The Remarkable SaaS Podcast

This podcast interview focuses on the entrepreneurial journey of persistence and adaptation. My guest is Maximus Greenwald, CEO of Warmly. After working at Google, Max and his co-founders quit their jobs to start a company with what he calls "the world's worst idea" - Tinder for co-founders.  What makes his journey fascinating is how he navigated through six pivots over three years, each time confronting the challenges of product-market fit, customer alignment, and sustainable growth.  Throughout this process, Max grappled with the central question many founders face: when to explore new ideas and when to commit fully to execution. And this inspired me, and hence I invited Max to my podcast. We explore the challenges of finding focus in startup chaos, the tension between vision and execution, and the counterintuitive reality that momentum often precedes perfection. Max's leadership principles cut through typical startup fluff with refreshing directness, challenging conventional wisdom about when to sell, how to pivot, and what metrics truly matter for early-stage companies. Here is one of his quotes  “In any company revenue is oxygen, and you need oxygen to live and to succeed. And so as we were starting to make money and make money fast, [..] we saw a excitement in the company and a devotion to work harder that we had never seen in our earlier six pivots. That's one of the most critical things: having momentum gets everyone excited to keep pushing along.” By listening to this podcast you will learn: The hidden pitfalls of pursuing product-market fit over generating actual revenue Why standard metrics often mislead early-stage founders away from what truly matters The real challenge of knowing when to stay the course versus when to pivot Why some customers might be holding back your company's growth potential For more information about the guest from this week:  Maximus Greenwald  Website: warmly.ai Learn more about your ad choices. Visit megaphone.fm/adchoices

This podcast interview focuses on the entrepreneurial challenge of revitalizing a 20-year-old SaaS business in a market with hundreds of competitors. My guest is Ash Didwania, CEO of Workzone. Ash took the helm of Workzone in December 2023 after the company was acquired by Big Band Software. Despite being profitable with a sticky customer base (7-year average customer lifetime), long-tenured employees (9-year average), and a must-have product, Workzone had been experiencing a six-year decline in revenue. Instead of the typical turnaround approach of immediate disruption, Ash took a counterintuitive path - learning first, focusing on existing strengths, and engaging deeply with customers before making changes. And this inspired me, and hence I invited Ash to my podcast. We explore what it takes to reverse a multi-year revenue decline while maintaining 40%+ EBITDA margins in a highly commoditized market. Ash shares how he challenged the conventional wisdom about business turnarounds by taking a path few would dare to follow. His counterintuitive approach transformed not only the company's financial trajectory but also reshaped how the entire team viewed their mission, their customers, and their path to growth. Here is a quote that captures one of Ash's most striking business lessons: "Throwing money at a problem can get you short-term results. It will not get you long-term sustainability. And so again, one of the thesis here was because we want to grow in a sustainable fashion while also improving our EBITDA margins, in some ways that acted as a forcing function, which is despite the fact that we were profitable, we did not want to tap into the profit pool and start deploying investments before identifying levers of growth that already existed." By listening to this podcast you will learn: How to turn around a declining SaaS business without sacrificing profitability or disrupting what works Why deep customer understanding can be more valuable than new feature development  How to create organizational focus through a single metric that aligns every team member The power of planning for multiple contingencies (Plans A, B, C, and D) in sales and go-to-market For more information about the guest from this week: Ash Didwania Website: workzone.com Learn more about your ad choices. Visit megaphone.fm/adchoices

This podcast interview focuses on transforming how B2B companies leverage customer interactions for growth. My guest is Krishna Raj Raja, CEO of SupportLogic.  From his early days as one of VMware's first support engineers, Krishna discovered something the industry had missed - the most valuable customer insights were being lost in departmental silos. Yet instead of accepting conventional solutions, he chose to build something the market initially rejected but customers immediately embraced. This inspired me, and hence I invited Krishna to my podcast. We explore the counterintuitive approach of building a B2B software company by deliberately ignoring what investors and the market considered essential. His journey reveals how challenging established industry assumptions can uncover massive business opportunities that others miss, while creating natural barriers to competition through a unique product philosophy. Here is a quote that captures one of Krishna's most striking business lessons:  "If customers are excited and investors are not seeing it, this is the right opportunity to go after, because this is an opportunity they're not going to fund."  By listening to this podcast you will learn: How to identify massive market opportunities in the disconnect between investor skepticism and customer excitement Why focusing on six wildly successful customers yields better results than chasing rapid-scale When deliberately ignoring industry "must-haves" creates stronger market positioning How to turn early customer enthusiasm into effortless enterprise sales For more information about the guest from this week:  Krishna Raj Raja  Website: supportlogic.com  Book: supportexperience.ai Learn more about your ad choices. Visit megaphone.fm/adchoices

