Episode 528: Sleepy family software business and leaving after an acquisition

In this episode, Dave and Jamison answer these questions:

1. A listener named “Will angel answer my question?” asks,

   Hi, I recently joined a new company about 1.5 months ago. It is the technology arm of a family-owned business group that has existed for over 30 years, providing technology services to all the other companies in the group.

   After a one-week onboarding, I was assigned to a team. After 2–3 days, I still had no tasks, so I asked a coworker to pair program with me so I could learn more about the processes and continue learning. The task was easy, and we finished it in less than a day. For the next 2 days I did nothing, asked my boss for tasks but he just told me to wait.

   Two days later, we finally had a planning meeting, and they assigned me three tasks for the upcoming two weeks. I finished the first one in 25 minutes and other ones in not much more time. It has been like this ever since. I’m really enjoying all the free time, but I’m also feeling anxious that I may eventually be part of a layoff.

   Apparently, the company is doing well, and they’re hiring a lot of people. Should I ask my manager what’s going on? Maybe everyone on my team is pretending to work and going to the gym at 3 p.m.? What might be happening? What would you do?

2. I’m a staff software engineer at a fully remote, 300-employee US SaaS startup. It was just announced that we are being acquired in an all-cash deal by a publicly traded tech company more than 10 times our size.

   I’ve been here for 8 years and absolutely love this job. Over my tenure, I’ve risen from a junior to a staff engineer, built critical customer-facing features, and developed internal tools used company-wide. I’ve also renegotiated my salary such that LinkedIn recruiters can rarely match it. While my stock options aren’t enough to let me retire early or fund Jamison’s yacht, I know I’m ludicrously lucky to be getting a six-figure payout.

   But what comes next? Leadership says we will operate as a standalone division for at least a few quarters, meaning no massive backend migrations immediately. However, I’ve never worked at a publicly traded company—only at consultancies and startups. My pessimistic expectation is that corporate bureaucracy will sanitize the culture I helped build.

   Should I lean in, try to hold on to some of the startup magic, and lead the inevitable integration work to ingratiate myself with the senior engineers at the parent company? Or should I take advantage of my golden handcuffs being unlocked and finally move on?