Of Staff / Operations Lead Jobs in Toronto, Ontario, Canada
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Chief of Staff
Artificial Intelligence (AI), Financial Services, Insurance, Real Estate, SaaS (Software as a Service), Software, Technology, Telecommunications, Venture Capital
Type Full-Time
Location(s) Oakville, Ontario, Canada
Hybrid
Compensation CAD $160,000 - CAD $180,000 Annually
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Description
Full-Time
Oakville, Ontario, Canada Hybrid
Important Location Requirement
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 important 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.
Our Hiring Process
Every application is reviewed by our recruiting team.
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.
What You’ll Be Responsible For
Working directly with the Founder & CEO, you will help drive execution across multiple operating companies by:
Translating strategic priorities into clear execution plans
Coordinating initiatives across operations, technology, finance, legal, HR, recruiting, marketing, media, leasing, brokerage, maintenance, and property management Establishing clear ownership, deadlines, accountability, and follow-up for strategic initiatives 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 Preparing concise executive summaries that allow the Founder & CEO to quickly understand priorities, progress, blockers, and decisions requiring attention Identifying opportunities to improve workflows, communication, reporting, and operational execution across the organization Helping build scalable systems that support the continued growth of multiple businesses
What We’re Looking For
The Successful Candidate Will Have
15+ years of experience in executive operations, business operations, strategy, program management, founder’s office, or similar senior leadership roles Significant experience working directly with founders, CEOs, ownership groups, or executive leadership teams 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 Advanced experience using ClickUp, Jira, Asana, Monday.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
The Kind of Person Who Will Succeed Here
We’re looking for someone who naturally creates order in fast-moving environments.
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.
You enjoy solving problems, improving systems, and bringing clarity where others see complexity.
Compensation & Opportunity
This position offers a base salary of C$160,000–C$180,000, depending on experience, executive leadership background, and overall fit.
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.
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About Rothenbury Group
Rothenbury Group is a privately held diversified holding company that builds, owns, and operates permanent businesses across real estate services, professional services, staffing, media, and technology. We are not a fund, a flip shop, or a syndicate. We are a long-term operator of operating companies, headquartered in Panama City, with portfolio companies and capital partners across North America and the broader Americas.
Our investment thesis is simple. The most durable returns in the modern economy come from boring, fragmented, operationally intensive markets where most competitors under-invest in systems, accountability, and customer experience. We build and back operating companies in those markets, equip them with senior operators and modern infrastructure, and hold them as permanent businesses for decades.
Each operating company in the Rothenbury portfolio runs as a stand-alone brand with its own service standards, customer commitments, and operating leadership. Independence is by design. Each operating company evolves at its own pace, and every customer relationship has a single accountable counterparty.
What our operating companies share is operational backbone. Centralized accounting, compliance, technology, governance, and capital allocation are run from Rothenbury Group. Operating companies focus on the work. The platform handles the rest.
Our capital partners include family offices, accredited private investors, and institutional allocators who want exposure to durable operating returns without the friction of running businesses themselves. We provide structured access through equity, structured debt, and operating partnerships. Capital is patient. Reporting is monthly. Audits are independent.
Rothenbury Group is led by a senior operating team with decades of combined experience in real estate, capital markets, and services operations. To engage our investment team, capital partnerships group, or media office, contact us.