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Decoding Sales

Episode 41: Piloting Sales at Pilot.com with Founder, Waseem Daher

Decoding Sales

Peter & Alex

Enterprise Sales, Business, Virtual Selling, Sales, Entrepreneurship, Software Sales

520 Ratings

🗓️ 5 February 2025

⏱️ 47 minutes

🧾️ Download transcript

Summary

Send us a text Waseem Daher (Ex-Dropbox and Founder of Pilot.com) sits down with Peter Ahn and Alex Allain of Decoding Sales to discuss learnings from his founder-led sales journey. They discuss: • The importance of founders being involved in closing a startup's first customers • How to think through hiring your first salesperson • What the right profile is for sales hire #1 • How to know when to fire salespeople who aren't working out • Lead gen tactics for startups and the power of w...

Transcript

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0:00.0

Welcome to Decoding Sales, a podcast. We're an engineer. That's me, Alex, and salesperson.

0:16.3

That's me, Peter. Talk about the art and science of sales as relates to life and business. In this

0:21.6

episode, we have another guest. Very excited to welcome Waseem to the show. Waseem is the co-founder

0:27.4

and executive chair of Pilot.com, a company that does accounting and tax prep for startups and

0:32.7

growing businesses in a tech-inabled way. Prior to pilot, Wissim also co-founded CaseFleis, which updated your software without rebooting,

0:41.7

and it was acquired by Oracle in 2011, and Zulup, a group chat for business,

0:46.2

which was acquired by Dropbox in 2014, which is how Peter and I know Waseem.

0:51.0

And prior to that, of course, graduated from MIT.

0:53.4

So, Waseem, welcome to the show.

0:55.2

We're very excited to have you.

0:56.6

First of all, thanks for having me on the show.

0:57.8

Great to be here.

0:58.5

I'm a big fan of both of you.

0:59.8

And so it's really a pleasure to kind of be able to chat with you all.

1:03.8

I mean, we all met at Dropbox was it was the first time that I really got to see a high

1:13.1

growth startup like from the inside at the scale it was operating at. Like our prior companies were,

1:18.5

you know, 10 or 20 people. So I had a fairly good read on the super early stage. And then my first

1:25.0

company was acquired by Oracle. So I guess I had a good read on like the

1:28.1

100,000 plus person stage or however it is, however big Oracle is. But, you know, when I joined Dropbox,

1:33.3

it was 600 people. When I left Dropbox, it was 1,200 people. And it was really interesting to kind of

1:37.8

observe that in hypergrowth across a bunch of different functions. And in particular, I think one

1:43.0

of the things was really exciting is that I as as a product manager at the time, actually did get to spend

...

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