Tech Entrepreneur on a Mission Podcast

<p>Welcome to the Tech Entrepreneur on a Mission podcast.</p><p><br></p><p>My name is Ton Dobbe. I am the founder of Value Inspiration and the author of ‘The Remarkable Effect’.</p><p>I envision a world where every B2B SaaS business succeeds because they're creating software their customers would miss if were gone</p><p><br></p><p>𝗛𝗲𝗿𝗲'𝘀 𝘄𝗵𝘆: </p><p><em>Research consistently shows 90% of all startups fail. That's bad. </em></p><p><em>What's worse however is that +75% of SaaS Scaleups fail - companies that are supposed to have product-market-fit.</em></p><p><br></p><p><em>Far too few Scaleups create the traction they aspire for and fail for the wrong reasons</em></p><p><br></p><p>I believe this should stop - and hence I started my business and this podcast</p><p><br></p><p>The goal I have with this podcast is two-fold:</p><ol> <li>to inspire new forms of value creation by sharing compelling ideas and stories about the potential we can unlock when technology and people blend in the right way.</li> <li>Share experiences from tech entrepreneurs like you about what it requires to create a remarkable software business and how to overcome the roadblocks to do so.</li> </ol>

#343 - Aytekin Tank, CEO Jotform - on continuous innovation and momentum

This podcast interview focuses on the entrepreneurial journey to build a global SaaS company with 25 million users without venture funding. My guest is Aytekin Tank, Founder and CEO of Jotform. Aytekin founded Jotform in 2006, creating a pioneering WYSIWYG online form builder that has grown to serve over 25 million users worldwide today.  What's remarkable is that he bootstrapped the company from the ground up. This allowed Jotform to remain 100% independent and define its own rules and company culture as it grew. Under his leadership, Jotform has experienced impressive international growth, with offices in seven different cities around the world. Their growth and style were recognized as Jotform was named one of the "Best Privately-Owned Companies in America" by Entrepreneur Magazine. Aytekin is not just a successful entrepreneur but also an automation enthusiast. He recently published a book titled "Automate Your Busywork. His book shares his insights on the automation philosophy he applied to grow Jotform. This inspired me, so I invited Aytekin to my podcast. We explore his biggest lessons learned from bootstrapping a form-building tool to leading a global company with 25 million users. He elaborates on his approach around continuous innovation and maintaining momentum (rather than worrying about competitors) and shares his insights on prioritizing product development and growth. Last but not least, he talks about how he recently gave new meaning to his 'Founder’ role and why every SaaS entrepreneur should do that. Here's one of his quotes Being a founder is not just about leading a team, coaching a team, managing a team. But it's also about improving myself, growing myself. Because being a founder is about growth. It's about growth mindset. It's about growing yourself with the company. It's about growing your company. And it requires some dedication to do that - growing knowledge and learning. During this interview, you will learn four things: How he's working with customers to ensure JotForm's success His first principles for managing growth and avoiding getting bogged down in busy work. How he's organized his development teams and their rituals to ensure momentum on the one hand and optimal alignment on the other hand. How he approached competition from Google Forms to come out stronger themselves.  For more information about the guest from this week: Aytekin Tank Website: Jotform 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

12-18
58:00

#342 - Ozan Unlu, CEO of Edge Delta - on solving critical business problems.

This podcast interview focuses on the entrepreneurial journey to eliminate the risk that cost businesses thousands of $ per second of downtime. My guest is Ozan Unlu, Founder and CEO of Edge Delta. Ozan has had an unconventional career path that spans multiple disciplines. He started as a nanoscientist and researcher before transitioning into the tech world. His professional journey includes roles at major tech companies. He worked as a Software Development Lead and Program Manager at Microsoft, and as a Senior Solutions Architect at Sumo Logic. In September 2018, he founded Edge Delta after recognizing the need for a new approach to handling the exponential growth of data in modern organizations. Their mission: Change the way enterprises manage their data - particularly in mission-critical systems. And this inspired me, and hence I invited Ozan to my podcast. We explore what it takes to navigate the complexities of building a successful B2B SaaS company in a competitive landscape. He elaborates on his approach to solving mission-critical problems and building credibility in deep-tech enterprise markets around a new category. Ozan also shares how he's maintaining a long-term vision while addressing urgent needs - and what he's doing differently to assemble and align a world-class team. Lastly, he discusses the challenges of market education, gaining early adopters, and scaling efficiently.  Here's one of his quotes If you're at an early-stage startup, look at how you're solving problems. Don't put more problems on other people's plates. Say, “Hey, this is how I'm solving a problem. This is what I think is the best approach.” And if people disagree with you, just make sure you're walking away with a mutual commitment.  We do this all the time, whether it's myself or someone else at the company where you say, You know what, I disagree, but I'm committed. Let's go do it that way.  That's super important because when you're dealing with companies that make hundreds of millions of dollars in profits a day, that is very hard to fight against if you aren't all in lockstep and marching forward. During this interview, you will learn four things: What he learned from their rapid growth period (6x employees in one year) and what he'd do differently next time. Why he's saying no to companies like Apple (even though they might be able to help them). Why he continues to focus on solving big technical problems rather than taking an easier route. What he's done to build credibility and trust in the market. For more information about the guest from this week: Ozan Unlu Website: Edge Delta 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

