Location: Toronto, In-Office Role, 5 days per week

Company: Our client, OSF Partners

Posting type: Existing vacancy

Compensation: $90,000 - $100,000 CAD + annual performance-based bonus

Use of AI: We do not use AI in the screening and interviewing process. A member of our team reads your resume and meets with you.

About this Role

Most Executive Assistant roles are about managing a calendar. This role is about owning the execution. At OSF Partners, you aren't just an Assistant; you are the primary navigator for our Founder’s professional and personal world. You are the high-impact partner who bridges the gap between high-level ideas and daily reality.

You are the gatekeeper who ensures the Founder is always in the right place, at the right time, with the right context. By taking full ownership of the logistical complexity across both a high-growth insurance firm and a high-demand family life, you bring structure to his daily life allowing the Founder to stay focused on high-value sales, strategy, and being present with his family.

What Your Day Looks Like

Morning: You arrive at our downtown office and triage the Founder’s work and personal inboxes. You’ve already anticipated the "buffer time" needed between his early morning emails and his first 9:30 AM client meeting, ensuring he isn't booked back-to-back.

Mid-Morning: You’re translating a high-level idea the Founder shared into a clear, documented project plan. You check in with the back-office operations team to ensure a client file is moving through the sales pipeline without Dan needing to ask or get wrapped up in the administrative pieces of the file.

Afternoon: You shift gears to coordinate personal and business priorities.



You might be researching a specialized vendor or a new sports camp, taking the Founder’s ideas and thoughts, building out a clear plan for family logistics. Simultaneously, you're ensuring the kids' school and extracurricular schedules are aligned with the Founder’s calendar, so he can easily move from a late-day client meeting to a family commitment.

Evening: While the workday has officially ended, you remain a reliable point of contact for the unexpected. A text comes in about a last-minute change to a dinner reservation or a field change for a lacrosse game, and you handle the logistics immediately so the plan stays on track.

You’ll Thrive Here If...

- You Are a Natural Navigator: You don’t just follow a schedule; you create a flow. You anticipate needs three steps ahead and "pick up the rhythm" of a fast-moving leader before anything is said.
- You Are a "Translator" of Ideas: You love taking a half-baked thought or a high-level vision and building the structure around it. You know how to provide the "why" and the "how" so others can succeed.
- You Possess Professional Guts: You are confident and honest. You aren't afraid to provide direct feedback to the Founder about schedule feasibility or to push back when things aren't working. You're a partner, not a "yes" person.




- You Have a High Bar for Discretion: You handle sensitive financial data and family dynamics with total integrity. You understand that in this world, trust and integrity are what matters.
- You Are "Tech-Fluent": You navigate CRMs, family calendar apps, and modern productivity tools with ease, always looking for ways to use technology to create more time for the Founder.

The Trade-Off The pace here is fast, and the expectations are exact. This role requires you to be on-site and fully present in our downtown Toronto office because the Founder and the business rely on your immediate partnership. You are the person who keeps the wheels turning, and that requires a "no-task-too-small" attitude and a sense of ownership over the outcome, not just the task.

The Perks

- High-Impact Partnership: You aren't support staff; you are a primary navigator. When the Founder’s day is seamless and the business is growing, it’s because of you.
- Total Rewards: A market-competitive salary of $90k–$100k plus a performance-based bonus tied to the success of the business.
- A Growing Legacy: Work with a firm that is entering its next iteration. You will be a key part of building the team structure from the ground up.
- Beautiful Downtown Space: We are currently near University Ave and moving soon to a current, modern space in the King East/Bay area.

If you need any accommodations or support to participate in our recruitment process, please let us know. You can reach out to Ashley at [email protected] and we’ll work with you to make sure you have what you need to do your best.

📌 Executive Assistant (Toronto)
🏢 Primary People Group
📍 Toronto