olivia_rossi

Hello

What I'm looking for next.

If you're reading this — thank you. Thank you for keeping me in mind, sending opportunities my way, or making an introduction when something feels like a fit.

I run operations for mission-driven organizations and creative businesses — building the systems, running the programs, and untangling the mess that comes with fast growth. Lately that's pulling toward organizations working on technology's impact on people: platform accountability, digital literacy, and the broader civic-tech space. I'm open to both fractional mandates and the right full-time role, wherever that lands.

The engagements I take on.

Where this is headed.

Engineer's rigour, founder's instincts.

I'm increasingly drawn to organizations working on technology's impact on people — platform accountability, digital literacy, digital privacy, and the society-technology intersection more broadly. My background runs from engineering through large-scale delivery across live events, media, and digital platforms, and I've spent the last few years as business manager for creators and independent media working in culture and media literacy.

If you have a funded program in this space and nobody to run it, that's the conversation I want.

The work I want to be doing.

Own high-stakes, cross-functional initiatives end-to-end
Build the operating systems and program architecture that let teams scale
Get stalled work moving again when the blocker is structural, not effort
Lead launches and time-boxed programs against a date that actually matters
Turn misaligned stakeholders into a working system for decisions and delivery
Bring operational rigour to organizations working on technology's impact on people
Step in as embedded senior leadership — whatever the title needs to be

A few examples.

Titles vary a lot from company to company, so I care much more about the work than the exact title. These are a few that make me think, yep, that.

Fractional / Consulting

Fractional COOChief of StaffStrategic Advisor

Full-time

Program DirectorHead of Program ManagementDirector of OperationsExecutive Producer

What I'm looking for in a client or company.

Engagement

Fractional, typically 2–3 days/week
Project-based, 6–10+ weeks
Or the right full-time role

Scale

Comfortable across the range
Independent creators to startups
Through established institutions

Industry

Education, events, media, and
mission-driven orgs — plus a pull
toward responsible tech & civic tech

Logistics

Based in Montréal
Open to remote, hybrid, or
in-person, depending on the work

Know of something that sounds like this?

If there's a good-fit mandate or role in your network, an intro would be incredibly helpful. And if you come across a company, project, or person you think I should know about, please send it my way.

Looking for ongoing program or operations support instead? See services. Building something and want a sharp second opinion? advisory.

I appreciate the help while I figure out what's next.

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