Episodes

  • #340 - Mark Kosoglow, CEO of Operator - on critical thinking in sales

    #340 - Mark Kosoglow, CEO of Operator - on critical thinking in sales
    Nov 27 2024
    This podcast interview focuses on the entrepreneurial journey to transform toxic sales automation. My guest is Mark Kosoglow, CEO of Operator. Mark is a tech entrepreneur on a mission. A big mission. He's a sales expert who played a crucial role in helping scale Outreach from zero to over $230 million in revenue in just 8-years. Being part of the rising growth of sales automation, Mark realizes how too much automation and the mantra of Growth at all Costs has wrecked outbound. It's created a massive problem, which he refers to as ‘The Great Ignore.’ This inspired the idea of founding an operator in April 2024. Their mission is to make outreach more human, insightful, and valuable for both sellers and buyers. And this inspired me, and hence I invited Mark to my podcast. We explore how The Great Ignore has not only created a sales execution problem for all of us - but has also fueled a much larger Societal problem. He shares a masterclass on the art of what effective sales is really all about. He elaborates on what he's done differently to build rapid traction - with buyers that stay and become fans from the start. Last but not least, he talks about his lessons learned in harmonizing work-life priorities. Here's one of his quotes "Most platforms, good advice is the antithesis of how they create revenue. So if I'm like a ZoomInfo or someone like that, I make money by people buying more accounts and more contacts. Therefore, for me to suggest something that would require less contacts and less companies would be the antithesis of what I'm supposed to be doing, which is growing my business." During this interview, you will learn four things: What sales skills to home in on to succeed in the evolving sales landscape How he's staying sane, flexible and performing better in the crazy world of building a startup in a market that's overwhelmingly crowded. How his Waitlist grew to 1,500 people within 24 hours of announcement. How building a personal brand is of value to any sales to stand out - not only top management. For more information about the guest from this week: Mark Kosoglow Website: Operator Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices
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    42 mins
  • #339 - Griffin Parry, CEO of m3ter - on taking the pain out of billing operations.

    #339 - Griffin Parry, CEO of m3ter - on taking the pain out of billing operations.
    Nov 20 2024
    This podcast interview focuses on the entrepreneurial journey to build mission-critical billing infrastructure for complex B2B SaaS pricing models. My guest is Griffin Parry, Founder and CEO of m3ter. Griffin Parry is a serial Entrepreneur. In 2013, he founded GameSparks, a backend-as-a-service platform for video games, which he sold to Amazon in 2017. Combining his firsthand experience with the challenges of usage-based pricing at GameSparks with the problems he encountered at a much larger scale at AWS became the founding idea behind m3ter. He founded m3ter in October 2020 - it's a platform that helps B2B Software companies manage complex pricing and automate complex billing calculations. Their mission: To enable B2B Software companies to deploy and manage usage-based pricing intelligently. This inspired me, and hence, I invited Griffin to my podcast. We explore what it takes to build a successful pricing and billing infrastructure company. Griffin shares his experience identifying and solving real market problems. He talks about the importance of a strong founding thesis and continuous iteration and why he opted to build for operational complexity and enterprise integration from the start. Last but not least, he shares some of his big lessons on how he defined his ideal customers and what not to do when approaching those customers if you want to gain traction. Here's one of his quotes Early on, we overdid it. We would go, 'We are revolutionizing your pricing. And they go, 'Okay, why?' And we go, 'It's going to allow you to ship product faster because you're gonna have more pricing agility. We just weren't talking the same language as them. We just pulled it back, pulled it back, simplified the story, and now we meet them where they are. We go, 'Billing operations is a real pain point for you, isn't it? And they go, 'YES.' During this interview, you will learn four things: Griffins' 3 success factors in growing his business. How he's building trust with his ideal customers from the start. What he's doing differently to give development a headstart when it comes to building new products. Why he hired a data scientist from day one - and why you should possibly too. For more information about the guest from this week: Griffin Parry Website: m3ter Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices
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    50 mins
  • #338 - Hadassah Backman, CEO of Guardoc Health - solving critical industry problems

