The Sales Development Podcast Episode 219 with guest Hilmon Sorey from Coach CRM

How do we not only do the job, BUT do the job, and do the job well?

Sales is simple, right? Maybe better described as “Deceptively simple” is a better way to talk about it. Its as simple and a moving target.

Join us as we borrow from the knowledge of Closeloop and now the Sales Coach of CRM Hilmon Sorey. After more than 10 years of training, we are happy to say that persistent is still key, but lets look at the new trends.

Together we answer the question of “How do we make the most of our people, processes, and technology advances?” Together we drive the pipeline and revenue forces in your business. Share in our discoveries!

Leave a rating if you enjoy this episode and tell a friend to listen!



David Dulany: Hello, hello, hello everybody. Welcome to another edition of The Sales Development Podcast. I am honored and blessed to have my next guest on the show, Mr. Hilmon Sorey, cofounder of CloseLoop and cofounder of CoachCRM. How are you doing today?

Hilmon Sorey: I’m great, David. I’m happy to be here. I’ve been actively following you for many, many moons.

David Dulany: Oh, man. OK, yeah. It has been many moons.

Hilmon Sorey: Hey, that’s good. The whole – what is it? Persistence is key, right?

David Dulany: Oh my gosh. Yeah, exactly. Yeah. We’ve been trying to figure out sales development and all the new trends and how to do the job for a long time and it keeps changing, right? And it keeps getting harder and more in-depth to try to get the best practices out there. So we’re hopefully scratching the surface after five years.

Hilmon Sorey: Well, you know, I think the important thing is that it evolves, right? I mean that’s part of the challenge is it’s a moving target. It would be great if these cats would stay in one spot and you wouldn’t have to hurt them. But they keep jumping and leaping and moving and, you know, yeah, it’s a constant thing and your contribution to the field has been immense and so I’m appreciative of it.

David Dulany: Yeah. I mean it keeps me – like it keeps me going every day to try to learn about this because at the end of the day, it’s pipeline and revenue and all the different – like that sounds so simple but it’s all the different pieces of the puzzle that you have to put together from the people, to the processes, to the technology and there’s so much involved and like you said, it’s always changing. So it’s an interesting topic. So here we are.

Hilmon Sorey: And then there’s that other piece that you can’t control which is the marketplace, right? And what your customer is doing and how they’re evolving and how they want to be interacted with and what their journey looks like and what channels they’ve decided to go deaf on. Yeah, absolutely.

David Dulany: Oh my gosh. It’s constantly changing and now we’re – especially in the tech industry, like we’re in the first to get hit by macroeconomic shocks. It’s almost like crossing the chasm. Like we’re the early adopter of whatever bad news.

Hilmon Sorey: That’s exactly right. We embrace it wholeheartedly, don’t we?

David Dulany: It’s just like just as fast as it goes off, it goes down. So, you know, just responding to all those and learning the new approaches that we need to take to be able to continue to build pipeline and revenue, right? It’s never-ending, man.

Hilmon Sorey: It is, it is. That’s what we love, right? Drinking from that well every day.

David Dulany: OK. So you’ve got such an interesting background and working especially with Cory Bray who like is another legend in our industry and you guys have been great partners for a long time. Tell me about how you got involved in CloseLoop and then now building CoachCRM.

Hilmon Sorey: Yeah. So CloseLoop really – going back to – I guess just a little of my background, right? I had been in sales for a number of years both professional services, management consulting sales. There was media sales working with a large digital media entity and then tax sales. You had, you know, increasingly more responsibility. It started off kind of like an inside sales, moved up to – it wasn’t called SDRs back then. It was telemarketers back then.

But yeah, yeah, I go that far back. We’re not going to talk about that. But, you know, moved into account executive and just strategic. Went down the whole path and then eventually had my own team and I got to a point where I could not move the needle anymore with my team. I was great as an IC. You know what I mean? And then with the team, I got to a point where despite the tips and tricks that I was immersing myself in, read every book under the sun, tried different methodologies to a certain extent and I realized it was a me thing, that I just could not get it done.

Then of course my employer realized it was a me thing too. So I was shown the door and I vowed to never let that happen again. I was that kid who for Christmas, I would get a remote control car and let’s say that’s seven o’clock in the morning when I have gone under the tree and I’ve opened the present.

