Live Better Sell Better April Highlights

Highlights reel from Live Better Sell Better (host Kevin 'KD' Dorsey) featuring April clips from interviews with Thomas Cherrion (sales enablement and buyer-centric selling), Ankara Huja (venture capital—cap tables and dilution), Ellie Twigger (video prospecting and SDR tactics), Townsend Wardlaw (coaching mindset), and David Weiss (pricing/negotiation). Key takeaways: align sales to buyer processes and stakeholders; dilution reduces early ownership over fundraising rounds (example: $1M at $5M = 20%); use personalized video early in cadences to improve outreach; coaches guide perspectives rather than give directives; avoid negotiating price before procurement to preserve margin.
Chapters
Foreign.
What up, everybody? Welcome to a special episode of live Better Sell Better podcast. This is your host, Kevin Dorsey, AKA kd. And today we're actually having a recap of all the amazing talks we had this April. Let's be honest, not everyone's got time to go through every 45 minute episode. So we're bringing the best of the best into this episode. And what an epic April it was, right? So these are five of the biggest highlights from some of the episodes that we did in April that really got me fired up and should get you fired up as well. So one, we learned the power of feedback and how it brings sales enablement to the forefront with Thomas Cherrion. This dude killed it. One of the best enablement leaders, I think in the game. So definitely check out his stuff. He dove into venture capital, right? And debunking some of the myths and what people believe with Ankara Huja and, and making sure that you understand how equity actually works. We talked human to human selling through video with Ellie Twigger and we talked to my coach, my mentor, Townsend Wardlaw about what it means to be in sales and then went super tactical on Medpick a modern day selling checklist with David Weiss. This is just some of what happened in April. So let's take a drive down memory lane with some of our best moments from April. And I'm so excited to pump up to kick off Marvelous May only here live Better Sell Better podcast.
I think, look, it's kind of hard because like when you're first of all as a rep in any company, like you're taught, hey, this is our sales process. These are the sales stages. You have to do step one, step two, step three, and you feel like you're stuck in this box and you have to do these things in a consecutive way. And that's how the magic happens. That's how you get the deal done. And I think the frustrating part, and I see it with the hundreds of vendors that are trying to solicit to me and my team, they're not selling to me the way that I want to buy. And I think that's the disconnect, right? I respect your process and how you need to do what you need to do. But as a buyer, I also have a process in how I buy. I'm not the only buyer, right? And actually the reality is I'm not a buyer. I just said it. I don't have a budget or I do, but I'm not, I'm not the one signing the order point or the Contracts, right? It's, you know, you have to talk to legal, you have to talk to my cfo, my CRO, all of these other stakeholders. And again, at the end of the day, even if I'm your user or your champion of this product, it's like, are we creating a connection?
So at the end of the day, everyone gets paid. That's on the cap table, right? And what you get paid is basically at the end, you know, after you get diluted, it's what your proportion of the company that you own is. So you know, you made, you gave an example, right, that we invest a million dollars at a five million dollar valuation, so we own 20% of the company. That's very early on. And as you take new money on, you get diluted. And so at the end you get some sort of calculation that this is what your ownership was after all your dilution. After all this, other investors came in and pump money, right? Because your denominator is getting larger. So you break that down real quick.
For people so they understand like the 20% at the beginning why it's no longer 20% 10 years later.
Because 10 years later, if the company's raised an additional $100 million now this 100, it's collectively the company raised 120 million bucks. And my 1 million was 1 over 120. Right. And so that's what my proportion would be of that billion dollar payout. And so it's something that VC funds, especially early stage investors, they are really trying to get a certain target ownership in the beginning. So our target ownership is typically like 10% a lot of times because we know we're going to get diluted over rounds. But you do also at every round, if you have pro rata rights, which is something that we want on every one of our deals, you're able to keep your same percentage as long as you're investing your pro rata share. On follow up rounds.
We've reached this new level and you know, in the, there's a book called the Challenger Sale and it talks all a bit about, you know, like obviously how like people buy from people. I think it's now humans buy from humans. And what better way to show you're a human than by sending a video of yourself smiling, saying, hey, I genuinely want to have a conversation with you for X, Y, Z. Feel free to pop some time in my calendar. And I think something we did here at Salesloft when I started off as an sdr, obviously with the cadences, you can see the analytics and reporting and we actually had video as our fifth step. We then were booking all our meetings on that step, so we moved it to our first step. What I'd then start to do is hit them up on LinkedIn. Hey, I've actually just dropped you a video to your email. The subject line is this. Go check it out. Give them a call. What did you think of the video? Oh, my God, you haven't got it. Let me send it again. And what I'd do is I'd ask them their favorite color, so green. And then whatever day it was. So I'd say, oh, I'm gonna send it now. It's green Wednesday. And then that is the subject line, so you know that it stands out in their inbox. Because that's the whole thing about kind of prospecting with SDRs. The main thing you need to think of is, how can I be unforgettable? And video is an amazing way to be unforgettable.
When you talk about having a coach, right? This idea of coaching, real coaching, real coaches don't tell you what to do. They don't even tell you how to be. They help you calibrate where you're looking at the world and guide you to look at it differently. Because when you see it differently, you start thinking differently, you start acting differently, you produce different results. So it's a very different methodology than training or even what a lot of people call people think coaching is like, let me give you advice in this deal. In the most purest form of coaching, I don't give advice. I don't tell people anything. I work to help make sure I grasp what do they see from where they're looking, and then give another view. And to be honest, after having done this for a lot of years with a coach, I'm pretty good at it. I'm pretty good at saying, okay, what do I see from where I see and let me see it differently and taking different views. But I still go work with this guy, and he shows me something like, man, I would have never looked there. But now that I'm looking from there, what I see changes everything.
Never negotiate before you get to procurement. That's like one of. If I'm gonna. If I'm gonna make any recommendation, any sales be worth it if someone says, hey, you guys are.
We want to keep you in the.
Game, but we need to drop your price 20%. And that's like mid cycle. Just pause there and say, we're gonna get there. We're gonna get there. But until I understand holistically every single thing that new procurement legal teams are gonna ask for. I can't. Let's just not do it. Let's focus on us being the right solution for the business, and then let's let them negotiate. This will save you so much. Anybody who's misquoted by 10 or 20%, inspect all your previous deals. See if you negotiated before you got to procure. If you did, and you stop that and just wait there, you'll make up the 10 to 20% on your annual quota just by changing that one behavior. So right there, like, those are some things to think about.
More from Kevin

#shorts THE POWER OF RECOGNITION: How Do You Empower People with Zoe Hartsfield









