Episode 517: Is it good for my career to work at a SaaS company and why am I being asked to manage two teams?

Episode 517: Is it good for my career to work at a SaaS company and why am I being asked to manage two teams?

June 15, 2026 · 32 min

About this episode

Dave and Jamison discuss the benefits of working at a SaaS company versus a non-software-focused company and address a listener's concerns about managing multiple teams.

In this episode, Dave and Jamison answer these questions: Hey guys. This question comes all the way from New Zealand. Recently discovered your podcast about a month ago, and have been catching up with older episodes on morning walks ever since - you guys are awesome. Anyway - the question: Is it more beneficial to work for a company where the software itself is the product (SaaS etc) or does it no longer matter given the rise of the robots anyway? For context - I’ve been working for a telco/internet company for just over five year. Initially when I joined there was a huge roadmap of software to develop internally - things like customer facing portals, diagnostic tools, and of course internal tooling. However over the past couple of years, it has just been cost cutting and downsizing. Given that the company is not in the business of selling software, our department has been stripped to skeletal level just to ‘keep the lights on’. So, I’ve started applying for jobs at SaaS companies on the basis that even with AI, there will at least be a continuous roadmap to work on. Or, is this a case of ‘snakes in the greener grass’… or whatever the idiom is. Keen to hear your thoughts! I’m an…

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