12-11
50:37

#341 - Daniel Saks, CEO of Landbase - on reclaiming your day with AI

This podcast interview focuses on the entrepreneurial journey to redefine software's role from engagement-driven to impact-driven solutions. My guest is Daniel Saks, CEO of Landbase. Daniel's entrepreneurial journey has deep roots in a 100-year-old family business. He grew up in Niagara Falls, Canada, where his family owned a furniture store founded by his great-great-grandparents in 1908.  However, the 2009 recession forced the century-old family business to close, which became a pivotal moment in Daniel's life. Instead of lamenting the loss, he was inspired to explore how technology could have saved small businesses like his family's store.  This experience led him to co-found AppDirect, a B2B subscription commerce platform that grew to generate over $3 billion in annual transaction revenue. In May 2023, he co-founded Landbase, which he leads as the CEO. He sees Landbase as his "second business" with a continued mission of "helping B2B businesses or entrepreneurs thrive." This time, the focus is on applying agentic AI to go-to-market strategies.  And this inspired me, and hence I invited Daniel to my podcast. We explore what's broken in the way companies still automate today. Daniel shares a compelling vision for the future of B2B SaaS powered by agentic AI - thereby creating a 5x lager market than today's software industry. He discusses how companies can achieve significantly better results while allowing executives to "reclaim their day." He also explains how this new technology can help build digital credibility, which is essential for companies to stand out. Here's one of his quotes I think that era of software, including business software, was all driven by what is the amount of hours that someone spends in your tool. And I think those are all the wrong metrics. My kind of goals with Landbase and agentic AI is the opposite. It's actually: how few, how little amount of time does a human have to spend in the software, but how much impact does the software make for the human so they can have more time to do what they love. During this interview, you will learn four things: What he's doing differently to create defensible differentiation.  His approach to helping his customers avoid waste of resources and money as they speed up their Go-to-Market activities. Why he advises against imposing previous playbooks/values on new ventures. What he learned from speaking to customers about their biggest painpoints that helped him to build far better products. For more information about the guest from this week: Daniel Saks Website: Landbase 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

12-06
56:23

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

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

11-27
42:09

#339 - Griffin Parry, CEO of m3ter - on taking the pain out of billing operations.

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

11-20
49:37

#338 - Hadassah Backman, CEO of Guardoc Health - solving critical industry problems

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

11-13
47:16

#337 - Dan Uyemura, CEO of Pushpress - on Vertical SaaS differentiation

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

11-06
47:00

#336 - Victor Kristof, CEO of DemoSquare - on resilient customer-driven innovation.

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

10-30
41:54

#335 - Joaquim Lecha, CEO of Typeform - on creating SaaS products customers love.

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

10-23
55:03

#334 - Bridget Harris, CEO of You Can Book Me - on the art of Bootstrapping.

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

10-16
45:52

#333 - Caitlin MacGregor, CEO of Plum- on successfully navigating market change

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

10-09
56:01

#332 - Matt Van Itallie, CEO of Sema - on executive Insight into code quality.

