Brad Jacobs designs org charts based on the optimal structure for achieving goals, defining necessary roles first. He resists shaping the chart around existing employees and their "fiefdoms." This role-first approach means leaving a seat empty is preferable to filling it with a poor fit, ensuring the structure dictates personnel, not the other way around.

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Don't think of AI as replacing roles. Instead, envision a new organizational structure where every human employee manages a team of their own specialized AI agents. This model enhances individual capabilities without eliminating the human team, making everyone more effective.

Founders often believe they can hire one "integrator" (like a COO) to handle all operational details. This is a myth. True scaling requires hiring specific, talented functional leaders (e.g., Head of Sales, Head of Product) who can solve a single, major business constraint, not a generalist helper.

Recoiling from Flipkart's complex leveling system (which spawned an "SD 2.5" role), PhonePe's CTO implemented a flat hierarchy with minimal titles. This structure aims to focus engineers on impact and capability growth, rather than chasing promotions and labels.

In his review of thousands of org charts, serial acquirer Brad Jacobs flags managers with only one direct report as a key indicator of organizational bloat. He calls this "companionship" rather than management, highlighting it as an inefficient layer that slows communication, adds cost, and ultimately harms shareholder value.

Optimal product leadership structures separate the long-term, visionary role from the tactical, execution role. One person focuses on the big picture and selling the future ("the house"), while the other translates that chaos into immediate, actionable work ("fixing the walls").

Treat organizational structure as a product designed to solve a business problem. The combined CPTO role isn't inherently good or bad; it is often a specific solution for when a non-technical CEO needs a single, decisive tie-breaker between product and technology.

To avoid bureaucratic bloat, organize the company into small, self-sufficient "pods" of no more than 10 people. Each pod owns a specific problem and includes all necessary roles. Performance is judged solely on the pod's impact, mimicking an early-stage startup's focus.

Ather's founder learned that hiring senior leaders for non-core functions too early fails due to value system clashes. Founders must first build the function themselves, establish principles, hire into that mold, and only then step back. This ensures cultural alignment.

Instead of asking employees what they do, map your core business processes (e.g., customer acquisition). Then, assign each step to a person. This bottom-up approach reveals who is truly driving value and who is overburdened, leading to more accurate role definitions based on business impact.

Shift from departments staffed with people to a single owner who directs AI agents, automations, and robotics to achieve outcomes. This structure maximizes leverage and efficiency, replacing the old model of "throwing bodies" at problems.

Build Your Org Chart Around Ideal Roles, Not Existing People | RiffOn