ScaleWise, Tom Glason
Making The Grade
Less than 1 in 100 Startups manage to achieve funding beyond Series D or an exit. Investors typically expect 8 out of 10 of the businesses they invest in to fail. It’s time to make building a business less depressing and scale more wisely. Tune into Making The Grade to hear first-hand experiences of venture-backed software companies in their journeys from Seed to Series B funding. Every week, we’ll be joined by Founders, Investors and senior Go-To-Market Leaders to explore the factors driving the decline in graduation rates, misaligned go-to-market operations and ineffective sales and marketin...
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Autor
ScaleWise, Tom Glason
Categoría
Web del podcast
Último episodio
29 de oct. de 2026
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Episodios
The Human Advantage - Laura Moniz de Aragão on why AI will make enterprise sales more human 29.10.2026 32:22
Laura Moniz de Aragão has spent her career in long, complex enterprise sales - the seven- and eight-figure deals that take 12 to 24 months and live or die on trust with a handful of executives. So when the conversation turns to AI making sellers redundant, she pushes back hard: in her world, she argues, AI is about to make the human seller more valuable, not less. Buyers were never asking for more...
The Hostage Negotiator's Secret to Winning Deals - Tom Castley on the sales signals everyone ignores 22.10.2026 35:13
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 talk...
Building a plan your board will believe - Shabri Lakhani on separating real bets from AI hype in your 2027 planning 15.10.2026 36:29
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 e...
Scaling Revenue Teams & Rebuilding Sales Processes - Adam Kay’s Playbook for AI-era Sales 08.10.2026 34:49
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, hav...
25 Years of Sales Leadership rewritten by AI - Jeremy Radcliffe on balancing human touch and automation in Sales 01.10.2026 29:42
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...
Transitioning from CMO to CRO - Hannah Garner on stepping into the CRO seat & hiring in the AI era 24.09.2026 36:03
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...
The Coaching Relationship That Changed Everything - Alex Olley on building Go-to-Market rigour at Reachdesk 17.09.2026 32:12
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 hi...
Season 3 Trailer: What it takes to be a CRO in 2026 and beyond... 15.09.2026 5:51
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...
The GTM Playbook that works in 2026: Amelia Scott on scaling Culture Amp from $15M to $170M without sales commission 09.04.2026 39:53
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, regi...
Bootstrapping to $45M ARR: Guillaume Moubeche on scaling efficiently without any VC trade-offs 02.04.2026 47:40
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 Gr...
What Investors Really Look for: Hillel Zidel on the moves and decisions that make or break the One to Ten Million journey 26.03.2026 39:47
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 g...
From Chaos to Predictability: Pete Crosby's Honest Lessons on the One to Ten Million Journey 19.03.2026 41:48
If you're building a venture-backed software startup and trying to navigate the messy, exhilarating, often brutal stretch from $1M to $10M ARR, this episode is essential listening. In this Making The Grade episode, we’re joined by Pete Crosby , Founder of Revelesco and one of the most experienced revenue coaches in the UK startup ecosystem. Pete has helped countless founders and CROs find clarity...
Reshaping GTM in the AI Era - Harrison Rose on repeatable GTM and scaling beyond Founder-Led Sales 12.03.2026 44:50
Harrison Rose has lived the journey most founders only see from the outside. As Co-Founder of Paddle, he helped scale from zero to $100M+ revenue - without the “overnight success” story everyone loves to tell. Now he’s doing it again with GoodFit , turning the market-mapping and ICP systems Paddle built internally into a product built for modern GTM teams. In this episode, Harrison breaks down the...
From Inception to Acquisition: Natasha Ratanshi-Stein on scaling Surfboard, stage-fit hiring and the importance of founder-led sales 05.03.2026 49:09
Natasha Ratanshi-Stein has seen startups from almost every angle, as a VC, Operator, and Founder. After scaling customer service operations at Bulb, she saw firsthand how broken legacy workforce management tooling really was. That pain became Surfboard, and in today’s Making The Grade episode, Natasha is refreshingly honest about what founders underestimate in the £1 to £10M ARR journey, and her...
Ego, Cash & GTM Discipline: Paul Fifield’s unfiltered lessons from building scalable businesses 26.02.2026 44:27
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...
Designing an AI-first Business - Bethany Ayers on hiring stage-fit leaders & the GTM playbooks that actually work in the AI era 19.02.2026 42:18
Bethany Ayers isn’t experimenting with AI at the edges of Metomic; she’s using it to redesign how the company operates, with an ambitious goal of becoming an AI-first company. In this episode of Making the Grade, Bethany Ayers, CEO of Metomic , joins us to unpack what it really means to build an AI-first organisation, and how it impacts hiring decisions, GTM design, and leadership accountability....