This podcast interview focuses on the entrepreneurial journey to make complex code understandable for business leaders. My guest is Matt Van Itallie, Founder and CEO of Sema. Matt has a diverse background spanning law, consulting, education, and tech, and he has held leadership roles at edtech and govtech companies like Social Solutions, and PeopleAdmin.  He earned his J.D. from Harvard Law School after studying history at Swarthmore College. He's also a thought leader on the impact and responsible adoption of AI in the tech industry. This multidisciplinary experience gives him a unique perspective as a tech founder and CEO. In September 2017, he founded Sema, a codebase scanning tool.  Their mission: to bridge the gap between the technical and non-technical worlds, particularly in the context of software development. And this inspired me, and hence I invited Matt to my podcast. We explore how most tech organizations carry more debt in their codebase - and the business risks that brings. Matt shares his vision of how to solve this - in a world where AI-generated code and Open Source are rapidly gaining popularity. He discusses the learning process he had as a founder in creating a singular, non-consensus vision for the company - and how their unusual approach upfront helped them gain deep differentiation and first-mover advantage.  Here's one of his quotes What I know now that I didn't know as a baby entrepreneur was there are so many different versions of 'No,'  except 'Here is some money.' Everything else is 'No'  "I love it. So interesting. I can really see this helping. This is a pain point. Yes, I want to pilot Yes, I want to tell my friends." That's all No. It's all versions of No, except "here is some money." During this interview, you will learn four things: How he uncovered a new, totally overlooked, target market where his product quickly became mission-critical, rather than a nice to have. Why he's prioritizing building trust-based relationships with key players in the industry and how he's achieving this. What he's doing differently around creating a team that is more than the sum of its parts. His recommendations on choosing your business model wisely.  For more information about the guest from this week: Matt Van Itallie Website: Sema 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

10-02
50:07

#331 - Christian Klepp, host of the “B2B Marketers on a Mission” Podcast - on how curiosity drives B2B marketing.

This podcast interview focuses on the entrepreneurial journey to drive change and adapt as a B2B marketer in an evolving business landscape. My guest is Christian Klepp, Co-Founder of EINBLICK Consulting and Host of the B2B Marketers on a Mission podcast.  Christian is a global citizen, entrepreneur, podcast host, and B2B branding expert with over 13 years of experience across diverse markets. Throughout his career, he worked with major global brands like Philips, Caterpillar, Samsung, and Logitech.  He is a true "third-culture kid." He grew up in Austria, the Philippines, Singapore and China - and is currently living in Canada, giving him a multicultural perspective and ability to bridge East and West. In 2019, Christian took a leap of faith and co-founded his own B2B branding and marketing consulting firm called EINBLICK. He's also the host of the popular "B2B Marketers on a Mission" podcast, where he interviews talented professionals in the B2B space and provides a platform for sharing cutting-edge insights with the B2B community. Being a regular listener of his podcast inspired me to invite Christian to my podcast. We explore why marketing isn't optimally leveraged inside many B2B SaaS companies. He shares insights from well over 100 podcasts on what marketers should do differently to increase alignment and buy-in across the organization to make a larger impact. Last but not least, he explains how to avoid complacency in marketing and how, by leveraging different perspectives, the company can stand out more and increase resilience to adapt faster to market change. Here's one of his quotes The way that marketers need to deal with addressing buy-in is they need to understand how their organization works. How does your company generate revenue? Where is the most revenue coming from? Which industries? Which customers? Do you understand what EBITDA is? Because if you don't understand, you better start learning about it quickly because that's what your board cares about. During this interview, you will learn four things: How to turn marketing into a core driver for the business.  How to get insights that matter beyond just interviewing customers. How to approach podcasting strategically, get instant value, and what to prioritize first to get going. How to go about analyzing competitors' strategies to further strengthen differentiation. For more information about the guest from this week: Christian Klepp Website: EINBLICK B2B Marketing on a Mission Podcast (Spotify / Apple) 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

09-25
45:20

#330 - Thomas Wulff Wilhelmsen, CEO of Less - on creating a customer-funded business.

