Strategic Operations Chief of Staff

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

Benefits offered by this job

Unlimited paid time off

Flexible working arrangements – remote

Pension contributions

Fringe benefit stipend

Wellness benefits

AI productivity tools

Job summary

Leo Berwick, an innovative mergers & acquisitions advisory firm, seeks a Chief of Staff to partner with the Managing Partner and leadership. Build operating rhythm, data visibility, and execution discipline to keep leadership focused on clients and deals.

The role is hybrid with a minimum of three days per week in our Toronto office. You will drive strategic programs, governance readiness, and cross-functional collaboration while shaping a data-driven culture and scalable processes.

Qualifications

• 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.
• 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

Responsibilities

• 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
• Design and run the leadership cadence (weekly, monthly, quarterly), tracking decisions, owners, and follow-through.
• Define core KPIs with leadership, own dashboards, and set quality standards for pipeline, staffing, utilization, and margin data.
• Triage demands on the Managing Partner, prepare briefings, and represent leadership in working sessions.
• With Finance, prepare reporting packs, board and investor materials, and the policies expected of a firm with outside capital.
• Map and improve how work is requested, scoped, and handed off between practices so processes are repeatable and not dependent on a few individuals.
• 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 to keep our culture intact as we grow.

Skills

KPI reporting

Strategic leadership

Communication skills

AI productivity tools

Change management

Data visualization

Tools

Claude (AI)

Copilot

Notion

Job description

Leo Berwick, an innovative mergers & acquisitions advisory firm, seeks a Chief of Staff to partner with the Managing Partner and leadership. Build operating rhythm, data visibility, and execution discipline to keep leadership focused on clients and deals.

The role is hybrid with a minimum of three days per week in our Toronto office. You will drive strategic programs, governance readiness, and cross-functional collaboration while shaping a data-driven culture and scalable processes.