The CEO team

I often half-joke that at least a billion dollars of our valuation comes from creating the CEO team. And it’s only a half-joke because, while it’s hard to isolate the value of a single decision, I know with certainty that we’re a much better company because of it and that the CEO team is now an intrinsic part of how we operate.

But to fully understand how it works and why it exists, let me first explain the problem it’s solving and why we had to create it to enable our operational model.

Founder Mode doesn’t scale. Unless...

The CEO team solves a fundamental paradox of scaling: how do you execute “founder mode” (1) without becoming a bottleneck? Because regardless of how good you are, you are limited by the commonplace of human existence which is the fact that everyone has 24 hours in a day. No matter how talented you are, you can’t be in every meeting, review every decision, or guide every project. You need leverage to extend your presence without diluting your standards. That’s exactly what the CEO team provides: a way to scale your judgment and maintain your hands-on approach across the entire organization. In essence, the CEO team serves as a force multiplier, extending your reach and the impact of each 24-hour day.

Seven Samurai

But how do you structure the CEO team to maximize leverage without creating bureaucracy? If you're at scale (100+ people), start with a team of seven samurais (2), which seems to be the sweet spot. Larger teams require coordination over outcomes; smaller teams limit your leverage. This critical mass of seven gives you reach without the overhead. If you're not yet at scale, begin with a traditional Chief of Staff role and expand the team as your bandwidth decreases and the number of challenges that require your attention grows.

Now, what type of profile is able to provide this kind of high leverage? Although creativity is very much welcomed, what you need in your CEO team are execution machines. The ideal CEO team member is a generalist who thrives on operational excellence: defining plans, executing flawlessly, and solving problems on the fly. They work hard and adapt quickly.

In this regard, we found that the best candidates come from top-tier consulting or investment banking. Why? They’re trained to work at intensity, switch contexts rapidly, dive deep into new verticals overnight, and deliver under pressure (which is the basic day-to-day of these profiles) . Most importantly, they excel at pattern recognition across domains, essential because the CEO team touches every part of the organization. And although this is the prototypical CEO team member, I don’t think there should be a strict rule for defining the ideal profile. You should remain open to bringing in people from diverse backgrounds, not just those with a pedigree from a top-tier consulting or investment banking firm (3). 

The ultimate goal in setting up this team is to forward-clone your operational DNA into seven highly capable executors who can extend your judgment into every corner of the company. I believe that the constraints in terms of team size and the versatile nature of the profile to hire maximize the likelihood of this happening.

The finest steel has to go through the hottest fire.

Given their direct exposure to the leadership team and their proximity to the most critical challenges at Sword, the CEO team ends up being the best training ground for learning the Sword way.

In an organization set up for success, the problems that reach the leadership team are, by definition, the hardest ones—everything easier has already been solved as it goes through each rank. That means the CEO team, by supporting the leadership team, is constantly interfacing with the most complex, high-stakes issues. It’s a trial by fire which results in the best possible environment to learn and grow.

As a result, profiles on the CEO team tend to develop extremely quickly. Their rapid growth and high visibility make them highly sought after by other leaders at Sword, who often recruit them into senior operating positions where their skills can have the greatest impact.  As an added bonus, CEO team members who demonstrate exceptional creativity are also ideally positioned to lead the launch of our new solutions, as outlined in the Planting Seeds of Innovation Manual.

This dynamic is both expected and welcomed. In fact, success for the CEO team is paradoxically defined by the expectation that every 18 months there’s a full refresh of the team. This results in a virtuous cycle where we bring strong talent into the CEO team, they learn the Sword way by working on the toughest problems, they get pulled into other parts of the business, start creating value there which then open positions for new talent to join the CEO team. 

Dynamic elasticity

Another important contribution the CEO team brings to Sword is its ability to provide dynamic elasticity to each leader’s execution bandwidth.

One of the most common pitfalls in a high-growth company—where fires are constantly burning and opportunities are constantly emerging—is that leaders often lack the bandwidth within their existing teams to tackle every problem or pursue every high-impact opportunity. That’s where dynamic elasticity plays a powerful role.

Dynamic elasticity refers to a company’s ability to expand a team’s capacity as needed to meet the challenges it faces. The CEO team provides this elasticity by acting as a flexible pool of talent that can be rapidly deployed to the areas of greatest need.

This is especially important because not every team faces the same intensity of problems or effort requirements at all times. Effort levels fluctuate – at any given time, some teams will be operating at peak load while others are not. So how do you scale teams up or down in real time based on their current demands?

That’s where the CEO team plays a critical role. It provides dynamic elasticity by serving as a pool of high-quality talent that can be quickly deployed to whichever team needs it most – sometimes for just a few weeks, and in other cases, for as long as six months. The bigger the problem, the longer the commitment. And it's not just about deploying into other teams. It’s also about filling functional gaps where no one currently has direct ownership. That can happen when you're pursuing a new opportunity, opening a new area that needs interim leadership, or dealing with attrition that leaves a role vacant. In any of these cases, someone from the CEO team can step in and lead temporarily.

This is actually a critical piece, as it removes one of the biggest blockers to eliminating subpar managers. It’s natural for a leader to hesitate before letting someone go if there's no one ready to step in (doing so can create an even bigger problem). But when they have the option to tap the CEO team for interim leadership, that fear disappears, making it easier to build a higher-quality team.

And that’s why it’s so important that these profiles are generalists because they need to be able to work across domains equally effectively.

Mirror, mirror on the wall

An interesting phenomenon we've observed is how different leaders perceive the CEO team. Reactions to its existence and the way it operates across each vertical at Sword are often deeply polarized.

On one end, the best leaders embrace the CEO team. Like the CEO himself, they see it as a force multiplier – a way to extend their own bandwidth and accelerate progress on the problems they're eager to solve. They proactively engage, seek help, and use the CEO team as an operating partner.

On the other hand, the weakest leaders see the CEO team as a threat. For some, it undermines their narrative that their success is solely their own. For others, it’s the fear of being exposed – of having an external lens highlight everything they’ve been doing wrong. These leaders tend to operate like kings in castles: protective, opaque, and defensive. To them, the CEO team is a magnifying glass they’d rather avoid.

Ultimately, the CEO team’s presence becomes a mirror. Strong leaders use it to grow and be more successful. Insecure or weak leaders see it as something to fear.

One legitimate critique of this model is that the CEO team can create distance between the CEO and leadership team. Leaders may find themselves communicating primarily with the CEO team rather than directly with the CEO. This is a good argument against the model because the importance of leaders reporting directly to the CEO is clear: they align directly with the CEO on what's important, and nothing gets filtered in the process. Intermediate layers will always create some degree of this filtering. That said, I believe this is a fair price to pay in exchange for the leverage that Sword and I gain from the CEO team.