This podcast interview focuses on the entrepreneurial journey to empower business users, especially in SMEs, to easily find insights in their data without technical complexities. My guest is Thomas Wulff Wilhelmsen, Co-founder and CEO of Less. Thomas and his co-founder Daniel previously worked as consultants in the data space before founding Less. Their experiences and frustrations in this role inspired them to create an analytics product for people like themselves. And that led to the birth of Less in September 2022. The name "Less" embodies their goal of stripping away complexities to build a product that focuses on the end goal and takes care of the technical aspects behind the scenes. Their mission: Set doers free to do what they do best: Roll up their sleeves and solve problems.  And this inspired me, and hence I invited Thomas to my podcast. We explore what's, after decades of development, still broken in the Business Analytics solutions market. Thomas shares his lessons learned from steering Less' journey as a customer-funded startup. He shares how he got early traction with paying customers and how he's creating a culture of analogical thinking to solve problems in creative ways.. Last but not least, he'll inspire you with his fresh perspective on crafting a compelling narrative that sells.  Here's one of his quotes "We've been focusing more on the persona than on the sector or industry. We call them doers. People that are curious by nature, that are frustrated with being dependent on other people and want to build cool things that they can show to other people in their teams and drive that change internally." During this interview, you will learn four things: Where he finds inspiration from taking Storytelling for his business to the next level. What he's done differently from the start to get traction and stay in control as the business grows.  How he ensures everyone understands what's important, and does the right things right to create fans from the start. Why he embraces being "customer funded" rather than just bootstrapped. For more information about the guest from this week: Thomas Wulff Wilhelmsen Website: Less 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

09-18
47:07

#329 - Angelo Coletta, CEO of Zakeke - on becoming a global leader in visual commerce.

This podcast interview focuses on the entrepreneurial journey in identifying an emerging opportunity and building an innovative, fast-growing company that transforms how we shop online. My guest is Angelo Coletta, CEO and Co-founder of Zakeke. Angelo is a serial entrepreneur who has founded and exited multiple companies.  In 2017 he co-founded Zakeke, an AI Visual Commerce platform. It's doing groundbreaking work in transforming the B2B customer journey and shopping experience. With this focus, it's now  serving 10,000+ eCommerce brands worldwide across 400+ industries Their mission:  To improve the industry's environmental footprint through the use of technology in the display process, the shopping experience, and the purchasing experience. And this inspired me, and hence I invited Angelo to my podcast. We explore how the shopping experience is still broken today - and why. Angelo shares his how he's building an organization to fix this and shares anecdotes about his lessons learned in choosing the right team, fostering a culture of innovation, and setting ambitious long-term goals. He then elaborates on creating resilience across the business, customer-centric product development, and how strategic acquisitions and investment in eco-system helped to scale their business. Here's one of his quotes I wanted to create a company that was totally based on a long-term vision. This is one of the most difficult choices to make when you start because it means you burn more money in the first years of the company. My opinion is that if you don't start as a long tail business, it's difficult to transform a company with 200 or 300 big customers into a company able to serve 1000s of customers, maybe most of them small customers. During this interview, you will learn four things: Why have a global mindset from day 1. Why focus on product excellence first before you consider a marketing push? What Angelo specifically prioritizes when it comes to hiring the right people that will help the company grow in good and tough times.  The strategies he applied to establish trust and leverage their growth opportunity via the e-commerce ecosystem.  For more information about the guest from this week: Angelo Coletta Website: Zakeke 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

09-11
48:53

#328 - Matthew McGrory, CEO at Arwen AI, on solving a problem of global scale.

This podcast interview focuses on the entrepreneurial journey to make social a positive place again - for everyone. My guest is Matthew McGrory, CEO of Arwen AI. Matthew is a tech- entrepreneur on a big mission. He has held tech leadership roles: IT Director at Logicalis, Director Managed Services at Acora, and Managing Director at Carrenza (a cloud service provider acquired by Six Degrees Group),  In the period from July 2018 and September 2020 he took a break from his corporate life to become a House Husband. In that period he developed a passion for using AI to drive positive change. That led him to cofound Arwen AI in September 2020. Arwen AI is a platform that helps its customers actively moderate and manage their community, across both paid and organic. Their mission: to make social media a more positive place by filtering out hate speech and toxicity.  And this inspired me, and hence I invited Matthew to my podcast. We explore what's broken in today's Social Media world. Matthew shares his vision to make Social a place without toxicity and spam. He then elaborates on his hard-won lessons from his journey to speed up direct sales and benefit from using ecosystems to grow even faster. Last but not least, he shares his framework to increase resilience across the organization.  Here's one of his quotes I thought, 'This is great, we'll create some technology, fix the problem and everyone will buy it.' I was so wrong on that part. I got to about demo number 200, it was with a US broadcast news organization. And the head of digital said, 'Listen, I'm protected by the First Amendment, I can let anything go up on my channels. I don't have to get rid of it. You're giving me an extra job to do. An extra cost. Tell me why this is valuable to my business. Tell me how it makes me money or saves me money.' During this interview, you will learn four things: How he gained traction in a market where customers resisted to buy because they saw the solution as an extra job and an extra cost.  What he did differently to gain technical and commercial momentum. What he invested in early on to get access to strategic accounts and speed up the commercial contracting process in enterprise sales situations. How he goes about to keep the business humming, and keeping everyone aligned and motivated - especially in tough times. For more information about the guest from this week: Matthew McGrory Website: Arwen 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) Learn more about your ad choices. Visit megaphone.fm/adchoices

09-04
59:03

#327 - Josh Ellars, CEO of OpenGTM - on Differentiation and growing efficiently.

