Yesterday was Star Wars Day — aka “May the Fourth be with you” — and it got me thinking, so I put together this blog post.
You might notice my title is “Operating Partner,” not “General Partner,” “Managing Partner,” or “Board Partner.” That’s intentional because I spend most of my time working directly with portfolio CEOs.
The Operating Partner role has its roots in private equity. Historically, Operating Partners are often former CEOs or COOs who use their experience to guide leadership teams, improve operational execution, and drive results, ultimately increasing the value of portfolio companies.
As far as I know, I’m the only former scale-up CEO in Canada who plays this role in an early-stage VC. At least, ChatGPT and Perplexity couldn’t find anyone else! Even in the U.S., this is very rare.
That said, I’ve always felt the “Operating Partner” title is a bit misleading. Unlike many private equity Operating Partners, I don’t step into full-time or part-time leadership roles within portfolio companies. I don’t give advice or directives either. Instead, I help CEOs solve their own problems rather than solving problems for them.
My single objective is to help portfolio CEOs improve the quality of their decisions by leveraging my experience.
Why? Most CEOs don’t need to be told what to do—they already know. Telling a CEO to grow their KPIs faster or hire great people is useless.
No CEO intentionally grows slower or hires bad people!
The real challenge for CEOs isn’t the what—it’s the how. This is where I come in, helping them navigate the how: strategic thinking, future-proofing, and decision-making that drive tangible progress, while staying alert to blind spots that could undermine success.
Hiring is an example. Many venture firms have talent partners who assist portfolio companies with recruitment. These partners, often from recruitment backgrounds, are excellent at sourcing candidates once roles are defined. However, they usually lack deep business context and may not fully understand the culture of the companies they’re supporting. This can result in untargeted candidates who don’t fit. I experienced this issue firsthand when I was a CEO.
That’s why I strongly favour internal recruiters who have an intimate understanding of the business and culture. Even so, recruiters typically get involved after roles are clearly defined. Before that, to design the organization, we need someone who has visibility into the broader perspective of the business. Only one person truly has it: the CEO. Besides, CEOS usually can’t ask their leaders about organizational design for obvious reasons.
That’s where I step in—well before recruiters are involved. I act as a sounding board for organizational design, considering not just immediate hiring needs but also how roles and teams will evolve over time. What level of talent should they hire now? When will this position need to level up? What downstream implications will these decisions have?
By addressing these questions early, I help ensure hiring decisions are aligned with the company’s long-term strategy and culture.
Of course, hiring is just one area where I provide support. Design future-proof stock option plans? Manage internal and external communication challenges? Interact with strategic conglomerates? Navigate inbound acquisition offers? Resolve leadership dysfunction? Handle unreasonable investors? Make board meetings more effective? Fend off super aggressive competitors or internet giants?
And yes, one of the most frequent requests I get is: “Can you help me with my pitch deck?”
Bring them on!
I’ve faced these challenges firsthand multiple times, and when CEOs bring them to me, I’m ready to share my war scars.
At the minimum, I help narrow the options from “I don’t know how” to a set of multiple choices. I don’t make decisions for CEOs; I help them make better ones. They are ultimately responsible for their decisions, and I see my role as a guide, not a decision-maker.
Being the CEO of a fast-scaling company is an enormous challenge that people should not underestimate—the level of experience, capacity, intensity, and mental strength that one needs to cope with. That’s why it is the loneliest job. Empathy is not enough. The best help I ever got was from a more experienced CEO than me at the time — someone who had walked the road ahead — and now it’s my turn to pay it forward. It is payback time for me.
The more I think about it, the less “Operating Partner” seems to fit. I don’t step into the spotlight or take over operations. My role is more like Yoda—helping Skywalker fight the battles while staying behind the scenes.
So perhaps my title shouldn’t be Operating Partner after all. Maybe it should just be… Yoda.
May the Force be with you!
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