TCG085: Enterprise Salescraft with Drew Meli
The Everything Feed - All Packet Pushers Pods
September 30, 2026
William Collins and guest Drew Meli explore the realities of buying enterprise SaaS and infrastructure. They cover the common engineering misconceptions about enterprise sales, navigating rigorous security reviews, establishing clear proof of value criteria, and how AI is reshaping buying behaviors.
Speakers William Collins, Drew Meli
TopicsTechnology
William Collins (0:12)
Head of Infrastructure and Operations, AI is rewriting your cloud architecture, your operating model, and your budget. Gartner IOCS is happening December 8-10 in Las Vegas, and this is where you figure out how to adapt. Register at gartner.com/io and use CodeCloud for $450 off. That's gartner.com/io, CodeCloud.
Hello, and welcome to another episode of The Cloud Gambit. I am your host, William, and we don't have Yvonne today. Yvonne is traveling. Yvonne has been pretty busy, of course, at the day job. And as we see this weather transition from nice and warm and maybe a little too hot, a little too humid to, it's kind of chilly this morning. I had to wear a jacket on the way to school.
Yeah, where the seasons are changing, everything's changing, and with me is Drew Meli. And I've worked with Drew in the past, and I guess before we kick things off, this is a topic I've really wanted to talk about because it's one that kind of drives me nuts. And we're going to talk about sales, which isn't the normal conversation point that we usually go through on this podcast, but it's an important one because if you've worked with good salespeople, which are a, you know, just not, they're very hard to find these days, but there's a lot of sales folks out there that are just very pushy. Like there's just a dynamic here, but anyway, how are you doing today, Drew? Welcome to the show.
Drew Meli (1:55)
I'm good, man. Great to see you again, and appreciate you having me on. Pleasure to be here. So looking forward to this topic. Like you said, we got to debunk some stereotypes and misnomers and whatnot, and look forward to unpacking the topic.
William Collins (2:10)
Yeah, absolutely. By the way, how's the weather in your part in the Northeast? In Kentucky now, anyway, it happened like overnight. It was like, you know, like 100 degrees one day, and then you wake up the next day and it's like, oh, it's like 50 degrees, you know, kind of cold. So how's it where you're at?
Drew Meli (2:29)
I'm at home today in Virginia, so be careful. This is not Northeast. That's a very fine line there. No, but it's fall. I got the long sleeves on. It's feeling pretty chilly. I think it's not getting in the 70s anymore and it's chilly at night. So it's my favorite time of year. So I welcome it. Love it.
Can't wait for the fire pits and all that sort of thing that really kick off.
William Collins (2:54)
Likewise, I got mine ready to go too.
We have young kids, you have a fire pit. It's so much fun for them. They love it.
Drew Meli (3:05)
All we talk about is Halloween costumes. What exactly this is going to all my girls and what they're going to wear and it's awesome. So best time of year.
William Collins (3:15)
And I mean, I'm not even going to talk about hockey because the Red Wings are just screwed this year. It's going to be pretty rough, but hey, I'm not a bandwagon fan. I'm going to stick with them. I'll just say that. So you've spent your, I guess, your entire career really working with, I guess, enterprise network buyers predominantly, but also some cloud centric stuff recently.
And I want to get into the part of that process.
Engineers don't always see, or maybe it would be helpful for them to just get a little more insight into. Like we can spend weeks kind of validating a product and still have no idea whether maybe a company is actually ready to buy it. If they have the right kind of funding, there's just a lot that goes into it. It's not as simple as, oh, hey, I like a thing. Okay, here's procurement, sign a check, let's go. It's, of course, it's much more complicated than that. So, I guess starting now, tell us a little about yourself, like where you started and kind of like how you got into enterprise sales.
Drew Meli (4:33)
Yeah, great, great question. So not on purpose to start with, it kind of backed into that one, if you will. I was fortunate enough that I was at a junction of kind of looking at different career paths after college and trying to figure out what I wanted to do.
And I was able to work for my family had a small value at a reseller. And we got to, I got to go as an opportunity there to just get started. I used it one day where I was building a resume and I wanted to go use one of the conference rooms. Got excited about what was happening in the rooms adjacent to me and just said, man, I want to learn more about this and think I can help out. And just really fell in love with it. And it's gone from there and had an opportunity to work for a lot of cool companies then and ever since.
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