Had lunch with my friend today regarding Job D and it sounds like it would be a relatively 'easy-in' if I want it; just because the group is revamping and I have a connection. After talking with him, he sounds convinced that I'd fit the role pretty well, and he is pretty much architect/director level at this point but more on the development/engineering side (whereas I'm more on the infosec side of things). It sounds like it could be a really good opportunity for ground-up experience, and so it's unique in that way. Financially, the company (privately-held) is stable with good year-over-year growth. They're looking to drastically expand out their product line and offerings to be a front-runner, rather than playing it conservative and sticking with supporting current and legacy stuff. The potential drawbacks, especially compared to my current job and other places I might be interested in, is that the benefits don't seem like they're as good (e.g. from what I gathered researching on their site and glassdoor, there's no 401k matching and salary is typically under-market for the relative role). It also sounds like it could be super-busy the first year too. Now if they can accommodate the 'golden handcuffs' I have from my current company, that might make things more appealing but well just have to see.
I haven't reached out yet about Job B but that could potentially be another easy-in since I'm already at the company and it would be more of just transition, as I mentioned. Again this would probably require more of my time, energy, stress, and pressure of going a pretty different direction in terms of career path.
I haven't heard back yet on Job A but that seems like it might potentially be the most 'laid back'/least demanding with pretty good benefits. The part about being "laid back" and even receiving an offer is yet TBD, however. And as far as career growth and experience, I'm not sure what the opportunities would be (again, this is yet TBD)
The interview with Job C is tomorrow, and I'm relatively intimidated but should I pass the phone screen I'll just consider it good interview practice at a minimum. The company is pretty high-profile and is an industry-leader, and the position seems to be pretty high-profile and extremely demanding. I spoke about it with a previous coworker who's now working on the team that I'm applying to be on, as well as another friend who works on a different team. Both have indicated constant busyness and long work-hours too. He also told me that the other infosec guys on his team tend to have many years (close to or decades of infosec experience). So you can see what it seems so intimidating and demanding. Work hard play hard, literally...
I did solicited by another recruiter who I initially sort of 'turned-down' by indicating to him that I felt under-qualified for a position he originally reached out to me regarding. He got back to me after a week or two and said in more or less words "I still really think this would be a good fit" which was surprising. Either he's desperate or he really truly believes it, haha. I have my doubts though - it's also a 100% telecommute position with a pretty high profile healthcare company HQed in the midwest. But the title of the position and what is implied within is not something that *entirely* appeals to what I want to do... the role/position is just one facet of what I would want to do in my day-to-day... otherwise, I think I'd get really frustrated (given past experiences...which is why I told him I thought I was under-qualified). I felt weird telling him that, and it's even stranger that he actually replied back and is still trying to convince me to go for it.