Chief of Staff - Private AI

Location: Toronto, Canada (Hybrid – onsite 2-3 days/week)

Private AI is hiring a Chief of Staff to serve as the operational backbone for our Managing Partner and CEO. This is a hands-on role for someone who thrives on bringing order to chaos, building systems that scale, and freeing up executive capacity so leadership can focus on the highest-leverage work.

We're looking for someone who can own everything from calendar architecture and inbox management to vendor negotiations and team coordination—while also contributing to our social media presence and external communications. You'll be the routing layer between the CEO and the rest of the organization, ensuring nothing falls through the cracks and that systems exist to handle anything that comes up twice.

This role is ideal for someone with early-stage software experience who understands the pace and demands of a startup environment, and who wants to grow alongside a company building at the frontier of AI.

What You'll Do In This Role

Own the CEO's operational infrastructure

• Build and manage the calendar architecture: know when calls should be booked, when deep work is protected, and what types of meetings belong where—without needing to ask.

• Implement an EA-managed email system: triage inbox, prioritize, draft responses, and surface only what requires direct attention.

• Create and maintain SOPs for everything done more than once—travel, hiring, vendor management, meeting prep, and more.

Be the routing layer for the organization

• Serve as the primary point of contact between the CEO and internal teams, portfolio companies, and external stakeholders.

• Parse unstructured brain dumps into organized, actionable tasks using tools like Asana and Zapier.

• Ensure follow-ups happen, deadlines are met, and nothing important gets lost.

Build systems that scale

• Document institutional knowledge so operations don't depend on any single person's memory.

• Create onboarding materials, playbooks, and templates that let new team members become productive in days.

• Own security and access documentation—know who has access to what, and ensure proper oversight.

Support social media and external presence

• Assist with content creation for LinkedIn, Twitter/X, and other relevant channels.

• Coordinate with leadership on thought leadership content, announcements, and founder-facing communications.

• Help build a repeatable cadence for external visibility.

Manage vendors, logistics, and special projects

• Handle vendor selection, negotiations, and relationship management.

• Coordinate travel, events, and any tasks requiring in-person execution.

• Take on high-priority projects as they arise—this role will evolve as the company does.

Who You Are

• You have 2-5 years of experience in operations, chief of staff, executive assistant, or similar roles—ideally at an early-stage software or AI company.

• You're obsessively organized and love building systems that make things run smoother.

• You can take a messy brain dump and turn it into clear, prioritized tasks without needing hand-holding.

• You're comfortable with ambiguity and can make judgment calls when the playbook doesn't exist yet.

• You communicate clearly and directly—written and verbal.

• You're based in Toronto and willing to be onsite 2-3 days per week.

• You already use AI tools to accelerate your work—research, drafting, automation, whatever gets the job done faster.

Bonus points if:

• You've worked directly with founders or executives in a high-trust, high-access capacity.

• You have experience with social media content creation or managing executive presence online.

• You've built SOPs, playbooks, or operational documentation from scratch.

• You're familiar with tools like Asana, Notion, Zapier, and calendar/email management systems.

• You've worked in venture capital, startups, or adjacent ecosystems.

Why Join Us

Private AI has raised tens of millions of dollars from top-tier investors including Microsoft, and we're growing fast with major enterprise customers you'd recognize. We're not dependent on external funding to survive—we have real revenue, real traction, and a sustainable business.

Our technology is built on differentiated PhD research in one of the hottest spaces in tech: the intersection of data privacy and artificial intelligence. As AI adoption accelerates, every company is grappling with how to use these tools without exposing sensitive data. We're solving that problem.

In this role, you will:

• Work directly with the CEO and Managing Partner, gaining exposure to both company-building and investment decision-making.

• Own a high-leverage role where your work directly multiplies executive capacity.

• Build systems and processes that will scale with a company on a steep growth trajectory.

• Have the autonomy to shape the role as you grow into it.

• Join a team that's building something that genuinely matters—not another nice-to-have SaaS product, but critical infrastructure for the AI era.

If you're someone who finds satisfaction in making things run, building systems that last, and freeing up brilliant people to do their best work, we'd love to hear from you.