This podcast interview focuses on the entrepreneurial journey to take GTM efficiency to the next level for enterprise SaaS companies. My guest is Josh Ellars, CEO of OpenGTM. Josh has over 15 years of experience leading successful go-to-market (GTM) functions at high-growth SaaS companies like Metalogix, Qualtrics, and OpenGov. This extensive background gives him unique insights into scaling SaaS businesses. In 2021 he founded Patri, which was rebranded OpenGTM in 2023. OpenGTM is platform to create content buyers love, capture high-intent leads, and uncover the truth behind your buyers and pipeline.  It's mission: to unite sales, marketing, customer success, and product around the attributes of highly-retained customers in order to boost revenue and retention. And this inspired me, and hence I invited Josh to my podcast. We explore what's broken in today's world of Go-to-Market (GTM). Josh shares his wealth of experience in scaling SaaS businesses. He emphasizes the importance of the "sell, design, build" methodology, where market demand pulls product development. He also explains, how their approach helps companies cut through the noise of the crowded go-to-market tech landscape. And last but not least he shares some big lessons learned on differentiation and growing efficiently. Here's one of his quotes Too often in Go To Market and in company building in general, we're driven by product market fit. And that's wonderful. But a big portion of that is really identifying: Is there security and regulatory fit? Is there a financial fit? Can we get some sort of return out of this investment we're making in this customer? And I absolutely saw that I had to learn the hard way and lose some very large deals. That got me thinking that I think there's a better way to to vet these opportunities.  During this interview, you will learn four things: What B2B SaaS companies should look for beyond product-market fit to grow more efficiently. Their framework that drives product strategy in order to build remarkable products.  How they avoid getting caught up in tech-stack rationalization.  How to expand market scope gradually while maintaining a narrow focus on the ideal buyer profile.  For more information about the guest from this week: Josh Ellars Website: OpenGTM 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

08-28
46:33

#326 - Niklas Hanitsch, CEO of SECJUR - on balancing culture and growth challenges

#326 - Niklas Hanitsch, CEO of SECJUR - on balancing culture and growth challenges A story about maintaining a blue ocean market in the rapidly evolving compliance automation landscape. This podcast interview focuses on the entrepreneurial journey to sustain in a heavily competitive market. My guest is Niklas Hanitsch, Co-founder and CEO of SECJUR. Niklas is a tech entrepreneur on a Mission. He was an idealist punk who turned lawyer, then SaaS founder. He's got deep expertise in data privacy, compliance, and agile product development. And entered the prestigious Top 40 under 40 list by Capital Magazine in November 2023.  Over the years, he grew the belief that while data protection and compliance requirements are important, the implementation should not become a stumbling block for companies. And that became the big idea behind SECJUR, an AI-driven compliance automation platform, which he founded in December 2017. Their vision: A world where businesses are always compliant, but never have to think about it. And this inspired me, and hence I invited Niklas to my podcast. We explore how personal tragedy grew into entrepreneurial drive. He shares how he bootstrapped the company towards growth, navigated fundraising during a recession, and built a resilient team culture from the start. Beyond that, he elaborates on his frameworks for strategic decision-making, hiring for values fit, and relentlessly delivering customer value. Last but not least he shares practical advice on how to stay motivated and sane in the crazy world of building a software business. Here's one of his quotes "Bootstrapping was definitely something that made us successful because we had time to really focus on the business and not focus on fundraising, on report creating reports and stuff like this. So we learned a lot about what customers really want in that time, because we could spend all our time with customers." During this interview, you will learn four things: How Bootstrapping gave him an advantage you cannot get when you start your venture with VC backing.  His approach to staying ahead of the competition as the market gets more crowded.  His advice (having been a lawyer himself) on how to go about committing to contracts His 3-step framework for hiring talent For more information about the guest from this week: Niklas Hanitsch Website: SECJUR 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

08-21
45:00

#325 - Matt Achariam, Co-CEO Clay - on fueling organic growth through Remarkability.

