The Work Item - Real Talk on Tech's Toughest Career Choices

In this week's episode, I sat down not with one, but two brilliant guests - the duo behind the brand-new venture known as SaaS Marketing Gym, Lianna Patch and Colleen Schnettler. As coaches and community leads for SaaS founders, they offer a refreshing counterpoint to the doom-and-gloom narratives trending on YouTube and other social channels about AI rendering software businesses obsolete. Through Lianna's conversion-focused (and delightfully humor-filled) copywriting expertise and Colleen's technical background, they're equipping SaaS founders with marketing strategies that prove software businesses aren't just surviving the AI revolution—they're positioned to thrive alongside it. What made our conversation so compelling was their evidence-backed optimism (a rare treat, I know) about the future of SaaS. While tech pundits predict AI will replace traditional software services, Lianna and Colleen articulate exactly why human-designed software solutions remain vital and how founders can use AI as an enhancement to what they're building rather than a replacement. Our discussion covers both the challenges of the current landscape and the surprising opportunities AI creates for SaaS companies that want to ride the wave. We talk about their origin stories and how they continuously evolve their skills to stay ahead of the curve. I guarantee you that you'll walk away with immediately actionable tactics and insights regardless of your company stage, and perhaps most valuably, a renewed confidence that SaaS remains a business model with staying power. You can find Lianna and Colleen on the following sites: 🌐 SaaS Marketing Gym 🦋 Lianna on Bluesky 🦋 Colleen on Bluesky 🐦 Lianna on Twitter 🐦 Colleen on Twitter 💼 Lianna on LinkedIn 💼 Colleen on LinkedIn The podcast was produced by Den Delimarsky. Feedback If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Chief Technology Officer - a few people I've talked to in the past year expressed some degree of interest in reaching, what seems like, the pinnacle of an engineering career. That three-letter title carries weight in boardrooms and across the industry alike. But beyond the fancy business cards and the seat at the executive table, what does it actually mean to hold the technical helm of an organization? Is it the promised land of pure architectural decisions and strategic vision, or something messier, more complex, and perhaps more rewarding in unexpected ways? Today, we're peeling back the curtain on the CTO role with Taiwo Oyeniyi, who'll share his journey from engineer to executive. Rather than relying on generic career advice or job descriptions, we'll hear firsthand about the transition, the challenges, and the realities of the position. Taiwo will explore the skills that matter most (spoiler alert: they might not be the ones you're cultivating now), the hurdles he faced along the way, and how the role has transformed his relationship with technology. You can find Taiwo on the following sites: 📽️ YouTube 🖼️ Instagram 📼 TikTok The podcast was produced by Den Delimarsky. Feedback If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

User research is an underappreciated art - we in tech are so used to being immersed in an ocean of quantitative data that we can forget that on the other side of the screen are real humans who want to solve very specific problems. And often times, their problems are extremely hard to put a number on. Why did they abandon their cart right before checkout? What made them start creating a new newsletter but then abandon it but come back a month later? Not everything can be answered with a SQL query against the telemetry database. Marisa Morby, a Principal Researcher at Observable, sat down with me to help me better understand what it means to be great (not just good) at user research, and how that can help produce a whole new range of unexpected product insights. And Marisa definitely knows what the impact of great user research can be on the product - she previously worked at such notable companies like Netlify, Gatsby, and Accenture Song, where she honed her skills and UX instincts. You can also find Marisa around the web: 🌍 Website 📷 Instagram 🦋 Bluesky 📰 Newsletter The podcast was produced by Den Delimarsky. Feedback If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

This is the last episode for 2024. To make it special, it's a supercut of all the unconventional advice from every single guest that was on the show this year - Kent C. Dodds, Jerod Santo, Rob Walling, Adrienne Tacke, David Khourshid, Saron Yitbarek, Rachel Andrew, Katie Fujihara, Lena Reinhard, Miriam Suzanne, Kirupa Chinnathambi, Craig Hewitt, Jennifer Wong, Jason Lengstorf, Michael Kennedy, and Asia Orangio. This turned out so well, that I will be definitely re-visiting the format in the new year. I hope you have a successful and adventure-packed 2025, with plenty of room for career growth. See you next year! The podcast was produced by Den Delimarsky. Feedback If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Asia Orangio, CEO of DemandMaven, shares her journey from marketer to founder, emphasizing a data-driven yet empathetic approach to growth. She discusses common mistakes that SaaS founders make and the importance of understanding customer insights. The conversation delves into the pitfalls of corporate growth strategies, the challenges of freemium models for bootstrap founders, and the necessity of merging quantitative data with human insights. Asia also highlights the iterative nature of effective growth strategies, encouraging a holistic view of business development.

If you are listening to this show, you have likely heard of a programming language called Python. And if you are a Python developer, you've likely heard of a podcast dedicated to this programming language - Talk Python To Me. It was started by none other than Michael Kennedy, a Python Software Foundation fellow who managed to turn his expertise into a viable bootstrapped business. In this show, we talk about ways to plan a training business from scratch, what tactics worked best to grow a podcast audience, and how to make sure that you have a viable idea before you quit your day job. You can find Michael on the following sites: 🌎 Website 😺 GitHub 🐘 Mastodon 💼 LinkedIn 🎥 Video 📚 Talk Python Training 🎙️ Talk Python To Me Podcast The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay. Feedback If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Jason Lengstorf, founder of Learn With Jason, shares insights from his journey in tech, transitioning from musician to developer advocate. He discusses the importance of building political capital and visibility while tackling business problems to forge trust in leadership. Jason emphasizes that the tools developers use are less crucial than understanding desired outcomes, and highlights the unique challenges of being a founder versus an executive. Embracing setbacks and individuality is key to personal growth in a constantly evolving industry.

In this discussion, Jennifer Wong, a seasoned engineering manager with roots in civil engineering, reflects on her unique journey into the tech world. She shares the thrills of quick project turnarounds in tech compared to construction delays. Jennifer emphasizes the value of user engagement and empathy over formal education in tech roles. She dives into the importance of mentorship and networking in transitioning to management, advocating for unconventional career paths as a key to long-term growth and success.

Craig Hewitt, the founder of the podcasting platform Castos, comes from generations of entrepreneurs, and his own journey builds on the experience and stamina of those that came before him. In this show, we chat about best practices for hiring developers for your bootstrapped startup, finding the right approach to deliver hard news, and how to ensure that your relationships aren't hurt as you embark on the entrepreneurship treadmill. You can find Craig on the following sites: 📝 Blog 💼 LinkedIn And of course, make sure to check out Castos! The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay. Feedback If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Kirupa Chinnathambi, a Product Manager at Google and creator of kirupa.com, shares his journey from hobbyist to professional. He discusses the unexpected path that took him from web development inspired by a physics assignment to a successful career in product management. Kirupa highlights strategies for balancing work and life, the importance of supportive management, and how to turn interests into impactful careers. He also emphasizes building a community around personal passions and the role of luck in navigating career growth.