Chief of Staff

About the Role

Rothenbury Group, a private owner of diverse businesses across real estate, technology, financial services, and other industries, is seeking a senior leader to join as Chief of Staff. This is a full-time, hybrid role based in Vaughan, Ontario, Canada. Although remote, candidates must reside locally to attend in-person meetings or events when needed.

Key Responsibilities

• Collaborate directly with the Founder & CEO to convert strategic goals into actionable plans.
• Coordinate projects spanning operations, technology, finance, legal, HR, marketing, product development, leasing, brokerage, maintenance, and property management.
• Assign clear ownership, deadlines, and accountability for strategic initiatives.
• Track active projects, identify risks or delays, and highlight operational bottlenecks.
• Ensure alignment among executives, managers, external vendors, software teams, and partners.
• Lead regular project reviews, executive updates, and follow-up processes.
• Support technology-driven efforts, including software development, AI implementations, CRM systems, automation, integrations, reporting, and platform upgrades.
• Create concise executive summaries to inform the CEO of key priorities, progress, blockers, and decisions requiring attention.
• Identify improvements for workflows, communication, reporting, and operational processes across the company.
• Develop scalable systems to support multi-business growth.

Candidate Profile

• Extensive experience (15+ years) in senior executive operations, program management, strategy, or founder’s office roles.
• Strong background partnering closely with founders, CEOs, or leadership teams.
• Experience working within technology-enabled sectors such as SaaS, PropTech, AI, automation, CRM platforms, or marketplaces.
• Deep understanding of software development lifecycles, product roadmaps, implementations, technology operations, and system integrations.
• Proven ability to manage complex cross-departmental initiatives.
• Advanced proficiency with project management tools like ClickUp, Jira, Asana, Monday.com, and CRM software.
• Exceptional organizational skills, communication competence, stakeholder management, and discretion with confidential data.
• Bachelor’s degree required; an MBA or graduate degree is a plus.

Traits for Success

We seek a proactive individual who excels at creating structure amid rapid change. The ideal candidate independently identifies priorities, organizes tasks, follows through consistently, resolves obstacles, and drives results. Comfort engaging with executives, software teams, legal advisors, and vendors with professionalism and urgency is essential. A passion for problem solving and streamlining complexity is highly valued.

Compensation and Additional Details

The annual salary ranges from CAD 160,000 to CAD 180,000, based on experience and fit. Performance bonuses will reward impact on project execution, operational improvements, and accountability. This position offers a strategic opportunity to be a close business partner to the Founder & CEO and contribute significantly to the growth of various technology-driven companies within the Rothenbury Group.

Additional Information

Candidates must be located in or near Vaughan, Ontario, and be available to attend local meetings or company events as required. The application process includes a pre-recorded online interview focusing on leadership, operational management, project execution, technology background, and collaborative ability with a Founder & CEO.