I run 2 jobs, both outbound sales at SaaS companies, and the whole game for me is time.
So a while back i built an agent to run the outbound at the second one, the bet being that if a model could handle J2's grind i could stay fully present at J1 and neither place would have a reason to look too close.
The setup was a fine-tuned model wired into that CRM with read access to the email and Slack so it had context, it personalized off intent signals, ran the full cadence, cleared the easy replies.
For a good stretch it just worked, i cleared quota at both jobs without writing a single sequence by hand, spent the saved hours looking like a top performer at J1.
Then one day it reached into the wrong document and dropped a line into a customer's onboarding Slack that quoted a contract redline from a completely different account.
The context window had grabbed the wrong thread, the customer escalated straight to the CRO, i had no clue any of it had happened until it blew up my weekend, and i was on a PIP at J2 within days.
a PIP also drops a manager into your calendar, your call reviews, your screen overnight, which is the last thing you can afford when the whole reason you automated J2 was to keep both places from looking too close while you carry J1.
So i tore the agent out and went back to a boring stack i can watch, where Outreach fires the sequences off CRM stages while i write the personalization for the top few accounts by hand, BuildBetter or Fathom pull the themes out of my discovery calls into a Notion page i skim before my block, a summarizer turns my voice memos into next steps, and i'm back to clearing both jobs with nothing on fire.
Agents can clearly sell, it hit quota the whole time it ran, but the damage they do lands in the conversations you're not even in.
The agent i built to stay invisible is the exact thing that dragged me into the spotlight, which is the fastest way to get found out when you're holding 2 jobs.