u/Large-Bad-8735

Through my 12ish year career I’ve only worked at 2 large hyperscalers

Started Google cloud as an SDR, left to try my own thing with a friend, didn’t work out.

Got a job at AWS as an SDR then after a few years became an AM mid market, got stuck there for years, hard to move up.

Hitting quota almost every year, but probably middle of the pack on the team. The issue was I started on a lower salary as an SDR so got screwed when I became an AM (quota 25x base).

Base is well below 100k (UK) and it’s roughly a 65/35 split.

I’m not going to increase my earnings here any time soon so I’m looking to move.

My fear is, I feel like AWS and Google basically sell themselves and my success is largely due to the name rather than my skill. Literally every prospect had heard of Google and most had heard of AWS.

Am I being overly worried here? Anyone else experience the same when moving to a smaller name?

I’m applying for some roles after doing a solo gig for 2 years and I’ve got connections in multiple companies (including my previous multinational where I’d go back).

A few people have checked various role openings for me to give me the names of the both the recruiters and the HM (can’t use the full word do to sub rules).

But, these are not publicly known so technically I shouldn’t know.

If you’re currently or have been a manager, how would feel about a DM on LinkedIn?

In general what do people think of DMing the recruiter or manager? Do they not get annoyed that you didn’t follow the process (I.e. apply through the application).

I’ve tried a few different businesses since I was in university, none of them very successful.

Always jumped back into tech roles in between.

This last business I’ve ran (consulting) has been the most successful and sustained me for two years but it’s not scalable/profitable enough to continue and I don’t really enjoy it. Scaling would mean that the parts I do like, I’d no longer do (delivery) and I don’t see myself doing this for the next 5/10 years.

Applying for jobs is getting harder as recruiters keep thinking I’ll bounce (I have a decent resume in terms of companies I’ve worked for). So I can’t keep the trend if I’m to get a decent job.

Part of me thinks I really don’t want a job (just money) and I’ll just want to quit as soon as I get another idea. It’s not a nice feeling. Most of my school friends who stuck out a career have much greater finances than I do now, unsurprisingly.

I know most entrepreneurs fail a few times but I assume there’s an element of survivorship bias and some always fail and not quitting is just one element. I’m finding it hard not to tell the difference between delusion and keep trying versus success is around the corner if I keep my eyes open.

Has anyone had a business, closed it then found peace at a company? Will it be the case that it will always be difficult now to work for someone else?

Do I take a step backwards to go forward?

Mid 30s worked in big tech companies up until 2024, last finished as an account manager selling tech.

Decided to leave for a mix of reasons but I ended up starting my own business in a different field as well as pursuing a doctorate part time. I’d been doing the business as a side hustle.

Fast forward two years and I really just don’t enjoy working as a solopreneur, or at least the business I’m running isn’t one I enjoy. Pay, extra hours, lack of colleagues and stability. The pros are just not worth the cons.

I’ve been applying for about 6 weeks to roles very similar to what I used to do but I’m struggling to even get a screen from a recruiter. Even jobs which I thought I’d easily get an interview for via referrals have let me down.

I don’t feel like I’ve went backwards in my career (I’ve learned a lot in my business and it’s way more challenging to do everything including sales) but I feel like maybe it’s a flag.

Should I apply for roles that were more junior to my last tech role or do I wait it out and keep looking? I’m not in a major rush but would like it to happen this year? Ideally I would have liked to have matched salary I left with, I thought have a professional doctorate and having ran my own business would have helped me stand out, even if not in the direct area (who does a doctorate in tech sales).

Mid 30s worked in big tech companies up until 2024, last finished as an account manager.

Decided to leave for a mix of reasons but I ended up starting my own business in a different field as well as pursuing a doctorate part time. I’d been doing the business as a side hustle.

Fast forward two years and I really just don’t enjoy working as a solopreneur, or at least the business I’m running isn’t the one. Pay, extra hours, lack of colleagues and stability. The pros are just not worth the cons.

I’ve been applying for about 6 weeks to roles very similar to what I used to do but I’m struggling to even get a screen from a recruiter. I don’t feel like I’ve went backwards in my career (I’ve learned a lot in my business) but I feel like maybe it’s a flag.

Should I apply for roles that were more junior to my last tech role or do I wait it out and keep looking? I’m not in a major rush but would like it to happen this year?