This podcast interview focuses on the critical decisions that define successful scaling. My guest is David DeWolf, CEO of Knownwell. After growing Three Pillar Global to 2000 employees across nine countries, David learned that sometimes the best way to scale is to deliberately slow down. During COVID, he made the bold choice to retain all employees despite revenue decline - a decision that led to tripling the business within a year. Now with Knownwell, he's applying these scaling lessons to build an AI company with intention, starting with 500 customer interviews before writing a single line of code. Their mission: To help professional services firms prevent "surprise churn” by elevating human relationships and experiences. And this inspired me, and hence I invited David to my podcast. We explore what it really takes to build an AI company that elevates rather than replaces human relationships. His approach challenges conventional wisdom about scaling, product development, and leadership - drawing from lessons that helped him grow his previous company from startup to 2000 employees and survive multiple market crises. But what's most fascinating is how he's applying these insights to tackle one of the biggest pain points in professional services: the struggle to see relationship problems before they become relationship crises. Here's a quote from David: We had an inbound lead that found us through the podcast and ended up signing a rather large contract before we even not only wrote a line of code, but before we had an engineer on staff. By listening to this podcast you will learn: How to secure major contracts before writing a single line of code (and why this might be smarter than building first) Why CEOs should never delegate customer relationships, even when scaling rapidly How staking your brand position before having a product can accelerate your go-to-market strategy Why implementing lightweight business systems early gives you an unfair advantage in scaling For more information about the guest from this week: David DeWolf Website: knownwell.com   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

A story about transforming a horizontal solution into targeted value propositions This podcast interview focuses on the entrepreneurial journey to build sustainable growth by deeply understanding customer needs over chasing broad market opportunities. My guest is Nick Wassenberg, CEO of Cludo. Nick is a marketing veteran turned CEO with an entrepreneurial mindset shaped by working closely with founders. Previously, as employee #12 at Fulcrum, he experienced rapid-growth dynamics firsthand. His diverse background spans manufacturing, healthcare, financial services, and global consulting – driven by an insatiable curiosity to understand how different businesses work. In June 2023, he became the CEO at Cludo. Their mission: To get website visitors of critical organizations the most relevant, timely, and trusted answers. And this inspired me, and hence I invited Nick to my podcast. We explore his strategic decisions in his first 90 days. He shares how he's transforming Cludo's approach from serving everyone to deliberately focusing on specific customer segments where they can deliver the most value. Last but not least, he shares his insights on how understanding the hidden patterns in customer behavior shapes both product development and go-to-market strategy. Here's one of his quotes: “If I were going to start from the beginning, I wouldn't say 'let's have 27 different industry categories.' We would pick one and build a product that was amazing for them, and then pick another, and then broaden out from there. That's an easy mistake - your eyes get pretty big, especially in a solution set like ours. Some amount of it is universal and universally applicable - but you still have to close the niche down and find your way that way.” By listening to this podcast you will learn the following: The importance of aligning your solution with your customer's top priorities rather than trying to elevate the priority of your specific solution Where he's investing his marketing budget to solve the current challenges of trying to make outbound work in complex B2B sales The strategic advantage of focusing on input metrics that drive outcomes rather than just measuring outputs The importance of building strengths in areas outside your comfort zone to drive business growth For more information about the guest from this week: Nick Wassenberg Website: cludo.com  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

