Sam Hillestad
Product Marketing at SetSail
Table of contents:

Join Kaylee Chappelow, Mid-Market AE at Greenhouse, for a discussion on why personalization and engaging performance is the ultimate key to every demo (plus, how she learned this from the master, Taylor Swift). She also discusses the one question you should never ask in a sales demo, and why a softer approach is key to building rapport with a prospect.

The following transcript has been roughly edited for clarity. Please excuse any errors.

Michaela: Hi, Kaylee. Thanks for coming in on the hot seat.

Kaylee: So good to be here. Thanks for having me.

M: Yeah, let's get into it. First, I want to learn a little bit about you. So tell us about your career, how you got into sales and what do you love about it.

K: Yes, it's a good question. I feel like mine's a little bit different. I started selling from the time I was like, little girl. I won my Girl Scout troop trip to this indoor water park because I sold, like the most Girl Scout cookies in our troop. So I was like a salesperson. Since I can remember. I think I love it because it's like when you get, when I get passionate about something, I want to tell everyone and that's what this is like. I found a product I only sell at companies that I really believe in. The product that you drew me. I get to share about it and also help people solve problems. And a big problem solver in my own life. So talking to people who have issues and being able to help them out is a couple of reasons that I love sales. I also think you have to be a little crazy to be in sales. I don't know.

M: All of that. Okay. Do you still have an end with the Girl Scouts? Like, can I get a discount on cookies or is it over? Is it over now?

K: Sadly, the ship has sailed. However, I'm a big believer. Like if I see Girl Scouts selling cookies, I'll buy like four boxes from them. So I'm like, Keep it up. And it really did. Weird, like, shape me into getting into knocking on doors, you know, going back to the overseas every year, like developing relationships. So yeah. Discounts but for the girls.

M: Amazing, amazing. I'm a big fan, mints fan and always will be with you. I'm always back, never whenever they're available. All right. So I want to talk today about how to run an engaging demo. You are Swiftie. I am Swiftie. You had a great LinkedIn post about how running an engaging demo is a lot like how Taylor puts on her Arias tour. So let's start with the big picture. Why is it so important to run an engaging demo, and what is the connection to Taylor Swift?

K: Yeah, good question. I also love to talk to a fellow Swiftie. We talked about this and from Kansas City you got the T Swift Travis Kelce rom com going on another time, but not her arrows. Her arrows tour. I was absolutely phenomenal. And I walked away and I was like, my gosh, this is literally a roadmap for me to do my job and to sell software, particularly a couple of things come to mind. The first is how personalized the show felt to us. She did over 100 shows and I felt like it was her and us. And I feel like that's the same thing when you're doing a demo. Usually your buyer is evaluating lots of systems, so they're seeing lots of these demos and having these conversations. It has to feel personalized to them and their problems. So some examples of that are: I always like to ask their pain and I make sure I know exactly what they're looking for in a system, what their pain points are, what their industry is, how big of a company are they, how are they thinking about hiring social hiring software before I have that conversation? So my demo is very personalized to their specific problem. Hey, you said this. I know all the names of their team. Charlotte can come in here and see all of our tasks and this will help because you said that time savings is really important. So really making sure it's personalized, just like Taylor did for us. She addressed us by name. She took little moments to have in between real life personal conversations instead of just singing from song to song, song or showing feature from feature feature feature. So that was the first thing. And I think the second thing is she gave us a real show, like lots of pizzazz and dancers and, you know, different transitions that were really, really cool. And I think it can be really easy to give like a canned demo that's just here's this feature rather than this button and it's boring. And like, I don't want to hear myself talking to the boring demo for an hour eight, 8 to 9 times a week. So it's all about giving a show, right? Like making them feel like it's a performance. It really is. So I have slides that I switch back from and I show visualizations and intriguing things versus just talking about it. So I think that that really helps me know. I'm always thinking about how I can make this a performance and keep it engaging, ask questions and actually show them cool little things like I try not to stay on the same screen for too long because it's boring when someone's talking and not moving the screen. So even just clicking from talking about email notifications, I can go out to an actual example of an email, right? And saying, Hey, this is what I could look like to help people visualize and really connect to the product.

M: No, that is such a great mindset. So before I go on to the next question, what was your favorite live song from Taylor?

K: I can't even pick. I love all too well, the ten minute version, and she did all 10 minutes of it and I was just eating it up. It was funny, like how I got to get tickets was a whole other thing. I actually demoed Taylor Swift as my demo candidate in our software. So I think I was like, it was just meant for me to get together. I mean, we didn't sit down like we sat down at the very end because we were just tired because as a three and a half hour long show, probably something we wouldn't do. And demos probably should be something we shouldn't take away from Taylor is how long she did it. But I just heard that song come on and it was just amazing. 

