Sam Hillestad
Product Marketing at SetSail
Table of contents:

Join Blake Gleason, Senior Account Executive at G2, for a discussion on why he likes to be transparent and open about pricing early on in prospect conversations, and how to prep for tough sales calls.

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

Michaela: Hi, Blake. Welcome to The Hot Seat. Thanks for coming on. 

Blake: Yeah, no problem. I was excited about the opportunity, Michaela.

M: Well, first off, tell us a little bit about you. How did you get into sales and what do you love about it?

B: Yeah. So sales in general, right? Right out of college, the job I basically got referred to actually by my sister was So I started the SDR role. The BTR role, Mid-Market Enterprise, Gateway and now Senior A all sales process. I guess I think it's fun. It's stressful, but it's fun. The winds are extremely amazing. And then losses you have to learn to kind of put behind you. But I mean, my sales, I just like to talk to people. I think it's fun. I think it's like this, For instance, like I saw you, you asked about this and I was like, this is awesome. Totally happy to join and talk about the different topics and talk about won't give them away. But yeah, I think it's just mainly, you know, like moving up the ladder and I think a lot of sales reps, you know, starting in the last year, well, it's very important to get to that in a year or so. Anyway, I can help do that. That's why we're here today, I guess, right?

M: Yeah. Congrats on career growth. That's really something to be proud of. It's not easy to be in sales, and that's why I'm over here in marketing. 

B: Marketing is not easy either.

M: Well, that's good. Thank you. We have empathy for each other. That's good. All right. So our topic today is pricing. So you posted something on LinkedIn about how you believe it's important to talk about pricing. And you said that you prefer to talk about pricing earlier on in the sales process. So let's set the stage. Big picture, why is it important to address the pricing topic with your prospects on the earlier side of things?

B: Well, the first thought is and I feel like it's probably everybody's thought is the fact that, like you want to know how much something cost before having a conversation about buying it. Right. And everybody's going to want that. They're going to want to look at your website, see what it costs instantly. They're going to be like, That's too much. I understand that concept, but multiple different sources. You know, like I listen to attacks upon me, I follow all the gang research. And when it comes to sharing pricing on the first call. So when you look at those stats and they're taking those gang videos from thousands of people, different companies, and they have a massive company base, of course, I just thought it was interesting seeing that. And then once I started checking pricing on that first call, whether it's the and the metal really just helping them understand, I think the biggest thing is you have to earn the right first. You have to understand their business model, understand what they're looking for. But I also don't like to be that person that's like, I'm going to force you into another call. Even though everybody's sales role, That's great, right? You want that next caller, you want to actually have that SBC, you want to build a relationship. But if you have the rapport, if you're in the right, I think it's fair in the beginning of the call and then just talk about value, what's important you go to the side. That's my company that I work at, but I'm really just understanding what they're looking for is the biggest thing. And then once you walk through that, you share some pricing. I think that's the best foot forward. So success rates have been going way out just because of that, because people trust you and people don't trust sales and marketers like ourselves these days, Right?

M: So true. It's so true. We got to just lay our cards on the table, right? Yeah. Yeah. I love that. That's a great answer. And putting myself in the shoes of a buyer, I definitely have more respect and trust when someone will just tell me what it costs. Right? Walk me through your strategy for introducing pricing. We'll get a little more granular so you start the call. Maybe it's the first call or second call, right? What is your strategy for introducing pricing? How do you start that conversation?

B: So starting the conversation, it kind of depends on how the beginning and the middle starts, right? So typically towards the end of the call, I'll say I'm happy to walk through pricing and I'll still show pricing, but I'll still ask for that next car, right? So you want to make sure they know how much it costs, show them, you know, what each tier is. You know, this means, you know, brand awareness, this means driving revenue, etc.. I think my strategy is typically, you know, just being straight and not from what I'm saying, like, I'll show you that, but I need to also understand what you're looking for. So when it comes to best strategies, it's asking me value based. The recommendations is a big piece. I like to go in having a recommendation. If I don't, then I don't recommend anything like those calls where I literally be like, maybe they're looking at intent and they're looking at like one of our higher tiers. I'll tell them straight up. I'm like, Maybe we take a crawl, walk around approach and we start at the entry level and that doesn't really necessarily help me in my numbers, my quota, what have you for like the next step there are Amazon. It's to good upsell opportunity for the company and also it builds trust and it's like, let's get started, let's build up your profile, let's build up, you know, say it's a gong. Let's start with Gong. But like at the entry level, right? I know I keep using them as an example, but we get to Salesforce, any of the other large car companies, but I like to start with recommendations and then explaining why. But I also like to pause for a second, let them look at it, understand it, and read it. Typically they're going to have like three or four questions, and that only gives you the opportunity to dive in more. So like this there they are questions of, you know, like, how are you doing this? What did I miss here?

M: Right. So I'm getting two things from this answer. And one is pricing alone. You don't just throw it up on the screen, you pair it with the value that you're going to get from whatever recommendation you're providing. And then the second thing it sounds like using pricing as an opportunity to go deeper with a prospect, is that right?

