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Matt MacInnis: Why he deliberately understaffs every project

How Rippling stays lean with the PICL checklist and escalations: overstaffing breeds politics, cruft, and slowdown that block 99th-percentile outcomes.

Matt MacInnisguestLenny Rachitskyhost
Dec 27, 20251h 36mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Rippling CPO on intensity, understaffing, and ruthless product leadership

  1. Matt McInnis, Rippling’s CPO and former COO, shares a blunt, systems-driven view of leadership, insisting that extraordinary outcomes demand extraordinary, sustained effort and that organizations must be deliberately understaffed to avoid waste, politics, and bloat.
  2. He explains how he moved from COO to CPO to fix a locally optimized but globally incoherent product org, emphasizing bottom‑up systems thinking, lightweight process that lowers volatility without killing creativity, and an almost religious use of escalations and feedback.
  3. McInnis challenges common Silicon Valley narratives around “never quitting,” product‑market fit, and early‑stage startups, arguing you learn far more from winning teams than from failure and that founders often stay too long on ideas without true pull from the market.
  4. He also outlines why AI plus bundled, data‑rich platforms like Rippling will crush isolated point solutions, and why leaders must mirror founder-level intensity while remembering that business is ultimately “just a sport” on a tiny blue marble.

IDEAS WORTH REMEMBERING

5 ideas

Deliberately understaff projects to avoid waste and politics.

McInnis argues it’s always better to understaff than overstaff: extra people create politics, work on low‑priority items, cruft, and slowdown. The leadership art is knowing when you’ve gone from “lean” to “too lean,” but the default should be deliberate understaffing.

Extraordinary results require relentless, often uncomfortable effort.

If you want 99th‑percentile outcomes, you must accept 99th‑percentile effort—frequent escalations, late‑night problem solving, and running the organizational engine in the red for long stretches. When work feels consistently comfortable, something important is being missed.

Fight entropy with constant, visible intensity and feedback.

Systems naturally decay and teams drift toward local comfort. Leaders must continuously inject energy—escalating issues, calling out bugs, enforcing hiring rigor, and publicly modeling urgency—because each concentric layer away from the founder risks a 10x drop in intensity.

Use process to reduce volatility, but avoid suppressing creativity.

Borrowing the “alpha/beta” concept from finance, McInnis views process as a tool to lower beta (volatility) in mature, high‑reliability areas (e.g., payroll), while protecting alpha (upside/creativity) in zero‑to‑one and exploratory work. Over‑processing kills innovation; under‑processing creates chaos.

Anchor product quality in simple, evolving checklists.

Rippling’s PICL (Product Quality List) is a lightweight, evolving checklist of standards every product must meet before ship (e.g., test coverage, feature flags). Each real incident adds a new line item, steadily lowering volatility without drowning teams in bureaucracy.

WORDS WORTH SAVING

5 quotes

It is really important to me that we feel that we've deliberately understaffed every project at the company.

— Matt McInnis

If you want to be in the 99th percentile in terms of outcomes, it's gonna be really uncomfortable. If you ever find yourself in the comfort zone at work, you are definitely making a mistake.

— Matt McInnis

Teams will always optimize for local comfort over company outcomes. Your job as an executive, as a leader, is to fight that entropy tooth and nail every single day.

— Matt McInnis

We talk in Silicon Valley about never quit, but that is complete, absolute venture capital bullshit.

— Matt McInnis

Life is amazing... If you remember how insignificant we are and all of this is, it brings this levity to what we do. Play the sport, play it with everything you've got, but never forget that it's just a sport and that none of it matters.

— Matt McInnis

Extraordinary outcomes requiring extraordinary, sustained effortDeliberate understaffing, prioritization, and anti-bloat culture at RipplingTransition from COO to CPO and rebuilding a dysfunctional product orgFrameworks for hiring, process design, and product quality (alpha/beta, SPOTAK, PICL)Real product‑market fit vs. delusion, and when founders should quitPower laws, entropy, and preserving founder-level intensity in organizationsAI’s impact on SaaS, bundled platforms, and the centrality of first‑party data

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