Senior Manager, Founder’s Office, Strategic Projects

We are hiring a Senior Manager, Founder’s Office & Strategic Projects to work closely with the Founder & CEO across a growing group of technology-enabled companies.

This role is for someone who can help keep projects organized, people accountable, and execution moving across multiple companies, departments, vendors, and strategic priorities.

This is not an Executive Assistant, basic administrative, or note-taking role. It is a hands-on project execution role for someone who is highly organized, tech-savvy, direct, and strong with follow-up.

The successful candidate will turn priorities into clear tasks, track progress, follow up with team members and vendors, identify delays, escalate blockers, and make sure important projects do not fall through the cracks.

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 projects, priorities, follow-ups, and execution across multiple companies
• Turn high-level direction into clear tasks, owners, deadlines, deliverables, and next steps
• Track projects across technology, product, operations, real estate, property management, brokerage, leasing, maintenance, staffing, media, finance, legal, HR, recruiting, marketing, and administration
• Maintain project visibility inside ClickUp or similar project management systems
• Make sure tasks are assigned, updated, followed up on, completed, and escalated when needed
• Follow up with executives, managers, employees, contractors, developers, vendors, agencies, and external partners
• Track product roadmaps, integrations, bugs, feature requests, automation projects, AI initiatives, CRM projects, internal tools, and system improvements
• Prepare clear daily and weekly updates showing priorities, progress, delays, blockers, and decisions required
• Attend meetings, document decisions, assign action items, and follow up until items are completed
• Identify unclear ownership, missed deadlines, vague updates, repeated delays, and operational gaps
• Help organize workflows, dashboards, reports, and processes that improve accountability across the group
• Support multiple active companies, launches, integrations, hiring initiatives, technology projects, and strategic priorities

Requirements

• 7+ years of experience in project management, operations, business operations, technology operations, product operations, founder’s office, executive operations, strategic projects, or a similar role
• Experience working directly with founders, CEOs, executives, or senior leadership 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, vendors, and system implementation
• Bachelor’s degree required
• Strong experience managing projects across multiple departments, business units, or companies
• Strong experience with ClickUp, Asana, Monday.com, Jira, CRM systems, or similar project management and operating systems
• Strong written and verbal communication skills
• Strong organization, documentation, follow-up, and accountability skills
• Ability to manage multiple priorities, urgent tasks, ambiguity, and fast-changing direction
• Comfortable following up with senior people, developers, vendors, contractors, and internal teams in a professional and direct manner

Nice-to-Have

• MBA, PMP, or similar certification
• Experience supporting technology, real estate, property management, brokerage, leasing, maintenance, staffing, media, or service-based businesses
• Experience working in a founder-led, high-growth, multi-company environment
• Experience tracking AI, automation, CRM, product development, platform operations, integrations, or internal systems projects
• Experience creating dashboards, project reports, operating rhythms, and accountability systems

Ideal Candidate

The ideal candidate is a hands-on operator who is organized, tech-savvy, direct, and relentless with follow-up.

They are comfortable working in a fast-moving, founder-led environment where priorities change quickly and execution matters.

They can take direction, ask the right questions, organize the work, assign next steps, track progress, and follow up until the work gets completed.

They are comfortable dealing with executives, managers, developers, product teams, finance teams, legal teams, HR teams, recruiting teams, marketing teams, vendors, contractors, and internal staff.

They understand that technology is central to the company’s growth and can help create visibility across product development, platform operations, integrations, automation, AI, CRM, internal systems, and business launches.

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.