We're often operating under the false illusion that the career track we have now is the career track that we somehow have to follow under any circumstances - it's easy to snap to common conventions around progression, where you work, and how you work. But what if there's more to the "choose your own adventure" track that we do not know about?

To get to the bottom of this question, I sat down with Lenn Pryor, a seasoned executive who used to work at many well-known companies, but decided to carve out his own niche where he found both joy and professional satisfaction. It's a risky bet that paid off, and I was keen to learn more about how he justified it and what decision points helped him navigate the overwhelming ambiguity. What I really enjoyed about recording this episode is that the learnings are broadly applicable no matter what role you are in or are looking to jump into.

You can find Lenn on the following sites:

 * 🌎 Personal Website [https://www.lennpryor.com/]
 * 💼 LinkedIn [http://www.linkedin.com/in/lennpryor]

The podcast was produced by Den Delimarsky [https://den.dev].

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!

#92 - You're Thinking Wrong About Your Career - Lenn Pryor (Executive Coach, Author)

Every year, millions of students try coding for the first time through Hour of Code [https://hourofcode.com/us]. 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 [https://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.

You can find Simon on the following sites:

 * 💼 LinkedIn [https://www.linkedin.com/in/simonguest]

The podcast was produced by Den Delimarsky [https://den.dev].

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!

#91 - The Future Of Software Engineering - Simon Guest (CTO, Code.org)

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 [https://saasmarketinggym.com]
 * 🦋 Lianna on Bluesky [https://bsky.app/profile/punchlinecopy.com]
 * 🦋 Colleen on Bluesky [https://bsky.app/profile/leenyburger.bsky.social]
 * 🐦 Lianna on Twitter [https://twitter.com/punchlinecopy]
 * 🐦 Colleen on Twitter [https://twitter.com/leenyburger]
 * 💼 Lianna on LinkedIn [https://www.linkedin.com/in/liannapatch/]
 * 💼 Colleen on LinkedIn [https://www.linkedin.com/in/colleen-schnettler]

The podcast was produced by Den Delimarsky [https://den.dev].

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!

#90 - The Death Of SaaS Has Been Greatly Exaggerated - Lianna Patch & Colleen Schnettler (Co-Founders, SaaS Marketing Gym)

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 [https://www.youtube.com/@techiefarmer]
 * 🖼️ Instagram [https://www.instagram.com/thetechiefarmer/]
 * 📼 TikTok [https://www.tiktok.com/@techiefarmer]

The podcast was produced by Den Delimarsky [https://den.dev].

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!

#89 - So You Want to Be a CTO - Taiwo Oyienyi (CTO, Distrobird)

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 [https://marisamorby.com/]
 * 📷 Instagram [https://www.instagram.com/marisamorby/]
 * 🦋 Bluesky [https://bsky.app/profile/marisamorby.com]
 * 📰 Newsletter [https://marisamorby.kit.com/posts]

The podcast was produced by Den Delimarsky [https://den.dev].

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!

#88 - Best-Kept Secrets on Becoming a Great User Researcher - Marisa Morby (Principal Researcher, Observable)

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 [https://theworkitem.com/episodes/going-solo-kent-c-dodds/], Jerod Santo [https://theworkitem.com/episodes/give-people-what-they-came-for-jerod-santo/], Rob Walling [https://theworkitem.com/episodes/put-the-passion-aside-rob-walling/], Adrienne Tacke [https://theworkitem.com/episodes/q-and-a-adrienne-tacke/], David Khourshid [https://theworkitem.com/episodes/starting-startup-pandemic-david-khourshid/], Saron Yitbarek [https://theworkitem.com/episodes/cash-money-with-saron-yitbarek/], Rachel Andrew [https://theworkitem.com/episodes/write-about-things-you-learned-rachel-andrew/], Katie Fujihara [https://theworkitem.com/episodes/i-left-hawaii-startups-katie-fujihara/], Lena Reinhard [https://theworkitem.com/episodes/how-to-get-promoted-tech-lena-reinhard/], Miriam Suzanne [https://theworkitem.com/episodes/web-development-is-theatre-miriam-suzanne/], Kirupa Chinnathambi [https://theworkitem.com/episodes/make-hobby-a-career-kirupa/], Craig Hewitt [https://theworkitem.com/episodes/stop-building-landing-pages-craig-hewitt/], Jennifer Wong [https://theworkitem.com/episodes/dont-take-the-easy-path-jennifer-wong/], Jason Lengstorf [https://theworkitem.com/episodes/tools-do-not-matter-jason-lengstorf/], Michael Kennedy [https://theworkitem.com/episodes/building-a-business-from-python-expertise-michael-kennedy/], and Asia Orangio [https://theworkitem.com/episodes/growth-strategies-with-asia-orangio-demandmaven/].