Building for efficient growth - Pavilion’s honest growth journey & the real problem behind the short CRO tenure with Sam Jacobs 12.02.2026 42:13
Most growth stories celebrate momentum, but very few actually share the behind-the-scenes of what happens when momentum stalls. In this Making The Grade episode, we’re joined by Sam Jacobs , Founder & CEO of Pavilion - the community built to give in-seat GTM leaders the peers, frameworks, and rooms they need to operate under real pressure. Sam takes us on a journey from the early days of Revenue...
What it really takes to win in the US - Honest lessons from Natalie Johnson 05.02.2026 43:26
US expansion is one of the fastest ways for a venture-backed SaaS company to accelerate growth…or blow up months of momentum, burn a painful chunk of cash, and leave a trail of “scar tissue” behind. In this Making the Grade episode, Tom Glason sits down with Natalie Johnson , a seasoned revenue leader who’s lived the 1 to 10 million ARR journey multiple times - across the UK and the US - and now l...
Making The Grade - Season 2 Trailer 03.02.2026 6:08
Welcome back to Season 2 of Making The Grade. This season, we’re digging into what it really takes to scale beyond early traction… the ups and downs of the journey from £1 million to £10 million in ARR… and why so many startups are struggling to make that leap. Each week, we're joined by experienced Founders, Investors, and senior Go-To-Market leaders to unpack the lessons, trade-offs, and decisi...
From CMO to CRO: Florence Broderick on balancing growth with efficiency and the metrics that actually matter 02.10.2025 51:22
What does it really take to make the leap from CMO to CRO and to build a revenue function that actually scales? In the final episode of Season 1, Tom is joined by Florence Broderick , CRO at General Index , to unpack what it actually takes to make the transition to CRO and what founders should know before hiring their first CRO. Florence shares candid insights from her transition to CRO, why she...
From $60m Exit to Building an Era-Defining AI Company: Sean Williams on lessons from a start-up exit to building again with AutogenAI 25.09.2025 43:26
What do you think of when you hear ‘exited Founder’? Someone travelling the world or sitting on a remote island sipping cocktails? Today’s Making The Grade guest may change your perspective… We’re joined by Sean Williams , Co-Founder & CEO of AutogenAI , the AI bid writing software. Before AutogenAI, Sean co-founded Corndell Ltd, which he grew from scratch to 350 people and sold to THI Holdings...
Scaling Lean in a $500B Market: Ed Bartlett on going from zero to one & transitioning out of the CEO seat 18.09.2025 42:50
In the start-up ecosystem, there are a few truths that never change - scaling is harder than it looks, over-hiring can kill momentum, and knowing when to hand over the CEO reins might be the hardest call of all. In this episode, Ed Barltett , Founder & CEO of Hicomply , unpacks how to successfully scale with a lean team and build a GTM engine that actually produces an intent-led pipeline. Ed bre...
Running Your Own Race: Tom Lavery on going from bootstrapped to venture-backed 11.09.2025 37:15
What does it take to build a category-defining SaaS company when your biggest competitors have raised 40x more funding than you? In this episode, Tom Lavery , Founder & CEO of Jiminny , joins us to share how he bootstrapped for years before raising, why staying in control beats chasing hype, and how to layer AI into GTM without over-engineering your stack. Expect pragmatic tactics for capital-effi...
Bootstrapping Agorapulse to over $20M ARR with Emeric Ernoult 04.09.2025 38:28
Start-up headlines are often dominated by fundraising announcements and the latest valuation. But the Venture Capital route isn’t the only option or the best to take. In this episode, we’re joined by Emeric Ernoult, Co-Founder & CEO of Agorapulse, one of Europe’s most successful bootstrapped SaaS Founders. Emeric is a serial entrepreneur and has seen Agorapulse through several pivots and interna...
The 5 Silent Killers of Go-To-Market with Keji Mustapha 28.08.2025 33:54
Every founder thinks they’re focused on growth. But too often, hidden mistakes in their go-to-market (GTM) strategy quietly erode their chances of success. In this Making The Grade episode, we’re joined by Keji Mustapha , CMO at Partech , to unpack the 5 Silent Killers of Go-To-Market. From undefined ICPs and premature scaling, to misaligned leadership and ignoring the voice of the customer, Keji...
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