The 3 Profiles of a Sales Rep

Look, I knew I wanted to be in sales straight away. In college, I worked for a company selling knives in people’s homes, the opposite of the job you’d ever go for. I ended up running an office as a college student. I was 20 years old. Had 75 people working for me in Palm Beach, Florida. It was like getting a PhD in sales. So in undergrad, I’m in finance. It’s an overloaded degree everyone’s getting at, so I started to pick up some programming classes just to try to find some separation, and then IBM picked me up.

And I’ll you one thing, as soon as I got to sales training, realized most people didn’t have any proper sales experience. And then my first role at IBM was a competitive sales rep. So every account I talked to didn’t wanna talk to me. So you get to kinda have this, like, bulletproof skin on you, which is a really great way to get into sales.

rank recruiting, the art and science of recruiting, a big part of it is how do you recruit a college student to go sell knives. You sell them to your mom, your aunt, their friend, and then at some point, they end up fizzling out. But the ability to recruit, if you can recruit good people, you’re gonna have a lot of success. And that’s carried on with me my entire career, which is if I get the best people and I treat them great, by definition, they hit their goals.

I’m hitting my goals in the company sappy. The idea of recruiting the best people, and it stuck with me. And then I was an intern for a recruiting firm, and I enjoyed that a lot. That’s kind of the bedrock of my whole approach as a sales leader.

It’s about resistance and persistence. Think my job every day is to solve problems, and I think if you have a problem with a problem, you’re not going to persevere. If you’re okay tackling something that’s super difficult, how you respond to that is going to help define you. So for me personally, when I was a kid, my father passed away when I was eight. My mom remarried. I picked up an incredible stepfather, and then years later, my brother passed when I was 30. But what it does is it makes you really grateful for what you do have to look for the positive, but it always kinda produced a chip on my shoulder and a feeling of being unstoppable.

And it’s like, hey, I made it through that. Let’s go. That’s just carried on with me through my professional career.

think that it creates a bold mindset and encouraged you to go for jobs, for example, that you’re unqualified for or go for deals that you’re not in a position to win, but the best teams take three point shots, and it encourages you to take three point shots. So, yeah, you’re going to take more risks. I would argue the outcome is going to be significantly better than if you have a more conservative mindset in your career, so I think it just

relevant. So I think first, it’s client relevance. So clients don’t care about you, your gear, your product, your orgas they care about them, their metrics, their firm. And so it’s gotta be client oriented. And then for the rep, it’s really hard to ramp in a new firm. Like, probably 50% of reps out there they’re something new. It’s a new company. It’s a new team. It’s a new client. It’s a new industry. And so it takes six to twelve months to ramp up. If you can have something that’s super relevant, it allows the client to get immediate interest in the firm, and it allows the rep to ramp way faster.

So, like, for me, I always start with the money, and I work backward. And I focus on TAM, and then I start to build the playbook back from there. So at least I know if I’m on a treasure hunt, and I’ve got a shovel, and we’ve got people digging, are they digging in the right spot? And I think that’s the question that a lot of sales teams miss. They find it later in the year when it’s a bit too late. That makes sense?

I think a TAM, there’s three elements to it. It’s either near or far. Right? It’s either big or small, and it’s either known or unknown. That might be, like, overly simple, but let’s break that down. It’s either near or far. So I’m either gonna go on a twelve, eighteen month sales cycle for a larger deal, or there’s some create and close. Customer needs something, and I’m gonna go sell it to them. It’s either big or small in the sense that I’m either gonna take down something that helps my quarter, or am I gonna have a great year?

I probably need to go for a transformational deal that might take a year or two. And I wanna prioritize and run an AN business, where I’m at all times going for something big, but I’m chipping away along because you can’t always count on a big deal. The third part is the part that I never hear people talk about. It drives me kinda nuts, which is it’s either known or unknown. When Steve Jobs creates the iPhone, goes out, does the keynote, no one ever knew they had it, and then they had to immediately have what he offered.

And so it’s about identifying problems a customer has that they don’t know how to solve, creating a vision, and then encouraging them that you have an opportunity to solve that problem for them. And now you’re hunting for a way larger pot of money, and you’re actually aligned to what they’re solving for, and you immediately differentiate. Because then it’s not you versus a competitor. You’re the only one that’s gonna solve it because you actually uncovered the opportunity for them, and you’re bringing them along in a journey and building a vision.

