SaaS ScaleUps: Pearls of Wisdom from Entrepreneurs

John O’Connell, tech entrepreneur, founder, and investor
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SaaS ScaleUps: Pearls of Wisdom from Entrepreneurs

SaaS ScaleUps – Pearls of Wisdom from Entrepreneurs is the go-to podcast for B2B SaaS tech founders looking to scale. Hosted by tech entrepreneur, founder, and investor John O’Connell, we dive into fundraising strategies, the power of AI in SaaS, and growth insights from top entrepreneurs. Whether you're securing Series A funding or planning a successful exit, get actionable wisdom from those who’ve been there. Brought to you by ScaleUp Group—helping B2B SaaS tech scaleups secure Series A funding, co-investing alongside institutional investors and providing post-investment support.

Episodes

  1. Behind the Raise: Inside Blackdot Solutions' Funding Journey

    JUN 17

    Behind the Raise: Inside Blackdot Solutions' Funding Journey

    From investor prep to post-deal growth—lessons in trust,timing, and scaling smart. Adam de Courcy Ling is the Executive Chairman at BlackdotSolutions - the UK technology company behind Videris, the most powerful investigations software for fighting serious, organised and economic crimes. An experienced software sector investor and director, Adam was an investor and director in fintech software vendor Multifonds, sold in 2015 to Temenos AG, and lead investor and director at an artificial intelligence vendor, Expertmaker, sold in 2016 to eBay Inc. Tune into this episode to hear Adam and John dive into thestory behind Blackdot’s recent £4.7M Series A fundraise—led by Maven Capital Partners with support and co-investment by ScaleUp Group. They discuss the realities of navigating a complex investment journey, the importance of thorough preparation, strong advisory guidance, and managing due diligence with precision. The conversation highlights the benefits of involving multiple funds to validate valuation and market appetite, the critical role of building trust with global investors, and the need for transparency post-investment. Adam also shares how the raised funds are being used to scale Blackdot’s engineering capabilities, boost sales, and support international growth.

    34 min
  2. AI – Beyond the Hype with Martin Neale, ICS.AI

    JUN 11

    AI – Beyond the Hype with Martin Neale, ICS.AI

    Martin Neale, is CEO and co-founder of ICS.AI, a company dedicated to revolutionising public sector services through innovative AI solutions. Having bootstrapped ICS.AI with his pension, Martin took abold personal leap to realise his vision of AI’s transformative potential. Recently recognised in Parliament as a Leader in Public Sector AI Innovation, ICS.AI is pioneering conversational AI as the new digital gateway for public services. In this episode, Martin and John dive into how conversational AI is reshaping the public sector. Martin shares a compellingcase study from Derby City Council, where an AI-powered voice platform delivered substantial cost savings and enhanced service with multilingual, high-deflection call handling. They also discuss AI’s rapid evolution, its impact on the workforce, and why human oversight remains crucial in critical decision-making. Don’t miss this insightful conversation exploring the real-world benefits and challenges of AI in public service transformation.

    34 min
  3. Scaling to Selling a SaaS Business: Insights on Board Dynamics, Product-Market Fit and Knowing Your Buyer

    APR 29

    Scaling to Selling a SaaS Business: Insights on Board Dynamics, Product-Market Fit and Knowing Your Buyer

    David Cocks co-founded CloudTrade in 2009 and managed the company as CEO from day one. He grew CloudTrade into a global provider of intelligent data capture and document automation services, delivered by its own patented, machine-learning technology. David shares some incredible insight, tips and advice for fellow entrepreneurs. David dives deep into the realities of startup life, from not paying himself for the first three years to navigating complex board dynamics down the line. Learn how developing your product alongside your first client can help secure that crucial product-market fit and hear about the impressive growth from £1m ARR (within 9 years) to £3m (within 3 years), after securing growth funding. On selling the business 12 years later, David notes, “One of the reasons we succeeded so well with the sale to Advanced is we understood why they wanted to buy us: why Advanced wanted the tech and where it fitted in. Understanding your buyer, is really key because then when you hit a problem, you know why and what you’ve got to negotiate around.”

    41 min
  4. Scaling to Selling a SaaS Business: Acquire a business for a £1 and sell it for more than £100 million!

    APR 22

    Scaling to Selling a SaaS Business: Acquire a business for a £1 and sell it for more than £100 million!

    Matthew Elson acquired Evotix (a health, safety and sustainability SaaS business) in 2011 and sold the business in 2023. He remains CEO, where he has led the company through commercial dispute, going from 10 to 150 staff, international expansion, growth funding, pricing strategies and much more. Today, Evotix is the leading player in its space in the UK and Ireland. Throughout this incredible journey, Matthew notes one of the keys to success is, “building up that network of external advisors and supporters for the business. Your job as CEO, as the entrepreneur is to take the decisions, you don’t always have to take the advice, but it’s always good to listen to the advice and consider it carefully. Frankly the external support and advice that we’ve had along the way has been absolutely invaluable to the success of the business.”

