Executive Function: Building Systems that Can Make Decisions without You | Jeanne DeWitt Grosser (COO, Vercel)

Why It Matters

Understanding these executive practices helps scaling tech firms build accountable leadership teams and align metrics with growth, reducing costly hiring missteps.

Key Takeaways

• Executive hiring requires rigorous, data-driven interview process.
• Driver trees align metrics with strategic objectives.
• COOs often oversee marketing to own customer experience.
• Scaling demands shifting from deep dives to high-level delegation.
• Feedback loops shape executive performance and culture.

Pulse Analysis

In today’s hyper‑competitive SaaS landscape, the ability to construct autonomous decision‑making systems is a hallmark of elite leadership. Jeanne De Witt Grosser leverages her decade at Stripe and her current role at Vercel to illustrate how executives can embed strategic intent into everyday operations. By treating the organization as a network of interlocking "driver trees," leaders translate high‑level goals into measurable actions, ensuring every team member understands how their work fuels revenue, reliability, or user growth. This metric‑centric mindset reduces ambiguity and accelerates alignment across product, engineering, and go‑to‑market functions.

The COO’s expanding remit, as highlighted by Grosser, often includes marketing because owning the end‑to‑end customer experience eliminates silos and creates a single source of truth for performance data. Vercel’s interview process reflects this philosophy: candidates are evaluated on their ability to think in systems, articulate metric drivers, and demonstrate cultural fit through scenario‑based workshops. Such rigor weeds out candidates who excel in isolated tasks but lack the holistic perspective needed to steer multi‑disciplinary teams. The driver‑tree framework also provides a transparent language for cross‑functional collaboration, enabling rapid decision‑making without constant senior oversight.

For fast‑growing tech firms, the transition from a hands‑on manager to a manager of managers is fraught with pitfalls. Grosser stresses the importance of stepping back, delegating deep‑dive analysis to trusted leaders while maintaining a high‑level view of strategic objectives. Continuous feedback loops—both formal reviews and informal coaching—anchor this shift, ensuring executives remain accountable while fostering a culture of relentless improvement. Companies that adopt these practices can expect higher retention of top talent, clearer strategic execution, and a reduced risk of costly executive mis‑hires, positioning them for sustainable scale.