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Are you ready to take the next step in your legal career? Do you have experience with various aspects of employment and labour law? Do you want to advise and represent clients at the forefront of their industries, as well as exciting and promising new tech start-ups? Join Osler’s highly regarded Employment and Labour Department as an associate in either our Toronto or Ottawa office for the opportunity to partner with a broad range of companies, in a wide variety of industries, as part of a team that delivers clear, practical and results-oriented legal advice on all aspects of workplace law. Requirements Position Requirements 3 to 6 years of employment and labour law experience gained from a leading law firm; Experience advising and representing employers in key areas of employment and labour law, such as: implications of corporate transactions and reorganizations; employment contracts and executive compensation; advising on emerging and high growth company employment issues, including company formation, founder employment agreements and venture-backed financing transactions; structuring employee dismissals/layoffs and responding to wrongful/constructive dismissal claims; advising on new labour and business structures, including “gig economy” issues; human rights, workplace accommodations, and workplace investigations; employment standards and workplace policies; occupational health and safety, workers’ compensation, pay equity and employment equity; collective agreement administration, collective bargaining, union certification/decertification, strikes, lockouts and grievance arbitration; and Superior communication and drafting skills and strong attention to detail. How To Apply Consistently ranked as one of Canada’s leading business law firms by clients and leading independent reviews, Osler prides itself on attracting and developing the brightest talent in the legal field. With a firm culture that nurtures mentoring and the open exchange of ideas, Osler is a dynamic and exciting place to continue building a career or carve out a new path. Osler’s Labour & Employment Department plays an integral role in supporting our national-leading Emerging and High Growth Companies practice and you will have ample exposure to the unique employment and HR risk management issues in this expanding sector. If you’re ready to take your next step and join our growing team, please submit your cover letter, detailed résumé and academic transcripts in confidence directly to our online application portal. Applications submitted outside of our online application portal will not be reviewed. Compensation Compensation offered will be based on a variety of factors including year of call, job-related knowledge, education, skills and experience. Accessibility and Accommodation We thank all applicants for their interest in Osler; however, only chosen applicants will be contacted. Osler is committed to fostering a diverse and inclusive work environment, and we welcome and encourage applications from people with disabilities and individuals with diverse backgrounds, identities, and cultures. Accommodations are available upon request for candidates in all phases of the selection process. Background and Reference Checks Please note that any offer of employment will be conditional upon background and reference checks, including a criminal record check, credit check, social media check, and employment and educational verifications. Please note that we use artificial intelligence throughout our recruitment processes to screen, assess or select applicants.

Location: North York - Toronto, ON (Hybr, CA Wawanesa, MB (Hybrid), CA Ottawa, ON (Hybrid), CA Kitchener, ON (Hybrid), CA Winnipeg, MB (Hybrid), CA Company: Wawanesa Insurance Job ID: 10337 Employment Type: New Role   Work Environment: We offer a hybrid work environment that offers flexibility to our employees in balancing in-office (2 days per week OR 15 hours per week in a Wawanesa office) and remote work. You may work from any of the following locations: Winnipeg, MB, Wawanesa, MB; Toronto (North York), ON; Kitchener, ON; Ottawa, ON. Working Business Language : English Salary: At Wawanesa, salary is only one component of a holistic, comprehensive and competitive offering that we provide to our employees. In addition to salary, full-time and part-time permanent employees are eligible for an annual bonus plan, leave of absence top-up programs and provided with generous vacation time, personal days, premium free benefits and pension plan. The salary offered for this role is determined with consideration to various factors, including but not limited to: your work location, local labour market conditions, external market salary data, internal pay equity and the knowledge, skills, experience and anticipated proficiency in the role. The salary offered is estimated to be within the following range: $120,000 - $160,000. Candidates with salary expectations outside of the range are still encouraged to apply.   About The Wawanesa Mutual Insurance Company Founded in 1896, The Wawanesa Mutual Insurance Company is one of Canada’s largest mutual insurers, 100% owned by its members, with more than $4.1 billion in annual revenue and $12.5 billion in assets. Headquartered in Winnipeg, Wawanesa is the parent company of Wawanesa Life, which provides life insurance solutions throughout Canada, and Western Financial Group, a leading national distributor of personal and business insurance. In March of 2026, Wawanesa entered into an agreement to acquire Everest Insurance Company of Canada to strengthen its commercial insurance capabilities and advance its long-term growth strategy. Wawanesa proudly serves more than 1.8 million members and we are home to more than 3,000 employees across Canada. The company actively gives back to organizations that strengthen communities, donating more than $4 million annually to charitable organizations, including more than $2 million each year in support of people on the front lines of climate change. Learn more at wawanesa.com.   