You know, by 11 o’clock, that thing was taken apart and I’m trying to figure out how it works. So I kept that – yeah, my parents loved that. But – and sometimes I was even able to get it back together. The idea was I did figure out how it worked.

David Dulany: Thanks a lot, Hilmon.

Hilmon Sorey: Yeah. They still keep giving me gifts though. You know, the gifts got a little more intricate as time went on. But, you know, the gift of that to me is that I’ve always been someone who likes to take things apart, figure out like what is the core essence. You know, what’s necessary to put back together and how you make it faster, stronger and better, lighter, cheaper, whatever it may be.

So after leaving that gig, what I did is I decided, hey, I’m going to go work for one of the top sales training organizations in the world and that’s what I did in the Bay Area for one of the top franchises and did that for nearly 10 years, learning the ins and outs of training, working with literally thousands of companies and tens of thousands of sales reps and really getting immersed into what the challenges were that were facing folks in Silicon Valley because that’s where I was and how to go best about addressing those and how to build an organization that can do that effectively.

It got to a point where I realized, you know, what we were doing in that organization was no longer effective. We were kind of riding the fumes of old methodologies that have been created in the ‘70s and ‘80s and while human beings didn’t change, to your point, as the way you started to show, a lot of these things with respect to process and technology and rules of engagement and channels and all of these other things, the buyers themselves and intent data, things like these, have changed.

So I decided I was going to just take some time off. In the interim, Cory had become a client of mine. He was a head of sales for a legal tech company in the Bay Area. He was looking for a coach and I tried everything I could not to work with him as an individual because I wasn’t working with individuals at this point. I was like, oh, big time. These big companies are – there’s this kid from Texas, right?

And being Cory as he is, you know, he’s of course – his nature, he doesn’t take no very easily. So I made him meet with me after five o’clock on Mondays every week and we forged this spot.

David Dulany: So you can make him go away.

Hilmon Sorey: I couldn’t make – I really tried. I would be – and I would get a – I got to a point – here’s the interesting piece. We got to a point where we had tried so much with this company that I actually had to fire him. It wasn’t a Cory thing. It was a product thing and shortly thereafter he realized, well, Hilmon is firing me. Then I’m probably on the wrong horse. So he left that and, you know, to make a long story a little less long, we forged a bond and understanding that there’s very little overlap in our Venn diagram with our skillsets and we both have a lot of passion and we think a lot of expertise around the areas that we have capabilities.

So we looked at the world of sales enablement, the world of sales training, the world of professional development and management consulting in the same way and decided that we could come at this from a more powerful, more modern perspective. So CloseLoop was born and we’re about four and a half years into it now. We won at Selling Power Top Training Firm Award this year which is great and we’ve helped a lot of people grow. So that’s where we are today.

David Dulany: Oh, man, congrats. That’s awesome, dude.

Hilmon Sorey: Thank you, yeah. Thank you.

David Dulany: And, you know, I won’t mention. I just looked at your LinkedIn. I won’t mention the training provider that you were with for a long time. But people can look it up.

Hilmon Sorey: Yeah. I try not to name names.

David Dulany: Yeah, no, you’re totally good. With our mass audience of listeners, I think you will be good. So when you’re working with these companies, what discoveries have you made of working with sales teams? Like how has their needs changed and how do you enable sales teams within what you developed at CloseLoop?

Hilmon Sorey: You talked a lot about the nature of sales development specifically and how that’s a moving target and how the technology, the people, the adaption of management, the understanding of the marketplace, all of these things have changed.

It has the same impact on training and professional development and that’s what’s really interesting is that we take that and then we compound it with the fact that hey, you’ve got a team that could be hybrid. It could be remote. They might be in the office. If they’re in the office, they’re staring at screens all day long. They’re not in some sort of call center where you just buy and have these conversations.

There’s automation where the velocity of business is moving at such a significant clip that it’s well beyond what it was 10 years ago and, you know, obviously 20 years before that.

The impact is significant because particularly in the SDR world, your top of funnel demand gen is critical for proving out all of these hypotheses that venture capital has invested in, right? Most SDRs are in a B to C type organization that has got a high hockey stick expectation of revenue growth and scaled to get to the next gate, next tranche of revenue and fund development.