And I think that kinda goes back to the iPhone analogy of, I didn’t know

need

think about an industry playbook, right, what I do is think about the first quarter as a sales rep. The first thing that you’re asked to do is create an account plan. That’s good. It gets you organized. It gets the whole squad and team organized. I would argue that you wanna have an account hypothesis, and you wanna go back and finish that in q one. So let’s take this apart piece by piece. First, you wanna identify where the TAM is. Where is everyone gonna mobilize and drive an ANZ business?

So where are the dollars? Known, unknown, big, small, near far. From there, then you wanna have a set of industry sort of assets. So if you wanna drive client relevance, and you’re gonna show up to an insurance firm, and you’re gonna work with, like, an insurance claims adjuster, they don’t wanna see a demo of technology. They wanna know how do you the life of an a claims adjuster easier? How do you get to the scene of the accident faster? How do you detect fraud? How do you ensure payment comes faster?

Like Rosetta stoning everything from technology into the use case and the persona of the person. Now, boom, you have an immediate set of client relevance where they go, well, this person really understands my industry. On the rep side, they’re not thinking so much about the technology. They’re immediately identifying, is there a problem? Can I solve it? And then you’re ramping them in weeks instead of months and quarters, and now you jump to stage two in the sales process. So the funny thing is if you identified a TAM and you create a vision and you put an industry lens on it, the client gets engaged faster and the rep gets to go a lot faster.

It actually compresses the sales cycle, And now you’re finding where the dollars are in April, May, or June, not in September or October. You actually have

patience. Yeah. That’s a big part of it, working with them. But I think the fastest and easiest way to do it is, let’s say you’re going to have an established team that has two or three people on it. You’re going get someone up front leading, like the quarterback that owns the whole process that’s been there, done that. You’re going to take the high potentials, put them inside that team. Then over time, they’re naturally gonna learn that process because they’re following the leader, and they’re gonna get there a whole lot faster.

So doing it one by one as a sales leader would be really hard to, like, literally teach every seller. But if you selectively build teams in the right way, then you’re having the team teach the team, and that starts to drive scalability and repeatability, and you’re not doing everything yourself. So I think that’s the way that you do that at scale. And also, if you get really good people that care about each other and they’re competitive, even if they’re not on the same team, they wanna help each other, and you wanna reward that and incent that and ask people to step up and help you.

What you find is the best people, they wanna teach. They’re proud of their crap. They’re proud of what they tried and worked.

Here’s a challenge. If you want the environment where people perform at their best, you need safety. If you want safety, they have to know that you’re trusting them, that you’ve got their back. And if you have two different people competing in the same environment, I don’t know if that creates the right environment. I would prefer to go all in and have their back, and if need be, I’ll go on sales calls. I’ll do all the work with them until they’re ready to go out on their own.

And that takes a lot of effort, but if you get the right person with the right potential, absolutely, I’ll invest in that person for a few quarters or a year, and then they’re off on their own. So I would probably just go with one. That’s just my gut.

that are just super competitive, it’s like athletes on the field, they have the energie and the competitiveness that’s gonna far exceed any pressure that you could ever apply, full stop. That’s just the way that I operate. And so for me, if you get the right people involved, a lot of those problems go away. So how do you find fast horses? You hire a fast horse, and guess who they run with? They run with Fast Horse. Go find the best sales rep that you’re gonna go find, and see who they hang out with in the office and socially.

They hang out with top performers. They hang out with winners. And so whenever you’re in the interview cycle, first question I always ask full stop is, hey, top rep, who are your friends? And should I have an opportunity to meet them? Because they are always gonna know the best talent. And I think when you bring them in and you drive that competitiveness, all those problems go away. How did I meet you, my friend?

For me, it depends on the account. And so you look at a spectrum of SMB to strategic sales, the answer’s gonna be wildly different. I’ll probably talk about the enterprise. So for me, it’s about fit. So if I’ve got an account that has multiple reps on it, the team chemistry is really difficult, but I always want the closer upfront because they have to carry it all the way from one end of the field all the way down. But I’m also gonna wanna bring in, like, a visionary.

Sometimes they’re more academic. They’re super right brained, very creative. They can build a vision, and bringing the organization along, they may not be as comfortable closing. And then the third profile of people I wanna pick up is the person that wants to go hunt and take down every deal. Let’s see a bear shoot a bear. That’s not something that I was, like, super talented at. I wanted to go big game hunting, but you if you’re gonna run an ant business, you need a collection of those different skills, and you put them all together.