    46 min
  5. AI – Beyond the Hype with Stuart Clarke, Blackdot Solutions

    APR 15

    AI – Beyond the Hype with Stuart Clarke, Blackdot Solutions

    Stuart Clarke is the CEO of Blackdot Solutions – the UK technology company behind Videris, the most powerful investigations software for fighting serious, organised and economic crimes. A globally respected expert in investigations and cyber security, Stuart brings extensive experience in business leadership, consultancy, and operational intelligence. Blackdot’s mission is to empower investigators to use open-source intelligence (OSINT) for good, providing cutting-edge software to combat criminal activity effectively. In this episode, Stuart and John explore the transformative role of generative AI in business intelligence and decision-making. They discuss how Blackdot leverages AI to unlock insights from open-source data, delivering tangible impact across investigative and compliance sectors. The conversation also covers data integration, the challenges faced by larger organisations with legacy systems, and why smaller, more agile companies are often better placed to seize the opportunities presented by AI.

    33 min
  6. Scaling to Selling a SaaS Business: Insights on AI, Empowerment, and Resilience

    APR 8

    Scaling to Selling a SaaS Business: Insights on AI, Empowerment, and Resilience

    Our guest – Frank Reeves, a distinguished entrepreneur and innovator in the travel technology sector, best known for his role as the co-founder and CEO of the bootstrapped travel tech firm, Avvio.com, from 2002 to 2022. Frank has a powerful story and some memorable points emerged from their conversation, which every self-respecting tech entrepreneur should heed. Frank recalls one of his biggest go-to-market initiatives, which reminds us that aligning your proposition directly with your clients is paramount, “we just bravely went into the market and said, look, this is what working with us means, right? Everyone’s got great technology, that’s fine. But when you boil it all down, working with Avvio means that you get at least 25% growth in your direct channel, which is your most cost-effective booking channel, and that then is tied directly to a PNL impact. So that was a very differentiated go-to-market strategy – talking about business outcomes rather than how great we were as a company and how great our tech was. That really resonated in the market. We worried, of course, that some competitors would follow us into that value prop. But none ever did, which was wonderful.”

    41 min
  7. AI - Beyond The Hype with Simon Black, Lexical Labs

    APR 1

    AI - Beyond The Hype with Simon Black, Lexical Labs

    Simon Black is the Co-Founder and Chief Commercial Officerof Lexical Labs, the company behind Tiro—the world’s leading AI-powered contract review software. With 25 years at a major law firm, primarily in Asia, Simonloved negotiating deals but grew frustrated with inefficiencies that wasted time and resources. Determined to drive change, he champions AI’s role in handling repetitive tasks, allowing professionals to focus on strategic thinking, decision-making, and innovation. In this episode, Simon joins John to explore how AI istransforming legal workflows, reducing costs, and making contract management more efficient. They discuss the opportunities and challenges of automation, from streamlining negotiations to addressing data security concerns. Packed with insights into the evolving legal tech landscape, this is a must-listen for anyone interested in the future of AI in law.

    31 min
  8. AI – Beyond the Hyhpe with Greg Wildisen, Panoram

    MAR 25

    AI – Beyond the Hyhpe with Greg Wildisen, Panoram

    Greg Wildisen is the founder and CEO of Panoram, a leadingGenAI software specialist for business and legal sectors. Panoram’s mission is to develop cutting-edge GenAI-powered solutions that enhance efficiency, ensure compliance, and drive profitability. By transforming how law firms and corporate legal departments operate, Panoram empowers them to deliver expertise seamlessly—anytime, anywhere. In this podcast episode, John and Greg explore the transformative role of AI and generative AI in the legal industry, highlighting their potential to streamline processes, reduce costs, and enhance accuracy. Greg discusses the benefits of using multiple large language models (LLMs) to ensure the best fit for specific legal tasks. He also examines AI’s ability to process vast amounts of data, from document reviews to cybersecurity applications, and emphasises the importance of selecting scalable, cost-effective AI solutions tailored to client needs.

    28 min
  9. AI – Beyond the Hype with David Williams, KAI Conversations

    MAR 18

    AI – Beyond the Hype with David Williams, KAI Conversations

    David Williams is the founder and CEO of KAI Conversations, the industry-leading Conversational Intelligence (CI) platform which uses AI to analyse and reveal the impact of human conversations, providing real-time, actionable insights that drive better outcomes in pharma and healthcare.  David has founded, invested in, built and sold consulting and SaaS technology businesses in the customer management space. He is passionate about using AI to transform the way organisations understand their customers and improve their interactions with them. In this episode, John and David cut through the noise to explore the real-world impact of Generative AI. They break down how KAI is delivering measurable benefits to clients, the challenges and strategies of AI-driven sales tools in the pharmaceutical industry, and why AI should be seen as a co-pilot—enhancing human potential rather than replacing it. Whether you’re an AI enthusiast or a business leader navigating digital transformation, this discussion is packed with valuable insights. https://scaleupgroup.co/

    30 min
  • 9 Episodes

About

SaaS ScaleUps – Pearls of Wisdom from Entrepreneurs is the go-to podcast for B2B SaaS tech founders looking to scale. Hosted by tech entrepreneur, founder, and investor John O’Connell, we dive into fundraising strategies, the power of AI in SaaS, and growth insights from top entrepreneurs. Whether you're securing Series A funding or planning a successful exit, get actionable wisdom from those who’ve been there. Brought to you by ScaleUp Group—helping B2B SaaS tech scaleups secure Series A funding, co-investing alongside institutional investors and providing post-investment support.

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