    #338 - Hadassah Backman, CEO of Guardoc Health - solving critical industry problems
    Nov 13 2024
    This podcast interview focuses on the entrepreneurial journey to change the way healthcare nurses can work to improve patient safety. My guest is Hadassah Backman, CEO of Guardoc Health. Hadassah has nursing roots: She started her career as a registered nurse and has built hands-on experience in emergency room and hospice care. This clinical background gives her unique insights into the challenges faced by frontline healthcare workers. Besides that, she holds a master's degree in public health policy and management from Columbia University. At this intersection, the big idea for Guardoc was born - which she founded in July 2021 - in the middle of COVID-19. Guardoc is a clinical data integrity solution that uses artificial intelligence to address nursing challenges. Their mission: to prevent medical errors, reduce wasted nursing hours, and improve care for chronically ill older adults. And this inspired me, so I invited Hadassah to my podcast. We explore what's broken when it comes to supporting nurses in preventing medical errors. Hadassah shares her vision of how to solve it and how she bootstrapped her way to delivering a solution that nurses just kept talking about. She elaborates on some of her big lessons learned (and the resilience needed) in getting traction and attracting funding. Last but not least, she advises on building momentum through laser-sharp focus and smart product development decisions. Here's one of her quotes We have apps streaming to our phones. You can watch your kids on your phone remotely. You can open doors and close doors and lock people out. There are all these things - but we still haven't figured out how to help what, to me, is the most important workforce. Because they really deliver holistic care to patients so that they can provide the care that they were trained to do and that they want to do. And so that really compelled me to ask: why isn't there a solution that captures mistakes? During this interview, you will learn four things: Why taking a 'user-centric' approach is not enough to succeed in building a successful software business. How she started to deliver remarkable value without having built any product yet - and how that helped accelerate the journey. What she did differently to put a flywheel for growth in motion for her business - in a world that requires a high-touch GTM approach. How she's built a resilient mindset to navigate the challenges of entrepreneurship successfully. For more information about the guest from this week: Hadassah Backman Website: Guardoc Health Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices
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    47 mins
  • #337 - Dan Uyemura, CEO of Pushpress - on Vertical SaaS differentiation

    #337 - Dan Uyemura, CEO of Pushpress - on Vertical SaaS differentiation
    Nov 6 2024
    This podcast interview focuses on the entrepreneurial journey to build deep vertical business solutions that deliver 10x value for every 1x in price charged. My guest is Dan Uyemura, CEO of Pushpress. Dan has had an entrepreneurial spirit from a young age. He was a Dot-com era pioneer: During college, he founded Mixture.com, a platform that was ahead of its time and preceded social media giants like Myspace. After working in tech, including a stint at Myspace, he made a dramatic career pivot by opening his own CrossFit gym. He quickly got frustrated with the poor software options available for gym management. So in January 2012, he leveraged his tech background to create PushPress and rebel against manual paperwork and complicated, overpriced software. Their mission: to make gym management
 the easiest part of starting a fitness business. And this inspired me, and hence I invited Dan to my podcast. We explore his journey from MySpace coder to gym owner to software entrepreneur. Dan shares his insights on what it takes to create a competitive advantage that's hard to beat. He elaborates on empathy-driven support, value-based pricing, and the "layer cake" approach that makes his SaaS products invaluable. He emphasizes the importance of focusing on customer value over traditional SaaS metrics and shares innovative strategies to outmaneuver competitors. Last but not least, he shares his data-driven decision-making framework and lessons on team building. Here's one of his quotes "Money is an output. It's the result of energy spent somewhere else. So the problem is, a lot of people build those businesses around money. How do I make more money? How do I generate more money? How do I increase my top line? Or bottom line? The reality is that's an output, and you can never affect an output. You can only affect the input. And the input is the order of magnitude and the sheer volume of value you provide to customers. That's what you got to focus on." During this interview, you will learn four things: How he's tuning his product strategy to grow a highly defensible position against competitors. His framework for building conviction and speeding up decision-making in feature development How he overcame the balancing act of horizontal feature breadth with vertical depth improvements His approach to innovating pricing models to outmaneuver competitors and accelerate growth. For more information about the guest from this week: Dan Uyemura Website: Pushpress Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices
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    47 mins
  • #336 - Victor Kristof, CEO of DemoSquare - on resilient customer-driven innovation.

