Making The Grade

Tom Castley built his reputation launching European operations for US-based SaaS companies, and after years in Revenue leadership, he's landed on an idea that cuts against almost everything sales training tells us: that the answers a prospect gives you are the least reliable part of a sales conversation.

The theory came from an unlikely place...hostage negotiation training with a man who once talked a protester down off a crane on Tower Bridge. Tom realised that almost everyone moderates their answers, especially in high-stakes conversations, but questions are different. Nobody can lie when they ask a question. Over the past year, he's rebuilt his methodology for reading a deal, not around what prospects tell his reps, but around what prospects ask them.

In this episode, Tom unpacks why deals where pricing questions arrive before value questions are twice as likely to be lost, why questions that repeat across calls are a red flag nobody looks for, and why silence is often the loudest signal of all. 

📚 Episode Chapters

03:10 - Why Questions beat Answers in Sales Conversations 
08:00 - Reading Deal Signals in 2026 
15:50 - Operationalising with AI 
21:10 - Rethinking team capacity in the age of AI 
25:00 - The Six Levels Framework 

🎧 Continue listening… 

Make sure you listen to Pete Crosby’s Honest Lessons on the One to Ten Million Journey
 

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If you're a CRO in the middle of 2027 planning, there's a good chance your board has already asked what AI is going to do for your conversion rates. 

Shabri Lakhani, CRO at ScreenCloud, got the same question. She's finished her plan, and shares the ins and outs of how she got there and what to keep in mind when it’s your turn, in today’s episode. 

Over the next 30 minutes, you’ll hear exactly how she built that plan: how she separated genuine strategic bets from AI hype, the "what are you going to stop doing" exercise she ran across her whole leadership team, and how she'd make the case for an enablement leader, which she thinks is still one of the most under-argued investments in Revenue leadership. 

📚 Episode Chapters

02:05 - Planning before the benchmarks 
04:15 - Assumptions, uncertainty & AI for FY27 
11:10 - AI’s impact on sales productivity and planning 
24:55 - The role of enablement & ROI measurement 
33:30 - Advice for future CROs

🎧 Continue listening… 

Make sure you listen to Adam Kay on scaling Revenue teams & rebuilding sales processes in the AI-era 

Enjoyed today's episode of Making The Grade?

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Adam Kay has built his career joining early-stage, founder-led businesses, most recently as CRO at GoodFit - the intelligence layer behind modern go-to-market. 

In this episode, Adam shares the biggest lessons that now shape everything from hiring to how he builds sales processes from scratch and how AI has become both a validator and a leveller. 

No matter if you’re an aspiring CRO, have recently stepped into the role or are currently navigating the ever-changing scope of the role, Adam candidly shares his biggest lessons, mistakes and shifts in the industry he’s witnessed over the last 20 years. 

📚 Episode Chapters

02:30 - Lessons from scaling sales teams
05:30 - Building sales processes 
09:00 - Mapping the buyer’s journey
16:20 - Frameworks and customisation in sales methodology 
18:00- Misalignment between sales & buyer behaviour 
31:30 - Nailing your ICP & common pitfalls 

🎧 Continue listening… 

Make sure you listen to Harrison Rose on repeatable GTM and scaling beyond Founder-Led Sales

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Jeremy Radcliffe has led revenue teams for over 25 years. Long enough to have watched several waves of "the next big shift" come and go. In this episode, we dive into what’s actually different about this current shift and the AI era. 

Jeremy walks through three ways AI is reshaping the CRO role: workforce design questions that barely existed a few years ago, product and revenue converging as product usage data becomes a better predictor of growth than CRM activity, and the CRO increasingly operating as a change leader rather than a pure sales manager. He's candid about where AI has genuinely changed his own day-to-day thinking, and equally candid about which parts are just hype and won’t stick in the long run. 

📚 Episode Chapters

02:15 - The evolving role of CRO in the age of AI 
05:30 - AI’s impact on day-to-day operations
07:30 - Navigating AI hype vs reality 
11:00 - Balancing automation and human touch 
12:30 - The future of SDRs in an AI-driven world 
24:00 - Lessons from a fractional CRO
 

🎧 Continue listening… 

Make sure you listen to Natalie Johnson on what it really takes to win in the US
 

Enjoyed today's episode of Making The Grade?

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Hannah Garner didn't set out to become a CRO. She joined Arctic Shores as VP of Marketing with an eye on the CMO seat, but found herself stepping into revenue leadership instead. 

In this episode, Hannah shares what that transition actually felt like - from the imposter syndrome that came with the transition to the advice from fellow CROs that helped her push through it. She also unpacks how to differentiate in an AI-saturated market and how AI is changing what “good hiring” actually looks like. 

📚 Episode Chapters

03:30 - Hannah’s journey to CRO
09:00 - Insights on Revenue Leadership
15:00 - Navigating Imposter Syndrome
20:50 - The importance of Brand differentiation 
31:00 - Hiring in the AI era 
 

🎧 Continue listening… 

Make sure you listen to Robert Newry’s transition from CEO to Chief Explorer at Arctic Shores 
 

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What happens when the investor everyone expects to say ‘yes’ tears your Go-To-Market plan apart in front of 15 people?

