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Toronto

Toronto

Welcome to the Toronto Chapter of the Chief of Staff Network — Canada's largest hub for operational leaders and strategic right-hands. Our chapter brings together Chiefs of Staff from Toronto's booming tech scene, financial institutions, and growing startups. Whether you're in the Financial District or the innovation corridor, this is your community to build genuine connections, share best practices, and navigate the evolving Chief of Staff role together.

Want to be a part of the CoS community?

We are an invite only community welcoming new members who meet the following criteria.

You are currently a Chief of Staff*
You work in the private sector (non-government)
You’re ready to actively participate in the community
*Your job title should include Chief of Staff in your public profile.
Join Us
Not a Chief of Staff yet? Contact Us

Toronto

Connect with senior Chiefs of Staff driving global business leadership.

Our chapters are supported by a network of top organizations across industries.

Toronto

Welcome to the Toronto Chapter of the Chief of Staff Network — Canada's largest hub for operational leaders and strategic right-hands. Our chapter brings together Chiefs of Staff from Toronto's booming tech scene, financial institutions, and growing startups. Whether you're in the Financial District or the innovation corridor, this is your community to build genuine connections, share best practices, and navigate the evolving Chief of Staff role together.

Join the Community

The Chief of Staff network has been incredibly helpful for me, and I honestly started seeing immediate value on Day 1 of joining.

The network offers numerous opportunities to further growth, development, and camaraderie - I think it'd be challenging to navigate the CoS role alone without this group of people.

Ali Sardinia

Chief of Staff, Order.co

An invaluable network offering impactful connections and a vast pool of knowledge. The ultimate brain trust for a generalist looking to learn and grow.

Alexandra Coleman

Chief of Staff at Hudson Valley Property Group

Our Chapter Leader

Mila Vukojevic leads the Toronto Chapter of the Chief of Staff Network. A five-time Chief of Staff who has supported seven CEOs and over ten founders, Mila is an operations, talent, and go-to-market expert with broad experience spanning Wall Street to startups. She has built 20+ key partnerships generating over $20MM in sales, hired 50+ early-stage operators, and advised 100+ VC-funded startups. Mila brings this depth of operational experience to the Toronto chapter, creating a space where Chiefs of Staff can share real-world strategies and grow together.

Chapter Events

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Toronto Chief of Staff Mixer (Wed Feb 18)
Feb 18

Toronto Chief of Staff Mixer (Wed Feb 18)

We’re excited to continue growing the Chief of Staff Network (COSN) community in Toronto. Despite winter weather challenges, the Toronto CoS community has shown strong momentum, with a committed group continuing to show up and engage. This next meetup builds on that consistency as we keep strengthening relationships and laying the groundwork for deeper programming later this spring. A special thank you to Mila Vukojevic for generously hosting and continuing to champion the Chief of Staff community in Toronto. Date & Time: February 18, 2026 at 5:30 PM Location: Shared upon confirmation of attendance This informal, in-person gathering will bring together Chiefs of Staff and adjacent operators across Toronto for relaxed conversation, meaningful connections, and candid discussion about the realities of operating in strategic leadership roles. As we maintain a regular cadence through the winter months, the focus is on community-building and connection, with plans for a more structured panel discussion once the weather improves. There’s no formal agenda — just a brief touchpoint on COSN and what’s ahead for the Toronto chapter, followed by open networking and shared stories from your experiences supporting founders and senior leadership. What to expect: A casual, welcoming environment Meaningful conversations with fellow Chiefs of Staff and operators Updates on upcoming Toronto programming, including a planned spring panel A small, curated group to encourage deeper connection Who is this event for? This meetup is for operators currently serving as Chiefs of Staff, Founders’ Associates, or in similar BizOps, strategy, or operations roles. Please include your current job title and company so we can verify your role and approve your registration. If you’re interested in helping shape the next phase of the Chief of Staff community in Toronto, we’d love to have you join us. Attendance will be capped to keep the group intimate — please RSVP to save your spot. For more information about the Chief of Staff Network and our upcoming events, programs, conferences, and more, visit: https://www.chiefofstaff.network/

Register
Chief of Staff Toronto Mixer (Wed Jan 21)
Jan 21

Chief of Staff Toronto Mixer (Wed Jan 21)

We’re excited to continue growing the Chief of Staff Network (COSN) community in Toronto. A special thank you to Mila Vukojevic for generously hosting and supporting the continued growth of the Chief of Staff community in Toronto. Date & Time: Wednesday, January 21, 2026 5:30 - 7:30 PM ET Location: Shared upon confirmation of attendance This informal, in-person gathering will bring together Chiefs of Staff and adjacent operators across Toronto for relaxed conversation, meaningful connections, and candid discussion about the realities of operating in strategic leadership roles. As we continue to build momentum locally, this meetup is focused on strengthening relationships and fostering a committed core community. There’s no formal agenda — just a brief touchpoint on COSN and what’s ahead for the Toronto chapter, followed by open networking and shared stories from your experiences supporting founders and senior leadership. What to expect: A casual, welcoming environment Meaningful conversations with fellow Chiefs of Staff and operators Updates on plans for strengthening the Toronto chapter A small, curated group to encourage deeper connection Who is this event for? This meetup is for operators currently serving as Chiefs of Staff, Founders’ Associates, or in similar BizOps, strategy, or operations roles. Please include your current job title and company so we can verify your role and approve your registration. If you’re interested in helping shape the next phase of the Chief of Staff community in Toronto, we’d love to have you join us. Attendance will be capped to keep the group intimate — please RSVP to save your spot. For more information about the Chief of Staff Network and our upcoming events, programs, conferences, and more, visit: https://www.chiefofstaff.network/

Register

Don't miss the next Chief of Staff Event in Toronto

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How the Toronto Chapter Connects

Our events are intentionally designed to foster trust, insight, and meaningful relationships.

Intimate Dinners

Small group dinners curated by topic or industry to foster deepconnection.

Roundtables

Facilitated discussions on specific challenges Chiefs of Staff face.

Happy Hours

Casual gatherings to meet new members and reconnect with old friends.

1:1 Coffee Chats

We match you with other local members for individual connections.

PRO+ Members Get Access to all Chief of Staff Network Community, Events & Programs

COSC events are exclusive experiences designed for PRO members bringing together curated conversations, expert insights, & high-value networking within the global community.
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