    #336 - Victor Kristof, CEO of DemoSquare - on resilient customer-driven innovation.
    Oct 30 2024
    This podcast interview focuses on the entrepreneurial journey to democratize political data and anticipate regulatory changes. My guest is Victor Kristof, Co-founder and CEO of DemoSquare. Victor is a fascinating individual with a unique blend of academic excellence, entrepreneurial spirit, and a passion for leveraging technology to enhance democratic processes. He holds a Ph.D. in Machine Learning from Ecole Polytechnique Federale de Lausanne, where he developed algorithms and statistical models to study human behavior within social and political systems. That research became the foundational idea behind DemoSquare, a SaaS startup he co-founded in November 2022. Their mission: to "democratize democracy" by making political and regulatory data more transparent and accessible with artificial intelligence. It will change how companies and their public affairs teams navigate the complex world of politics and regulation and, potentially, how citizens engage with democracy. And this inspired me, and hence I invited Victor to my podcast. We explore the journey of transforming academic research into a change-making political data platform. Kristof shares his lessons learned by doing customer interviews and pivoting in the right direction. He highlights the value of sharing ideas openly, adapting to constant change, and maintaining resilience in the face of rejection. Last but not least, he offers practical advice on investor relationships, sales strategies, and personal stress management. Here's one of his quotes I've heard several times people saying, "I have this super cool idea. I don't want to share it with anyone until I do it. I had the complete opposite experience. Even when it wasn't completely ready, we were not selling it, just talking about it to people, not even in a professional or formal context. You go to a party, you go to a family gathering, and you meet with some friends. You just share your ideas and see what's happening. The most important feedback I got came from these informal discussions. I cannot count how many introductions to potential customers I've gotten through these informal discussions. During this interview, you will learn four things: How to gather feedback and validate your idea - and use both positive and negative feedback to refine (or even pivot) your product. How finding the right co-founder can have a multiplicative effect on your business. How to stay resilient in the Face of Rejection from both customers and investors. What to look for to select investors who will make a difference for your business. For more information about the guest from this week: Victor Kristof Website: DemoSquare Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices
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    42 mins
  • #335 - Joaquim Lecha, CEO of Typeform - on creating SaaS products customers love.

    #335 - Joaquim Lecha, CEO of Typeform - on creating SaaS products customers love.
    Oct 23 2024
    This podcast interview focuses on the entrepreneurial journey to help all of us to have conversations that drive action and meaningful connections. My guest is Joaquim Lecha, CEO of Typeform. Joaquim (Kim) is a tech entrepreneur on a big mission, bringing over 20 years of experience in high-growth companies. He started his career in M&A, strategy, and financial advisory. In 2012 he joined the tech world as the CFO of Socialpoint, a world-renowned mobile game developer, later taking on the role of Chief Operating Officer. In 2018 he joined Typeform as Chief Operating Officer and quickly rose to become the CEO. Their mission: to create a world where conversations drive action and meaningful connections. Under his leadership, Typeform has grown impressively (+$1B valuation), now serving well over 150,000 paying customers worldwide and achieving profitability. He recently got recognized as one of the Top 50 SaaS CEOs of 2023 by The Software Report. This inspired me, so I invited Joachim to my podcast. We explore what it takes to profitably scale a SaaS business as it experiences rapid growth. He discusses what fueled their initial growth and what strategic changes he had to make to ensure growth won't stall. Last but not least he offers practical wisdom on product development, customer-centric innovation, and maintaining resilience in the face of challenges. Here's one of his quotes I was coming from games. I had not heard from those types of products so many times the word 'Love'. People love Typeform. So my most immediate reaction to all of that is, how can we make more people aware of this great product? And I even thought, since I come from a financial type of background; 'if we can find that scalable with quick feedback loop type of motion, and in addition to that, it's got a less than 12 month payback period. Then we can fund it.' So with that in mind, we got to work. We grew our customer base by 2.5x and our revenue by almost 4x. During this interview, you will learn four things: How to ensure your pricing reflects the true value your product provides to customers - so you don't undervalue your offering. How to choose marketing and sales approaches that can bring in thousands of new customers and provide quick feedback loops. How he found a segment in the market where Typeform provided the most value - and what that meant to their growth trajectory.. What to focus operations and hiring strategy on - if you aim to create a sustainable, resilient, and easily scalable business over time. For more information about the guest from this week: Joaquim Lecha Website: Typeform Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) Learn more about your ad choices. Visit megaphone.fm/adchoices
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    54 mins
  • #334 - Bridget Harris, CEO of You Can Book Me - on the art of Bootstrapping.

