In this episode, Ben sits down with Casey Graham, Co-Founder and CEO of Gravy Solutions, the first-ever payment recovery solution for subscription-based businesses. Prior to launching Gravy, Casey founded the Rocket Company, which he successfully exited in 2016. During this episode, Casey opens up about how his grandfather’s suicide initially led him to the path of entrepreneurship, how his successful company exit resulted in a deep depression, and his overall perspective on company culture...

In this episode, Ben sits down with Alexa Gates, Demand Generation leader at Catalyst. During their conversation, Ben and Alexa discuss the value of being direct and upfront in all communications, and why it’s essential for organizations to have a clear mission in mind from the get-go. Alexa explains how a role in demand generation can be compared to putting together the pieces of a jigsaw puzzle, and how in many ways, the function acts as the connective tissue for all marketing teams. They...

In this episode, Ben sits down with Sara Masson, the VP of Customer Success at leap tools, a company that’s on a mission to revolutionize the retail experience through AR technology. Sara recently joined the company following the birth of her daughter. During their conversation, Ben and Sara discuss a wide variety of topics including parenting, customer success, company culture and even juggling work with breastfeeding. They offer candid views on building psychological safety in the...

In this solo episode, Ben discusses various aspects of tech culture. He shares his perspective on recent scripted drama series that have depicted tech startup culture like Super Pumped featuring Joseph Gordon-Levitt, about the founding story of Uber, WeCrashed featuring Anne Hathaway and Jared Leto, about the founding of WeWork, and The Dropout featuring Amanda Seyfried, about Elizabeth Holmes and the story behind Theranos. Exploring the narratives surrounding these companies and their origin...

This brief episode was recorded on the day Russia invaded Ukraine, and in it, Ben shares his thoughts on compartmentalizing work and life, making the most out of the time you have, and how people can best support each other at work when things like this happen. 

In this episode, Ben broaches more hot topics in the tech landscape today. He discusses LinkedIn’s new filter option, which allows users to remove political content from their feeds, the ongoing hiring crisis in the workforce today, the Metaverse and more. Ben also emphasizes the need for clearer pathways towards building a career in tech to usher in the next generation of the workforce.

In this episode, Ben offers his take on some of the most controversial headlines in the business world today. He discusses how Peloton recently laid off 20% of its staff (2,800 people), and why people are saying the way the leadership team handled the layoffs was tone deaf. Ben also discusses how Apple classifies every employee as an “associate” after they leave the company, regardless of what their title was while they were there, and why this could affect future job prospects. Last but not...

In this episode, host Ben Winn is back to discuss more key trends and developments happening in the SaaS community right now. He explores the impacts of inflation on wages and company-wide pay increases. Ben also discusses remote work and mental health, touching on a recent UK poll of 2,000 employees which found that only 41% were willing to raise their concerns with management. 

In another special solo episode, host Ben Winn is back to discuss more key trends and developments happening in the SaaS community right now. He explores the idea of sabbaticals, which are now being offered as an employee perk at companies like PayPal, Adobe, Dropbox and more. Ben also discusses the overall sustainability of the remote work movement, and how it can be balanced with in-person collaboration and community. Finally, he touches on the importance of staying loyal to your company...

In this special solo episode, host Ben Winn discusses new key developments happening in the SaaS community. He explores the concept of the four-day workweek and how it may help to boost productivity, different time-saving strategies, and tips for any professionals who are hoping to make a change in their career in 2022. Finally, Ben rounds out the episode by emphasizing the importance of placing a strong focus on employee satisfaction for companies looking to make their mark this year.

In this episode, Ben sits down with Lloyed Lobo, the Co-Founder and President of Boast.AI., a company that automates access to research and development, tax credits and innovation incentives so companies can fuel their growth while preserving equity and avoiding red tape. During the episode, Lloyed shares the details of his non-linear founding journey, his thoughts on building brand equity, and how creating a strong sense of community can magnify a business’s impact.

In this episode, Ben sits down with Liz Willits, the owner of Liz Willits marketing consultancy and the number one marketer on LinkedIn (according to her mom). Liz specializes in email marketing, copywriting, content marketing and demand generation, and she works across customer success, sales and marketing teams. During the episode, Liz explains the reasons behind her decision to operate as an independent consultant, why she uses LinkedIn as a tool for self-promotion, and the steps she took...

