Making The Grade

ScaleWise, Tom Glason

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. What Investors Really Look for: Hillel Zidel on the moves and decisions that make or break the One to Ten Million journey

    17 HR AGO

    What Investors Really Look for: Hillel Zidel on the moves and decisions that make or break the One to Ten Million journey

    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 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!

    40 min
  2. From Chaos to Predictability: Pete Crosby's Honest Lessons on the One to Ten Million Journey

    19 MAR

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

    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, fix alignment, and scale with real commercial rigour. In this conversation, Pete shares the patterns he sees repeatedly across the companies he works with, and the frameworks he uses to help them break through. Pete also shares the human side of scaling - why team alignment is the silent killer of otherwise great businesses, what makes a true builder in the one to ten phase, and how the best GTM leaders think about culture, hiring, and diversity. Whether you're a founder, a CRO, or a revenue leader trying to level up, Pete's insight is the kind of hard-won wisdom you'd normally only access through years of experience.  📚 Episode Chapters 01:40 - The root cause of stalled growth  05:30 - Finding your ICP with discipline 10:30 - The four phases of scaling internationally 18:00 - Defining true predictability 21:30 - Team alignment & hiring diverse teams  🎧 Continue listening…  Make sure you listen to Reshaping GTM in the AI Era - 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!

    42 min
  3. Reshaping GTM in the AI Era - Harrison Rose on repeatable GTM and scaling beyond Founder-Led Sales

    12 MAR

    Reshaping GTM in the AI Era - Harrison Rose on repeatable GTM and scaling beyond Founder-Led Sales

    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 real inflexion points that unlocked Paddle’s growth, why founder-led sales is often misunderstood, and how teams get trapped at $2–3M ARR when “founder privilege” masks the lack of a scalable playbook. You’ll also hear Harrison’s clear-eyed take on bootstrapping vs VC, and how AI is moving from “more output” to actually making GTM decisions, including the coming tension over who owns the top of funnel: CRO or CMO. 📚 Episode Chapters 05:15 - When to hire experienced Sales Leaders 08:45 - A focus on cold outbound 11:25 - Seeing ICP as a spectrum19:30 - Building true repeatability  25:15 - Funding & the future of AI  🎧 Continue listening…  Make sure you listen to From Inception to Acquisition: Natasha Ratanshi-Stein on scaling Surfboard, stage-fit hiring and the importance of 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!

    45 min
  4. From Inception to Acquisition: Natasha Ratanshi-Stein on scaling Surfboard, stage-fit hiring and the importance of founder-led sales

    5 MAR

    From Inception to Acquisition: Natasha Ratanshi-Stein on scaling Surfboard, stage-fit hiring and the importance of founder-led sales

    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 own journey from inception to an acquisition by Dialpad, which was all sparked by an SDR’s mis-targeted outbound message.   📚 Episode Chapters:  02:00 - Building Surfboard from idea to acquisition14:40 - Lessons from selling before a finished product 30:15 - Transitioning out of being a Founder 38:00 - Hiring the right Sales Leaders for growth   44:15 - Navigating funding challenges  🎧 Continue listening…  Make sure you listen to Ego, Cash & GTM Discipline: Paul Fifield’s unfiltered lessons from building scalable businesses  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!

    49 min
  5. Ego, Cash & GTM Discipline: Paul Fifield’s unfiltered lessons from building scalable businesses

    26 FEB

    Ego, Cash & GTM Discipline: Paul Fifield’s unfiltered lessons from building scalable businesses

    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 failures in his career, and the patterns he now sees repeatedly in early-stage SaaS: messy data, woolly ICPs, uncontrolled SDR targeting, false confidence from renewals, and leadership decisions driven by ego rather than fundamentals. Paul also shares why the GTM playbook is changing fast, what modern CRO capability looks like in 2026, and why AI won’t save teams that haven’t done the foundational work first. If you’re a founder, CRO, VP Sales, or an Operator trying to help a business graduate from Series A to Series B - this one is a masterclass in what to do, what to avoid, and what to take seriously before the market forces you to. 📚 Episode Chapters 03:04 - Lessons from Failures and Successes 24:04 - The impact of ego in leadership28:13 - Scaling strategies from $1M to $10M 35:05 - The evolving role of the CRO   41:06 - Leaning into fractional talent as a startup   🎧 Continue listening…  Make sure you listen to Designing an AI-first Business - Bethany Ayers on hiring stage-fit leaders & the GTM playbooks that actually work 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!

