Strategic Initiative Operator

The vision exists. What's missing is someone who owns the distance between here and done.

I work with founders, executive directors, and operations leads at lean, ambitious organizations in content, media, education, and nonprofit. I embed, take structural ownership of the work that matters most, and stay until something tangible exists.

Let's talk about what you're building

The Problem

It's not a capability problem. It's a bandwidth and ownership problem.

In lean organizations, important work gets distributed across people who all have full plates. Without someone holding the whole thing, decisions don't happen and the work drifts. By the time there's a real problem, a lot of time has already been lost.

  • High-priority initiatives stall because no single person holds the full picture

  • The strategy and intent get lost as they move into execution

  • Accountability is so distributed it effectively belongs to no one

  • Leadership spends time coordinating things that shouldn't require them

  • Launches slip because there's no shared definition of what ready looks like

  • Progress sounds fine until the deadline, then suddenly it isn't

What I Do

I take ownership of the work your team can't afford to let drift.

Not as an advisor. Embedded, inside your systems and timelines, with accountability to outcomes and not just deliverables.

  1. 01

    Scoping and structuring from the start

    Turning a mandate into a real, executable program. Clear scope, sequenced milestones, mapped dependencies, and defined ownership before anything moves.

  2. 02

    Holding cross-functional work together

    Making sure the connective tissue between teams actually holds. Decisions happen, accountability is real, and the strategy that got approved is the one that ships.

  3. 03

    Getting stalled programs back on track

    Figuring out what actually broke and not just what looks broken, then building a credible path forward from wherever you are.

  4. 04

    Building the operating systems for next time

    Designing the rhythms, structures, and accountability patterns that make the next initiative run without constant escalation.

Who It's For

Built for lean, ambitious organizations where something real is on the line.

The context

Smaller independent organizations in content, media, education, and nonprofit. Places where the ambition is real but the infrastructure hasn't always caught up.

The moment

A high-priority initiative is behind or stalled. A launch is coming with no one accountable for making sure it actually happens. Something important has fragmented with no one holding the whole.

The person

A founder, ED, or operations lead who knows the work matters and is honest enough to recognize they can't give it what it needs right now.

Not the right fit if the environment is already fully optimized, there's no real mandate, or the initiative doesn't have the resources to see it through.

Who I Am

I've spent my career inside the gap between strategy and execution.

My background spans mechanical engineering, project and program management, event production, and two years of work alongside content creators, influencers, and larger brands on complex productions. I'm a generalist by design and not by default. What connects it all is a bias toward structure, a low tolerance for drift, and a track record of shipping things that weren't moving. I'm based in Montreal. I work with teams across North America.

Let's talk about what you're building
Olivia Rossi speaking at an event

Proof of Impact

Outcomes, not outputs.

50%

Reduction in implementation overruns within 90 days of operating model redesign

97%

On-time delivery rate across programs managed over the past three years

$40K+

In recovered annual spend identified through process audit on a single engagement

20%

Increase in team capacity after eliminating low-value coordination overhead

Startupfest · FWD50 · belairdirect · Intact Insurance · National Bank · Danone · Moët Hennessy · Independent content creators

Tell me what's stalled.

No pitch decks. No long intake forms. Just a conversation.

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