You wanna find those people, and then at a chemistry level, figure out, can they work together, or do you have two alphas? If you have two alphas, it’s never gonna work. And I’ve screwed this up a few times, by way.

If you ask them what their passions are, what they’re most proud of, what’s a deal where they create a demand that never existed before, and someone’s either gonna get excited and passionate, or they’re gonna look at you like you’ve two heads. When you ask those qualifying questions, it’s very easy to determine where do they fit in. If you’re gonna move into the enterprise and do material deals that are gonna break records, you’ve gotta have a closer that’s super passionate. So I just ask those qualifying questions, and people will

When we talked about the TAM example, where demand is known or unknown, I think, how do you create money that doesn’t exist? You go look at the demand that’s inbound, and then you look at the latent demand that doesn’t exist. That’s an immediate way to increase the TAM that you’re pursuing without hiring any more people. And so, when I think of creating demand that doesn’t exist, and you ask someone that, what problems does a customer have that they don’t understand how to solve where you’ve created an answer to them?

So go back to, like, the Frank Fillmann example. He worked with different firms where he’d ask clients what they thought about the product, and they were using it in very diverse ways that surprised organization. So at a product level, they’re like, hey, we didn’t design it that way, but customers are using it. Lean in on that and ask them, well, how are you using it? Why are you using it that way? You go back and align that to the long range plans of the organization, chances are there’s a big gap in execution where they’ve got a big vision and a big target.

They don’t know how to get there. So how do you take a malleable platform and create a vision around that that says, oh, you’re trying to align and move upmarket? What if you had better insight into the customer profile that you’re pursuing? And then you align a malleable platform and create a solution that says, we can help you get better visibility into how to pursue that so you’re chasing larger deals and you’re moving upmarket to the enterprise segment. And now all of sudden, you’re a consultant.

And you’re not starting with tech, you’re ending with technology. So for me, it’s like every conversation starts through the lens of the customer and great empathy. What are they trying to do? And then how do we reverse engineer the product to fit it? It never starts with product.

think the biggest mistake is when you just send a price over, and then you end up arguing about numbers. You ever see this, you send a proposal, and whether it’s a percentage savings or the absolute number, it’s human nature in negotiation to look at that and then want that number to be smaller. And so sometimes you get lost on all the wrong details. So if it’s me, my preference would always be start with a blank canvas, find your buyer, and spend some quality time. And I think you’d ask questions of her like this.

Number one, how are you measured? What are the metrics that you as an organization, an individual, are measured by at the organization level? And you start to really unpack how they define value and values and what their priorities are. And then you go, like, a level deeper. What’s most important? Is it cash flow? Is it TCO? Is it year one fees? Is it exit fees? And you can start to kinda profile what financial levers do you have to play with that matter to them. Commensurately, you’ve gotta be super transparent with your organization.

Here’s how we’re measured. Here’s how we report. These are the prioritized levers that we have. Here’s what we want. If you do that, and then you start to align on deal structure, whether it’s like, is it a flat or is it a ramp, when you start to really categorize all the different ways to package a solution, if you do your job right and you’re authentically looking for ways to create a win for them while being transparent about what a win for you looks like, then by the time they get the first offer, it’s gonna land well because it’s very predictable.

And then when they counter or you counter, it should be very predictable because they’ve already told you what they’re interested in and so have you. And it takes something like the gamemanship out of it where you’re just trying to find a win on both sides. When you start with price, it’s really hard to get there.

have changed over the last twenty years. Protectionism, I think things are a lot more transparent. Customers have access to all kinds of data about your organization, about products, about negotiation. The idea of being closed ended like you have all the information and you don’t wanna share it, we’re twenty years past that. It’s about being really transparent. But if it starts with you, I don’t think it’s really authentic. It’s gotta always start with them. I was reading a book called The Go Giver, and it’s like, how do I serve the person I’m working with and working for genuinely as the priority, and then you back into what’s good for you.

So I start with what are your priorities? What are the mistakes? What do you not wanna see? What’s really gonna irritate you? If you’re gonna try to sell this internally, where are you gonna catch a lot of flack? And then I say, great. Now that I understand this, here’s how we are generally measured, and here’s some overlap. And then what I wanna do immediately upfront, Harry is say, what are the friction points that we can acknowledge? We’re probably gonna bump heads here, so let’s just identify it.

