Why Hiring - not Coaching - Is a Sales Leader's #1 Job | Shaun Priest, Promptly #sales #salestips

Sean, good to see you. Appreciate you joining today. As a way of getting started, tell us a little bit more about yourself and how you got here.

Dustin, always appreciate your time and thanks for the invitation. So I'm Sean Priest. I'm blessed to be a 30-year technology salesperson with the last 20-plus years being in sales and go-to-market and marketing leadership. And then I've spent the majority of my time in Awesome.

Appreciate that. And good, good to see you again. Tell us a little bit more about where you're at now and what you focus on. You know, healthcare can be an interesting industry. It's— there's a lot of opportunity, but it also can be tough to get new disruption and innovation there. But yeah, tell us a little bit more about what you do now, if you don't mind.

Oh, so yeah, as you say, so 19 cents of every dollar goes into healthcare today. So it is the largest individual industry and driver in the economy. And then, so what I do today, so I work with Promptly. Promptly is a patient experience vendor. So essentially what we do is we connect to the electronic health record, and then we become that seamless patient experience, giving the patients the ability to schedule appointments, get appointment reminders. In our healthcare system today, the patient is responsible for sometimes up to 100% of the procedure. They've got a copay. We help manage, help the finances part for that. And then we also help practices grow, whether in a fee-for-service model and help finding the right patients, or in a population health model. How do I make sure my patient population is healthy? So it's a great business. Promptly is doing a lot of exciting pieces and we don't have any meetings without talking about AI. So Promptly is making a big investment in AI. And one of the things we see in the market today is a convergence of digital and voice and those 2 pieces rapidly coming together.

Love that. That's really cool. I can relate for sure because my dad's a doctor and I understand all the stuff you're talking about and definitely a lot of opportunity there. So really cool. What, from a sales standpoint, You've been doing it in a lot of different areas at a high level. What, what has changed, you think, the last, let's say, 5 or 6 years? You mentioned AI, but what, what else have you seen change in recent years? Or maybe it's been staying the same.

Well, so there's been so much change in the industry. So if we go way back, right? So then we've added, I'm old enough that I started selling, there was no internet. So the buyer needed me to get information. Then obviously the internet was a big revolution. We don't need to go through that. But probably the biggest dynamic was the pandemic, and part of the pandemic made just huge structural changes. One of the biggest ones that I talked about prior to the pandemic, you'd have to go on site for almost every single sale, right? Whether it was a $10,000 sale or a $5 million sale, you really had to go on site. And then the pandemic really moved things to an online piece. So I think that's been a big change, right? So right now we're doing this on Zoom. If we did this meeting pre-pandemic, either we'd be in person or we'd just be on the phone doing it. All right, so all of that technology has been a big change. And then I think the piece that the buyer is now really insulated. So that's probably been the biggest fundamental change that as sales teams and marketing teams and go-to-market teams have gotten smarter and more aggressive and so on, they're forcing the buyer to be more insulated. So how can you provide value to the market? And then this is where successful companies make big investments, and they're still out there. Cold callers are still out there for sales teams. But how can I create content? One thing that I talk about at Promptly is we're actually making investments in TikTok and Instagram Not so much that we believe our buyer is going to go find information on Promptly there. You know, they'll actually go to Google, they'll go to large language models. And because they're going to large language models, we actually now believe we have to put our content in other places for the large language models to find them.

Oh, that's really cool. I definitely want to dive a little bit deeper on that because I know you post quite a bit on LinkedIn. Sounds like your company is heavily invested in social media, which is awesome. And all that stuff you're saying is 100% true because the buyers just have everything at their fingertips and they're getting protected to not talk to salespeople, unfortunately. But I do think you mentioned in-person though, because I think you're pretty big on trade shows. You also do in-person hikes sometimes just with friends and whatnot. But do you think there's like this— there's this online push with AI, but then there's also a need to be in person? I feel like a lot of people just want to be in person as well. Are they both kind of converging together? What do you think?