So all of those implications are sitting there and they’re wholly dependent upon being able to hire and train and execute and promote folks into the organization. So what has changed? Well, a number of things. Training delivery can happen in workflow. Coaching can happen in myriad ways whereas coaching used to be just a one-on-one conversation.

The retention of those assets and data can happen in different ways. The assessment of individuals can happen in different ways. So all of this is critically important to the function of performance management because that’s your ultimate goal and what we found in CloseLoop, this is kind of segueing into CoachCRM, what we found in CloseLoop was that the greatest fulcrum, the lowest-hanging opportunity with the biggest value reward was getting folks in that frontline manager role, competent around coaching, right?

If you’ve got competent coaches, a number of things happen. One, you’re more liable to hit your goals. You’re more liable to keep that manager. You’re more liable to keep your team. You’re more liable to be able to promote folks from within and it goes on and on and on the list here and this is a sunken cost because the individuals are in your organization anyway. You don’t have to go externally to bring in somebody to do this and then have them go away with their knowledge base.

You can build this internally and what we found was that when we were able to achieve this inside of our client organizations, they developed consistent and significant competitive advantage and that competitive advantage is something that they have retained ongoing and that’s really where we began to see an opportunity for a software tool platform like CoachCRM to exist in the marketplace.

David Dulany: Got it, OK. So this is so interesting because especially in a remote environment, the kind of the pathway to sales at least in the software industry is you’re an SDR and then you’re kind of up or out to some extent and then you become an AE if you’re doing well and you get promoted. Then they come in and they’re working from home and they don’t even have the sort of the bullpen like office where you could turn to the guy next to you or the gal next to you and ask the question and get some help.

So it’s very isolated and then the coaching might be just a little bit of training, you know, coming in and then a one-on-one. Maybe like once a week and some Slack messages. So it seems like it’s very isolated these days with …

Hilmon Sorey: Absolutely. Huge problem. You know, it’s – we named the company CoachCRM for a reason. CoachCRM stands for “coaching results management”. Sometimes people believe it’s a misnomer that it’s actually a CRM but it’s really “coaching results management”. The way we look at it though is if you were to pattern match against a typical CRM, you know, a typical CRM is looking at revenue and retention as the external goal of performance, right?

Well, if you look internally and you say, “What is your internal currency from the standpoint of human capital and what are you trying to do with relation to that team?” what you’re really focusing on is performance and professional development and it’s the same thing. You have opportunities their just like you have sales opportunities. You have leads in the form of challenges that if you can convert those challenges into resolution, you’re actually significantly impacting that person’s ability to perform, which should have a reciprocal impact on the business, right?

So how do you take these things? And David, you nailed it. There are myriad conversations taking place in everything from Slack to your CRM to the notes that your dribbling in. You know, in your call recording software to email, wherever it might be. They’re all disparate. They’re all over the place and the problem with that is it doesn’t create any consistency. It doesn’t afford any opportunity for activity progression and understanding the direction, moving the needle on something.

You can’t share it as tribal knowledge. It’s the bane of everyone’s existence. You know, we hopped on a little earlier and we were bemoaning what Slack looks like and where the messages are and Slack is looking more and more like email even though that’s what they were supposed to be assuming early on, right?

David Dulany: Right.

Hilmon Sorey: So great tool for some things, right? Not for coaching performance, right? So how do you create a tool that is not a burden to front level management or to leadership but instead is a tool that managers can sink into as a platform that’s going to help them to leverage a one-to-many way of moving performance both individually and for the entire team? That’s where we saw the opportunity and so the alignment here between CloseLoop and CoachCRM was that we did have this group of really fantastic, really top level, fast-growing clients who had these problems at CloseLoop and, you know, one of the best testing beds for software is a spreadsheet.

If you know Cory Bray well, he never met a spreadsheet he didn’t like. So he took our coaching training methodology which we wrote a book on, The Five Secrets of a Sales Coach, dropped it into a spreadsheet which we used in our training engagements and in those spreadsheets, we would work with management teams around here’s how you effectively coach in 20 minutes or less. Here’s how you go about holding folks accountable. Here’s how you go about ensuring that you’ve got outcomes. Here’s how you go about ensuring that to understand consequences and here it is in a spreadsheet.

