Paul Fifield shares brutally honest lessons from scaling companies - why renewals can mask product risk, why cash discipline matters, and what CROs must master in 2026 as AI reshapes GTM.
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