This podcast interview focuses on the entrepreneurial journey to make effective leadership development available for everyone. My guest is Smadar Tadmor, CEO of Claro Mentor. Smadar Tadmor is a visionary leader who's on a mission to change the way organizations develop their managers. With over 30 years in HR and organizational development, she founded three successful consulting companies before spotting a critical gap: most leadership development programs weren't driving real behavior change.  This insight led her to found Claro Mentor in 2022, creating a platform that makes personalized leadership guidance available for every layer of an organization.  What makes her story particularly compelling is her transition at this stage in her career - moving from being a top-tier consultant to a first-time tech startup CEO, embracing a beginner's mindset while leveraging decades of domain expertise. And this inspired me, and hence I invited Smadar to my podcast. We explore her remarkable transition from successful consultant to first-time tech CEO, where she had to unlearn decades of habits to build something entirely new. She shares candid insights about the struggles of perfectionism, the surprises of product-market fit, and how bootstrapping forced tough but transformative decisions that shaped their innovative approach to leadership development. Here's one of her quotes: “I left behind an amazing 30 years of career where I was top-notch consultant, well known... and start from a place where I know nothing. And it's very humbling to be at this point. From that perspective, I could be very open to explore and take risks that I think in a different way I wouldn't be doing.” By listening to this podcast, you will learn the following: Why starting with 'knowing nothing' became Smadar's biggest advantage The surprising reason their initial AI coaching approach failed - and what insight changed everything How bootstrapping revealed a truth about their product they wouldn't have discovered otherwise The counterintuitive approach that doubled their customer adoption For more information about the guest from this week: Smadar Tadmor Website: claromentor.com 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

This podcast interview focuses on the entrepreneurial journey to transform thoughtful validation of the problem into confident scaling of his SaaS business. My guest is Robbert Lodewijks, Co-founder and CEO of Hulo AI. Robbert Lodewijks is an entrepreneur who understands the delicate balance between patience and ambition. His journey began with a profound realization during his studies in Taiwan - that impact requires more than just good technology. What makes Robbert's story intriguing is his methodical approach: spending four years in research before launching, then bootstrapping to validate, and only then accelerating with venture funding. This disciplined progression showcases a rare blend of scientific rigor and entrepreneurial instinct. And this inspired me, and hence, I invited Robbert to my podcast. We explore how early-stage founders can build confidence through validation rather than rushing to scale. His insights reveal how methodical customer development, thoughtful bootstrapping, and strategic timing of funding can create a stronger foundation for growth. What's particularly fascinating is his scientific approach to sales and his insights on avoiding the common pitfalls of enterprise customer development. Here's one of his quotes:  "We have one really clear definition [of success], and that is in the amount of water that we have saved. In the end, that relates to all our goals, because if we save so many Olympic-sized swimming pools of drinking water, which is 4 million (our BHAG), then it also means that we will probably build a very profitable company and make a huge impact on the world.” By listening to this podcast you will learn the following: That patient validation beats premature scaling because it builds stronger foundations. How to avoid pure sales hustle and having to rely on individual talent to secure the growth of your SaaS business. How to get everyone aligned in your company to create business velocity (not just departmental speed) Why you should always start your validation processes with end-users rather than just decision-makers. For more information about the guest from this week:  Robbert Lodewijks  Website: hulo.ai 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

This podcast interview focuses on the entrepreneurial journey to transform messy wearable data into standardized enterprise gold. My guest is Marco Benitez, CEO of Rook. Marco is a tech entrepreneur on a mission. He's a former Tae Kwon Do champion who transformed his athletic discipline into entrepreneurial success.  At just 22 years old (while still in college), he and his co-founder built a machine learning system for hospitals, which they successfully sold in 2006. This got him involved in clinical research - thereby working for pharmaceutical giants like Roche and Novartis. This is where stumbled across big challenges that were caused by the absence of enough meaningful health data. And this became the founding idea behind ROOK, which he founded in June 2017.  What began as a heart rate monitoring platform in 2018 evolved into a sophisticated B2B platform that now integrates with over 300 wearable devices.  Their vision: to create a healthier world by making health data accessible and meaningful.  And this inspired me, and hence I invited Marco to my podcast. We explore the journey of building a groundbreaking health data platform. Marco tells the story how COVID destroyed their fitness-center business model, and what lessons he learned in the process of pivoting. He shares his insights on enterprise sales cycles, pricing strategy, and team building. Last but not least he explains how he's deliberately portraying the startup's challenges to find the right cultural fit and his mantra of "cut through the noise and keep walking" when it comes to facing tough decisions.  Here's one of his quotes Once you switch your mind, instead of selling a product, you are selling data, and you are really selling a problem, that's when they put your price on you. Because if you are selling a very good solution to their problem, that's when they are will say, ‘This is a no-brainer. I don't care how much you are going to charge to me.’ During this interview, you will learn four things: What insights changed their ability to charge premium prices in enterprise deals? What's he's doubling down on successfully to shorten the typically long sales cycles.  Why he emphasizes radical transparency, sharing financials and challenges with potential hires. His secrets to staying persistent and disciplined, even when facing doubts or lack of motivation For more information about the guest from this week: Marco Benitez Website: Rook  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