Yeah. So I agree. So I actually, we do think a shift of the next phase is the buyer's going to want us to come on site more again. So I think went for a phase, obviously in the, in the depth of the pandemic, things were 100% remote. And I think things slowly, slowly coming back to being in person. I also think the technology piece is buyers want to be connected with other buyers. Like I tell stories all the time. I was just with one of our clients and I'm like, I could say the same thing. But if you, if the client says the same thing, it means so much more. So like, what are their trusted resources? So now they're actually spending more time in different user groups, different forums to get information. So ironically, the more we do with technology, the less the buyer needs us in the near term. So there's a popular book out there, The Challenger Sale. I know you're familiar with The Challenger Sale. I know other people are familiar with The Challenger Sales. But one of the things they talk about When I first started selling pre-internet, right, in a 9-inning game, you had to involve the salesperson in inning 1 because you needed us for data. Then with the internet, you probably had to bring us in at inning 4. Now with large language models, forums, user group meetings, you may not bring us into inning 7 or 8 on the baseball analogy, right? So like you have to bend in. How do you support the buyer or support the prospect? In their decision-making process when you're not there. And then ultimately, any successful company, I want the buyers to make the right decision. So in many scenarios, I believe Promptly is the right decision. In other scenarios, we're not the right decision. And that's okay too, right? Because we want to have long-term successful relationships. So how can we help them find us when we're the right decision? And how can we help them not include us when we're not the right strategic fit for them?

That's great. Yeah, you definitely want to have that long-haul mentality and connect those buyers with, with previous customers, get it from their perspective, because no matter how good you are, myself or whatever sales rep, they don't always believe everything they hear. But if they hear it from someone else who's been using it for a while, that's fantastic. And on that note, you're right. Now it's harder than ever probably to be a sales rep because you get pushed off until those late innings, as you put it. So when you're trying to hire folks, whether that be in the past or now at Promptly, What do you think separates the best sales reps from other people out there?

So I think you have to provide value to the prospect or the buyer, right? So how can you do— so again, so I'm a 30-year HIT person, like I understand the space, like I can bring value in regards to what are they doing with their electronic health record today? What are they doing with their payers, different IPs? How can we bring value? So I think that's a big part is you need to bring value. And then I think also having the discipline to go through the discovery process of what business challenges are we helping them solve. So like at the end of the day, to make an investment in any company or make an investment in Promptly, it's either one of two things. We're helping them solve a business problem or we're helping them achieve a strategic initiative. So I believe the nice-to-have days, unless you're selling a very low-value or low-dollar solution, The nice-to-have days are long gone, right? So they're gonna make a decision today. It's a have-to-have decision. So then how can you, how can you understand? And then I think the hardest piece, and I'll just do this for me personally too, is when do you need to push and when do you need to pull back?

Right?

Because if you're following up twice a day, you're just annoying them and you're not adding value. And if you just give them the data and you leave, You're not providing value, you're expecting them to figure it out themselves. So I think that's a big challenge in certain prospects and buyers you need to follow up with a lot, and some of them you got to find that right balance, and it's really hard.

Agreed. I think I would call that judgment. Which deals are you working on? Which deals are you pushing a little bit more or pulling back? It's really hard because what ends up happening is sometimes we spend a lot of time on deals that don't close. And that can mess with your mindset and just cause burnout and all that. And then the other thing you touched on is being very outcome-focused, focusing more on the value, which is 100% correct. I think you need to be more like a peer, not a salesperson. They're already trying to come up with ways to not talk to salespeople sometimes. So if you're more of a peer bringing that industry knowledge or whatever niche that is for you, that's great. So find a differentiator because you need it for sure. The other thing about healthcare, just knowing it from doing that device back in the day, my dad being a doctor, it tends to be very complex sales, longer sales cycles, and that can be tough, right? So what, where do you, where do you think is the hardest part of the sales cycle from your standpoint? Is it just keeping the momentum in the middle of it? Is it just not giving up after the 6-month process, or what do you think is the hardest part? for reps to navigate?

Well, I think your answer is yes. And then we look at it as kind of 3 phases: top of funnel, middle of funnel, bottom of funnel. So top of funnel is how do we break through that initial crust to get them interested in Promptly? Do they know about us? Are we out there in the market? Is there a problem that they have that we can solve? Is it a problem that they don't know that they have that we can identify in advance that they have the problem? That's the top of the funnel. And then once you've got them to raise their hand or some level of interest, can then you get them to the next stage, right? So again, they've got to make good decisions. How do you provide value to them? Then how can you, like, do you live in Missouri, the Show-Me State? Can you give them case studies? Is it, I'm sorry, there's so much new stuff going on with AI. Can you show them that you're doing a new technology? And then ultimately, once you get to the bottom of the funnel, how can you, you know, work with them directly to say, okay, because anytime the buyer makes a decision, they're taking a risk. Right? You know, so they're taking a risk betting on your product or betting on Promptly. How can we help them manage that risk? And we also need them to make a commitment. Right? So I talk a lot about Promptly does a lot of great things. And one of the things I say is we sell change. So if you're having a business problem, you wanna solve that problem, you actually have to change. Right? So ultimately, how can you get the The prospect or the buyer to get, because they're gonna, they're gonna have to take risks. There's no doubt about it, right? And you have to show them that there's a bigger risk of not doing something that versus, you know, going with your company.