    #334 - Bridget Harris, CEO of You Can Book Me - on the art of Bootstrapping.
    Oct 16 2024
    This podcast interview focuses on the entrepreneurial journey to build a successful bootstrapped SaaS company in the highly competitive scheduling software market. My guest is Bridget Harris, Co-founder and CEO of You Can Book Me. Bridget has had three distinct careers, showcasing her versatility and adaptability: She started in the television and film industry. Then, transitioned to politics, serving as a political advisor focusing on constitutional reform and the House of Lords. Her political career culminated in a role as an advisor to the UK Deputy Prime Minister. Finally, she co-founded YouCanBook.Me, where she now serves as CEO. Their mission: To provide the best booking experience for businesses' clients and customers. Under Bridget's leadership, YouCanBook.Me has achieved impressive growth: The company has reached $5 million in Annual Recurring Revenue (ARR) without external funding. That route was a deliberate one. She decided from day one to avoid external funding that might have distorted business priorities, saying "I'd rather make a million dollars slowly than lose a million dollars fast", And this inspired me, and hence I invited Bridget to my podcast. We explore her bootstrapping journey over the past 12 years. She shares how she's successfully competing in a saturated market against well-funded competitors and tech giants like Google and Calendly. She elaborates on how she's maintaining a customer-centric approach while managing limited resources. Last but not least, she shares insights on how she overcame the challenges of pricing, overcoming feature bloat, refactoring legacy code, and adapting to market change. Here's one of her quotes Feature bloat is real. You can say, 'Let's be really generous about our free tool and have loads of features in the free tool.' All you're doing is confusing free users who need a really simple tool and don't want to think because they're not paying for the software. So they just literally want it to work. So if you have a problem that your free users can't contact support, it means that your free tool is more complicated than it needs to be. During this interview, you will learn four things: How she's aligning her entire team so they deliver on time and grow an eagerness to go above and beyond. What she learned from refactoring their pricing approach and the lessons nobody talks about is that How to avoid feature bloat in your development process. What she's doing differently to create the best customer experience. For more information about the guest from this week: Bridget Harris Website: You Can Book Me Bootstrappers Manual Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices
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    46 mins
  • #333 - Caitlin MacGregor, CEO of Plum- on successfully navigating market change

    #333 - Caitlin MacGregor, CEO of Plum- on successfully navigating market change
    Oct 9 2024
    This podcast interview focuses on the entrepreneurial journey from the last 5 years to turn Plum into the best Talent Intelligence solution on the market. My guest is Caitlin MacGregor, Co-Founder and CEO of Plum Caitlin MacGregor co-founded Plum in 2012 and has been an earlier guest on my podcast (#54 in February 2019). She was voted "most likely to save the world" in her high school yearbook, foreshadowing her future as an innovative entrepreneur. Before founding Plum, Caitlin built two other businesses, which gave her insights into the need for change around talent processes in the age of automation. Fast forward, she was recently selected for the EY Entrepreneurial Winning Women™ North America Class of 2024, a program that supports high-potential women entrepreneurs. Caitlin's drive to democratize access to psychometric data so that no one would have to rely on luck for someone to realize their superpower still underpins the core of the company - although how this is brought to market has evolved a lot. And it's noticed - HR Tech voted Plum the best Talent Intelligence solution in the market in 2023 This inspired me, and hence I invited Caitlin back to my podcast. We explore the journey over the past 5 years. How did the market change in general - in particular in relation to how we attract and manage talent? She also shares what this means to all of us in the coming years. She then drills into how this has changed their priorities around product strategy and Go To Market. As we discuss this, she reveals some valuable lessons learned in product development, positioning, and segmentation, and how her role as CEO changed in this period of rapid change. Here's one of her quotes 12 months ago, we were working on how we best resonate. It was really just about how you get to that Aha moment, and it really has nothing to do with the product and the solution. It was really like the Why. Why should you care about Plum? How do we align to a top three boardroom problem? And how do we connect to that strategic problem [....] so we were able to get into a strategic conversation with the right people that had the power to decide to do things differently. During this interview, you will learn four things: How Plum expanded from talent acquisition to full employee lifecycle management What made them decide to bet on Enterprise instead of SMBs What internal capabilities organizations need to develop and prioritize to gain competitive advantage and become the winners of the future? How her role as a CEO had to change to effectively lead the rapidly growing organization that Plum is today. For more information about the guest from this week: Caitlin MacGregor Website: Plum Plum Flourish Assessment Subscribe to the Daily SaaS Reflection Get my free, 1 min daily reflection on shaping a B2B SaaS business no one can ignore. Subscribe here Yes, it’s actually daily. And yes, people actually stay subscribed (Just see what peer B2B SaaS CEOs say) My promise: It’s short. To the point. Inspiring. And valuable. Learn more about your ad choices. Visit megaphone.fm/adchoices
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    56 mins