytics - **Target customers**: Accounting firms (from small to large), corporations, and government regulators (B2B) - **Mission or purpose statement**: To deliver trusted outcomes through workflow-embedded intelligence, helping customers answer the key question: “Why?” ## Products & Services - **[Caseware Platform]**: An end-to-end cloud-enabled platform that serves as the system of record for modern engagements. It integrates AI agents and intelligence directly into workflows. - **[Caseware Verity]**: An AI-powered tool operating within engagements and across the full assurance workflow. It understands context, applies a firm’s methodology, and helps navigate complexity. - **[Caseware Agents]**: Purpose-built AI agents that perform real work across every phase of an engagement—from preparation to reporting—automating tasks, generating outputs, and accelerating delivery. - **[Data Analytics Solutions]**: Tools for digging deeper into financial data to transform insights into impact. ## Market Standing - **Valuation/Market Cap**: Not publicly disclosed - **Key Metric**: Annual Revenue of $55M (estimated); serves 23k+ organizations and 475k+ users across 130 countries. - **Notable Investors/Partners**: Backed by “one of the world’s leading private equity technology investors” (specific name not disclosed in source materials). - **Growth Signals**: Headcount of 460 employees (+6.8% YoY, +40 people); expanding quickly in multiple markets globally; LinkedIn followers growing at +21.8% yearly. ## Competitive Advantages - **Deep Domain Expertise**: 35+ years focused exclusively on assurance and financial reporting, giving them unmatched domain depth. - **Governed AI**: Every AI-assisted decision is reviewable, explainable, and defensible, with context preserved and authority explicit—critical for regulated industries. - **Measurable ROI**: Reports 107-167 hours of AI time savings per engagement, and 35-50% reduction in evidence collection time. - **Embedded Intelligence**: AI operates directly inside existing, trusted workflows rather than as a separate tool, reducing friction and adoption barriers. ## Strategic Focus - **AI-First Platform**: Continuing to embed frontier intelligence and purpose-built AI agents into every phase of the audit and accounting lifecycle. - **Global Expansion**: Scaling presence across multiple markets worldwide, backed by private equity resources. - **Talent Growth**: Actively hiring across technology, product, customer experience, sales, marketing, finance, and people operations to support growth. ## Why Work Here - **Work Flexibility**: Offers flexibility to work remotely, from one of their global offices, or a combination of both. - **Global Collaboration**: A truly global company with team members and partners across 130+ countries, offering a diverse and connected work environment. - **Learning & Development**: Invested in employee development at every career stage through training programs, conferences, educational opportunities, and meaningful projects. - **Comprehensive Benefits**: Provides healthcare and wellbeing benefits tailored to local standards, plus retirement savings and long-term financial planning benefits. - **Engineering Culture**: Technology teams design, build, secure, and scale the platforms customers depend on daily, working with cloud, ML, and AI technologies. - **Growth Trajectory**: Backed by a leading private equity investor and expanding quickly, offering opportunities for career advancement in a growing company. ## Sources 1. [caseware.com](https://www.caseware.com/) 2. [caseware.com/about](https://www.caseware.com/about) 3. [caseware.com/careers](https://www.caseware.com/careers) 4. 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