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 perspectivesDrawing on Apple experience, Matt argues teams must stay relentlessly engaged with no organisational downtime, or hungrier competitors will seize any gap.
AI as Non-Judgemental Thought Partner for Executive Communication
leadership perspectivesMatt treats ChatGPT and Gemini as non-judgemental collaborators to refine executive communication, keeping only the best 20% of suggestions.
Learning From Success Outweighs Learning From Failure
quotesMatt cites Parker’s view that successes teach far more than failures.
Drucker's Effective Executive Remains Relevant After 70 Years
strategic thinkingHe highlights Peter Drucker’s The Effective Executive for timeless, practical advice on leading teams that has stayed relevant for 70 years.
High Alpha, Low Beta Framework
strategic thinkingUse alpha for outsized upside and beta for volatility to balance creativity versus reliability in products and processes.
Feature Flag Limitation Reduces System Volatility
case studies lessonsAfter a blank-screen bug, adding a single-flag rule to the checklist lowered future risk while keeping iteration speed.
Notion's Narrative-Violating Persistence
case studies lessonsNotion iterated for four years, even relocating to Japan, and succeeded in a Google-Microsoft-dominated market through relentless craftsmanship.
Conway's Law: Teams Ship Their Org Chart
strategic thinkingLocally optimised, globally incoherent teams will inevitably ship a similarly incoherent product, per Conway's Law.
When to Quit Your Startup
leadership perspectivesIf after four to five years and two or three pivots growth still isn’t obvious, shut down and start fresh.
Rippling's Tough PM Case Study Evaluates Problem-Solving Depth
leadership perspectivesRippling gives every PM the same tough case to judge depth, curiosity, and seniority by how far they drill into a hard problem.
Extraordinary Results Require Extraordinary Efforts
quotesMatt credits Dan Gill for the core principle driving his leadership.
Rippling's Escalation Team Traces Root Causes
case studies lessonsRippling created a specialist team that relentlessly traces customer-reported errors back through software and processes to eliminate underlying causes.
Two Ways to Make Money in Software: Bundling and Unbundling
quotesMatt cites a classic maxim on software monetisation.
Move Fast In Proper Sequence
leadership perspectivesMove fast yet in sequence, grounding decisions in firsthand observations and first-principle reasoning instead of imported frameworks.
Deliberate Understaffing Prevents Politics
strategic thinkingMatt McGinnis advocates deliberately understaffing projects because overstaffing breeds politics, waste and slows delivery, with wisdom in not under-understaffing.