Chief of Staff

Spectrum Search is partnered with an established legal services business expanding its AI-enabled technology offering. The company is seeking a commercially focused Chief of Staff to work directly with the Chief Operating Officer, turning strategic priorities into measurable growth and stronger operational performance.

About the opportunity

This is a hands-on role within a profitable business developing its consumer services offering. Working across sales, finance and operations, the Chief of Staff will combine analytical depth with direct responsibility for delivering commercial initiatives.

The opportunity offers a potential route into a General Manager position with full profit and loss ownership, subject to performance and business needs.

The role

Reporting to the Chief Operating Officer, you will lead cross-functional projects from initial analysis through implementation and measurement. Your remit will include growth experiments, pricing, financial planning and the operating processes that keep teams accountable.

You will work closely with senior leadership to identify opportunities, prioritise investment and translate complex data into clear decisions.

Key responsibilities

• Own strategic growth projects, including pricing experiments, additional services and new service-line opportunities.
• Partner with sales leadership to design tests, track performance and improve conversion across the customer journey.
• Establish weekly scorecards, functional key performance indicators and a shared goals dashboard.
• Identify underperforming initiatives, clarify ownership and coordinate corrective action.
• Produce monthly business-unit profit and loss reporting, financial forecasts and headcount models.
• Prepare executive decision memos, presentations and board-ready performance reporting.
• Assess market opportunities, competitor positioning and pricing, then launch and measure resulting initiatives.

Essential requirements

• Experience in strategy and operations, investment banking, management consulting or a comparable analytical commercial role.
• Hands-on operational experience within a technology company, scaling business or your own venture.
• Evidence of owning growth or revenue projects from initial assessment through delivery and evaluation.
• Strong financial modelling skills, including headcount planning and operational forecasting.
• Ability to design experiments, select meaningful performance measures and assess statistical significance.
• Commercial judgement and an understanding of the factors that influence revenue, conversion and profitability.
• Clear, concise writing and presentation skills, with the ability to turn incomplete or complex data into practical recommendations.
• Sound judgement when handling confidential financial, compensation and people information.

Nice-to-haves

• A combination of investment banking or consulting experience followed by an operating role in a technology business.
• Founder experience or responsibility for building a new business initiative.

Interview process

The process includes interviews with the Chief Operating Officer and Chief Executive Officer, followed by a practical take-home exercise expected to take two to four hours, with a short recorded walkthrough.

Location and remote setup

Full-time position based in Toronto, Ontario, Canada, with approximately three days per week in the office. Candidates must be able to meet this hybrid requirement. Visa sponsorship is not available.