This podcast interview focuses on the entrepreneurial journey to finally solve the problem of managing all your personal and professional relationships. My guest is Matt Achariam, Co-Founder and Co-CEO of Clay. Matt has a diverse background in product development and design.  He was a principal at design agency FortySix, working with clients like Disney, BBC, Expedia, and the University of Pennsylvania and held product roles at Custora (acquired by Amperity) and LayerVault (acquired by Tiny Capital) and  He has a lifelong obsession with the craft of design, sparked by childhood curiosity about why certain objects elicit feelings of joy. This led him to question the status quo in relationship management software - and that's how the vision behind Clay was born. In 2018, he and his co-founder, Zach Hamed, founded the company, an app for managing personal and professional relationships.  Their mission: to help people be more thoughtful and helpful with their relationships, ultimately helping them achieve more and be happier by putting others first. And this inspired me, and hence I invited Matt to my podcast. We explore his journey of building Clay. Matt shares how he and his team create meaningful differentiation beyond just solid functionality. He elaborates how they gained early traction and created strong organic growth that enables them to now manage over 100 million relationships. Last but not least, Matt shares his insights on navigating tradeoffs, maintaining confidence in decision-making, and staying true to company values while scaling rapidly. Here's one of his  quotes Be very clear about the values and the lines that you will cross and won't cross because when things start speeding up, momentum is something very precious.  When you move really fast, you have to move with confidence. And if you don't have the confidence and that foundation, you're not going to be able to make decisions rapidly. During this interview, you will learn four things: His unconventional approach towards creating a "minimum remarkable product" instead of a "minimum viable product"  How they strengthen their differentiation by focusing on things other than just functionality, and where he focuses to find inspiration. How they've managed to achieve all their growth to be entirely organic and driven by word-of-mouth What signals, he in hindsight, wishes they had paid more attention to in order to grow even more. For more information about the guest from this week: Matt Achariam Website: Clay 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

08-14
38:41

#324 - Lee Rubin, Founder and CEO of Confetti - on designing for business resilience.

This podcast interview focuses on the entrepreneurial journey to build a business that can survive crises and emerge stronger every time. My guest is Lee Rubin, founder and CEO of Confetti.  Lee is a visionary culture leader with over a decade of experience in B2B sales. In 2014 she founded Wekudo - a remote corporate event planning agency. The idea behind it came while working at ZocDoc, where she struggled with the bureaucracy and logistics of planning team-building events.  Soon after that, she founded Confetti, realizing that the problem could only be solved through a combination of technology and people (not just people).  Under Lee's leadership, Confetti achieved exponential 600% growth during the COVID-19 pandemic and grew it as the leading solution for virtual team-building through a relentless focus on quality experiences. Their mission: to simplify event planning while empowering organizations to build stronger, happier, and more holistic teams through unforgettable shared experiences that make work life more memorable. And this inspired me, and hence I invited Lee to my podcast. We explore her journey to build a successful B2B SaaS company in a period when most of her competitors ceased to exist. Lee shares her story about a remarkable pivot during Covid, and why she decided to do nothing when "back to work" kicked in again. She also shares how she wasted 3 valuable years at the start, and what she could have done differently to avoid that. Last but not least, she elaborates on what ingredients she doubles down on to build a product people just keep talking about. Here's one of her quotes The main contributor to our success is that we built a platform that had a very strong form of agility. The platform can support various different use cases if we really want it to. It allowed us to pivot super quickly [during Covid]. The last invoice that we got from an in-person event and the first invoice that we got for a virtual was 10 days. We didn't spend time sitting in sadness that our events business was in shambles. We got right back to the drawing board, back to playing and having fun and trying to see what sticks - and the virtual events stuck. During this interview, you will learn four things: What she has done differently to survive during & post-COVID when other competitors closed their doors. How she managed to pivot her entire business in less than 10 days when Covid started.  What she learned from niching down, where everyone else was widening the net - and how that played to their advantage.  How she's embedded delivering "wow factor" in every aspect of her company - and why this has become unnegotiable for her.  For more information about the guest from this week: Lee Rubin Website: Confetti 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

07-31
43:10

Recommend Channels