We’ll try to work through those with a very unique solution. And I think if you do that authentically, someone’s gonna say, alright, they’re showing up trying to help me out. And I don’t know that every negotiation starts that way, but the best ones I’ve been involved in start that way.

feedback loop, which is I think where you’re going, it’s less about recording and dissecting. It’s also less about waiting a whole quarter and giving feedback. It’s really hard, and it never lands well. I like to do an obsessive in the trenches process with my team where we spend a lot of time prepping. We do a lot of time role playing. We go to the meeting together, and the first thing we do when when we’re done is we go debrief. And the first thing is, like, alright.

Give me some criticism. What did I do wrong? So it’s not like me as a leader talking down to someone. All of us have an opportunity to learn. We’re all in this thing together versus, like, how am I being evaluated or critiqued? Because you go back to safety. If I feel like I’m being critiqued, I’m gonna get defensive, and I’m not gonna get the best output. So I don’t like the formal process. I like just to say, how do we get better at our craft so next time it’s gonna land even better?

Yeah. I’ve certainly over my whole career, I’d say the biggest mistake I made was trying to team people together that were both alphas. I think being an alpha in sales is really good. You want the natural leader, but if they do it at the expense of other people, and there’s an ego involved, and then you have two of those together, it will crash and burn immediately. Stylistically, that’s where the hair on the back of my neck stands up, and I say, I don’t wanna go through that again.

And I wanna be able to pair that person with someone who might say, you know what? I don’t have as much at bats. Pair me with them. They’re gonna exponentially learn. They’re gonna get three years of education in a year when they get paired up with the alpha. So it’s healthy. It’s just not healthy together.

for me. It’s always hypo, one, experience, two. There’s always an exception to that, though. I think when you have, like, a big, mature customer and a big brand with a lot of visibility, you’ll always have to take experience first. You don’t want someone learning on the job in a very high profile environment, because then you might be setting them up for failure, and that’s not fair to them as a sales rep.

With the exception of that, I’ll always hire for potential, and I want to take someone who’s got a tremendous amount of adaptability and future potential, give them a job they might be a year away from, watch them be a little bit nervous and stumble for a quarter, but what’s gonna happen is they’re gonna get there way faster. I’ll always go potential first. My question is, what’s a stumble and what’s a stumble too far? It’s almost when you outsource to someone to say, hey, I think you’re really good.

You’ve got good potential. There’s a big meeting coming up. You’ve got this. That’s crazy. For me, what I wanna do, whether it’s me or one of my leaders, it doesn’t matter who in the stack does this, someone who’s more experienced, get in the trenches with that person and say, look, you’ve never had a CEO meeting before. Let’s figure out how they’re gonna operate and run the meeting. First off, they might run the meeting, and you’re just gonna have to go along with it. So whatever you’re gonna plan for, you can just toss right out the window.

And you don’t know that until you go through During the preparation and the role playing, having that senior leader step by step with them to say, here’s an experience I went through, but also, ideally, you have a senior leader go with them on that meeting, and they play the role. So maybe they’re teeing them up with a softball question that they can hit out of the park, or they’re there in case it goes off the rails, they can hop in. But I think having someone riding shotgun with you in the car, and then giving the freedom to go take the wheel a little bit is really important.

Once you get through that handholding process, you get a few at bats, you’ll find the reps like, I think I got this. And then you go, great. You’ve demonstrated the experience. Go. But I think if you start there, you’re kinda leaving them out in the wind, and that’s not fair for them.

is you’ve got a big account that you’re pursuing, and it you’ve got two or three reps. First The thing I do is grab the hypo and put them inside of that organization. So they’re teaming along with it. If not, I think there’s a level of babysitting, and I say that as a positive term, not a negative term, where I’m gonna sit side by side with that rep. A big part of my day is I clear two to three hours that I have no plans for, specifically so a rep says, hey, I’ve got a big account meeting coming up, and I feel stuck.

Or I have an account meeting coming up, and I want you to join. I can immediately, and I will immediately clear my calendar and say, let’s get in the trenches. So I’m literally, personally teaching them and bringing them along, and never letting them out on their own until they’re ready to go. I don’t think there’s any substitute for on handholding, on the ground training, and so the only way that you do that is personally getting involved. That’s why we just run a super flat organization. I could care less what my title is or what yours is.

