Making The Grade

ScaleWise, Tom Glason
  • 5.0 (1)
  • Entrepreneurship
  • Weekly

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 marketing strategies. All while making you leave every episode with actionable insights and expert advice to help you navigate these common Startup hurdles and thrive in a competitive market, showing that it can be done differently.

  1. 3d ago

    More Reps doesn’t mean more Revenue - Rob Massa on the new rules of scaling sales

    Rob Massa has been a CRO four times over more than a decade, seeing the role shift and change many times, and he's blunt about it: the old SaaS playbook is dead. At Juro, he's building the opposite.  A leaner team, higher quotas, no SDRs at all, and revenue growing faster than it ever has. The turning point came about a year ago, when Juro's CEO asked every department head the same question: if you were building your team from scratch today, knowing what you know now, how would you build it? In this episode, Rob shares what that actually looked like, including replacing SDRs with an AI system, flattening his management structure so senior people report straight to him rather than through layers, and promoting from within rather than betting on outside hires who don't know the business. He's equally candid about what didn't work the first time and the real challenges of turning peers into people you manage.  Tune in for candid reflections from a decade in the CRO seat.  📚 Episode Chapters: 04:15 - The evolution of the CRO role & skills needed 11:00 - Impact of AI on team structure and decision-making19:30 - Promoting talent from within the org 24:50 - The future of SDRs & AI  32:00 - Advice for aspiring CROs 🎧 Continue listening…  Make sure you listen to Bethany Ayers on designing an AI-first Business 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 podcast@scalewise.com ✔️ 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!

    More Reps doesn’t mean more Revenue - Rob Massa on the new rules of scaling sales

  2. Oct 29

    The Human Advantage - Laura Moniz de Aragão on why AI will make enterprise sales more human

    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 sales activity. What they want is scarce: real judgement, real insight, real trust. And that's exactly what AI can't manufacture.  In this episode, Laura unpacks what AI slop actually looks like, why she thinks most AI-assisted selling is optimising for the wrong thing entirely and where AI can actually make sellers more impactful.  📚 Episode Chapters: 03:30 - The skills AI can’t replace 10:00 - Redefining hiring and onboarding in the AI era16:00 - Laura’s AI toolkit22:40 - How to actually build executive trust 30:00 - The future skills and qualities of enterprise sellers 🎧 Continue listening…  Make sure you listen to Amelia Scott on The GTM Playbook that actually works in 2026.  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 podcast@scalewise.com ✔️ 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!

    The Human Advantage - Laura Moniz de Aragão on why AI will make enterprise sales more human

  3. Oct 22

    The Hostage Negotiator's Secret to Winning Deals - Tom Castley on the sales signals everyone ignores

    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    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 podcast@scalewise.com ✔️ 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!

    The Hostage Negotiator's Secret to Winning Deals - Tom Castley on the sales signals everyone ignores

  4. Oct 15

    Building a plan your board will believe - Shabri Lakhani on separating real bets from AI hype in your 2027 planning

    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? 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 podcast@scalewise.com ✔️ 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!

    Building a plan your board will believe - Shabri Lakhani on separating real bets from AI hype in your 2027 planning

  5. Oct 8

    Scaling Revenue Teams & Rebuilding Sales Processes - Adam Kay’s Playbook for AI-era Sales

    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 teams05:30 - Building sales processes 09:00 - Mapping the buyer’s journey16:20 - 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 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 podcast@scalewise.com ✔️ 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!

    Scaling Revenue Teams & Rebuilding Sales Processes - Adam Kay’s Playbook for AI-era Sales

  6. Oct 1

    25 Years of Sales Leadership rewritten by AI - Jeremy Radcliffe on balancing human touch and automation in Sales

    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 operations07:30 - 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? 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 podcast@scalewise.com ✔️ 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!

    25 Years of Sales Leadership rewritten by AI - Jeremy Radcliffe on balancing human touch and automation in Sales

  7. Sep 24

    Transitioning from CMO to CRO - Hannah Garner on stepping into the CRO seat & hiring in the AI era

    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 CRO09:00 - Insights on Revenue Leadership15:00 - Navigating Imposter Syndrome20:50 - 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   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 podcast@scalewise.com ✔️ 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!

    Transitioning from CMO to CRO - Hannah Garner on stepping into the CRO seat & hiring in the AI era

  8. Sep 17

    The Coaching Relationship That Changed Everything - Alex Olley on building Go-to-Market rigour at Reachdesk

    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? 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 podcast@scalewise.com ✔️ 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!

    The Coaching Relationship That Changed Everything - Alex Olley on building Go-to-Market rigour at Reachdesk
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About

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 marketing strategies. All while making you leave every episode with actionable insights and expert advice to help you navigate these common Startup hurdles and thrive in a competitive market, showing that it can be done differently.

Information

  • Creator
    ScaleWise, Tom Glason
  • Years Active
    2025 - 2026
  • Episodes
    31
  • Rating
    Clean
  • Copyright
    © 2025 ScaleWise
  • Show Website
    Making The Grade

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