Chief of Staff

Leo Berwick; Toronto; Hybrid; CAD 150,000 - 200,000; Full time

Benefits offered by this job

Unlimited PTO

Disconnect time

Flexible work arrangements

Pension contributions

Fringe benefit stipend

Wellness benefits

Job summary

Leo Berwick, an advisory firm focused on M&A for infrastructure funds, is seeking a Chief of Staff to partner with the Managing Partner and senior leadership. You will build the operating rhythm, data visibility, and execution discipline that let our leaders focus on clients, deals, and the firm’s strategic direction.

This hybrid role, based in Toronto with a minimum of three days in the office, requires turning scattered data into a single trusted view of the business and coordinating

Qualifications

• 6–10 years in operations, strategy, chief of staff, or leadership roles at a high-growth company
• Hands-on experience building KPI reporting and preparing board or investor materials
• A track record of leading organizational change that delivers measurable business results
• Exceptional written and verbal communication skills, with the ability to turn complexity into clear, decision-ready summaries
• Advanced skills with AI-enabled productivity tools and repeatable workflows using LLMs and data sources

Responsibilities

• Own firm-level programs such as international expansion, new practice launches, operating model changes and systems rollouts
• Support M&A and acquihire activities
• Design and run the leadership cadence (weekly, monthly, quarterly) with tracking of decisions and owners
• Define core KPIs with leadership and maintain dashboards for pipeline, staffing, utilization and margin data
• Triage demands on the Managing Partner and represent leadership in working sessions
• Prepare reporting packs and investor materials with Finance
• Map and improve workflows and handoffs between practices for scalable processes
• Drive adoption of new processes with practice leaders and the implementation team
• Partner with the Chief HR Officer on onboarding, advisor engagement, and communication norms

Skills

KPI reporting

AI tools proficiency

Change management

Communication

Strategic thinking

Stakeholder management

Tools

Claude

Copilot

Notion

Job description

Leo Berwick is an innovative, commercially focused mergers and acquisitions advisory firm serving the world’s largest infrastructure funds, infrastructure and energy developers, pension funds, sovereign wealth funds, private equity firms and their portfolio companies, publicly listed corporations, and private strategic investors across a broad range of industries, with deep expertise in infrastructure and energy. Our team of more than 120 M&A advisory leaders and specialists from the Big Four and Big Law partners with clients throughout the deal life cycle to maximize value, minimize risk, and achieve superior outcomes through tailored, high-impact advice.

At Leo Berwick, we hire the best and the brightest. As a growth-stage company, we move quickly, work collaboratively, and value people who take initiative and thrive in a fast-paced environment. Our culture is grounded in high performance, continuous learning, and the shared ambition to build something exceptional together while delivering dedicated, customized service to every client.

What we’re looking for

Leo Berwick is hiring a Chief of Staff to partner with the Managing Partner and senior leadership team. You will build the operating rhythm, data visibility, and execution discipline that let our senior leaders focus on clients, deals, and the firm’s strategic direction. You’ll be a trusted advisor to the Managing Partner, an integrator across practices, operations, and people, and the owner of cross-functional initiatives as we scale.

This is a hybrid role, with a minimum of three days per week in our Toronto office location.

You’re the right fit for this role if you –

• Bring structure to a high-growth environment, knowing what to build and when.
• Keep a fast-moving firm focused on a short list of priorities.
• Turn scattered data into one trusted view of the business.
• Influence without authority across partners, directors, and advisors.
• Exercise sound judgment and discretion, knowing when to act and when to elevate.
• Redesign how work moves across teams, so it scales with the firm.

What you'll do

• Strategic initiatives: Own firm-level programs such as international expansion, new practice launches, operating model changes and systems rollouts. Building workplans, coordinating across finance, people, marketing and practice leadership, and reporting progress candidly. Before these initiatives reach leadership, you will do the analysis behind them, including business cases, practice economics and market and competitor work.
• M&A and acquihire support
• Operating rhythm: Design and run the leadership cadence (weekly, monthly, quarterly), tracking decisions, owners, and follow-through.
• Data and KPIs: Define core KPIs with leadership, own dashboards, and set quality standards for pipeline, staffing, utilization, and margin data.
• Prioritization: Triage demands on the Managing Partner, prepare briefings, and represent leadership in working sessions.
• Investor and governance readiness: With Finance, prepare reporting packs, board and investor materials, and the policies expected of a firm with outside capital.
• Workflow and handoffs: Map and improve how work is requested, scoped, and handed off between practices so processes are repeatable and not dependent on a few individuals.
• Change management: Drive adoption of new processes with practice leaders and the implementation team.
• People and culture: Partner with the Chief HR Officer on onboarding, advisor engagement, and communication norms to keep our culture intact as we grow.

What you bring

• 6 - 10 years in operations, strategy, chief of staff, or leadership roles at a high-growth company, professional services firm, or private equity-backed business.
• Hands-on experience building KPI reporting and preparing board or investor materials.
• A track record of leading organizational change that delivers measurable business results.
• Exceptional written and verbal communication skills, with the ability to turn complexity into clear, decision-ready summaries.
• Advanced skills with AI-enabled productivity tools (e.g. Claude, Copilot, Notion). Ideally you have built repeatable workflows that use LLMs, AI assistants, connected data sources to produce research, analysis and written output, and you can show the time and quality gains. You understand the limits as well as the strengths, including verifying outputs, handling confidential information appropriately and knowing when not to use a tool.
• Unlimited paid time offincluding 2 weeks of disconnected time each year
• Flexible working arrangements – remote and location flexibility
• Pension & retirement contributions
• Monthly fringe benefit stipend (up to $400)
• Additional benefits to support your physical and mental wellness

Compensation

This is a permanent full-time role offering a base salary range of $150,000–$200,000 CAD, commensurate with skills, experience, and alignment with the requirements of the role. Placement within this range will be determined based on experience relevant to this role and scope of responsibility.

Vacancy Statement

This posting reflects a new vacancy.

Use of Artificial Intelligence in Hiring

The firm uses artificial intelligence tools to screen candidates for this role.

Equal Opportunity Statement

Leo Berwick provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type with regard to race, age, ancestry, color, creed, disability status (physical or mental), gender, marital status, legally-protected medical condition (including pregnancy), national origin, religion, gender identity or expression, genetic information, sexual orientation, military, protected veteran status, or any other characteristic protected by applicable federal, state, or local laws.