We all have the client’s interest in mind. Let’s get together and go. I’m a rep. Put me to work. And that’s my mentality, and I think the team appreciates that. Now you’re not sitting in the Ivory Tower like you’re out there with them.

really good point. First off, you gotta set them up for success. If it’s a big account, and they’re gonna do a big buy every couple years, you can cyclically understand what the odds are of that person coming in. And I think if it’s a one to two year sales cycle, and you have someone new, maybe it’s more of an eighteen to twenty four month sales cycle. So if you put them in with the hope that they’re gonna land it in the first year, you’re setting them up for failure, so I think you can prohibit some of that.

So I think you either give that account to them in year two, or you don’t give that account to them at all. I think measuring the effectiveness along the way is predicated on setting them up for success at the beginning of the year. But I also think that if you’re a team and you’re going on sales calls together, you know if they’re doing the job or not. There’s no escape from that if you’re actually giving them ample time to prep, to go on the meeting with them, and to debrief.

Your job as a leader is to spot that. It shouldn’t be hard. You said about setting

a little bit contrarian, and we’ve talked about a couple pieces, but let’s take Humpty Dumpty apart and look at q ’1. The first thing I wanna do is I wanna build an account plan, but let’s call that a hypothesis. That way, we’re immediately starting to take action. We’re mobilizing both the sales team and the extended team. But immediately from there, I’m gonna pause and say, great. Let’s go do the TAM analysis. Where’s the money? Where’s the opportunity? From there, I’m then gonna align the sales process to where that revenue opportunity is.

And if I’m doing my job right, I’m running an ANZ business. I’m gonna pick off some of the small deals along the way. I’m gonna go for the big bet, and ideally, there’s a path to hit my quota both ways. So at the end of the year, if I intersect and both hit, I’m gonna have a monster year. If one of the two hit, I’m gonna have a pretty good year. From there, this third step is we’re gonna like, an industry playbook. I think playbook, it’s sort of disambiguous term.

So I don’t mean, like, the PhD version of a playbook. What I mean is, I’m a sales rep. I’m about to go on a call. What I don’t wanna do is go prepare all the materials. I just wanna go out and make the sales call. So let’s say you’re walking out, like, I’ve got four kids. So one of my kids is walking out in the morning to go to school. They don’t wanna prepare their meal. They don’t wanna pack the lunch. They wanna get the Capri Sun, the apple, the sandwich, put it in a paper bag, go out, and they wanna eat.

And so if I’m a new rep, I don’t wanna go figure out everything about my product, everything about the industry, the customer, and go build this whole thing that, by the way, all of their peers did. You gotta drive a level of repeatability. So what we do is we build industry playbooks. So if we’re covering an insurance company and the insurance adjuster, that example we used earlier, we’re gonna put together five slides. In the industry, with 80% accuracy, these are the problems they’re faced with. These are the solutions where we fit.

These are examples where it works. These are the outcomes of customers who have solved the problem with our technology and the outcome of it, and then here’s the success plan to get there. And what it does is, it doesn’t replace discovery, but it gives them a framework to say with 80% accuracy, you’re probably gonna land well if you use this process. Yeah. So number one, you know where the money is. You’re making the right sales call. You’re talking to the right person. You’re pursuing the right opportunity.

And when you show up, you’re talking the love language of the client. Immediately, you’re relevant. Immediately, you get ramped, and you’ve qualified out. The opportunity isn’t worth pursuing or it is, and you’ve jumped along in the sales cycle. Now you race back at the end of the quarter, and you rebuild your top account playbook. You rebuild your account plan. And then now, you’ve got 0.75 to find and close the revenue versus finding out in q two or q three, and now you’re in a race to the end of the year.

And I think when you’re in a race, it’s really hard to perform. How do you ramp them and give them some space to run? That’s how you do it. So I think what you do in Q1 completely determines the success of your year.

So first off, I drive people crazy. So, like, I did this personality test a few years ago with my coach, and what I found out is I’m full blown left brain and right brain at the same time. And the absence of focus, I’m everywhere. And so what I have to do is get really focused on what’s the idea, how do we prioritize, stay on message, and then execute with focus. So that’s one of those learnings as a leader that I’ve tried to get better at over time.