For Alex Olley, Co-Founder and CRO of Reachdesk, that moment at his Series B in 2021 became the inflexion point of his career as a Revenue Leader. 

In this episode, Alex tells us the full story from that shocking investor meeting to the coaching relationship that changed his career and Reachdesk forever. We also touch on how Alex is deploying AI today - from surfacing high-intent accounts to using outbound and business cases and why he believes efficiency without accuracy is a trap. 

It's a conversation about the line between the art and the science of selling, and what it actually takes to go from good to great as a CRO. 

📚 Episode Chapters

04:00 - The Series B wake-up call 
13:00 - Lessons on Sales Rigour 
23:30 - Art vs Science in Sales 
25:00 - Applying AI without losing creativity 
29:00 - The importance of unit economics for CROs 
 

🎧 Continue listening… 

Make sure you listen to Season 2 with Sam Jacobs on building for efficient growth

Enjoyed today's episode of Making The Grade?

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✔️ Leave us a rating and review on your favourite podcast platform.
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Every CRO has had this moment: the deal that should've closed and didn't, the board meeting where the numbers didn't add up the way you'd hoped, the realisation that what got you here won't get you to the next stage. 

This season of Making The Grade is built around that moment, and what the best Revenue Leaders do differently once they've had it.

This season, we sat down with CROs and Revenue Leaders across enterprise SaaS and early-stage scale-ups to find out what's actually changing in Go-To-Market. Alex Olley shares the wake-up call that reshaped how he runs revenue today. Tom Castley makes the case that the questions your prospects ask reveal more than the answers they give you. And Laura Moniz de Aragão argues that in enterprise sales, AI is making the best human sellers more valuable, not less. 

And those are just a few of the brilliant CROs we're sitting down with to really look under the hood of some of the fastest scaling businesses and the challenges they face, ready for you to learn from and apply to your day to day as a Revenue Leader. 

Don't forget to hit subscribe to be the first to listen to fresh episodes every Thursday morning, wherever you get your favourite podcasts.

Enjoyed today's episode of Making The Grade?

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What does it actually take to build a world-class sales culture? 

Amelia Scott knows better than most. She spent nearly seven years at Culture Amp, joining as a senior AE when the business was at $15M ARR and leaving as VP of Global Sales at $170M. 

During her tenure, she took the EMEA business from $1.5M to $40M, and learned some hard, invaluable lessons along the way about talent, culture, regional expansion and what revenue leadership actually requires.

Now working as a fractional CRO, Amelia is right at the sharp end of how AI is reshaping the GTM function. 

In today’s Making The Grade episode, she shares what she's learned across both sides of that journey, how to build sales teams without a commission structure and where AI is genuinely delivering ROI right now.

📚 Episode Chapters

02:10 - Culture Amp’s scaling journey 

08:50 - Scaling without sales commission  

11:30 - How to expand into multiple regions 

21:00 - The evolving role of the CRO  

28:45 - Where AI is adding value & where the gaps are

Enjoyed today's episode of Making The Grade?

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✔️ Leave us a rating and review on your favourite podcast platform.
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What does it actually take to build a $45M ARR SaaS business without raising a penny of VC money? 

Guillaume Moubeche, Founder of Lemlist, knows better than most. Starting with just €1,000 and rejections from 30 VCs, Guillaume built one of the most recognised outbound sales tools in the world, bootstrapped, community-led, and stubbornly focused on doing fewer things better.

In this Making The Grade episode, Guillaume unpacks the full journey from building in public before it was fashionable, why the constraint of having no money forced the creativity that capital never could have bought, and his refreshingly honest reflections on what didn’t work along the journey. 

📚 Episode Chapters

04:10 - Bootstrapping in a crowded market

06:20 - Repeatability, Community and Content

13:00 - Bootstrapping advantages VC money can’t buy

25:00 - GTM & Hiring lessons from scaling to $45M ARR 

37:00 - The future of GTM in an AI-native world

Enjoyed today's episode of Making The Grade?

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✔️ Leave us a rating and review on your favourite podcast platform.
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What does an investor actually see when they look under the hood of a 1 to 10 Million journey? And what really separates the companies that break through from those that quietly stall?

We’re joined by Hillel Zidel, Managing Director at Kennet Partners, to find out. Kennet Partners invests in founder-led, capital-efficient B2B SaaS companies at precisely the stage where growth either compounds or gets stuck, making Hillel one of the most informed voices on what this journey actually takes.

In this episode, Tom and Hillel dig into the predictors he uses to assess whether a company will scale, the hidden dangers of moving from inbound to outbound too aggressively, and why the "shiny shoe" CRO hire so often ends in disappointment. 

This episode is essential listening for any founder or revenue leader navigating the 1 to 10 Million journey. 

📚 Episode Chapters:

01:50 - What changes at the 1 to 10 Million stage 

05:00 - Predictors of early-stage growth 

09:50 - The inbound to outbound danger zone 

15:30 - US Expansion: When it actually makes sense 

29:30 - What ‘marketable’ looks like today

🎧 Continue listening… 

Make sure you listen to From Chaos to Predictability: Pete Crosby's Honest Lessons on the One to Ten Million Journey

Enjoyed today's episode of Making The Grade?

If you took something valuable from the episode, we'd love for you to...

✔️ Leave us a rating and review on your favourite podcast platform.
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See you again next week!