Making The Grade
by ScaleWise, Tom Glason
Latest episode
More Reps doesn’t mean more Revenue - Rob Massa on the new rules of…
More Reps doesn’t mean more Revenue - Rob Massa on the new rules of…
About this podcast
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.
Episodes
The newest 20 of 31 episodes
- More Reps doesn’t mean more Revenue - Rob Massa on the new rules of scaling sales · 37 min · Season 3 Episode 8Juro CRO Rob Massa on why he cut 20% of his team, replaced his SDR function with AI, and built a leaner, faster revenue organisation that's growing ARR quicker than ever. Candid…
- The Human Advantage - Laura Moniz de Aragão on why AI will make enterprise sales more human · 32 min · Season 3 Episode 7Unmind CRO, Laura Moniz de Aragão, on why AI is making the human side of enterprise selling more valuable, not less - from spotting AI slop to the test she uses to measure real…
- The Hostage Negotiator's Secret to Winning Deals - Tom Castley on the sales signals everyone ignores · 35 min · Season 3 Episode 6Tom Castley on the sales methodology he built around a simple idea: that prospects' questions reveal more truth than their answers, and how it's reshaping his forecasting…
- Building a plan your board will believe - Shabri Lakhani on separating real bets from AI hype in your 2027 planning · 36 min · Season 3 Episode 5ScreenCloud CRO Shabri Lakhani on why she refused to bake unproven AI productivity gains into her FY27 plan, how PE ownership changed what "defensible" means, and the case for…
- Scaling Revenue Teams & Rebuilding Sales Processes - Adam Kay’s Playbook for AI-era Sales · 35 min · Season 3 Episode 4GoodFit CRO Adam Kay on why he stopped trying to clone himself as a sales leader, how AI is reshaping sales processes and the two reasons most companies get their ICP wrong.
- 25 Years of Sales Leadership rewritten by AI - Jeremy Radcliffe on balancing human touch and automation in Sales · 30 min · Season 3 Episode 3Jeremy Radcliffe shares insights from 25 years of leading Revenue teams, how AI is reshaping the CRO role, and his own path as a fractional GTM Leader.
- Transitioning from CMO to CRO - Hannah Garner on stepping into the CRO seat & hiring in the AI era · 36 min · Season 3 Episode 2Arctic Shores CRO Hannah Garner on the unplanned move from marketing into revenue leadership, working through imposter syndrome, and why hiring for critical thinking matters more…
- The Coaching Relationship That Changed Everything - Alex Olley on building Go-to-Market rigour at Reachdesk · 32 min · Season 3 Episode 1Reachdesk Co-Founder & CRO, Alex Olley, on the brutal investor grilling that exposed his gaps as a CRO, and the coaching relationship that rebuilt how he leads revenue, from…
- Season 3 Trailer: What it takes to be a CRO in 2026 and beyond... · 6 min · Season 3Throughout this season of Making The Grade, we sit down with some of the most successful CROs and Revenue Leaders across enterprise SaaS and early-stage scale-ups to find out…
- The GTM Playbook that works in 2026: Amelia Scott on scaling Culture Amp from $15M to $170M without sales commission · 40 min · Season 2 Episode 10Amelia Scott scaled Culture Amp, from $15M to $170M. Now a fractional CRO, she joins us to share the leadership lessons, cultural principles and AI tools that are genuinely…
- Bootstrapping to $45M ARR: Guillaume Moubeche on scaling efficiently without any VC trade-offs · 48 min · Season 2 Episode 9Guillaume Moubeche, Founder of Lemlist, shares the unfiltered story of bootstrapping from zero to $45M ARR. From why constraints forced the creativity that fuelled Lemlist's…
- What Investors Really Look for: Hillel Zidel on the moves and decisions that make or break the One to Ten Million journey · 40 min · Season 2 Episode 8Hillel Zidel, Managing Director at Kennet Partners, shares what an investor really looks for in the One to Ten Million journey.
- From Chaos to Predictability: Pete Crosby's Honest Lessons on the One to Ten Million Journey · 42 min · Season 2 Episode 7Pete Crosby, one of Europe's most experienced revenue coaches, unpacks the biggest mistakes founders make on the $1M to $10M journey. From ICP discipline, team alignment, hiring…
- Reshaping GTM in the AI Era - Harrison Rose on repeatable GTM and scaling beyond Founder-Led Sales · 45 min · Season 2 Episode 6Harrison Rose shares his insights on approaching ICP as a spectrum, why founder-led sales must become repeatable, when to hire sales leaders, bootstrapping vs VC, and AI’s next…
- From Inception to Acquisition: Natasha Ratanshi-Stein on scaling Surfboard, stage-fit hiring and the importance of founder-led sales · 49 min · Season 2 Episode 5Natasha Ratanshi-Stein shared her hard-won lessons on founder-led sales, real PMF signals, stage-fit hiring and scaling ACV.
- Ego, Cash & GTM Discipline: Paul Fifield’s unfiltered lessons from building scalable businesses · 44 min · Season 2 Episode 4Paul 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…
- Designing an AI-first Business - Bethany Ayers on hiring stage-fit leaders & the GTM playbooks that actually work in the AI era · 42 min · Season 2 Episode 3Beth Ayers shares how to scale from $2-10M ARR with stage-fit hiring, tighter ICP, better operating rhythms, and what “AI employees” look like in practice.
- Building for efficient growth - Pavilion’s honest growth journey & the real problem behind the short CRO tenure with Sam Jacobs · 42 min · Season 2 Episode 2Sam Jacobs shares the real story behind Pailion’s rise, the mistakes that broke retention, and the real problem behind the short CRO tenure.
- What it really takes to win in the US - Honest lessons from Natalie Johnson · 43 min · Season 2 Episode 1In 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…
- Making The Grade - Season 2 Trailer · 6 min · Season 2This 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…