We would roll that out to folks and they would continue to use that spreadsheet and eventually we got to the point – you know, after being in business a certain number of years, you get to a point where your clients are still your clients and they hit you back and they’re like, “You know, the spreadsheet is getting broken. I’ve got so many tabs. I’ve got so many employees. I’ve got people who have come and gone. I’ve got people who have been promoted. I need a better way of managing. Can’t you do something better than a spreadsheet?”

And you know, what better pull or push to get someone to create software than from a nice corpus of your client base telling you that they need something more? And that’s really where CoachCRM was born.

David Dulany: That’s interesting. So for the product developers out there, if you hear my spreadsheet is broken, you know, that should make you think. OK.

Hilmon Sorey: It’s part of our mantra, David. Even from a management perspective, when we go in and do something called a “sales effectiveness assessment” where we’re looking at strategy systems, staff and skills in an organization, when we look at systems, what we often say is like, “Why do you have such poor utilization here?”

Well, you’ve got poor utilization because you’ve over-engineered the tool. Like break the spreadsheet first. Do an analog to the extent that you can. Understand your process. Get a process that works and then exceed the utility of a spreadsheet before you go investing in sales tech. I know that’s going to make some people very angry that are in that diagram that you created. Seven thousand sales and marketing automation tools. But …

David Dulany: Only 500. I’m talking about the market map.

Hilmon Sorey: Yeah, the market map. That’s it, yeah. But really …

David Dulany: Well, it’s funny. It just makes me think because we’re a small company and the renewal came up for and so the finance guy here at Tenbound was like, “You know, you could run this in a spreadsheet. You could save a lot of money,” and I go …

Hilmon Sorey: That’s it.

David Dulany: Oh, man. It’s hard to go back when you have …

Hilmon Sorey: It is hard to go back. It’s hard to go back.

David Dulany: It’s a great system and it’s like let’s go back to a spreadsheet but when you get that big bill, you’re like …

Hilmon Sorey: I will consider it, right?

David Dulany: Yeah, but that would break pretty quick. By the way, as you – you know, you’re rattling off all this stuff Hilmon. You guys have written like six books about this.

Hilmon Sorey: Eight.

David Dulany: Eight. OK, sorry.

Hilmon Sorey: Yeah. Yeah. I guess I need to ship you two

David Dulany: Yeah, dude. I mean – and everybody that – you have to read these books. I mean they’re very practical and you can tell that because of your work hands-on over the years with real sales and marketing challenges, that it’s not a bunch of fluff and theory. It’s like this – here’s exactly what we’ve seen be successful in coaching for example.

Hilmon Sorey: Yeah, it’s our big mantra there is we look at it like open sourcing. We’re like let’s just open the kimono. Not everybody can afford to work with ClozeLoop and not everybody is going to be a software customer. But everybody should understand what these practices are, where they came from and how they’ve been proven out and then make a determination around whether or not this is something that could be impactful in their organization.

So we have literally – we publish what we have proven, right? That’s our mantra and we publish it in a no-fluff way so that someone can take a book and get through it. In an airplane trip, that’s kind of our barometer, right? Can you fly cross-country, learn something and go buy it when you land, right?

David Dulany: Nice, OK.

Hilmon Sorey: And be able to take those things and move the needle. That’s the goal.

David Dulany: Yeah, yeah, and I think people, you know, they’re hesitant to like buy business books in general because they’re just like, oh, it’s another high level fluff that I can’t actually use.

Hilmon Sorey: Three pages of value, right?

David Dulany: Yeah. I mean it could be condensed down to like a blog post but with – your guys, it’s different. So it’s highly recommended that we check that out.

Another thing that made me think about what you’re doing is, you know, in the really old days and you said telemarketer. So I know that you’re with …

Hilmon Sorey: I’m really old, yes.

David Dulany: Yeah. So sales coaching was like if you’ve seen Tommy Boy or The Office, like the sales manager and the sales rep would drive out to the location, do the sales call and then drive back to the office and the coaching took place throughout that process as they were getting donuts and coffee and stuff and driving together.

I think it’s hard to replicate that in our digital environment. Just as you said, there are so many inputs and pieces of information. It’s like – it feels like people get kind of overwhelmed.

Hilmon Sorey: You know what’s interesting about that? I thought long and hard about this because we work with so many different types of teams and typically the SDR teams are a little younger in age. It might be closer to Gen Z and you got Gen Alpha coming along now. My kid is actually out there in her first job doing some stuff which is terrifying, terrifying and gratifying at the same time for obvious reasons. But here’s a thing that I’ve come to realize.

