Making The Grade

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 Chapters04:00 - 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? 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. ✔️ Share your ideas or guest suggestions with us at [email protected]✔️ Stay in the loop with the latest from Making The Grade and ScaleWise by following us on LinkedIn or YouTube. See you again next week!

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? 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. ✔️ Share your ideas or guest suggestions with us at [email protected]✔️ Stay in the loop with the latest from Making The Grade and ScaleWise by following us on LinkedIn or YouTube. See you again next week!

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? 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. ✔️ Share your ideas or guest suggestions with us at [email protected]✔️ Stay in the loop with the latest from Making The Grade and ScaleWise by following us on LinkedIn or YouTube. See you again next week!

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.  Plus, we look ahead and discuss what the future of outbound and the SDR realistically looks like in an AI-native world.    📚 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? 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. ✔️ Share your ideas or guest suggestions with us at [email protected]✔️ Stay in the loop with the latest from Making The Grade and ScaleWise by following us on LinkedIn or YouTube. See you again next week!

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. ✔️ Share your ideas or guest suggestions with us at [email protected]✔️ Stay in the loop with the latest from Making The Grade and ScaleWise by following us on LinkedIn or YouTube. See you again next week!