We are currently looking for dedicated, driven, and enthusiastic individuals who thrive in an environment that welcomes change and are looking for an opportunity for diverse experience and advancement on a growing team.   Job Overview This role is responsible for establishing and leading the enterprise framework for external counsel governance, performance management, and legal spend oversight. Leveraging insurance litigation expertise, vendor governance, and data-driven insights, the role drives the quality, consistency, and value of legal services while ensuring alignment between external counsel performance, claims strategies, and business objectives. As the organization's lead for external counsel management, the role provides strategic oversight of panel counsel relationships, performance standards, legal spend management, and vendor governance practices, supporting effective stewardship of external legal resources and improved claims outcomes across the enterprise. Job Responsibilities Lead the design and implementation of a structured external counsel performance management program, including governance frameworks, processes, tools, and reporting. Develop and maintain a claims-wide panel counsel strategy, including firm selection, specialization, and geographic alignment. Support vendor selection and onboarding processes, including participation in RFPs and evaluation of external law firms. Establish and maintain governance frameworks, including engagement guidelines, service standards, and escalation processes. Support the development of formal vendor agreements and contracting approaches, including rate negotiation strategies. Ensure alignment between vendor services and claims strategies and business priorities. Design and implement a structured performance management framework, including defined KPIs and service expectations. Lead ongoing reviews of law firm performance using quantitative and qualitative data. Conduct file-level reviews and audits to assess quality and alignment with internal claims strategies. Analyze litigation performance and identify opportunities to improve outcomes, consistency, and service quality. Partner with Claims and Finance to establish and support legal spend management practices, including cost tracking, reporting, and budgeting insights. Establish and oversee billing guidelines and invoice review processes, ensuring compliance and cost discipline. Identify and support cost optimization opportunities, including rate benchmarking and alternative fee arrangements. Develop and maintain performance dashboards and reporting to support informed decision-making regarding firm selection, file assignment, and continued engagement. Translate litigation, spend, and performance data into actionable insights that inform vendor strategy and program improvements. Serve as a key point of contact for external law firms, supporting effective and collaborative vendor relationships.   Qualifications Law degree and membership in good standing with a Canadian law society (preferred), or a combination of related education and experience. 7+ years of litigation experience, preferably within insurance defence, bodily injury, casualty, or complex claims litigation. Demonstrated expertise in external counsel management, vendor governance, legal operations, or related legal service delivery models. Strong relationship management, communication, and stakeholder influence skills, with the ability to build credibility across all levels of the organization. Experience establishing performance measures, evaluating service delivery, and leveraging data and insights to drive business decisions and continuous improvement. Experience reviewing, supervising, auditing, or managing external law firms or professional service providers. Strong analytical and financial acumen, including experience interpreting legal spend, performance metrics, and outcome data. Ability to collaborate effectively across Claims, Finance, Procurement, Vendor Management, and other cross-functional teams. Demonstrated ability to lead through influence, manage competing priorities, and drive strategic initiatives in a complex environment.   Diversity Equity, Inclusion & Belonging At Wawanesa, we are committed to Diversity, Equity, Inclusion and Belonging (DEIB) and believe that our strength lies in the diversity of our people – this is supported by having a representative workforce. We welcome applications from all qualified candidates, including racialized persons, women, Indigenous Peoples, persons with disabilities, members of the 2SLGBTQIA+ community, gender-diverse and neurodiverse individuals, and anyone who can contribute to the further diversification of thought and ideas. We aim to ensure our recruitment process is accessible to all candidates. If you require accommodations during any stage of the recruitment process, please reach out in confidence to jobs@wawanesa.com. All Wawanesa job applicants are subject to Wawanesa's Privacy Policy. Please note that the recruitment process for this position may involve the use of AI tools to screen, assess, or select applicants. All final decisions are taken or reviewed by human recruiters and human hiring leaders in compliance with all applicable legislation.  