We may think of it – and I’m going to call out to you here, David. I’m going to pull you in to my age group. Make some assumptions, right? We may think of it that way. We may be thinking it’s difficult because you don’t have that high tough. You don’t have that managed by walking around where everybody gets to hear a conversation and you stop by and you go, you know, “That was really good. But you got to do this thing over here,” or you hear Jennifer across the way say something that’s really gold.

There’s certainly value in that and I will tell you that there’s a generation that has never had that kind of exposure and has lived with a phone in their hand, has lived with a screen in front of them and has navigated to the best of their own ability into a place inside of your office – well, maybe not literally inside your office but at least inside of your company without ever having that.

So the sooner we’re able to kind of divorce ourselves of the idea of what was was better and realize that what is is what is, then we get to a point – and the onus is on us in management. You know, one of the first things that I said in starting the conversation was it was a me problem, a managing piece, right? So if we take ownership of that and realize, wow, we do have a decentralized workforce, we do have focus on either hybrid or remote or maybe they’re in the office, whatever the situation might be, we do have technology we can leverage.

I need to learn what the pieces were that were most critical because it wasn’t the doughnuts and it wasn’t necessarily the car ride. It was the storytelling that maybe took place in the car on the way to Dunder Mifflin’s next meeting, right? It was the ability of someone to witness what you’re doing, right? Which is still not the best way to train somebody. Like watch what I do and then go do it kind of a thing but there’s a certain level of emulation and then really being able to break that rubric into its parts that allow you to be effective in getting someone where they need to be in an organization.

I will tell you this. If you want to go thin and agile on a tech stack for any sales organization, I say go heavy on a learning management system where you can actually invest in owning your own training in a way that has got space repetition, reinforcement, certification and I don’t mean like the talking head videos of like the old sexual harassment videos and …

David Dulany: Oh god.

Hilmon Sorey: I mean you remember this, right? They’re still out there on YouTube by the way. I mean good training that’s really leveraging stuff and not just full-on gamification where it’s all fluff, right? You got to work with somebody who understands how to train people. Then you go heavy on coaching, on a coaching platform that is built for managers to be able to coach one to many, be able to track challenges, understand how to move those challenges through resolution, engages enablement and leadership in the process of imbuing the manager with a guidance and with the training that they need to be impactful as managers because that’s a critical piece too, right?

That rolls downhill to the actual IC and the individual rep and then holds the rep accountable to activity that’s going to move the needle and tracks their performance and the CRM, right? Where you’re actually tracking deal performance which is your output of the production. Those three things when done well and in concert and thoughtfully considered can significantly move the needle on performance for a team.

David Dulany: Well, it’s interesting because one thing you mentioned leveraging the manager and how underutilized that resource is that I see out there and that they don’t have a lot of guidance and structure on how to coach and how to be effective in that way. It just makes me think – this is totally off-topic but Chick-fil-A pays like 100 grand for a great manager at one of their stores or more because I think that they realize that the leverage points of those stores is an amazing general manager and – you know what I mean? Yeah.

Hilmon Sorey: Absolutely. McDonald’s, any – I mean you think of – I spent some time in retail and like the retail management track was a fairly highly compensated track where they understood and there was manager development because they understood that was critical to the proliferation of their stores to quality assurance, to the retention and attraction of employees. I mean that’s the whole thing.

It’s so interesting that’s we cut our nose off despite our face in sales management often by either promoting salespeople to – you know, their Peter principle to their position of least knowledge and competence, right? So that does two things. It takes an awesome salesperson off the sales floor because Hilmon was great at sales and now we’re going to make him manager because we’re going to keep him and we want more people like him but we’re not going to train him how to manage. We’re also going to get rid of his quota number that he was hitting really well and put him in an office somewhere where he’s tracking down some other thing.

I mean it’s just so counterintuitive and very seldom do you find organizations that have really clear rigor around not just the coaching piece but the whole management trajectory which could be account – I’m sorry, accountability. It could be leadership. It could be understanding how to articulate vision down to your team from a high level strategy, understanding how to hire people, how to retain people, how to coach people. You know, all of these types of things that are critical in a management construct. I mean there’s a reason why Fortune 500 companies are so successful when we spend so much – so many dollars and so many resources in ensuring that frontline managers and all the way up to high level executive leadership are consistently trained inside the organization on whatever that organizational philosophy is.

