Project Manager - AI First - Professional Services

PROJECT MANAGER - AI FIRST

(Remote/Hybrid, full-time, part-time or fractional)

Auger Hollingsworth is a high-growth personal injury law firm that operates at the intersection of legal excellence and technological innovation. We are transitionary—moving from a traditional practice to a modern, AI-First organization. We are looking for a high-agency Project Manager to serve as the "right hand" to our leadership team, executing strategic initiatives across every department of the firm.

The Role

The AI-First Project Manager is the firm’s "Force Multiplier." You are not a traditional coordinator; you are an implementation specialist who uses AI to accelerate every task you touch. Whether it is a marketing campaign, a financial audit, or a new HR policy, you apply an "AI-First" lens to ensure the project is executed with maximum efficiency and minimum manual drag.

Reporting directly to the Head of Operations and Leadership Team, you will take high-level objectives from the leadership team and turn them into finished products. You are a generalist with a "Builder" mindset (always from an AI First perspective) who can pivot from a technology roll-out in the morning to a marketing funnel optimization in the afternoon.

Your Support System

You will work in close partnership with the Head of Operations and the Leadership Team. You are the "Connective Tissue" of all growth initiatives, ensuring that the "Rocks" set by leadership are actually crushed with a sense of urgency. You will have access to the latest AI tools (Claude, specialized legal tools etc.) and a progressive leadership team that encourages radical experimentation.

What You’ll Do

First Month: Context & Tooling • Department Deep Dive: Shadow the leads of Marketing, Finance, HR, and Tech to understand their current projects and "bottlenecks." • AI Tool Integration: Establish your personal "AI Tech Stack" (centered on Claude) to manage project tracking, communication, and drafting. • Project Audit: Take over the tracking of the firm’s current quarterly "Rocks" to ensure total visibility.

First 90 Days: The Execution Sprint • Cross-Functional Wins: Lead and complete one major project in each core area (e.g., an automated lead-gen report for Marketing, a conscious onboarding sequence for HR). • AI Standardization: Create "AI Templates" for common firm tasks to ensure the team is leveraging LLMs for drafting and analysis. • Meeting Pulse: Manage the "Scorecard" for the weekly Level 10 meetings, ensuring all data is accurate and AI-summarized for leadership. • Research, Evaluate, Select and Implement market-based AI legal tools

First 6–12 Months: Scaling Operations • Process Automation: Work with the Leadership Team to "AI-enable" at least 5 major firm workflows. • Special Projects: Lead the launch of new regional initiatives or the implementation of new firm-wide software. • Financial Oversight: Assist Finance in using AI for predictive cash-flow modeling and disbursement tracking.

First Year and Beyond: Operational Excellence • Institutional Memory: Build an AI-searchable "Knowledge Base" of the firm’s standard operating procedures. • Strategy Support: Move from "Executing" projects to "Designing" them alongside the leadership team. • The Efficiency Benchmark: Demonstrate a measurable reduction in "Project Cycle Time" across the firm.

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

Skills • AI-Native Workflow: You don't "do" a task without asking how AI can do it faster. Expert-level Claude and automation skills. • Project Management Mastery: Expert in project management tools Asana; skilled in Agile or Lean methodologies. • Business Acumen: You understand P&Ls, Marketing funnels, HR compliance, business strategy and growth • High-Speed Execution: You move faster than the average professional. You "Get It Done" with high standards at high velocity.

Experiences • 3–5+ years in Project Management with AI First, ideally in a fast-paced startup or professional services firm. • Proven experience managing projects across diverse departments (Marketing, Finance, HR, Operations). • Demonstrated history of using AI to significantly improve project outcomes. • Must have a relevant university degree. This is mandatory. DO NOT APPLY if you do not have a university degree. • PMP qualifications in a tech setting ideal. • Must be expert level with all Claude AI tools.

Traits • High Agency: You don't need a map; you find the way. • Radical Responsibility: You live "Above the Line"—you own the outcome, regardless of the obstacles. • Calm Under Pressure: You bring structure to chaos and clarity to ambiguity. • Low Ego: You are happy to roll up your sleeves for any task that moves the firm forward.

What Won’t Set You Up for Success • Needing a granular, step-by-step "to-do list" from leadership. • Being "AI-Curious" rather than "AI-First." • Preferring to "consult" rather than "execute." • Lacking the "Grit" required to push a project through the "mid-project dip."

Why This Role Matters

Our leadership team has massive visions for the future in Ontario law practice. You are the engine that turns those visions into reality. By executing projects with AI-First speed, you allow the firm to scale at a rate that would be impossible for a traditional law firm. You are the key to our operational velocity.

Compensation, Perks & Benefits • Competitive Package: $100,000 – $150,000+ (comprised of Base + performance bonuses tied to project completion and firm growth). • Work Freedom: Remote/Hybrid flexibility across Ontario. • Unlimited Vacation: We focus on the "Done with velocity" pile, not the clock. • Full Benefits: Health, dental, vision, life insurance, and firm-matching pension plan.

Apply in Confidence by April 17, 2026 Please email your resume and a brief description of a relevant complex project you executed using AI in a professional services settling to Richard Auger at recruiting@augerhollingsworth.ca