So true. And I think people forget about that, though, that, that champion that has to go fight internally that gauntlet and get asked a million questions and all the naysayers that might be there. And it can be overwhelming. And if they haven't done it before, If you don't equip them the right way, they can get shut down pretty quickly. So you have to put yourself in their shoes, have some empathy, really try to be a peer and help with that change. And I, and I do think that's a great point too, is people underestimate the implementation, they underestimate the change management. Depends on what you sell, whether it's technology services, etc. But that's always the hardest part, especially when today we have our iPhone, we have AI, we have just so many distractions. It's— we can't even get people to focus on a A 10-minute call, let alone implement a new product or service. So that's very true. Very true. Now, from a sales leader perspective, a lot of people are leaders here that will listen to this. What do you think is some mistakes that you see leaders making out there today? You know, is there certain things that you've picked up over the years that, you know, if you could go back, you would change? Or do you just see a lot of leaders making certain mistakes in this day and age?

I guess I'd answer it a little differently. I'd like, I think the most important thing you do is hiring, right? So I think if you can have a top team, I'll tell Nick Saban for the football fans out there. Nick Saban was the coach of Alabama, I think, believe won 7 national championships. And he talked about hiring his staff and growing his staff and growing his people was like his number one job. You think it would be recruiting players? But he actually talked about recruiting his staff and how important they were. That way he can continue to grow and expand. So I would put that as the number one piece. And then I would say the biggest mistake people make is we're in such a complex environment. You have to have a multi-pronged strategy, right? And because you're just gonna be like, what type of salesperson do you have? Do you hire an industry knowledge person? Do you hire a relationship person? Do you hire, you know, more of a lone wolf person from a marketing and outbound strategy? Are you doing LinkedIn? Are you doing Google Ads? Are you doing trade shows? Are you doing case studies? Are you doing webinars? I think the reality is that you have to have a multi-pronged strategy because if one strategy worked, everybody would do it. So I think, you know, I think number one would be hiring and then Number 2 is you have to have a multi-pronged strategy.

I like it. I like it. And I agree, it's gotta be a 360 approach. I mean, everyone's gonna have their strengths and weaknesses, but there's not gonna be any magic out there. And today, maybe if you're a massive company like Salesforce or whatever, and you just have inbound, but that's unfortunately not the majority of us out there, and you have to be a lot more creative and put those dollars where, where it makes sense. What have you seen? So you guys obviously do a lot of disruptive change with your end user and the customers that you call on, and a lot of that is AI. What's, what's your sense been so far with AI in the sales world? Do you think it's been a lot of open reception to it, or do you think there's been a lot of pushback? Or what, what have you been seeing with AI so far from a sales standpoint?

I think from a, I think from a sales perspective, there's a fair amount of pushback. And I see these as tools. So again, just using Promptly. So we make big investments. So we have an investment in Gemini. We have an investment in Claude. We have an investment in ChatGPT, right? So, and that's just on the sales front. We use Fireflies to record our meetings. Fireflies now has Fred to ask Fred, how are you doing in the different meetings? So like that train is really coming quickly. So for individual contributors and sales leaders. I mean, if you're not using the AI, start and just do little things. It'll just amaze you on how quick it is. And I use this statement all the time, but today is the dumbest AI will ever be, right? So if you've used it 6 months ago and it didn't fit your need, try it again. Like, it's just, it's absolutely amazing on how quick. Just a personal story. So we're a big Google shop. when Gemini first came out, I was gonna switch from ChatGPT to Gemini. My first Gemini usage was a failure. And then I was doing stuff with Gemini, and our CEO and founder, Dr. Kapoor, said, hey, how come you're not using Gemini? And I said, well, I had these problems. Well, go try it again. And all those problems were gone.

Mhmm.

Right? So I think, like, that's the piece where it's just gonna get more and more integrated. And then just one, so In my role, I'm also a buyer. So not only am I out there, I talk about when the buyers are prospects, I'm a buyer. I guess I've done enough name dropping of companies, but we went through a process to buy a contact database and we actually selected Claude and we could not get a salesperson on the phone.

Hmm.

