Chief of Staff to the Founder, CEO

We are hiring a Chief of Staff to the Founder & CEO to work directly with the Founder and CEO across a growing group of technology-enabled companies.

The group operates across real estate technology, property management, brokerage, leasing, maintenance, staffing, media, and service-based businesses. Technology is a major part of the company’s growth strategy, and this role requires someone who can operate across multiple companies, projects, and teams at the same time.

This is a senior founder’s office role for someone who can turn founder-level direction into clear action, assign ownership, track progress, follow up relentlessly, identify blockers, and make sure important work gets completed.

This is not an Executive Assistant, administrative, note-taking, or traditional project manager role. The Chief of Staff will act as the Founder & CEO’s execution partner in a fast-moving, high-accountability environment.

How to Apply

• Apply with your resume
• If your background aligns, you’ll receive a link to a short pre-recorded video interview shortly after applying

What You’ll Do

• Work directly with the Founder & CEO to manage priorities across multiple technology-enabled companies
• Translate high-level founder direction into clear tasks, project plans, owners, timelines, deliverables, and follow-up systems
• Manage strategic projects across technology, product development, SaaS/platform operations, real estate, property management, brokerage, leasing, maintenance, staffing, media, finance, legal, HR, recruiting, marketing, administration, vendor management, integrations, and new business launches
• Own the operating rhythm for project follow-up, including daily updates, weekly reviews, status reports, executive summaries, and escalation tracking
• Maintain visibility into active projects, overdue items, risks, blockers, and decisions required
• Ensure ClickUp or similar project management systems are properly structured, updated, and used by the team
• Follow up with executives, managers, employees, contractors, developers, vendors, software teams, agencies, and external partners to make sure commitments are completed
• Work with technology and product teams to track roadmaps, platform development, integrations, bugs, feature requests, automation projects, AI initiatives, CRM projects, and internal system improvements
• Challenge vague updates, unclear ownership, missed deadlines, repeated delays, and projects without clear next steps
• Join key meetings, document decisions, assign action items, and ensure follow-through
• Identify operational gaps, communication breakdowns, accountability issues, bottlenecks, and execution risks
• Prepare clear daily and weekly reports for the Founder & CEO showing priorities, progress, delays, blockers, and decisions required
• Build systems, workflows, dashboards, reporting structures, and operating processes that improve execution across the group
• Support active company launches, integrations, hiring initiatives, strategic projects, technology projects, and urgent priorities

Requirements

• 15+ years of experience in operations, strategy, project management, program management, founder’s office, executive operations, business operations, technology operations, product operations, or a similar senior role
• Direct experience working with founders, CEOs, ownership groups, or senior executive teams
• Experience working in technology, SaaS, proptech, marketplace, platform, AI, automation, CRM, or technology-enabled businesses
• Strong understanding of product roadmaps, development cycles, integrations, bugs, releases, sprints, vendor management, and system implementation
• Bachelor’s degree required
• Strong experience managing cross-functional projects across multiple departments, companies, or business units
• Advanced experience with ClickUp, Asana, Monday.com, Jira, CRM systems, or similar project management and operating systems
• Strong ability to create structure in fast-moving, high-pressure environments
• Excellent written and verbal communication skills
• Strong judgment, discretion, confidentiality, and follow-through
• Ability to manage competing priorities, urgent issues, ambiguity, and high expectations
• Comfortable holding senior people, developers, vendors, contractors, and internal teams accountable in a professional, direct, and documented manner

Nice-to-Have

• MBA or similar graduate degree
• Experience working in a founder-led, high-growth, multi-company environment
• Experience supporting real estate technology, property management, brokerage, leasing, maintenance, staffing, media, or service-based businesses
• Experience tracking AI, automation, CRM, product development, platform operations, integrations, and internal systems projects
• Experience building executive dashboards, operating rhythms, reporting structures, and accountability systems
• Experience supporting launches, restructures, integrations, hiring plans, vendor transitions, or major strategic initiatives

Ideal Candidate

The ideal candidate is a serious operator who has worked closely with demanding founders, CEOs, or ownership groups before.

They are highly organized, tech-savvy, direct, calm under pressure, and relentless with follow-up. They understand how to manage both business operations and technology projects.

They do not need constant direction. They can take a broad instruction, break it into a plan, assign ownership, track progress, and make sure the work gets done.

They are comfortable working across multiple companies and departments at the same time, including executives, managers, developers, product teams, finance, legal, HR, recruiting, marketing, vendors, agencies, contractors, and internal staff.

They know how to create clarity where there is chaos. They are not afraid to chase people, ask direct questions, challenge unclear updates, identify excuses, and escalate issues when needed.

They understand that this role is about protecting the Founder & CEO’s time, creating visibility, driving accountability, and making sure execution happens across both technology and operations.

Important Location Requirement

This is a hybrid position based in Vaughan, Ontario. The role may begin with a hybrid schedule; however, the successful candidate must be available to attend the Vaughan office regularly and transition to primarily in-office work as required.

Please only apply if you are based in Ontario or are willing and able to commute or relocate to the GTA/Vaughan area.