In this episode, Ben sits down with Melissa Kwan, the Co-Founder and CEO of eWebinar, a tool that automates webinars to free up more of your time. Melissa shares the fascinating story of how she became a digital nomad to travel the world, and what she learned from the experience of building eWebinar on a completely remote basis. She also offers some insightful advice about prioritizing happiness and building your career around your life, not the other way around.

In this episode, Ben sits down with Guillaume Moubeche, the CEO and Co-Founder of lemlist, sales automation and cold email software that helps companies personalize cold emails, automate follow-ups, and engage with leads across all channels. During the episode, Guillaume shares the company’s unique growth strategy, the story of how the company nearly failed twice, and the philosophies he holds that have led him to success. He also shares the creative strategies the company used to bring the...

In this episode, Ben sits down with Eric Johnson, the director of the Center for Decision Sciences at Columbia University and the author of the newly released book, The Elements of Choice. During their discussion, Ben and Eric talk about the science of decision making, the tools that can be employed to steer decision making, and how it all applies to the larger context of tech and the customer experience. Eric provides an overview of the science behind human decision making processes, and how...

Fred Reichheld is a Bain fellow and the inventor of NPS, or Net Promoter Score, which is a system adopted by thousands of companies around the world to measure customer loyalty. He's authored several bestselling books that have helped companies thrive in a customer-driven economy, and according to the New York Times, his work has put loyalty economics on the map. In this episode, Fred and Ben discuss strategies for measuring customer success and strengthening customer loyalty, as well as some...

Jack Ryan is the Partner Manager at SaaStr, the world’s largest community of SaaS professionals. In this episode, Ben and Jack discuss Jack’s journey of suffering a broken neck and numerous strokes, which led to his paralysis and near death. Jack tells the inspiring story of how through sheer grit and determination, he was able to overcome his injuries to regain full mobility and even climb Mount Whitney, the tallest summit in the continental U.S.

Mike Roberts is the Head of Marketing at Catalyst Software, AKA Ben’s boss. In this episode, Ben and Mike discuss some of the projects they’re most proud of in their careers so far, the importance of reflecting on our progress overtime, and achieving optimal work/life balance. They also touch on how they’ve cultivated careers they love, and the correct pronunciation of La Croix.

Leah Chaney is the founder and Chief Experience Officer of BetterGrowth, a consultancy that helps companies gain clarity on why sales are decreasing, churn is climbing, and employees are leaving by providing a step-by-step action plan. She’s also the Founder of BreakoutCS, a community for CS professionals. In this episode, Ben and Leah discuss the stories behind BetterGrowth and BreakoutCS, some of the challenges she’s faced while navigating her career as a queer person in tech, and how...

Stacy Schmitz is an Enterprise Account Executive at Catalyst Software. In this episode, Ben and Stacy discuss how she has seen incredible success in her career so far, reaching 200% of her quota last quarter. Stacy also shares her unique approach to sales, what motivates her, and how the industry has evolved in recent years.

Bradley Liou is the Head of Customer Success at Acquire, an app that’s transforming e-commerce by creating unforgettable checkout experiences. In this episode, Ben and Bradley discuss the sabbatical Bradley took recently to support his wife who was struggling with postpartum depression and how it helped him realign his priorities. Bradley also shares the story of how he landed his new role at Acquire, and why the company is such a great culture fit.

Edward Chiu is the Co-Founder and CEO of Catalyst Software, a company that helps businesses centralize customer data, get a clear view of customer health, and scale experiences that drive retention and growth. In this episode, Ben and Edward discuss the company’s mental health initiatives, Edward’s “Hot Ones” video, and the incredible growth of Customer Success over the last 2 years. 

Kris Rudeegraap is the CEO and Co-Founder of Sendoso, the leading sending platform that helps companies engage with customers throughout the buyer’s journey. In this episode, Kris and Ben discuss how the best ideas often come from a problem that needs solving, working smarter not harder, and approaching business as a marathon, not a sprint.

Mike Murchison is the CEO and Co-Founder of Ada, the leading provider of AI customer support chat bots that automates millions of chat-based conversations per month for clients like TELUS, Coinbase and Shopify. In this episode, Mike and Ben discuss the company’s origin story, their recent partnership with Zoom, and why simplicity is one of their core values.