salesloser

Sales Loser: an anonymous sales diary

I started my first cold-calling job in 2018 and I was awful at it. So I got in earlier and left later than everyone else, until I was the best on the team. Within a year I was an AE. I made President's Club twice, and in my third year closed a six-figure deal, the biggest the company had ever done.

After four years I left to build my own business and raised over £6m. Now, after a break, I'm back in sales as a founding AE.

Sales has changed. I have far more information than I used to and less time to make sense of it, and AI gives me the answer before I've thought it through. This is where I slow down and write it up: what happened today, what I learned, and what I'd do differently. Mostly it's for me, as a record of what we've done.

Wednesday Recap

Tested messaging to both the IT and the Ops person today. Messaging just lands better with IT. Surprisingly they are far more open to a conversation than Ops are. Makes sense tbh, I have been in ops and always find cold callers very annoying when they are bad. And I’m not any good still. Way too rusty.

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Forward Deployed Market Research

I’m 5 weeks into my new job as founding AE at a startup. We’ve got 2 paying customers and a half-baked product that was supposed to be one thing, but now we’re testing lots of different things, as it feels like everyone has moved into the market for what we were originally selling.

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