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  1. Lenny's Podcast: Product | Career | Growth
  2. This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)
This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

Lenny's Podcast: Product | Career | Growth · Aug 2, 2026

Whatnot CPO Tom Verrilli explains his philosophy: 'We regret that product management exists,' advocating for fewer, senior, hands-on PMs.

Whatnot CPO Tom Verrilli Believes Product Management Should Be a Regretted Necessity, Not a Default Role

The standard 'pod' ratio (1 PM per 6 engineers) infantilizes engineers and designers by removing their decision-making reps. Instead, Whatnot only hires PMs for specific, high-leverage needs, forcing other roles to build their own product muscle and raising the bar for adding PMs.

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot) thumbnail

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

Lenny's Podcast: Product | Career | Growth·2 days ago

Whatnot's CPO Is Down-Leveling PMs Who Specialize in "Politics" Like Stakeholder Management

Candidates who over-emphasize 'driving alignment' and 'stakeholder management' are red flags. This often indicates a specialty in internal politics rather than customer-oriented or technical skills. Whatnot prioritizes PMs who demonstrate both macro systems thinking and a bias for rapid execution.

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot) thumbnail

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

Lenny's Podcast: Product | Career | Growth·2 days ago

Whatnot's VPs and Directors Spend Over 50% of Their Time on IC Work, Not Pure Management

The traditional model promotes top PMs away from hands-on work. Whatnot reverses this by having senior leaders, including the CPO, spend most of their time as individual contributors. This keeps the best 'players on the field,' leading to faster, higher-quality decisions and a stronger connection to the product.

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot) thumbnail

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

Lenny's Podcast: Product | Career | Growth·2 days ago

A Lean Team of Highly Paid Senior ICs Is More Efficient Than a Bloated Hierarchy

Instead of funding a large hierarchy (a VP managing directors who manage PMs), a company can pay a few top-tier ICs VP-level salaries. This model is often more cost-effective and drives higher leverage, as these ICs can deliver the impact of a much larger team without the management overhead.

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot) thumbnail

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

Lenny's Podcast: Product | Career | Growth·2 days ago

Improve Systems Thinking by Mentally Simulating Both Success and Failure Scenarios for Every Decision

To develop systems thinking, go beyond the immediate outcome. Constantly ask: What if this experiment succeeds? What if it fails? How does my strategy change? What are the knock-on effects at 1000x scale? This mental exercise builds more robust, scalable solutions and preempts future risks.

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot) thumbnail

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

Lenny's Podcast: Product | Career | Growth·2 days ago

AI-Powered Data Analysis Tools Provide a Greater Productivity Leap for PMs Than Code Generation

AI tools for data analysis, like Hex, are the single biggest productivity unlock for PMs. They allow PMs to independently conduct sophisticated analysis in minutes that once took a senior data scientist weeks. This direct access to data enables faster, more informed decisions with less organizational dependency.

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot) thumbnail

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

Lenny's Podcast: Product | Career | Growth·2 days ago

The "Hire Great People, Get Out of Their Way" Mantra Can Be a Symptom of Lazy Leadership

This common mantra is often an excuse for leaders to avoid staying in the details. Effective leadership involves getting into the trenches to verify assumptions and provide crucial macro-context. A leader who clears their day to go deep on a problem builds a stronger, truth-seeking culture than one who just delegates.

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot) thumbnail

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

Lenny's Podcast: Product | Career | Growth·2 days ago

Adopt the "Play the Accordion" Method: Alternate Between Broad Strategy and Focused Execution

Effective product development requires a constant rhythm between expansive strategic thinking (pulling the accordion out) and focused, rapid execution (pushing it in). Over-indexing on either long-term roadmaps or mindless iteration leads to failure. This model balances learning with shipping.

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot) thumbnail

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

Lenny's Podcast: Product | Career | Growth·2 days ago

When Big Decisions Languish for Years, Blame Weak Leadership, Not "Complexity"

Drawing from his time at Twitter, Tom Verrilli argues that when an obvious, critical decision is debated for years (like lifting the 140-character limit), it's not a sign of complexity but of weak leadership. Indecisiveness disguised as diligence stifles necessary progress.

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot) thumbnail

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

Lenny's Podcast: Product | Career | Growth·2 days ago

Deprecating Features Based on Low Average Usage Can Inadvertently Kill Your Power Users' Core Workflow

Averages lie. A feature with low overall adoption might be critical for a valuable niche of power users. Killing it based on a surface-level '3% usage' metric, without understanding its importance to that cohort, can alienate your most dedicated customers and create unforeseen negative effects.

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot) thumbnail

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

Lenny's Podcast: Product | Career | Growth·2 days ago

A CPO Serving a Product-Minded Founder Should Avoid Overlap and Focus on Uncovered Areas

To succeed with a product-focused founder, a CPO must not compete for vision. Instead, they should actively step away from projects where the founder is deeply engaged to avoid the 'two dads problem' of conflicting instructions. The role is to fill gaps and provide leverage elsewhere.

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot) thumbnail

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

Lenny's Podcast: Product | Career | Growth·2 days ago

Mandatory Hands-On Case Studies Expose "Product Theater" During Hiring

Many candidates are skilled at presenting product frameworks but lack deep thinking. Whatnot uses a mandatory, hands-on case study for all roles. This step effectively filters for substance over style, as candidates must defend their analysis, quickly revealing those who rely on 'product theater.'

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot) thumbnail

This CPO regrets that product management exists | Tom Verrilli (CPO of Whatnot)

Lenny's Podcast: Product | Career | Growth·2 days ago