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 [https://den.dev].

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!

#87 - A Wrap-Up Of 2024 Unconventional Career Advice

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.

You can find Asia on the following sites:

 * 🌎 Website [https://www.asiaorangio.com/about/]
 * 🦅 DemandMaven [https://www.asiaorangio.com/about/demandmaven.io]
 * 🦋 Bluesky [https://bsky.app/profile/asiaorangio.bsky.social]

Asia also recommended the following folks to check out:

 * Lenny Rachitsky [https://www.lennyrachitsky.com/]
 * John Cutler [https://cutlefish.substack.com/]
 * Jason Cohen [https://longform.asmartbear.com/jason-cohen/]

The podcast was produced by Den Delimarsky [https://den.dev]. Music by Wataboi [https://pixabay.com/users/wataboi-12344345/?tab=audio&utm_source=link-attribution&utm_medium=referral&utm_campaign=audio&utm_content=1165] from Pixabay [https://pixabay.com/music/?utm_source=link-attribution&utm_medium=referral&utm_campaign=music&utm_content=1165].

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!

#86 - The Only Real Way To Know Is To Talk To People - Asia Orangio (CEO, DemandMaven)

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 [https://talkpython.fm/]. It was started by none other than Michael Kennedy, a Python Software Foundation fellow [https://www.python.org/psf/fellows/] 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 [https://mkennedy.codes/]
 * 😺 GitHub [https://github.com/mikeckennedy]
 * 🐘 Mastodon [https://fosstodon.org/@mkennedy]
 * 💼 LinkedIn [https://www.linkedin.com/in/mkennedy/]
 * 🎥 Video [https://www.youtube.com/@mikeckennedy]
 * 📚 Talk Python Training [https://training.talkpython.fm/courses/all]
 * 🎙️ Talk Python To Me Podcast [https://talkpython.fm/]

   The podcast was produced by Den Delimarsky [https://den.dev]. Music by Wataboi [https://pixabay.com/users/wataboi-12344345/?tab=audio&utm_source=link-attribution&utm_medium=referral&utm_campaign=audio&utm_content=1165] from Pixabay [https://pixabay.com/music/?utm_source=link-attribution&utm_medium=referral&utm_campaign=music&utm_content=1165].

   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!

#85 - Building A Business From Python Expertise - Michael Kennedy (Founder, Talk Python Training)

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 [https://www.youtube.com/channel/UCnty0z0pNRDgnuoirYXnC5A]. 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.

You can find Jason on the following sites:

 * 📽️ Learn With Jason (YouTube) [https://www.youtube.com/channel/UCnty0z0pNRDgnuoirYXnC5A]
 * 🏫 Learn With Jason (Website) [https://www.learnwithjason.dev/]
 * 🕸️ Jason Lengstorf’s Website [https://jason.energy]
 * 🦋 BlueSky [https://bsky.app/profile/jason.energy]

The podcast was produced by Den Delimarsky [https://den.dev]. Music by Wataboi [https://pixabay.com/users/wataboi-12344345/?tab=audio&utm_source=link-attribution&utm_medium=referral&utm_campaign=audio&utm_content=1165] from Pixabay [https://pixabay.com/music/?utm_source=link-attribution&utm_medium=referral&utm_campaign=music&utm_content=1165].

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!

#84 - Tools Do Not Matter - Jason Lengstorf (Founder, Learn With Jason)

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.

You can find Jennifer on the following sites:

 * 😺 GitHub [https://github.com/jennz0r]
 * 💼 LinkedIn [https://www.linkedin.com/in/jenniferewong/]

The podcast was produced by Den Delimarsky [https://den.dev]. Music by Wataboi [https://pixabay.com/users/wataboi-12344345/?tab=audio&utm_source=link-attribution&utm_medium=referral&utm_campaign=audio&utm_content=1165] from Pixabay [https://pixabay.com/music/?utm_source=link-attribution&utm_medium=referral&utm_campaign=music&utm_content=1165].

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!

#83 - Don't Take The Easy Path - Jennifer Wong (Engineering Leader)

Building a fulfilling career is hard. With so many people around us taking on different adventures that propel their careers in unexpected trajectories, is there a path a person can take that is going to increase their likelihood of success? Can I build a career creating content? What does it take to make the transition from information technology jobs to space? Can I start a start-up and not lose my sanity? Every week, Den sits down with folks from a range of industries, roles, and backgrounds to learn more about their career journey, lessons learned, and what it takes to map out your own very unique track.

Den Delimarsky

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