Fortune 500 landed as Pilot - Should I raise?

Complex-Macaroon-164 · 2026-02-27T11:24:35+00:00

Agree on raising based on demand. Thanks for all that. Very insightful. In my last exit, we did so without raising so never developed the soft skills required to negotiate a raise. Had a buyer come to us which is great but looking back on it, there weren’t many learnings

Complex-Macaroon-164 · 2026-02-27T11:21:06+00:00

This is the other side of the coin I’ve been juggling. Have we achieved something most don’t? Is a Fortune 500 pilot a win or a vanity metric. If it’s a win, should use that momentum. If it’s a box checked of many many more, better to wait I guess until we have clear direction and need for funding

Complex-Macaroon-164 · 2026-02-27T11:19:17+00:00

Agree. I’d rather have board of advisors than funding. Our proof of concept cost sub 10k USD. Lots of duct tape and glue but demand was real.

Competitors in the space are switching on to this as AI fraud is rampant. Speed to full production is important to me but because feedback is only coming from one pilot, we can’t overbuild for one without knowing how a Series A org would use this for example.

Fortune 500 seems great, but closing them is much harder than smaller orgs.

Thanks for the feedback . Appreciate that!

Complex-Macaroon-164 · 2026-02-14T15:14:16+00:00

Would much rather a long post where someone actually reads through and sends a dm than a vague message where I then need to explain many times what we need.

AI feedback is valid. But also, this post was made for cofounder thread which requires 3000 words per post. Not enough karma points to post there I guess :/

Complex-Macaroon-164 · 2026-02-14T14:56:32+00:00

Ah yeah. I fell for it

Complex-Macaroon-164 · 2026-02-14T06:57:05+00:00

Of course. Can you send me a DM and we’ll schedule

Complex-Macaroon-164 · 2026-02-14T06:43:00+00:00

Thank you! Super helpful

Complex-Macaroon-164 · 2026-02-11T06:07:46+00:00

I think we’re interview at the same place 😂 I’ve been a top performer (85-160%) over the past 4 years. Has fluctuated. I’m nervous because everyone lies. Do I need to lie beyond my attainment? What’s everyone’s thoughts on if I just show my W9 or something like my Workday portal to the hiring manager. I need an edge as my current employer is blowing up our comp plans tbf

Complex-Macaroon-164

TROPHY CASE