The Core 4: What Separates Elite Execs from Everybody Else

Hi — Asad here!

SaaS-era marketing had gotten real boring. Webinars, reports and corny booths — easy to measure, but never built to delight.

That’s what made Kyle Lacy special. While marketing went numb, Kyle gave us the Lessonly Llama and built board games — and still hit his number, like a guy who came up carrying a bag. Sadly, there weren’t many like him, and we were worse off for it.

Now, things are getting interesting.

You could say brand marketing is having its Golden Age, and AI’s writing the check. Cinematic launch videos, founders channeling Palmer Luckey to control the narrative, and — naturally — the celebrity cameos. Apparently Jude Law is what SaaS was missing.

Or, you could say we’ve wandered into a sea of sameness. Messaging that blurs together. Copy that looks right and reads wrong. The Michelin experience, sub the good food.

Both are a little true, which is why this feels like a fork in the road. One path leads us somewhere worse than the SaaS era we just escaped. The other is the fun one — and the one I hope we take.

As AI turns innovation into a commodity, brand becomes more important. If that’s so, then the market will drag us there eventually; we’ll just take a few wrong turns along the way.

Does Kyle see it that way? Only one way to find out = ▶️

And now, without further ado… let’s hear about what makes for a winning exec from GTM veteran Cassie Young.

Most executives are completely forgettable.

I should know — hundreds of new ones cross my desk every year through my work at Primary.

Plenty have track records of hitting numbers and building strong teams. But after years of operating in companies, sitting on boards, and watching leadership teams navigate the hardest moments of company-building, I’ve come to see those as the price of admission, and not what makes someone elite. So, what actually separates the best from everyone else?

A few years ago, Sam Jacobs asked me to deliver a keynote at Pavilion’s first-ever CRO Summit with a simple prompt: how not to get fired as a CRO. I love a spicy conference topic, so I obliged. But the moment I started crafting it, I realized the pitfalls I warned of applied to any execution function, not just CROs. Back then, I focused on two specific gaps that cost executives their jobs: P&L fluency and the First Team leadership principle championed by Patrick Lencioni. In the years since, I’ve further expanded that framework into four attributes that separate the best from the rest.

I call it “the Core Four.” These traits are evergreen, but in a world where we’re all eating, sleeping, and breathing AI, the penalty for ignoring them has never been steeper.

Attribute #1: P&L Fluency

Back in 2019, when I was still operating, my Insight board member Shelley Perry made a comment over dinner that parked itself permanently in my brain: The number one reason leaders stall out before reaching the C-suite is that they can’t walk their way through an income statement. She meant it both literally and figuratively.

The literal side is straightforward enough: Can you actually navigate through an income statement? Do you know where your function sits above or below the line? Can you articulate — without a finance cheat sheet — how your team’s work maps directly to revenue generation and margin expansion?

I started my career in a Wall Street analyst program, where these capabilities were drilled in. Today, AI has democratized financial-statement analysis, so there’s truly zero excuse for not leveling up. And to be clear: “Income statement” was the pithy version of Shelley’s comment. Real fluency means understanding all components of the company’s financial operations, from the income statement to the balance sheet, and everything in between.

Equally important were the figurative implications of Shelley’s imperative. Too many smart, hardworking leaders get trapped working in the business, instead of on it (h/t to my friend Lisa Lewin for that one!). They’re so loyal to their teams, and committed to the cause, that they get stuck doing the work and optimizing toward local maximums, while accidentally becoming functional advocates rather than business owners. It derails their careers.

The fix is deliberate and not complicated. Every initiative you put forward should have a financially-oriented outcome attached to it. Not “this will improve customer satisfaction.” Not “this will drive adoption.” Those are vanity framings. The only question that matters is how the initiative flows through to revenue or margin.

Here’s a CS example: If your data shows that customers who complete live bootcamps have materially higher net retention curves, don’t pitch enablement budget by citing satisfaction scores. Say: “The retention curve for trained customers is X points higher. Multiplied across the install base, that’s $Y in incremental ARR for the segment that attends.” Same initiative, entirely different frame — and one that actually gets funded.

Then, take it a step further, creating a “walk chart” that connects your initiatives directly to financial outcomes. For example:

Note: My favorite hack for improving financial command involves humans, not AI: Take your CFO (or any leader on the Finance team!) to lunch. Ask them how the board is pushing them. How they’re grading your function. What’s keeping them up at night about your department. My Finance friends aren’t drowning in social invitations, so there’s a strong likelihood they’ll accept. And talking shop with someone steeped in your own business is infinitely more powerful than another chat with Claude.

Attribute #2: First-Team Mentality

Patrick Lencioni popularized the concept, so I’ll give you the operational version: Your First Team is the most senior team you sit on — your peers, not your direct reports. So, a Chief Customer Officer’s First Team is the executive team (i.e., the CFO, CTO, CRO, etc.), not people like the Head of CSMs, Head of Implementation, and Head of Support, who are each other’s First Team. The Head of CSMs should be prioritizing their relationship with the Head of Support over their CSMs — mind-boggling, I know!