It was 100% AI through the whole process. We were allowed to do a free demo. We were allowed to ask questions. And then at the end, I wanted to negotiate a better deal with the rep. And with our deal, we didn't talk to one per— and it was wild for me because I'm very pro-salesperson and I believe that salespeople provide great value in the ecosystem. And do I believe more and more is gonna get automated with AI and so on? But I still believe just having that communication with the person, like we believe Like with the Promptly product, right? So Promptly, we do a lot with AI that the winners are gonna be both AI and then how do you support the staff, right? How do you support the patient? How do you— if you're doing stuff around voice or digital chatbots, how do you give an exit to a person? If you're actually dealing with the staff, how do you actually have them spend more time with patients? So that's how we see Again, I'll, I'll, uh, hype Dr. Kapoor. He's doing a presentation in 3 weeks, uh, on AI and how we see it as a benefit to the staff versus replacing staff.

Love that. Real quick on the Claude implementation. So you, you got a discount without ever talking to a rep, like you were going back and forth with some, uh, email or bot, or how did it end with, with that?

Uh, sorry, not Claude. Clay, right? So Clay, sorry.

Oh, Clay, my bad.

Yeah, Clay. No, no, right. No, no, no, no, no. Sorry, Clay, but my bad, right? They, they run together. So Clay, the contact. We do use Claude, but, and, and so I would say that we did not get a discount. Alright.

Well, but that's a, that's a great story to see, like, how far some industries or some areas are going, and then you have the opposite. So real quick. So the, I do think there is a fair amount of pushback. I think part of it is because it's a little confusing out there. There's so many options. There's so many things getting thrown at us that changes daily and weekly, it can be a little overwhelming. And then sometimes someone might have a bad experience like you were talking about and give up. But, but that's not the right way to look at it. I think, you know, find stuff that is driving you crazy, right? Like whether it's meeting prep, research, follow-up, calendar back and forth, stuff that's not a good use of a salesperson's time. It's not necessarily revenue generating. Start small with that stuff. Get in the game with some of the tools you're talking about. And then You can start doing some more advanced things. So, but I think if you look at the stats, a lot of salespeople are not spending time in front of the customer. They're spending time doing a bunch of other stuff. So most leaders want their reps in front of the customer doing what they do best. So if you can automate some of that day-to-day stuff that's not a good use, that's a huge win and it should lessen burnout and make you perform better in front of the client, which is what we all want to do. Do you think that's like a good way to start for people that haven't done anything?

Yeah. I, I mean, I would agree. I mean, just start little, just help with your emails. Like, anytime you're stuck with an email, and I would also do the more content, the better. Right? So we had a big meeting yesterday. I needed to do the follow-up. I put our proposal, I was using ChatGPT, right? Or excuse me, I was using Gemini. I put our proposal in there. I put the recording of the meeting. Right? And then it did a great, but I still tweaked it at the end. Right? So I think, like, any, just to your piece, like, anywhere you're stuck, Right. Anywhere you're stuck, just try to use it to unstick it. Or like I'll use, there's a bottom of funnel deal that where the buyer has sort of ghosted us. So we went back in to listen to the meeting and we're, and instead of listening to the meeting, we're doing interactive dialogue with Fred at Fireflies, right? How did the meeting end? What did we do? What could we have done better? How did you rate the meeting? Fred, meeting, 9 out of 10. Right? Those types of things.

So true. And, and even if you get 80 or 90% of the way there, that's so much less work that you have to do. You can actually just think and be strategic that last 10 or 20% to your point.

If you have a busy day and you have 4 demos in a row, at the end of the day, they run together, right? I don't care who you are. Right? And then, then for us, which EHR group did this have? Which competitor did they have? What to when was their board meeting? Like, so we record all of the meetings and it just has great data in there. And now the good news is the buyer's used to it, right? So if you do like before, people used to fight recording meetings, right? When, you know, when we kicked off this meeting, right? Get the recorder in it, do the copy of it. So all that stuff, I think the— it's a win for them too, right? And as salespeople, they can hold us accountable. What did we say? You contracted with us. What did Sean say? Here, the meeting was recorded. Here's what Sean said.

100%. I agree. And I think, you know, the buyer wants good outcomes too. So they don't— in my opinion, if you're using AI for 90% of your output or using it not at all, if they're still getting a good service and outcome, that's, that's what they want. So I think if you, if you get AI to do the stuff on the back end that we're talking about, you perform at your A-level more often, right? You just can't do it all the time. You can't remember all this stuff. So it helps with that. So Good stuff, man. Well, we got like a few more minutes here left. I want to ask you a couple more things. So if you had to go back and give yourself one piece of advice, uh, starting out back when you did, uh, what would that be? If that might help others out there.

Um, I'm gonna go with a, uh, an interesting one. So Dustin, do you know what Winston Churchill's definition of success is?