David Dulany: Yeah, that is so true. Yeah.

Hilmon Sorey: And a lot of times one of the challenges is we’re moving at the speed of light if we’re talking about technology companies. If we’re talking about venture-funded technology companies, there’s not a lot of time to be thoughtfully considered in how you go about doing this. That’s where – you know, this sounds a little self-serving but that’s where you got to leverage an expert who has been doing this across multiple industries and has a lot of experience at this and can help you build what you need and pattern-matched towards where there has been some previous success rather than you out there trying to reinvent the wheel and losing great people in the process or missing targets.

David Dulany: Oh, 100 percent, yeah, and CloseLoop is still thriving, right? It’s still going.

Hilmon Sorey: Yeah. Oh, yeah.

David Dulany: So you got your whole advisory team on that end and then getting this intel into the CoachCRM to continue to build the product, yeah.

Hilmon Sorey: One informs the other, for sure.

David Dulany: Yeah.

Hilmon Sorey: Absolutely

David Dulany: It’s great and it’s interesting because, you know, a great platoon – you can have a great platoon but if you don’t have a great sergeant, they could be completely – you couldn’t imagine if a platoon didn’t have a great sergeant, you know.

Hilmon Sorey: You want to know what’s interesting about that analogy, David? So back to that story I shared where it was a me problem and they let me go because of it. Do you know what the parting words were of my CEO? He said, “Hilmon, this …” He actually said this with tears. He’s like, “I hate to let you go. But I need a sergeant, not another general.” That was his feedback and I was like – first I was like, “What the heck does that mean?” Right?

David Dulany: Yeah.

Hilmon Sorey: And then I pieced it together and it was absolutely the – I was not a leader of people at the time. I hadn’t developed those chops yet. I was instead very high level, strategic and I can do some things on my own. But I was not making my team better, yeah.

David Dulany: That’s funny. In the meltdown in 2008, 2009, our VP of sales came in at the company I was working with and he gave this kind of state of the union speech and he said, “We really need to focus on what we can control and let the rest go.”

We were just like, “Dude, whatever,” you know. But that fast forward like 20 years and I realized that’s a quote from Marcus Aurelius.

Hilmon Sorey: Oh, yeah.

David Dulany: A great stoic philosopher.

Hilmon Sorey: Absolutely.

David Dulany: And it’s one of the most useful things that you can think of. But at the time, this student has to be ready for the learning.

Hilmon Sorey: Isn’t that the truth? Absolutely. I wish I was ready when I was 22 but I had scraped some knees along the way.

David Dulany: I know. You got to learn at your own pace. It’s so frustrating because by the time you gain a little bit of wisdom, it’s like, OK, now retire and go …


Hilmon Sorey: … the pasture. That’s right.

David Dulany: You’re done, you’re done. So no, it’s interesting though. Just I think – like I always think if you had a magic wand and say you got some venture funding and you needed to put together a sales team. These days, the conventional wisdom is just hire like five AEs and an SDR to support that and they’re off to the races. But it would be better if you – say you had four head count that you hired a rev ops person, a coach, an enablement person and then an SDR and an AE. It’s like …

Hilmon Sorey: That will scale.

David Dulany: Yeah. You know what I mean? And then build the foundation and then add the individuals back into that.

Hilmon Sorey: You know what’s very interesting about that, we work with a lot of private equity firms as well and what we’re hearing from them is they are taking that piece. They understand the importance of it and they also understand – and obviously they have a different growth curve than with a venture-backed company. But they understand that piece and they’re building it in and that’s a place where we’re supporting them with frameworks and with rubrics and with metrics and with assessment tools and things like that that they can use.

But they find it so critically important and difficult to impress upon a CEO of a software company that’s growing that yeah, you know, put the money in rev ops and a coach instead of in these three heavy-hitting AEs and an SDR. Difficult argument to be made but, you know, again let’s go back to the spreadsheet. Put some of this stuff into a spreadsheet. See how things scale and don’t do the lemming mentality of just following what companies did 10 years ago because that was the path and you might be surprised.

David Dulany: Yeah, and it’s kind of like –