The same general situation has happened to me twice now and I am wondering if it’s something I can break free from or if it’s just the nature of the Startup beast - or what. There seems to be some kind of bubble that starts drying up investment in a startup where I am a technical lead. Both times, things seem to be going well and then 2 years in there are rounds of layoffs due to factors outside my/product’s control where the result is the same. I end up as the last tech generalist. It falls to me to write as much of the code as I can, manage (if any are left) engineers in my department, running support basically on my own, owning a large part of the product roadmap, working with the customers on support and implementations, working with integration partners, plus a slowly expanding list of responsibilities as new stuff falls on reduced teams. I pick up new domains pretty quick (finance, insurance, compliance), switch contexts well. I’ve always been the person who just figures it out - someone who takes ownership of something and just does it. But, instead of being rewarded, I just get to keep my job while absorbing the work of others less fortunate.

During these contractions, the work never shrinks. Same clients, same integrations, same support volume (for now). Something else I’ve noticed is the scrutiny goes up - not down. I think a big factor is you have founders and upper managers stepping in to be more engaged or attempting to cover gaps. This causes all sorts of issues.

After this last round of cuts, the company offered me a revised title and job description that focused on managing the department that now was essentially just me down from 6 a year ago. It was full of responsibilities like “leading team to meet targets”. I did kind of want to accept it since it is the sort of role I was hired for and would help in a job search later. Regardless, I couldn’t because I am basically the team. It felt like a trap (or at least, wishful thinking that has been proven as much time and time again due to factors beyond my control.)

I could just leave, but the job market and economy look scary as hell. It took me 8 months to find a role last time. This is primarily due to my experience and background. I’ve been involved in engineering, product, support, sales, customer success, integrations and user comms. I look like someone who could/did do everything but that comes off as someone who owned nothing. The reality is I owned way way too much as things evolved.

Three things I am trying to think through and could use some help with:

1. Is it just the companies and bad luck? Am I picking startups in industries or with offerings that are just vulnerable to VC trends and hype? They both seemed like great opportunities, and I completely understand there is always risk - but the current/former result as it pertains to my role and situation once cuts were made is surprisingly identical.

2. Should I stand my ground? I have a habit of trying to work things out and get scrappy. During the last contraction, I spoke out to the president of the company that I wanted to sit down and look at our team’s responsibilities and projects that were being used/sold and see what was essential, could be covered, etc. That never happened - should I have been more firm and demanded it versus just absorbing it?

3. Ignoring the company, should I lean into the role and try to develop it? Should I accept I am an amazing generalist “jack of all trades, but master of none” and make it a more deliberate role/career? I know these sort of people are needed, but no company can really put out a role description for them. I’m seeing AI helps cover a growing amount of the gaps that I can’t dedicate the time to developing. I also have enough experience and knowledge to know AI is a tool and needs to be closely guided and applied in focused/appropriate areas. (Case in point - I’ve spent the last two hours fighting it from going off the rails in our Go golden test framework because it wants to ignore our test patterns).

I’m curious if others out there have found similar issues with Startups. Also, if there are other “Red Mage” technical folks that have a hard time in the job market because they’ve been asked to cover such wide areas?