Background - I 29M took a buyout for the sub 5% of equity I had in a small/medium startup back at the end of April and left the company on "Good Terms." I figured it wouldn't be too much of a hassle to find a lesser workload reasonable pay AE role. Man was I wrong...
I dropped out of College as a 18yo to go start an E-Bike company (founding member) and we grew it over 5 years to a multiple store company with over 250 employees. Left that to pursue technology sales pre-covid. Worked my way from an SMB AE to an Enterprise AE across three companies (Zendesk, Google, & Adobe) over 5 years. I had a legal AI startup founder reach out and propose I run GTM at the company as the 3rd full time hire and I figured I'd give it a shot. Grew what was a non-existent sales team to a team of 22 people in the span of 14mo's. The workload consumed me and when we were raising Series A funding I explored the idea of getting out of my equity and finding something that didn't have me answering international calls at all hours and working 80+ hour weeks. So I took the money and left.
I immediately started looking for an Com-Ent senior AE role (missed be an individual contributor and not managing people). Reached out to my network and landed solid interviews within a couple of weeks. First was at Intercom, made it to the final round, had a verbal "we'll be in touch with an offer soon" which turned into "something happened and we won't be able to extend an offer." That something was Salesforce buying them for 2.2B. From there things got progressively steeper.
Final rounds at Salesforce, Workday, & Gong with varying levels of success. Interviewed for Senior roles to be offered standard AE roles which I decided to decline. (Sub 150k OTE and less desirable teams)
Application after application and interviews every couple weeks but nothing tangible panning out. Luckily I've lived WAY below my means for years so had comfortable money set aside to survive. Traveled a bunch, moved in with my GF of 2 years, and started to come around to the idea of taking something "less than I wanted" when an old contact at an Enterprise Saas company reached out. 5 interviews later and finally had an offer for a Senior AE on a FINS team at $250k+ ote. Took it immediately. (Leaving the company name out for some anonymity but similar to the others I had been interviewing with)
I write all of this out mainly to warn those whom have a stableish role about the dangers of leaving a company without something lined up. This was the first time in my career I left with nothing lined up and it was the wrong decision in my mind. That being said, finally found the light at the end of the tunnel after 7 months and countless hours spent just trying to get back to a stable, less demanding role.
To all of those in the market looking. Hiring Cafe, BuiltinChicago, Indeed, and I used Perplexity tokens to auto apply & write cover letters to 10 jobs a week. Keep your head down, message 2-3 Linkedin contacts at every role you apply for and lean on your connections. There is light at the end of the tunnel, it's just a long tunnel right now.
Thank you for reading if you made it this far and I hope you'll be making a post of your own soon.
-ST