    44 min
  6. Designing an AI-first Business - Bethany Ayers on hiring stage-fit leaders & the GTM playbooks that actually work in the AI era

    19 FEB

    Designing an AI-first Business - Bethany Ayers on hiring stage-fit leaders & the GTM playbooks that actually work in the AI era

    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.  Beth shares why her default is now AI before headcount, how Metomic is using AI coworkers to strip out busy work across SDRs, engineering, marketing, and leadership, and why one SDR can now deliver the output of two to three.  But this isn’t an AI hype conversation. Beth is equally candid about the fundamentals that don’t change: why stage-fit exec hiring still breaks scale-ups, why founders step away from sales too early (or not at all), and why clarity on ICP, pipeline targets, and operating rhythm matters more than ever. If you’re rethinking how to scale with fewer people, higher leverage, and sharper focus, this episode offers a clear, practical blueprint, without pretending the trade-offs don’t exist. 📚 Episode Chapters:  01:50 - Hiring the right Sales Leadership   03:22 - Evolving GTM Strategies  16:45 - The intersection of Product and Sales  22:04 - Leveraging AI in your Sales Team  30:35 - Future of Work: Balancing AI and People  36:10 - Diversity in Leadership  ⛳ Mentioned in today’s episode:  Metomic: https://www.metomic.io/   🎧 Continue listening…  Make sure you listen to Building for efficient growth - Pavilion’s honest growth journey & the real problem behind the short CRO tenure with Sam Jacobs 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!

    42 min
  7. Building for efficient growth - Pavilion’s honest growth journey & the real problem behind the short CRO tenure with Sam Jacobs

    12 FEB

    Building for efficient growth - Pavilion’s honest growth journey & the real problem behind the short CRO tenure with Sam Jacobs

    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 Collective dinners to Pavilion’s Covid-era surge. But there’s no skipping the hard bits in this episode. Sam shares the painful consequences of growing too fast, loosening ICP, and chasing scale for growth’s sake. This is a rare, unfiltered conversation about what happens when your biggest strength gets diluted, and how you rebuild when churn becomes the signal you can’t ignore. No matter whether you’re a Founder currently building or a GTM Leader facing the various challenges the market throws at you, there’s endless practical advice in this episode, ready for you to apply straight away.    📚 Episode Chapters 01:15 - Pavilion’s origin story  09:23 - Scaling mistakes & lost focus  19:08 - The short CRO tenure  22:20 - Building P&L Fluency for Revenue Leaders  29:00 - Sustainable GTM Strategies  39:34 - Planning for a successful exit  ⛳ Mentioned in today’s episode:  Pavilion: https://www.joinpavilion.com/Intro to P&L Fluency: https://www.joinpavilion.com/pavilion-university/intro-to-pl-fluency  🎧 Continue listening…  Make sure you listen to What it really takes to win in the US - Honest lessons from Natalie Johnson 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!

    42 min
  8. What it really takes to win in the US - Honest lessons from Natalie Johnson

    5 FEB

    What it really takes to win in the US - Honest lessons from Natalie Johnson

    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 leads revenue at one of Europe’s fastest-scaling AI companies, AutogenAI. In this episode, Natalie unpacks what actually works when expanding into the US, why outbound still works and why AI is not an IT rollout but an organisational transformation that rewires how modern revenue teams operate.  If you’re scaling through the messy middle and considering the US leap, this one’s packed with battle-tested guidance you can apply immediately. 📚 Episode Chapters 01:15 - Lessons from two scaling journeys  03:12 - US expansion mistakes  16:26 - Navigating the messy middle  26:08 - Autogen AI’s Growth Engine   30:46 - Outbound strategies that actually work  35:34 - Hiring Revenue Leaders in 2026 ⛳ Mentioned in today’s episode:  AutogenAI: https://autogenai.com/uk/Glyphic: https://www.glyphic.ai/ 🎧 Continue listening…  Make sure you listen to Season 1 Sean Williams - From $60m exit to building an er-defining AI company 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!

    43 min

Trailers

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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.

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