M: That's so cool. So you definitely know what you're talking about. You know, you're crushing it at GreenHouse. How did you learn how to run an engaging demo? Was there an experience or something that you came up against, a challenge that you overcame to really learn this lesson?

K: Yeah, I think this comes down to like just how I've learned to sell in general. Obviously, like I've sold as a kid, I'm always all things I studied sales in college. That was really cool. So I had some foundational learnings there. When I got into this tech sales, I was at a startup and had no real experience, so I did teach myself a lot and it kind of goes into how I would recommend anyone do like development if you got to take hold of that, right? Like joining a group. There's so much content and so many great leaders giving away or like charging small amounts, I think for the value, like all of this content that you can absorb on demo. So Chris, all that from Gong is really good. Scott is amazing. I joined his community early on in my career. I think I also learned by doing right, like at my first company, I remember giving my first and I had a whole script, I read the whole thing and I was like, Well, that was awful. So like, how do I want to do that better next time? You know? So I think one thing that I do for all my demos is I have a script that I follow, but now it's a lot looser, but I'm always tweaking my process as well. Like when I learn something on a podcast like this, I'm trying it out and testing results and I think you have to have a playbook and you have to be consistent in how you demo to know what hits and what doesn't, instead of just winging it every time. So I have a question and a bank and I listen to it. I do a lot of preparing. I probably prepare an hour before each demo so I can be very specific and very tailored and make them feel like I know them from the moment they get on the call because they've had a conversation with an SDR. So I'm doing a lot of time preparing and really trying to figure out what matters to them. How can I really make this tailored? And I think that I've learned from the best too. I watch a lot of gong calls of top reps at GreenHouse, and I think I take little pieces of people. I think that's something I do in life in general is like when I come in contact with someone amazing, I immediately take what I like that they do and I apply it to my life, you know? And I think that that's the same thing in sales. I find something I like, I emulate and I, you know, pull and take and then tweak and make it my own. So, yeah, a combination of finding my own development, learning, really engaging. I have 30 minutes a day where I sharpen my act, but I spend that 30 minutes a day either doing a podcast to do a gong, practicing some sort of like development, and then finding the best people who you want to sell. Like there's a rap cult named Drake Patterson at my company every year. Greenhouse, Frankly, amazing. But he's really concise, so I watch his demos to make sure that I can get better at that. Jake Bellamy He's actually I'm dating him, which is funny, but he's a good salesperson as well. Best salesperson. I know I learned a lot. He's so charismatic and really didn't show what I was talking about, So I learned a lot from him early on as well. So yeah, there's a little bit about how I learned and how I'd recommend tackling, learning the sales space.

M: Those are amazing pieces of advice. Final question about demos. So what should we not do when giving a demo? What are some of the common pitfalls and how do you of course, correct if you sense like it's starting to go off the rails.

K: Yeah, I love this question. So great work for you. I think the first thing is canned demos. Like you will lose people, They will glaze over. They're not paying attention. And now when they're deciding on what the sound, they're going to pick the cheapest option because they think you do the same thing as your competitor. Like we're not. We are the premium product for a reason. We're the best product in the market. I wouldn't work here if we weren't. But there's times where you have to sell that. You have to show them that. So I think where people go wrong is they just go through their same canned script and they have no idea what's important to that business. For example, a friend of mine on my team also has a phenomenal salesperson named Amanda. She was demoing a specific industry. She pulled up like a competitor of theirs that used our system and said, Hey, we work with a lot of people in your industry. And they told her afterwards they were like, that's amazing, because this other competitor, they felt like they really didn't know our business at all and they felt like they were more geared towards tech companies. We also work with a lot of tech companies, but because she identified them and made them feel good and special and it wasn't canned, she was able to really like bring them in and bring them on as a customer. So don't do canned demos. The other one is really specific and I feel really strongly about this. I literally hate the question does not make sense. I feel like a lot of people ask that and I feel like it can be a little bit condescending. So I learned that that I read this in a book. I think I can even remember. But instead of saying like, after you demo something and be like, So does that make sense? Like maybe saying something like, is that more, is that clear? Did that clarify or that answer your question? So I think that just comes across more like warm and professional. So that just felt like a little bit of a small pain point of mind that I don't love when people doing demos asking, Does that make sense after you?