Chief of Staff
Oakville, Ontario, Canada (Hybrid) · Full Time
Be the first to apply
- Experience
- 15+ yrs
- Salary
- CAD 160,000 – CAD 180,000 / year
- Openings
- 1
- Posted
- 1 hour ago
- Work mode
- Hybrid
- Education
- Bachelor's degree
- Resume
- Required to apply
Where you'll work
Job description
Overview
The Rothenbury Group, a private owner and operator of businesses spanning several industries including real estate, staffing, technology, media, and more, seeks an experienced Chief of Staff. This role involves close collaboration with the Founder & CEO to drive growth and operational excellence across multiple ventures in sectors such as Artificial Intelligence, SaaS, financial services, and telecommunications.
Position Details
- Employment Type: Full-Time
- Location: Oakville, Ontario, Canada (Hybrid remote with onsite presence required as needed)
- Compensation: Annual base salary between CAD 160,000 and CAD 180,000, plus performance-related bonuses
- Important: Candidates must reside locally to attend in-person meetings or training sessions when required.
Primary Responsibilities
- Convert strategic directives into actionable execution plans and monitor progress.
- Coordinate cross-departmental initiatives across operations, technology, finance, legal, HR, marketing, and other units.
- Assign clear responsibility, deadlines, and maintain accountability for key projects.
- Maintain transparency on active projects, identify risks, and mitigate delays.
- Align and ensure commitment among executives, managers, contractors, vendors, and partners.
- Lead project review rhythms including executive updates, action tracking, and follow-ups.
- Support tech endeavors such as software development, AI projects, automation, CRM integration, and system enhancements.
- Prepare succinct executive summaries highlighting priorities, progress, issues, and decisions.
- Identify and implement improvements to workflows, communications, reporting, and operational systems.
- Develop scalable frameworks to sustain growth across multiple business units.
Candidate Profile
- Over 15 years of senior leadership experience in executive operations, strategy, program management, or related roles.
- Proven track record working directly with founders, CEOs, or executive leadership teams in dynamic organizations.
- Background in tech-enabled businesses such as SaaS, PropTech, AI, automation, CRM platforms, or marketplace environments.
- Strong comprehension of software development cycles, product roadmaps, implementation, operations, and integrations.
- Experience managing complex, cross-functional projects spanning multiple departments or companies.
- Advanced proficiency with project management tools like ClickUp, Jira, Asana, Monday.com, and CRM systems.
- Exceptional skills in organization, communication, stakeholder engagement, and confidential information management.
- Bachelor’s degree required; an MBA or graduate degree is advantageous.
Ideal Attributes
The successful candidate is a natural organizer thriving in fast-paced contexts. They proactively identify priorities, manage tasks rigorously, eliminate impediments, and ensure commitments are fulfilled. Comfort engaging stakeholders from various disciplines while maintaining professional urgency and accountability is essential. A problem solver who simplifies complex environments and enhances systems is highly desired.
Compensation & Benefits
- Salary range: CAD 160,000 to CAD 180,000 annually, commensurate with experience and leadership qualities.
- Opportunity for additional bonus based on performance metrics including execution, project delivery, and operational impact.