DO NOT APPLY IF YOU ARE OUTSIDE OF CANADA AND THE US

Position Overview

The Strategic Operations & Executive Integrator is the CEO's trusted execution engine and operational anchor-responsible for unifying leadership direction, maintaining organizational accountability, and managing personal legacy structures. This role bridges business and life, combining strategic foresight with executional rigor to drive outcomes across multiple ventures and disciplines. The role demands high discretion, elite communication skills, and systemic thinking.

This individual must work seamlessly across multiple businesses or ventures-translating the CEO's entrepreneurial vision into integrated strategies, executional plans, and operational standards. They must unify and optimize systems, teams, and priorities across departments, creating a synchronized execution model that reflects the CEO's long-term intent.

Key Mandates

Operational Integration & Leadership Accountability

Design, manage, and enforce enterprise-wide accountability frameworks.
Create and maintain a dynamic, real-time tracking system for KPIs and strategic initiatives.
Facilitate weekly, monthly, and quarterly operating cadences including leadership check-ins, planning sessions, and retrospectives.
Coordinate executive dashboards, pulse updates, and exception reporting.

Strategic Communication & CEO Enablement

Act as communication proxy and synthesizer of the CEO's thinking across stakeholders.
Write executive memos, decks, and narratives for internal and external stakeholders.
Control CEO bandwidth by triaging inputs and resolving issues at the first pass.
Maintain situational awareness across all company domains and upcoming priorities.

Business Alignment & Cross-Venture Coordination

Ensure all business lines align with the CEO's strategic direction.
Coordinate between independent ventures, ensuring knowledge transfer and resource sharing.
Identify redundancies and inefficiencies across business units.
Lead special projects that span multiple ventures or stakeholders.

Personal Legacy & Life Infrastructure

Oversee personal scheduling, travel, family obligations, and health routines.
Coordinate legal, estate, and succession planning with external advisors.
Maintain updated records of wills, trusts, POAs, and key legal documents.
Act as liaison to family office, attorneys, wealth managers, and board advisors.
Experience & Education Requirements
Minimum 8-12 years of progressive experience in executive operations, management consulting, private equity operations, or high-level executive support roles.
Proven success working directly with founders, entrepreneurs, or C-suite leaders in high-growth, founder-led companies.
Demonstrated ability to manage multiple concurrent businesses, special projects, or family office structures.
Strong experience in building systems, enforcing accountability, and driving strategic initiatives from inception to execution.
Familiarity with legal structures, estate planning, governance, and succession documentation is a strong asset.
Bachelor's degree in Business Administration, Finance, Law, Engineering, or a related field is required.
MBA, JD, or other relevant advanced degree preferred.
Additional certifications in operations, project management, or family office management (e.g., PMP, FFI, CFM) are advantageous.

Job Type: Full-time

Pay: $120,000.00-$140,000.00 per year

Additional pay:
Bonus pay
Schedule:
Monday to Friday
Weekends as needed

Work Location: In person