So a big part of what we do as a team is we wanna bring the creative energy in. We wanna bring the right people, not to conform to our group, but bring in a lot of diverse set of of experiences and personalities and perspectives. So we do a lot of right brain creative whiteboard y stuff to come together on, hey, we try these five different points with a customer. Three failed, two worked. Let’s go in on those two. So it’s very much trial and error. Mistakes, very encouraged in our group.

So if you screwed up and the client meeting went poorly, great. Tell us so we don’t go do that again. And so whenever we build the Playbook, they’ll end up in slides. But the way that we build it, we call it by the people for the people. I’ll literally bring in my industry team, my sales reps, my engineers, me, and we’ll sit down and say, let’s bring together the last six months of learnings, and let’s go rebuild the industry playbook based on what’s actually working, what’s monetizable.

Even with COVID, the world’s changed a lot in two years. If you’re not adapting your cycle, it’s gonna be stale, so you have to do that. And then we put together five very simple point and shoot slides that a fifth grader could read and understand. And then you take that and you say, this isn’t the end all, be all. It’s a template. Make it yours. Make the questions yours, but let it inform the discovery so when you’re asking questions, the buyer is like, wow. They did their homework.

I appreciate that. I wanna lean in and help this person.

I think if it starts with you as an organization and what’s in the interest of the firm trying to sell it, they’re gonna see through that. I don’t think it’s gonna work. I think it’s gotta be through the lens of the client, full stop. So let’s take an example. I’m a customer. I’m trying to stand up a new program. That’s always gonna require people process and tech, but tech’s gotta enable something to get set up, and they go, hey, we have to go live next July.

We don’t need it yet. This is q four. Come back in six months. Well, we go, great. You need it in July. When do you do user testing? Well, we’re gonna do user testing in May. So when do you need to administer the technology? Well, we’d probably do that in February or March. Great. So when would you need to stand up the technology and have a contract in place? Well, maybe, like, January, February. And if you actually take that very logical objection of not now, we’re six months away, and you programmatically work back and you create a success plan based on their timeline, chances are they need to get going right now.

But you can’t make the assumption that they understand it because this is what your job is, not theirs. So you’ve gotta build out this, here’s a success plan over the next six months and requires you to start now. And by the way, take advantage of your enterprise buying power and our fiscal year end to get the best technology financial deal that aligns to your success. And if you focus on their success and their outcomes and a faster ROI table, then they might believe you and wanna lean in and buy earlier.

But I think if you do it based on what’s in the best interest of the firm that you’re representing, I don’t know that it’s gonna land as well.

Yeah. I’d say two things. Number one, in this environment, the first question is, have you adapted a lens on the buying cycle for the CFO to review it? Is there a quant element of value inside the proposal that a CFO who’s never met with you, who will never meet with you, who’s never used the technology, could look at, understand, and say, I like what I’m seeing financially? Because we have a new buyer in the cycle that was never there. That’s the CFO, and probably gonna get personally involved in an enterprise deal that’s material.

And if you haven’t evaluated that and haven’t, like, role played that, then you’re gonna fail.

Yeah. No. Here’s way I would do it. I was like, after you go through, what are your value and values? What is the problem we’re solving? What is the solution? What is the success and roadmap? What is the value, and then what is the pricing, and what is the next step? Like, that’s the logical process. Before you get to pricing is the value. And I think the value slide has a few different pieces to it. If you’re being really specific, Harry, it’s a Google Slide. But you gotta think through a few lenses.

One is the economic value of buying. Are they getting a good deal? Are they avoiding cost? Are they saving money? And part of that is fee reduction, as an example. Another part is, how do you consolidate and do cost reduction in this cycle where, hey, I have 15 vendors. How do I standardize on one? So cost reduction or cost savings has a lot of different pieces. The other piece of that is value. How do they drive value to the organization?

Now if you’ve done your homework right and you’ve asked the questions, you know how they’re measured, you’ve read the 10 k, you know what is important to that organization financially, and you’ve built a value framework that either says time to value is faster, ROI is there, this is gonna drive shareholder value in these meaningful ways. And then I think the qualitative value, which I don’t think a CFO is really gonna buy into, is as a side benefit, you might raise sales. As a side benefit, might have happier people.

