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Matt McGinnis

Chief Product Officer at Rippling

Matt MacInnis is the Chief Product Officer at Rippling, a company specializing in unified workforce management solutions. Formerly the COO, he has played a significant role in the company's growth to a $16 billion valuation. Matt brings expertise in product management and leadership strategies to his role, focusing on innovation and organizational efficiency.

Episodes (1)

Insights (15)

Relentless Intensity Prevents Competitor Intrusion

leadership perspectives

Drawing on Apple experience, Matt argues teams must stay relentlessly engaged with no organisational downtime, or hungrier competitors will seize any gap.

8m

AI as Non-Judgemental Thought Partner for Executive Communication

leadership perspectives

Matt treats ChatGPT and Gemini as non-judgemental collaborators to refine executive communication, keeping only the best 20% of suggestions.

1h 24m

Learning From Success Outweighs Learning From Failure

quotes

Matt cites Parker’s view that successes teach far more than failures.

14m

Drucker's Effective Executive Remains Relevant After 70 Years

strategic thinking

He highlights Peter Drucker’s The Effective Executive for timeless, practical advice on leading teams that has stayed relevant for 70 years.

1h 29m

High Alpha, Low Beta Framework

strategic thinking

Use alpha for outsized upside and beta for volatility to balance creativity versus reliability in products and processes.

25m

Feature Flag Limitation Reduces System Volatility

case studies lessons

After a blank-screen bug, adding a single-flag rule to the checklist lowered future risk while keeping iteration speed.

29m

Notion's Narrative-Violating Persistence

case studies lessons

Notion iterated for four years, even relocating to Japan, and succeeded in a Google-Microsoft-dominated market through relentless craftsmanship.

54m

Conway's Law: Teams Ship Their Org Chart

strategic thinking

Locally optimised, globally incoherent teams will inevitably ship a similarly incoherent product, per Conway's Law.

19m

When to Quit Your Startup

leadership perspectives

If after four to five years and two or three pivots growth still isn’t obvious, shut down and start fresh.

49m

Rippling's Tough PM Case Study Evaluates Problem-Solving Depth

leadership perspectives

Rippling gives every PM the same tough case to judge depth, curiosity, and seniority by how far they drill into a hard problem.

37m

Extraordinary Results Require Extraordinary Efforts

quotes

Matt credits Dan Gill for the core principle driving his leadership.

5m

Rippling's Escalation Team Traces Root Causes

case studies lessons

Rippling created a specialist team that relentlessly traces customer-reported errors back through software and processes to eliminate underlying causes.

1h 11m

Two Ways to Make Money in Software: Bundling and Unbundling

quotes

Matt cites a classic maxim on software monetisation.

1h 18m

Move Fast In Proper Sequence

leadership perspectives

Move fast yet in sequence, grounding decisions in firsthand observations and first-principle reasoning instead of imported frameworks.

23m

Deliberate Understaffing Prevents Politics

strategic thinking

Matt McGinnis advocates deliberately understaffing projects because overstaffing breeds politics, waste and slows delivery, with wisdom in not under-understaffing.

10m