Head of Operations in Toronto

Auger Hollingsworth is an accident and injury law firm with offices in Ottawa and Toronto. We are determined to become Ontario’s largest personal injury law firm, and we’re entering a pivotal stage of its growth—one where this role will play a key part. This full-time Head of Operations role will be a blend of remote work from anywhere in Ontario with some travel to our Toronto and Ottawa Canada offices. There will also be travel to professional leadership conferences because we want this professional to learn and grow.

The Head of Operations is the firm’s execution leader. This is the person who ensures initiatives move forward, teams stay aligned, issues get solved quickly, and the firm operates with rhythm and discipline. They oversee the business to create the conditions for scalable growth. This is a role for someone who thrives in complexity, brings clarity to ambiguity, and is energized by building operational systems that expand the reach of the team to make a real difference in clients’ lives. The Head of Operations must be comfortable designing processes, implementing technology, optimizing workflows, and building cross-functional capability. They are both a builder and a leader—a hands-on operational architect who can guide the firm from high-potential to high-performing.

The Head of Operations reports directly to the Managing Partner and works in close partnership with the founding team. They will collaborate with lawyers, paralegals, finance and administrative staff, and external vendors. This role becomes the connective tissue of the organization, ensuring the right conversations are happening, the right priorities are set, and the right people own the right processes.

What You’ll Do

• First Month
• Dive deep to understand the firm’s current workflows, culture, constraints, and opportunities
• Clarify operational priorities with leadership
• Design initial communication and accountability rhythms
• Begin ownership of planning, project tracking, and operational problem-solving
• Take the lead on the File Management System (FMS) selection and implementation
• First 90 Days
• Formalize reporting, meeting cadence, and role accountability
• Lead the requirements gathering, vendor demos, and selection process for the FMS
• Map key operational processes (Intake, Records, Case Management, Client Care) at a high level
• Reduce founder involvement in day-to-day operations
• First 6–12 Months
• Oversee the full implementation and rollout of the FMS
• Build workflows, dashboards, task structures, and quality checks
• Create a structure for Shared Services and define transition plan
• Pilot and refine Shared Services department
• Improve lawyer + paralegal capacity by rolling out Shared Services team
• Build operational transparency (metrics, dashboards, performance indicators)
• First Year and Beyond
• Improve file velocity through consistent processes and accountability
• Make the business scalable, predictable, and less dependent on founders
• Build and lead the firm’s long-term operational roadmap and continuous improvement engine

What Will Set You Up for Success (S.E.T.)

• Skills
• Operational excellence: process design, workflow optimization, system adoption
• Strong project leadership: turning strategy into clear execution steps
• Technology implementation experience, ideally in legal, medical, or service/regulated industries
• Ability to establish and enforce accountability structures
• Strong communication skills at all levels of the organization
• Ability to make decisions in ambiguity and create clarity where none exists
• Experiences
• 5–8+ years in operations, legal ops, professional services, or systems implementation
• Experience leading multi-phase transformation (systems + people + process)
• Proven ability to reduce operational bottlenecks and scale service delivery
• Prior leadership of shared services teams (or comparable centralized functions)
• Experience working with business operating systems such as Scaling Up/EOS is an asset
• Experience implementing case management or workflow platforms is an asset
• Builder mindset—excited designing new systems from scratch
• Calm, structured, and grounded—especially when others feel overwhelmed
• Relentlessly solution-oriented
• Low-ego, high-accountability operator who owns outcomes
• Comfortable with both rolling up sleeves and driving strategic change
• Strong facilitator who builds alignment in complex environments

What Won’t Set You Up for Success

• Preferring to operate as a consultant rather than a hands-on leader
• Avoiding conflict or hesitating to hold people accountable
• Discomfort with defining and enforcing standard processes
• Expecting stable requirements—this is a building phase with evolving needs
• Viewing yourself as an administrator instead of a strategic operator

Why This Role Matters

The firm can only scale if its operational foundation becomes stronger, more consistent, and less dependent on founders. The Head of Operations enables that shift by:

• Building systems that support predictable growth
• Reducing administrative burden on legal team
• Increasing file velocity and capacity
• Establishing accountability and structure
• Leading the firm through modernization and process transformation

This is the role that turns Auger Hollingsworth from a high-performing practice into a high-performing business. Enjoy the balance of remote, hybrid or in-office work environment. Unlimited Vacation policy. Full health, dental benefits and disability insurance. Competitive compensation in the $200k-$250k range comprised of base salary and incentive bonuses for meeting business growth targets.

Apply in Confidence by January 23, 2026. Please email a brief outline explaining how you meet the above requirements including your current resume and LinkedIn link to Richard Auger at richard@ahinjurylaw.com. All applications will be held in strict confidence. We thank all candidates for their application but will be contacting only those who we select to invite for an interview.