Chief of Staff Artificial Intelligence (AI), Financial Services, Insurance, Real Estate, SaaS (Software as a Service), Software, Technology, Telecommunications, Venture Capital Type Full-Time Compensation CAD $160,000 - CAD $180,000 Annually Full-Time This is a remote position; however, candidates must be located in the same country, city, or region where the job is posted. The successful candidate must be available to attend a local office, meeting, training session, or company event if requested. Please only apply if you are based in the location listed on this job posting. Remote does not mean the position is open worldwide. Help Build and Scale a Growing Group of Technology-Enabled Companies The Rothenbury Group is a privately held company that owns and operates businesses across real estate, property management, brokerage, leasing, maintenance, staffing, technology, media, and other service-based industries. As our companies continue to grow, we’re looking for an exceptional Chief of Staff to work directly alongside the Founder &

• CEO. This is a senior leadership role for someone who thrives in fast-moving environments where priorities change quickly, multiple companies are operating simultaneously, and execution matters more than meetings. You’ll work across strategy, operations, technology, finance, legal, HR, marketing, product development, and business launches to help ensure significant initiatives move forward with structure, accountability, and urgency. This is an opportunity to become one of the Founder &

• CEO’s closest business partners and play a meaningful role in the long-term growth of the organization. If your background aligns with what we’re looking for,



you’ll receive an email within 24 to 48 hours of applying with a link to complete a pre-recorded online interview . The interview helps us better understand your leadership experience, operational thinking, project execution style, technology background, and ability to operate effectively alongside a Founder &

• CEO. Candidates selected after the first stage will be invited to continue through our executive interview process. Coordinating initiatives across operations, technology, finance, legal, HR, recruiting, marketing, media, leasing, brokerage, maintenance, and property management Maintaining visibility into active projects, risks, delays, and operational bottlenecks Ensuring executives, managers, contractors, vendors, software teams, and external partners remain aligned and accountable Leading the operating rhythm for project reviews, executive updates, action tracking, and follow-up Supporting technology initiatives including software development, AI projects, CRM systems, automation, integrations, reporting, and platform improvements Helping build scalable systems that support the continued growth of multiple businesses 15+ years of experience in executive operations, business operations, strategy, program management, founder’s office,



or similar senior leadership roles ~ Experience operating within technology-enabled businesses, including SaaS, PropTech, AI, automation, CRM platforms, marketplaces, or similar environments ~ Strong understanding of software development, product roadmaps, implementation projects, technology operations, and system integrations ~ Proven experience managing complex cross-functional initiatives involving multiple departments or business units ~ com, CRM systems, or comparable project management platforms ~ Exceptional organizational, communication, and stakeholder management skills ~ Excellent judgment, discretion, and ability to manage confidential information ~ Bachelor’s degree required ~ MBA or other graduate degree considered an asset Someone who doesn’t wait for direction, but instead identifies priorities, organizes the work, follows up relentlessly, removes obstacles, and ensures commitments become completed results. You’ll be comfortable working with executives, department leaders, software developers, product managers, finance teams, legal counsel, vendors, consultants, and external partners while maintaining professionalism, urgency, and accountability. In addition to base compensation, you’ll be eligible for a performance-based bonus tied to execution, project delivery, operational improvement, accountability, and overall impact across the Rothenbury Group. This is more than a traditional Chief of Staff position. It’s an opportunity to help shape the future of a growing group of technology-enabled companies while working directly with the Founder &

• CEO on the decisions, initiatives, and systems that will define the organization’s next stage of growth. #

📌 Chief of Staff - Chief Executive Officer (Vaughan)
🏢 Rothenbury Group
📍 Vaughan