EPISODE · Dec 3, 2025 · 1H 18M
E.114 - In the AI Era, Weak Leadership Is Still Startups’ Greatest Risk w/ James Westlake
from WMYT - What makes YOU Tick? Tech Leaders Career Stories
Most people think startups fail because of product, funding, or go-to-market.But more often than not, it comes down to leadership.Not the big vision stuff — the day-to-day choices that shape culture, trust, and momentum.In this episode, Tolu and I sat down with James Westlake - a seasoned CRO and startup operator who helped scale Trustpilot and now works with SaaS founders to rebuild revenue, align boards, and lead under pressure.We talk about what actually breaks when leadership isn’t right, especially when you’re remote, scaling fast, and trying to harness the promise (and pressure) of AI.What we cover:– Why poor leadership is still the #1 reason startups stall– How to build trust and culture in remote, fast-changing teams– The real job of a startup CRO (and why most fail)– What to do when your GTM org feels off — but you can’t see why– The tension between speed, scale, and ethics as a leaderWho it’s for:Founders, CROs, and execs trying to grow fast — without burning people or breaking trust.If you’re leading a team in a remote, AI-shaped world… this one will hit home.Connect with James on LinkedIn https://www.linkedin.com/in/james-westlake/About Richard WashingtonRichard Washington is the host of Making Revenue Tick and a trusted authority for tech founders looking to hire and scale elite revenue teams. Known for his contrarian, practical approach, Richard helps startups avoid costly hiring mistakes, align GTM teams, and grow from early traction to sustained success.Follow Richard on LinkedIn: https://www.linkedin.com/in/richwash/Read Richard’s Newsletter Growth Magnet: https://www.linkedin.com/build-relation/newsletter-follow?entityUrn=7083793079794556928Subscribe for more conversations that go beyond tactics — and into what makes the people who build startups tick.#Leadership #StartupCulture #SaaSScaling #Trustpilot #CROInsights #GTMLeadership #RemoteTeams #AIandLeadership #WhatMakesYouTick #TickTalent #MakingRevenueTick
What this episode covers
Most people think startups fail because of product, funding, or go-to-market.But more often than not, it comes down to leadership.Not the big vision stuff — the day-to-day choices that shape culture, trust, and momentum.In this episode, Tolu and I sat down with James Westlake - a seasoned CRO and startup operator who helped scale Trustpilot and now works with SaaS founders to rebuild revenue, align boards, and lead under pressure.We talk about what actually breaks when leadership isn’t right, especially when you’re remote, scaling fast, and trying to harness the promise (and pressure) of AI.What we cover:– Why poor leadership is still the #1 reason startups stall– How to build trust and culture in remote, fast-changing teams– The real job of a startup CRO (and why most fail)– What to do when your GTM org feels off — but you can’t see why– The tension between speed, scale, and ethics as a leaderWho it’s for:Founders, CROs, and execs trying to grow fast — without burning people or breaking trust.If you’re leading a team in a remote, AI-shaped world… this one will hit home.Connect with James on LinkedIn https://www.linkedin.com/in/james-westlake/About Richard WashingtonRichard Washington is the host of Making Revenue Tick and a trusted authority for tech founders looking to hire and scale elite revenue teams. Known for his contrarian, practical approach, Richard helps startups avoid costly hiring mistakes, align GTM teams, and grow from early traction to sustained success.Follow Richard on LinkedIn: https://www.linkedin.com/in/richwash/Read Richard’s Newsletter Growth Magnet: https://www.linkedin.com/build-relation/newsletter-follow?entityUrn=7083793079794556928Subscribe for more conversations that go beyond tactics — and into what makes the people who build startups tick.#Leadership #StartupCulture #SaaSScaling #Trustpilot #CROInsights #GTMLeadership #RemoteTeams #AIandLeadership #WhatMakesYouTick #TickTalent #MakingRevenueTick
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E.114 - In the AI Era, Weak Leadership Is Still Startups’ Greatest Risk w/ James Westlake
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