This podcast interview focuses on the entrepreneurial journey to make buying and selling in B2B remarkably easier.  My guest is Mark Fershteyn, Founder and CEO of Recapped. Mark is a tech entrepreneur on a mission. He has a passion for building things from scratch. He specifically prefers going from "zero to one" rather than maintaining existing systems, describing himself as someone who enjoys "bushwhacking through the jungle" and forging new trails. His entrepreneurial journey includes diverse experiences: He co-founded Tryhard Games LLC. Led sales at App Academy, a coding bootcamp, and has a remarkable history of taking on challenging situations. At Citrix, he volunteered to manage their worst-performing sales team - one where no one was making quota. Within 6-9 months, he transformed it into a top-three revenue-producing vertical. In Jun 2019, Mark founded Recapped, a customer collaboration platform that helps B2B sellers work more effectively with buyers.  Their mission: to solve the "messy middle" of sales and change the way how B2B sales teams collaborate with buyers and close deals.  And this inspired me, and hence I invited Mark to my podcast. We explore how he transformed Recapped from a side project into a game-changing deal collaboration platform, achieving a remarkable 44% win rate for customers - far above the industry standard of 15-18%. He reveals counterintuitive insights from his sales process optimization at Citrix and elaborates on his approach to building a remarkable software company. Last but not least, he shares his unusual incentive approach that helped him and his team to significantly grow a high-quality pipeline. Here's one of his quotes I fundamentally believe 90% of your Salesforce data should be client-facing and should be shared with the prospect... if you're not on the same page, get them out of your pipeline and go focus on deals that are actually going to move the needle. During this interview, you will learn four things: Why he would split the focus 50/50 between product and distribution if he would ever start again? How he's increased close rates by deliberately blending in more professional services How 10% of features but 10x the marketing can outperform having more features but less visibility How the science of selling is 80-90% of success, while art is only 10-20% - making the process repeatable matters more than individual talent For more information about the guest from this week: Mark Fershteyn Website: Recapped 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

This podcast interview focuses on the entrepreneurial journey to successfully merge and integrate two distinct SaaS companies while balancing stakeholder interests, maintaining growth, and navigating complex market dynamics. My guest is Randy Wootton, CEO of Maxio. Randy is a serial CEO. Before becoming CEO, he held senior positions at industry giants like Microsoft and Salesforce, where he led sales, service, and marketing teams. His career has given him a truly global outlook. He has worked internationally, opening up divisions in England and Australia, and has hired teams across multiple countries, including France, the UK, the US, Japan, and Australia. In March 2015 he moved to Rocket Fuel, a first-generation AI company. He started as their CRO, quickly turned CEO, and took the company private 2 years later. He then became the CEO of Percolate, where he led the company's transformation from a mid-market social media product to an industry-leading content marketing platform.  And now, since May 2022, he is the CEO of Maxio, a billing and finance operations platform for B2B SaaS companies. Their mission: to help its customers amplify their recurring revenue and decipher their next stage of growth. And this inspired me, and hence I invited Randy to my podcast. He provides invaluable insights for B2B SaaS CEOs navigating growth and mergers by sharing candid experiences from this process. He discusses his strategic decision-making frameworks and highlights the challenges of brand management post-merger and the complexities of transitioning from sales-led to product-led growth. He also zooms into the complexities of expanding into new markets and how to go about that. He ends with advice on fostering innovation, managing stakeholder expectations, and personal development.  Here's one of his quotes As you think about your expansion strategy and your growth agenda, there's going to be a set of things you're just going to grow within your current segment. But then you're going to think about which category we should explore next. But as you start, you've got to get really clear about what you do better than anyone else. During this interview, you will learn four things: The four key support pillars for B2B SaaS CEOs. How to go about merging distinct company cultures so the business becomes stronger and keeps delivering on growth expectations. What he would have done differently if he could deal with the branding opportunity again. His framework for evaluating expansion opportunities to find the next area of growth for the company. For more information about the guest from this week: Randy Wootton Website: Maxio 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