First-Teamthinkers avoid what I call the “swim lane trap,” when leaders advocate for their functions irrespective of what’s going on in the business at large. An example: I once had to sit through a board presentation in which a marketing leader celebrated — with genuine enthusiasm — that 90% of closed-won deals were sourced by his own team QoQ (see sanitized chart below).

The missing context? The company missed its plan, and the business was literally shrinking QoQ. It was like watching a bad car accident in real time. The reason: Marketing can’t be crushing it if the business isn’t crushing it. But neither can Sales. Nor Product or Engineering. Every function is either winning together or losing together, and it’s incumbent on executives to make sure the whole team understands that. Rising Directors and VPs are typically the worst offenders, so educate them on this dynamic early and often.

The antidote starts with naming the First-Teammetrics explicitly — the handful of numbers that, if you’re moving them, the company is winning — then, ensuring that every employee knows what they are. When I was CCO at Sailthru, we used the same shared metrics dashboard in every monthly All Hands for five consecutive years. The targets evolved (e.g., cash became EBITDA once we were cash flow positive), but the buckets endured. Transparency helped us to explain to a support agent that a 9/10 average ticket resolution score was meaningless to the business if we missed churn and NPS targets. Even more importantly, we aligned the executive compensation pool to three shared metrics: exit ARR, NPS, and net burn. You haven’t seen a product leader’s behavior change until you’ve seen a comp plan like that one.

Attribute #3: Macro Market Pulse (Especially: AI!)

At a bare minimum, executives must read the news. And I don’t just mean listening to The Daily. They must follow industry coverage, benchmarks, and thought leaders to develop an informed perspective on how the macro climate is hitting their customers, teams, and businesses.

But reading the news isn’t enough. They also have to apply their new knowledge to evolve their playbook. The leaders I see plateau most frequently are stuck in the rinse-and-repeat cycle, running yesterday’s strategies in today’s environment. What worked in 2021 simply won’t work in our present climate, where AI is the macro trend that matters.

And a substantive view alone won’t cut it. Executives must roll up their sleeves and build with the tools themselves. AI probably won’t take most executive jobs tomorrow, but ignorance 100% will. As the proverb says, “the best time to plant a tree was 20 years ago, the second best time is right now.”

This isn’t peripheral to your company’s product roadmap. It’s the most consequential macro trend of our professional careers. Do you have a view on how your company will fare in the SaaSpocalypse? If it’s grim, why are you still working there? Back to the P&L: Do you comprehend how AI is reshaping yours? Not just where it stands to improve revenue and reduce costs, but how it changes your pricing strategy when your engineering team is investing in inference and deliberately taking a hit to gross margin?

Attribute #4: Strategic Network

Networking as an act misses the point. The work is curating a strategic network. Quality over quantity. As Amy Butte (former CFO, Navan) told 100 executives at a recent event I hosted, great leaders work “outside in, not inside out.” Your ability to push your own thinking based on external inputs is hugely important, and the juicy stuff comes from live interactions, not blog posts. (Note: If you work on a distributed team, you have to be 10x more deliberate.)

But cultivating this network can’t be passive. It requires the same prioritization as the other three pillars, yet time and again, executives weasel their way out of the networking dinner. The dinner you skip because your inbox is driving you crazy — don’t do it! The lunch you cancel because it’s not urgent today — don’t cancel it. Your network creates compound interest that, over years, determines whether you operate with genuine leverage or in an information silo. I have some very close friendships that have emerged from a second- or third-order introduction from a coffee I dreaded attending. Don’t cancel!

Your network has always been important, but in the era of AI it matters more than ever. Our portfolio company Chief recently published a study with Harris Poll that revealed 86% of women leaders leverage their peer network as a competitive advantage in navigating AI strategy. Though the poll focused on women, the takeaway is broadly applicable: To level up your macro perspective, you have to invest outsized time in expanding and grooming your network.

Why All Four, Why Now

The Core Four are evergreen. But the market has raised the stakes across all of them simultaneously — and in ways that have no historical precedent.

Boards in 2025 rewarded effort narratives. That’s over. They want P&L impact from leaders who can demonstrate it across the entire business, not just their swim lane.

The executives who are winning right now are executing across all four pillars at once. They understand what every market in flux eventually reveals: In a compressed, AI-accelerated market, information asymmetry and network access are among the last remaining edges available to a leader.

Hitting your numbers will always matter. But it will never be enough to make you remarkable.

Embrace the Core Four.

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Cassie Young is a General Partner at Primary, a $1.6B AUM early-stage venture capital firm that backs category-defining companies like Chief, Alma, K Health, Dandy, Etched, and Vestwell. She invests in founders disrupting the B2B P&L and also leads Primary’s firm operations. Before joining Primary in 2020, Cassie spent 15 years in GTM operating roles, most recently as CRO at Sailthru through its PE exit, and at Marigold, where she oversaw a $200M+ martech roll-up.