Are you ready to elevate your career with one of Ontario’s most respected law firms? Our client, a prominent firm located in Toronto, is actively seeking a Litigation Associate Lawyer to join their esteemed team. Known for their inclusive and progressive culture, this firm consistently ranks as a top workplace in the legal industry. Why This Role Stands Out This is an exceptional opportunity for a lawyer seeking meaningful, impactful work in a supportive environment. In addition to managing high-quality insurance litigation files, including Motor Vehicle Accident (MVA) claims, this role offers the unique chance to work on class action cases retained on behalf of a government client. The position features a flexible billing structure, hybrid work options, and access to valuable trial experience. You’ll manage a diverse caseload and collaborate with a team that values innovation and excellence in legal service delivery. Key Qualifications Experience : 2-8 years of post-qualification experience specializing in insurance litigation defense or class action work with a respected law firm. Expertise : Strong understanding of insurance litigation, conflict resolution strategies, and class action processes. Innovation : Interest in advancing legal service delivery and supporting the firm’s growth. Leadership : Initiative and readiness to take on leadership roles in projects. Flexibility : Hybrid work options available, promoting a healthy work-life balance. What Makes This Opportunity Unique Opportunities like this are rare in the legal sector, particularly with such a reputable firm. The chance to work on government-retained class action cases adds a level of significance and impact not often found in similar roles. Whether you want to refine your litigation expertise or explore leadership opportunities, this position offers a clear path to advance your career while enjoying the benefits of a hybrid work environment. Interested? Confidentially send your CV to: ben@cartelinc.com Contact Information Ben Higham, JD, LL.M. Director of Legal Recruitment Cartel Inc. | First Canadian Place, Suite 2550 About Cartel Inc. At Cartel Inc., we prioritize transparency and genuine support for our candidates. We’re known for helping candidates find the right fit and making a meaningful impact on their careers. Contact us today to discover how we can assist in your legal journey!

Position: Law Clerk Location: Durham Region, ON – Primarily Onsite Salary: $60,000–$70,000 per year, depending on experience Job Type: Full-time, Permanent Posting Type : Open Vacancy About the Opportunity Quantum is currently recruiting for an experienced Law Clerk to join a well-established and growing law firm in the Durham Region. The successful candidate will join a busy and expanding Wills & Estates practice and work closely with an experienced Partner, junior lawyers, and senior clerks. This is a newly added position created to support the continued growth of the practice and increasing workload The firm is looking to add another experienced professional to its established team. This is an excellent opportunity for a specialized Law Clerk who can manage probate and estate administration files with minimal training and enjoys working directly with clients. Responsibilities: - Manage and maintain multiple Wills & Estates and probate files from opening through completion - Act as a primary point of contact for clients and maintain regular communication throughout the estate administration process - Open files and organize client-provided documentation and information - Assist with the preparation and execution of probate and estate administration documents - Prepare correspondence, documentation, and other materials for lawyer review and execution - Assist with the preparation of estate accounts and Passing of Accounts applications - Attend client meetings and assist lawyers with client matters - Provide support on estate litigation files as required - Maintain accurate and organized physical and electronic files - Docket time and maintain accurate file records - Manage a high volume of files while ensuring accuracy, organization, and attention to detail Qualifications: - College diploma in Legal Administration, Law Clerk, or a related legal program - 3+ years of experience working as an Estates Clerk or Probate Clerk - Hands-on experience with probate and estate administration is required - Previous experience supporting a Wills & Estates practice is required - Experience preparing estate accounts and/or Passing of Accounts applications is strongly preferred - Strong client service and communication skills - Excellent organizational skills with the ability to manage multiple files and competing priorities - Exceptional attention to detail and accuracy - Ability to work independently with minimal supervision - Strong proficiency with Microsoft Word and Outlook - Comfortable working in a paper-intensive, documentation-heavy environment What the Firm Offers: - Competitive salary of $60,000–$70,000 per year, depending on experience - RRSP matching program of 2–3% - Comprehensive benefits after 3 months - 5 sick days - Stable, long-term opportunity with a well-established and growing law firm - Supportive and approachable leadership - Opportunity to work alongside a highly established and experienced team - Primarily onsite work environment, with some flexibility for the right candidate, including the potential for up to 1 day of remote work per week Please note: Due to the specialized nature of this position, candidates must have previous hands-on probate and estate administration experience within a law firm. Transferable experience from other areas of law will not be considered a substitute for direct Estates experience. To apply, please send your resume to Vanessa Tran at vanessa.tran@quantum.ca . REFER A PERM HIRE AND EARN A CASH BONUS! For details, click here . All applications are reviewed by our recruitment team, and hiring decisions are made by people. We may also use AI-enabled tools to support parts of the application review process.