How a Mediocre Sales Team Loses You Deals. Ones You Could Have Won

A vendor reached out to me last week for fund administration for SaaStr Fund. We are genuinely in the market for a vendor and it’s a $100k+ a year potential client. This should have been a real shot for them.

It started on LinkedIn, where they reached out. I said I wasn’t sure we were switching but give me your best shot. I was a warm, in-market prospect who had already signaled interest.

Being in the market is not the same as being an easy close. I already have a provider, and switching costs real time and carries real risk. The migration alone is a project I’d rather not run. For me to move, a new vendor has to clear a high bar: show me they’re better, show me they’ll be more attentive than what I have, and show me they’ll actually fix the problems I’m dealing with today. Fall short of any of those and switching isn’t worth it, no matter how good the deck looks.

Then the emails showed up.

First one: “Following up from LinkedIn, here’s a [link to a generic, uncustomized] overview of our back office solution. All good if you’re set with your current provider, but would love to connect if you’re open to learning more.” Second one, a few days later: “Checking in before the long weekend. I’d love to touch base next week if you’re open to learning more. Have a great 4th.”

Two emails to a prospect who had already told them he was interested in a six figure deal. The sales exec did zero research. No point of view. Nothing that showed they understood my setup, let alone that they could beat it. No reason to reply beyond politeness.

So I told the rep the truth. The email was crappy. Did you research me or my fund? Do you know my fund size? My goals? How your product could help me beat what I run today? Did you spend even a few minutes asking Claude what to write me?

This is what I got. Zero customization, zero work, zero anything put a generic prospectus behind a sign-in link.

A Generic Email to a Warm Lead Is Almost Worse Than No Email at All.