Head of Legal Ops & Transformation

Sterlington, PLLC • Toronto, ON

12h • Remote

About The Position

Sterlington is looking for a Legal Operations & EA Transformation Manager to build the next generation of executive support for a globally distributed law firm; and lead the team through that evolution with structure, judgment, and genuine momentum. Our Executive Administration team supports the attorneys of across our elite and demanding legal practice. As the firm scales toward its next phase of growth, we are building the operational infrastructure to match our ambition; and this function is at the center of our success. This role sits at the intersection of people leadership, AI implementation, and strategic operations. You will introduce customer success methodology into a function ready to evolve, deploy AI across workflows primed for automation, and redefine what excellent partner support looks like at a firm that competes at the highest level. You will work in alignment with the broader operational infrastructure of the firm, never duplicating it.

Requirements

• 10+ years of progressive operations experience, with direct people leadership of distributed teams
• Demonstrated experience redesigning or transforming an operational function;not just running one
• Genuine AI fluency: you use Claude, Copilot, or equivalent tools daily, and you have built or led AI workflow implementation in a real work environment
• Customer success or partner-facing service delivery experience; you understand what it means to treat internal stakeholders as clients
• Ability to operate with ambiguity and create structure
• Strong written and verbal communication in English

Nice To Haves

• Legal, SaaS, or professional services background strongly preferred; familiarity with how lawyers think and work is a meaningful advantage

Responsibilities

• Lead a world-class team of Executive and Legal Assistants at a defining moment of growth for the firm. This is a pivotal chapter; integrating AI-enabled delivery to empower our team as true Business Partners who don't just facilitate but actively enable partners to deliver elite client work at scale. By building tailored development paths and fostering a culture of excellence, you'll ensure our team remains the strategic engine of the firm's success in a future-ready landscape
• Introduce CS methodology into the EA function; treating partners as internal clients with defined success metrics, feedback loops, and service standards. Design and own the partner satisfaction framework. Build the cadence and culture of accountability that makes great support visible and continuously improving.
• Audit current workflows and identify opportunities to increase efficiency through automation. Introduce AI tools for scheduling, meeting prep, communications management, and document handling; integrated in a measured, high-judgment manner that enhances performance without adding complexity.
• Act as the bridge between Firm Management and the EA team. Own workforce planning, coverage models, and capacity strategy. Serve as a thought partner to firm leadership on how the administrative function evolves as the firm scales.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed