Dear SaaStr: What Was Your Experience At Your First Big Enterprise Pitch?

Mine was terrible:

  • My more technical co-founder didn’t show up to the meeting.
  • The interactive demo didn’t work (a browser bug).
  • They asked me about our LDAP integration. At the time, I had no idea what LDAP was. So I didn’t even know how to answer the question.
  • I had a deck to use, but it was more a VC-pitch type deck and not enough about the product. They asked me to skip the deck.

This was a Fortune 50 prospect and 20+ folks were in the room for the meeting.

We lost the pilot. Even after the SVP before the meeting said he’d make it happen. I blew it that badly.

It was rough.

But I learned. I was never unprepared again.  After that:

  • I always had the right team at the meeting.
  • I got better at demo-ing myself.  Not relying on someone else to do the demo
  • Most importantly, I had to hear the objections first to learn them. Then, you get better.

The next one like this — we closed.


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