Chief of staff - Managing Director

Division: Office of the Chairman

About the Job
The Office of the Chairman at 369 Global supports the governance, long-term stewardship, and external credibility of a rapidly scaling global enterprise with operations and partnerships across multiple jurisdictions.
As Chief of Staff, you will serve as the Chairman’s principal strategic integrator and governance enabler—ensuring focus, discipline, and institutional integrity at the highest level of the organization. This role is designed for a senior professional who can operate effectively in fast-paced environments characterized by high visibility, ambiguity, complex stakeholder dynamics, and elevated reputational standards.
The Chief of Staff plays a critical role in protecting the boundary between governance and management, enabling CEO autonomy, and ensuring that the Chairman’s time, presence, and judgment are applied only where they create the greatest long-term value for the institution.
This is not an operational management role. It is a judgment, coordination, and risk-calibration role.

What You Will Do
Strategic Prioritization & Chairman Effectiveness You will:

Translate Vision 2029 into a disciplined, rolling Chairman agenda aligned to approved performance frameworks
Filter, sequence, and prioritize all inbound requests to the Chairman to ensure focus on the highest-leverage governance and external matters
Actively manage trade-offs between opportunity, risk, visibility, and institutional impact.
Ensure the Chairman’s time allocation aligns with governance priorities, capital credibility, and enterprise reputation.

Governance Enablement & Boundary Protection You will:

Operationalize and enforce the Chairman–CEO Operating Covenant in day-to-day practice
Ensure strict adherence to role clarity between governance, executive management, and operations
Prepare governance briefings, board materials, and decision memoranda that are concise, evidence-based, and decision-ready
Track Chairman KPIs and enterprise scorecard signals, flagging early deviations or risks

External Interface & Stakeholder Discipline You will:

Serve as the single coordination point for the Chairman’s external engagements, including government, institutional, industry, and international stakeholders
Ensure message discipline, consistency, and appropriateness across all high-visibility engagements
Prepare the Chairman for complex external interactions where business, policy, and public-interest considerations intersect
Assess and manage cumulative exposure risk arising from public-facing activities

Reputational, Ethical & Risk Oversight You will:

Act as an early-warning system for reputational, governance, or boundary risks
Apply heightened judgment to matters involving public perception, conflicts of interest, or dual-use platforms
Ensure all activities of the Chairman’s Office meet standards that exceed legal minimums and align with best practices for highly visible leaders
Coordinate with external legal, ethics, or communications counsel as required

Office Leadership & Discipline You will:

Lead and coordinate the Chairman’s Office staff and advisors
Establish operating rhythms, information hygiene protocols, and confidentiality standards
Ensure the Office remains small, disciplined, and non-operational by design
Prevent mandate creep or the emergence of parallel decision structures

How Do I Qualify?
Leadership, Judgment & Professional Maturity You have:

• 10+ years of progressively senior experience supporting a founder, CEO, board chair, or public-facing institutional leader.
• Experience working across multiple jurisdictions, stakeholder groups, or regulatory environments.
• Demonstrated ability to operate with absolute discretion and professional restraint
• Proven judgment in environments where reputation, credibility, and perception materially affect outcomes.
• Proven comfort managing ambiguity, capacity to work irregular hours, manage competing priorities, and the confidence to say “no” when required to protect institutional integrity.

Experience operating within complex governance environments (public sector, regulated industries, global enterprises, or highly scrutinized organizations)
Proven exposure to board-level processes, governance frameworks, or enterprise-wide strategic coordination
Strong understanding of governance principles, fiduciary responsibility, and role separation
Experience navigating complex stakeholder environments where business, policy, and public interest intersect
Familiarity with ethical frameworks, conflict-of-interest management, and reputational risk mitigation
The ability to anticipate how decisions may be interpreted externally—not just internally

Strategic Thinking & Communication You demonstrate:

Exceptional written and verbal communication skills
Ability to synthesize complex information into clear, decision-ready briefings
Exceptional judgment and situational awareness
Strong narrative discipline and message calibration
Advanced stakeholder management and interface coordination
High emotional intelligence and professional presence
Comfort communicating with senior leaders across public, private, and international contexts
Outstanding prioritization, sequencing, and time-management skills
Ability to anticipate issues before they escalate
Willingness to undergo enhanced background, reference, and conflict-of-interest checks

Additional Information
This role carries no operational or line-management authority over business units Strict confidentiality, conflict-of-interest disclosure, and information hygiene are mandatory
The position requires availability outside standard business hours and occasional domestic or international travel.
The successful candidate must be comfortable operating under elevated public and stakeholder scrutiny

Why This Role Matters This role exists to ensure that:

The Chairman remains focused on governance, stewardship, and long-term value creation
The CEO retains full operational authority and independence
The enterprise scales institutionally rather than personally
Reputation, credibility, and trust compound rather than erode as visibility increases

What Success Looks Like
The Chairman is consistently effective, disciplined, and non-operational
Governance boundaries are respected without constant intervention
External engagement enhances credibility rather than creating exposure
Vision 2029 advances without dependency on any individual

Compensation
Base: CAD $130,000 - $155,000 per annum
Performance Pay: 0 - 5%
Vacation Pay : 4 weeks of vacation.
Benefits: Executive package - Dental care, Extended health care, Vision care, Life insurance, On-site parking, Some hybrid work.

Location: Ajax (Hybrid, Occasional Domestic/International Travel)

369 Global is an inclusive work environment and as such has a workplace accommodation policy in place. Accommodations are available, upon request, for the interview process and other selection stages for job applicants with accessibility needs.
***Artificial Intelligence (AI) tools may be used to assist in screening and assessing applicants.***