B: Yeah. And kind of like circling back to my point earlier too, is like, who's involved in this process? Like I'll talk to a marketer, say like somebody on the content side, like yourself and content strategy. I can talk to a content marketer, they want something different then the VP of sales does, right? So when you go into those conversations, it's not necessarily that you have to give a recommendation, but if they know that they want a smaller company, they're basically, you know, say a marketer and they have like 50 different hats, right? Content marketing, sales enablement sales in general. Honestly, I think understanding who's going to be involved because that's going to give you a better understanding of the recommendation, getting them involved. On another call. I think that's big because again, yeah, it's not cheap, right? No, no. SaaS company these days is cheap, so it's a big spend.

M: Yeah. So I think what I would assume again, I'm not a salesperson, but I would assume, you know, one of the worries and introducing pricing too early is, okay, I'm going to get ghosted or they're just not going to fully understand yet. You know why, why it costs this much. So how do you prepare for that? And how do you overcome those fears as a salesperson with a quota?

B: Yeah, I mean, at the end of the day, if you have the right people involved in this, they just don't see the value. They think it's too expensive. Yes, there's in any sales organization, for the most part, to my understanding, there's always going to be some lever that you can, you know, help them if you see the value. Otherwise, like I don't like to be pushy. The consultative approach is the only approach. Mentor Dan Button shouted out. He really helped me with that approach because I like understanding that if it's not like the right time for them, it's not the right time for me. So I have 600 plus accounts, right? Sorry for you. That's fine. Like maybe it's next year, but I still want to show you that pricing. I want to show you what that looks like right now so that when that time comes, I can value add and nurture. I can do everything, all the above, but also getting into other people in the company too. So I don't know if that answers your question specifically..

M: Yeah, no, totally. It's like not having that scarcity mindset of I need to close this particular deal because like you said, if you can't force them to have a budget for you, right? So that very way you can educate them.

B: That's insane. And so I guess I would ask you like, you know, like what are your ultimate goals? I would tell you right away, like, can you help? No. Yes. Depends. So I think that helps and it goes a long way, but, yeah, cool.

M: No, that's great. That's a great point. Okay, so we're on top called the Hot seat, so I have a hot seat question for you. Are you ready?

B: Let’s hear it. 

M: All right, so it's the pressure cooker question. Imagine you only have 10 minutes to prep for a pitch for a potential client and you have a feeling they're going to be very tough and discerning. What are the key elements that you are going to prepare for that pitch?

B: So I get 10 minutes, but I get 5 seconds here. Yeah, no, I'm just kidding. So I think given the times, like, I think the first thing that you have to understand and one I don't know if this is like a past stop that you already know is tough, right? Maybe they've just always been like there's ten opportunities in your, your CRM or something like that. And then it's never by I think the biggest things are starting it off bluntly if they're tough, like being tough with a mirror. I think mirroring is like one of the biggest things in sales. If you can mirror some of these attitudes, not like a fake way, but just if they're going to be blunt upfront with you and say like they are coming to the call, they're like, yeah, just final pricing, what that entails. The easiest question is, okay, what do you know? Already puts them in the hot seat per se, but like understanding that and like, what are you looking to do? Like we have multiple different packages, multiple different tiers. A lot of companies do, right? So who are you looking for, I guess, going after when it comes to, you know, like your ICP, stuff like that, making them answer those questions and kind of like getting back on track instead of just running the call, I think is important because it's tough prospects. They're going to try to run the call. They jump like I'm going to tell you what I need and that's fine. Hopefully they give me a lot of information, which sometimes they do, which is fantastic. But then you just fall back to, and by the way, I'm like, listen, I'm your account manager here. So. Right. The intros, which I like because that's relationship based rapport. I don't like to just jump into things, but again, I can't create a budget out of thin air. So if the pricing isn't right for them, it's not it's not going to work. So if they understand the product already, they've had multiple calls. Sure, it'll happen right away. I'll be like, here's a pricing pause. Let them look at it. They don't understand it. They'll have questions and then ultimately they'll be like, This is a lot. And it's expensive. There's a reason for that because we're going to drive this in this. So yeah, I'm trying to keep just saying, 

M: No, no, this is good. So it sounds like your best prep is knowing the questions you need answered in order to help them move forward with you. 

B: Yeah, And also, just like. Like just be straight out with them. There's a lot of people that are going to come in. They're going to be hard balling. They're going to be, I need this, this and this. Hopefully they say that because then I know and then I can just show examples. But I obviously looking at their LinkedIn, looking at past apps and these have pulled out, that is a driving force in most of your opportunities statistically that close. So yeah, I think just preparation is going to be like the biggest thing for those tough ones.

M: That's great, great advice. Well, Blake, where can people get in touch with you?

B: Where can people get in touch with me? Big reason that you two dot com hit me up. If you ever need some reviews on demand generation tools, I think they feel free to follow me on LinkedIn. I try my best to start posting more stuff on the sell side. So Michaela, I appreciate you.

M: Thank you so much for coming on The Hot Seat. This has been a great conversation. 

B: Yeah, absolutely Wonderful time. Appreciate you.