I do not. I should, but Go ahead.

It's going from failure to failure to failure with no lack of enthusiasm. Right? So I guess the piece would be, I've had some pretty major failures in my career. You're gonna have, you've been doing this 30 years, you're gonna have a bunch of them. And then those failures have all helped me in different ways. Right? I've learned a lot from each one of those. And then just, you know, go ahead, grind, You know, stand back up, dust yourself off, and then go into the next one with full enthusiasm. So it's kind of interesting, like in sales, my success or failure is based on how successful I am. But according to Winston Churchill, it should be how enthusiastic I am after each failure. How was that one, Justin?

That's a great one. I haven't heard that one yet. I haven't heard that one yet. And it's just making me think too, because It is a roller coaster. You get beat up so much. A lot of people don't wanna talk about their failures or they shy away from it, but then you have the chance of repeating them potentially, which you don't wanna beat yourself up on it too much. But I think that's a great quote. You gotta stay, stay positive.

You gotta have that growth. And sales isn't meant, sales isn't meant for everybody, right? Sure. Certain people just cannot take it. Like if you cannot take rejection, this is not the right market for you. It just isn't, right? I mean, no matter who you are, I don't, you know, whatever the, pick the best salesman in the world, you know, they're still gonna lose 80% of the time, right? So like, how do you then just, if the, if this is the right bid, just understand it's part of it. Be positive, go on to the next one, learn from it, right? Don't be negative on it. Ultimately, then put yourself in the buyer's shoes or the, you know, the client you lost shoes and what did, you know, why did they make that decision? What did they see that you didn't see? And then how can you go, how can you go, how can you go correct it?

Definitely, definitely. And a lot of people don't want to talk about their failures. They don't want to admit it, all that. I think it, from a leader standpoint or a sales rep, you get a lot more respect and, uh, it helps you keep staying positive in that growth mindset. That's a great one. All right, and then, you know, what's something you're really excited about the rest of this year? It could be personal, could be professional. Is there anything you're really looking forward to?

Uh, well, the wife and I are going on vacation in a couple of weeks, so that's, uh, That's one to look forward to. I just think the changes in the market. I mean, I think this is a great time to be in the space as a whole. I think we're gonna look and see how much transformation is going on here. And I know it sounds, you know, redundant. And so anybody familiar with the Gartner hype cycle? So if anybody that's not, go, you know, Google the Gartner hype cycle. And I think we're now kind of in, we're through the mega hype that AI was gonna take all the jobs. Right? We're going to have Terminators and this and that. And I think we're now heading into the trough of disillusionment, and then we're going to come out of it. Right? So, like the whole token, if you follow token maxing, right? At one point, we want to use all these tokens until the CFOs start getting bills on tokens.

Yeah.

Right? And then we went to that ChatGPT and Claude or Anthropic, we're going to go public at trillion-dollar valuations on $20 billion in revenue. Both of those have slowed down. But there's real value here. So I think we're gonna continue to see that value. And I think the biggest one is we're gonna see the merger of voice and digital. Whereas I think today they're 2 separate things that I think AI is gonna bring them rapidly together.

Voice and digital. Yeah, I might need you to explain that a little bit more because I, I—

And again, I think about from our business, right? So in our business, Right? If you're a hospital or a specialty practice or whatever, you have your online presence, which is pretty straightforward, right, of web and mobile. And then you have your call center or your voice, right? And those are 2 separate pieces today. Whereas we're gonna add AI to voice and we're gonna add AI chatbots to web and mobile, and then they're gonna come together. The investments you make in that are very similar investments. Whereas prior to that, voice was one piece and web and mobile was another. Does that make sense?

Yeah, for sure. You're, you're making a more seamless experience. It's everything in one place. It's much easier to probably work with you and, you know, one-stop shop for a lot of different stuff that's gonna help them be way more productive. So that's great. And then, yeah, there's that classic, I think it was Uber that spent a fortune on Claude tokens. And the CFO, like, freaked out. So that, that article was definitely going around. I know exactly what you're talking about. Well, cool, man. I appreciate you joining today. If people want to get ahold of you, what's, what's the best way? LinkedIn?

Or if they want to learn more about—

Probably LinkedIn.

I'm a big LinkedIn guy. Sean Priest just dropped a note that you got it through Dustin because I now also, I get prospected too because I'm big on LinkedIn. I, again, if you're gonna send me a LinkedIn invite with no note, I'm actually rejecting them these days. So if you're gonna reach out on LinkedIn or check out promptlycheckin.com, uh, if you want to learn more about our company.