Ego, Cash & GTM Discipline: Paul Fifield’s unfiltered lessons from building scalable businesses

What actually breaks a startup between £1m and £10m ARR isn’t usually the thing founders are obsessing over.

In this Making the Grade episode, we’re joined by Paul Fifield - one of the UK’s most experienced go-to-market leaders, and someone who’s lived the full spectrum from predictable revenue playbooks, to rocketship growth, brutal crashes, and the rebuild that follows.

Paul unpacks two defining failures in his career, and the patterns he now sees repeatedly in early-stage SaaS: messy data, woolly ICPs, uncontrolled SDR targeting, false confidence from renewals, and leadership decisions driven by ego rather than fundamentals.

Paul also shares why the GTM playbook is changing fast, what modern CRO capability looks like in 2026, and why AI won’t save teams that haven’t done the foundational work first.

If you’re a founder, CRO, VP Sales, or an Operator trying to help a business graduate from Series A to Series B - this one is a masterclass in what to do, what to avoid, and what to take seriously before the market forces you to.

📚 Episode Chapters

03:04 - Lessons from Failures and Successes 
24:04 - The impact of ego in leadership
28:13 - Scaling strategies from $1M to $10M 
35:05 - The evolving role of the CRO   
41:06 - Leaning into fractional talent as a startup  

🎧 Continue listening… 

Make sure you listen to Designing an AI-first Business - Bethany Ayers on hiring stage-fit leaders & the GTM playbooks that actually work in the AI era 

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