Chief of Staff to CEO

Location

Toronto, Canada (On-site)

International travel as required

Company Overview

We are a high-growth data and artificial intelligence consultancy headquartered in Toronto, partnering with Fortune 500 companies and global multinationals to design human-first experiences powered by data and AI. Our work enables organizations to unlock the full value of their data, deploy AI responsibly, and deliver measurable, enterprise-scale business outcomes.

With Canadian headquarters in Toronto, US headquarters in Austin and a growing presence in the UK, we are scaling internationally. As we enter this next phase of growth, we are building a leadership team capable of shaping our global strategy, strengthening our market presence, and representing the firm with credibility at the executive and board level.

Role Summary

The Chief of Staff to the CEO is a senior, trusted advisor and force multiplier to the Chief Executive Officer. This role operates at the intersection of strategy, execution, communications, and external engagement. Reporting to the CEO, the Chief of Staff will act as a representative of the CEO in required internal and external forums, help implement strategic initiatives across the organization, and play a central role in helping the CEO shape the company's public narrative, brand positioning, and relationships with media, customers, and partners.

This is a highly visible role requiring sound judgment, executive presence, and the ability to operate seamlessly across board-level strategy, market-facing communications, and day-to-day leadership execution.

Key Responsibilities

Strategic Leadership & Execution

• Assist the CEO in defining, refining, and operationalizing strategic priorities and long-term vision.

• Lead and coordinate cross-functional strategic initiatives, ensuring alignment with company objectives and measurable outcomes.

• Prepare strategic materials for the CEO, including internal & external presentations and executive briefings.

• Track progress against strategic goals and proactively identify risks, gaps, and opportunities.

CEO Proxy

• Represent the CEO, as required, in meetings, decision-making forums, and internal communications as a delegated authority.

• Act as a connective tissue across the executive team, ensuring clarity, alignment, and accountability.

• Facilitate executive operating rhythms, including leadership meetings, offsites, and planning cycles.

• Serve as a confidential sounding board and thought partner to the CEO on sensitive or complex matters.

Public Relations & Branding

• Steward the company's external narrative, positioning, and executive voice in alignment with CEO vision & strategic goals.

• Help define PR and brand strategy, including messaging frameworks, thought leadership themes, and market positioning.

• Oversee media relations, including press strategy, spokesperson preparation, interviews, and proactive media outreach.

• Partner with marketing and external agencies to ensure consistent, high-impact brand representation globally.

Media, Customer & External Engagement

• Act as a senior company representative in customer meetings, industry events, conferences, and partner engagements.

• Support the CEO in high-stakes customer and stakeholder interactions, including executive briefings and relationship management.

• Monitor industry trends, media coverage, and public discourse related to data, AI, and technology to inform positioning and response.

• Help manage crisis communications and sensitive external issues when required.

Required Qualifications

• 5+ years of experience in strategy, chief of staff, management consulting or corporate communications within technology, data, or AI-driven organizations.

• Demonstrated experience working directly with C-suite executives, preferably as a Chief of Staff or equivalent strategic advisor.

• Strong background in strategic planning, executive communications, and cross-functional leadership.

• Proven experience in PR, branding, media relations, or external communications at a corporate or agency level.

• Exceptional written and verbal communication skills, with the ability to translate complex ideas into clear, compelling narratives.

• High degree of discretion, sound judgment, and comfort handling sensitive information.

•  Executive presence and credibility with senior leaders, customers, media, and external stakeholders.

• Experience operating in international or multi-market environments is strongly preferred.

• Data-savvy strategic thinker with strong execution discipline, politically astute, emotionally intelligent, highly collaborative with an ability to pivot fast and juggle multiple priorities simultaneously.

• Comfortable operating in ambiguity and fast-paced, high-growth environments.

•  Confident representing the organization externally while remaining deeply aligned with the CEO's intent and values.

Candidates MUST be authorized to work in Canada & US without current or future sponsorship needs
.