Every year, millions of students try coding for the first time through Hour of Code. But most people don't know that the technology powering those experiences is ran by someone who didn't really have a plan to become a CTO. In the fourth episode of this season of The Work Item, I am talking with Simon Guest, CTO at Code.org. Simon walks me through how he actually became a CTO (not the LinkedIn version we commonly see), and what skills helped him succeed despite the fact that there was no pre-charted path he could follow. You'll be surprised to learn just how much serendipity and having the skills in the right place at the right time play a role in strapping one's career to a rocketship. We also talk about the future of coding, whether AI is truly going to make engineers obsolete, and what we can do to build a good career moat that sets us up for long-term success. And of course, if you've ever wondered what it takes to move into technology leadership, this conversation will give you a very realistic picture of what that path looks like.

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.

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.

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.

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!

Today, I'm thrilled to be joined by Asia Orangio, the brain behind DemandMaven, a growth agency dedicated to helping SaaS companies and their founders reach new heights. Asia's unique approach blends data-driven strategies with deep empathy for customers, making her a sought-after expert - from bootstrapped businesses to some of the most established companies. Whether you're a startup founder or a seasoned marketer, I promise you that her insights will challenge your thinking and inspire quite a few new ideas. In this conversation, Asia shares her journey from marketer to founder, unraveling the lessons she's learned while scaling SaaS companies and guiding others to do the same. We'll explore her philosophy on growth, the common mistakes founders make when trying to identify their growth levers, and the power of understanding your audience on a deeper level. This really ended up being a masterclass in sustainable growth and customer-first business foundations.

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.

If you've been immersed in the tech world for some time, you probably have heard one specific YouTube channel mentioned more than once - Learn With Jason. It's a project started by Jason Lengstorf, a former VP of developer experience at a web tooling startup (he was a head of developer relations prior to that too), that is aimed at helping everyone navigate the always changing landscape of developer tools and frameworks. Which, by the way, according to Jason do not matter. In this show, we dive deep in Jason's career path and focus on the less known aspects of climbing the career ladder - things like amassing political capital by doing great work, building visibility by meaningful means that can help cement your reputation, and being able to address business problems as a mechanism to build trust in your own leadership abilities.

Jennifer Wong is a seasoned engineering manager who started her journey in civil engineering. The fast pace of the tech industry drew her in, and she stuck with it for years since making that call. In this episode, I chat with Jennifer about her transition from a non-traditional career path into software, reasons to take on management instead of being an individual contributor, and why taking the road less traveled in terms of career progression might just be the recipe for 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.

In episode 81, Den Delimarsky chats with Kirupa Chinnathambi, a product manager at Google who has built his own personal brand in what is now known as kirupa.com. Kirupa is a talented web developer, designer, writer, and packs so much knowledge in his blog that you can learn how to create great web-based experiences on that content alone. We discuss best ways to balance everything in one's life and still have a successful career, finding the right angles to change a team culture, making your hobby your career, and how to increase your likelihood of building more luck in the day-to-day activities.

One of the things that Miriam Suzanne realized early in her developer journey is that web development is a tool - she wanted to build a website for her theater company and ended up building a career and a company around it. And not just that, but she also joined the CSS Working Group - the official standards body that determines how the CSS stack evolves. In this show, we talk about her early discovery of the power of the web, how she joins creativity with technical prowess, and how CSS is really like poetry written in the browser.

We often talk about promotions and growth, but the moment the conversation shifts towards paths to staff or executive positions, the advice goes blank. There is very little actionable information out there that can tell you how you can get to the highest echelons of leadership. To get a clearer picture on this topic, I sat down with Lena Reinhard, a seasoned executive with an extensive track record at CircleCI, Travis CI, and more. Lena shares her insights on the best ways to accelerate career growth in the tech space, answer thorny questions, such as “Why are executives hired from the outside?” and provide some candid takes on why taking things slow sometimes can pay off in the end.

One's journey from their early career to working at startups in Silicon Valley can take many forms. Some folks take the more traditional route of joining a company right after college. Others get tired of their corporate life and decide to try something different. Katie Fujihara, an engineer and a technical program manager amalgam, decided that her journey to the heart of “startup land,” San Francisco, would be an impromptu one - she just packed up her bags and set out on an adventure. I am delighted to share with you this recording, where I talk to Katie about her early starts in Hawai'i, how working in engineering was not the end goal for her career journey, and what the best practices are for overcoming impostor syndrome.

For today’s episode, I had the privilege of sitting down with Rachel Andrew, arguably one of the more influential folks in the world of web development. With a career spanning over two decades, Rachel has left an indelible mark on the web developer community. From her groundbreaking work on CSS to her role as co-founder of Perch CMS (she spent 20 years as a freelancer and a business owner), Rachel’s contributions have shaped the way we build and interact with the web. Throughout her career, Rachel has not only demonstrated technical prowess but also a remarkable knack for empowering others through her writing (and now, her team’s writing as well). As an acclaimed author, speaker, and advocate for web standards, she has tirelessly championed inclusivity and accessibility in the digital realm.

One of the things that is a bit taboo to talk about, both in the tech industry and outside of it is money. People just aren’t comfortable discussing openly the hard decisions that go into things like seeking funding, investing money into things that save you time, and scaling your own abilities with the help of, you guessed it, cold, hard, cash. Saron Yitbarek, entrepreneur extraordinaire behind CodeNewbie and podcasts such as Command Line Heroes, generously accepted my invitation to chat and talk about all these things, and more. And of course, we talk about Saron’s latest project - Big Cash Money 2024, something for folks that want to max out their income beyond just their salary.

In this episode of The Work Item, I had a conversation with David Khourshid, founder of Stately.AI. You might know him as @DavidKPiano on social media. Today, we’re breaking new ground around unconventional paths of building an engineering career, entrepreneurship, and leveraging your audience as the potential first customers for your product. And of course - we talk a bit more about state machines (David is also the developer behind XState) and lessons learned from launching and growing a startup in the midst of a pandemic.

Welcome back to The Work Item. Today we're exploring the ins and outs of remote work, writing, and community engagement with a show veteran, Adrienne Tacke. I'm delighted to welcome Adrienne Tacke back to the show, especially considering that since our last recording we received quite a few follow-up questions. Just like last time, Adrienne brings a wealth of knowledge and experience to our discussion, especially when it comes to remote work culture. And today, we're adding a new twist: a dedicated Q&A segment where Adrienne will be addressing your burning questions directly.

If you've ever listened to Startups For The Rest Of Us (which, by the way, is approaching seven hundred episodes), you might already be familiar with the energetic host of the show - entrepreneur, bootstrapper, and podcaster extraordinaire Rob Walling. Rob and I chat about his early days as an employee, the transition from the more traditional path of working for someone to starting his own business, building MicroConf, and how the trifecta of skill, hard work, and luck can help folks be on a more predictable path to success.

Today I got the pleasure to chat with Jerod Santo, the Managing Editor at Changelog Media. Picture this – a podcast that not only uncovers the intricacies of Jerod's career but also shares some unconventional lessons learned from his work. From navigating the ever-evolving tech landscape to spearheading Changelog, Jerod brings a wealth of experience that transcends your typical engineer expectations and taps into the heart of what it means to build a sustainable developer community. In this candid conversation, discover the 'aha' moments, the challenges met head-on, and the behind-the-scenes tales that shaped Jerod's path. Whether you're a seasoned developer or just embarking on your tech adventure, join us for an episode that's not just an interview but a personal expedition through Jerod's experiences and the impact of his work on Changelog.