As a side benefit, you might reduce your carbon footprint because you’ve moved to the cloud. Now, these are things that, like, a CFO would look at and say, first, they’ve done their homework. Second, my team has validated this. Third, now I wanna lean in and not object to it, but maybe ask some questions. You’re avoiding all of these inhibitors to a sale and maybe enlisting the support of someone that all they care about is financial value. So if you skip it, it’s gonna be problematic to a sales cycle.

wanna do more with less. Cost matters. Efficiency matters. This is when you’re gonna get more financial buyers as part of the process. If you haven’t organized your story around these new evolving priorities, shame on you, because their their priorities have shifted. Your messaging and your value prop should absolutely be shifting in alignment with them, or you’re gonna be irrelevant. Then that’s your fault.

I think there’s three pieces. One is you need a very left brained math model that looks at all the historicals and says, on an average ratio, this is our close rate to pipe. Like, there’s basic math that everyone should include as part of the cycle. Number two, everyone should be layering in AI to be able to at a predictable level. If you’re a big organization at scale, understand trends. Because if everyone else in the organization is seeing a downfall in forecast, technology is gonna pick that up where if you’ve got a team of five people in a small territory, you’re not.

You don’t have a chance to pattern match because you’re not talking to a thousand reps, but the tool is. The third is I think you need to have, like, a right brain qualitative review of everything in your cycle. So what we do is we do a bottoms up deal by deal analysis, and then we go back and compare it to the math model and whatever AI says. And and we go, do we believe the truth of this? And I think if you’re really involved in your business, if you’re, like, out talking to customers and listening to them and asking qualifying questions, I think between those three or four dynamics, you should be able to call your business.

But I think when you look at The Wall Street Journal, you can tell when there’s gonna be more cost pressures. So, like, we spend a lot more time forecasting and truing up and doing, like, checks and balances now as you should in this cycle. You’re So never gonna remediate all of the other risk. But I tell you what you can do is you can microwave it a little bit and take it out of the cycle and have a more predictable forecast.

Well, there’s two kind of super reps. There’s the good and the bad. So just go up from here. So I think if you’re a control oriented leader where you’ve always gotta be the person in the meeting or, hey, I did this, or I’m gonna get overly involved, or I’m gonna micro this person, that’s not great. But I do think if you wanna understand how to drive success in the field, if you look at your job as internal and the sales rep as external, and you’re too far removed from the customer, that’s terrifying to me.

All of our big deals, we do a weekly review, full stop, every single week. One of the biggest deals in the week or the quarter or the month or the year? And what I’m gonna do is I’m gonna get really involved. And the second I see something go off the rails, great. I have a two hour block in my calendar. Cancel whatever you got. Let’s get on the phone, and we’re gonna spend time rebuilding your entire value prop. And then next week, I wanna see how that goes.

And so I think that’s the way that I get sort of micro, but it’s in the interest of the rep. And the first question I ask on a big deal review is, what’s your goal, not your quota? What’s your goal? What do you need to be financially successful this year? Great. Now how do we get there? Here’s this proposal. You’re not gonna get there with this proposal. Let’s work together to bridge the gap so you hit your goal. And I think if you do that authentically, you’re helping that person, and you’re not being critical.

You’re not looking over the shoulder. You’re just trying to drive increased odds of success. But in so doing, you’ve gotta be, like, really in there with the rep. So you gotta be like a leader and a sales rep, and you just have to be able to fluctuate back and forth.

It’s an hour and a half a week. The first thirty minutes is free form. Maybe it’s because there’s an urgent deal, and we just need to pivot into whatever senior leadership might need that week, or I have a house on fire we need to solve. Great. Let’s identify it and swarm. The second hour is very structured, and it’s a little bit more looking forward. So I might have an hour broken into twenty minute slots, and I’ve got three reviews. Maybe that’s this quarter or next quarter.

And what they’re gonna do, very programmatic, is show me two slides. One is the why slide, and one is the big deal review slide. And the why slide, what I’m gonna do is say, I want you to tell me exactly through the lens of the CEO’s long range priorities. Maybe it’s a CIO or a CDO or a chief operating officer, but let’s take the CEO for the example and say, what are their long range plans? And then you say, great. What’s gonna inhibit them from hitting that?

What would be the value of accomplishing those goals? How would you quantify the value of solving that problem? And you kinda go left to right where what’s important to them is paramount. And far off on the right, if you have used your binoculars, is the technology that solves the problem, but it forces the rep to think through the client problem through the lens of the customer, not the lens of product. So it’s gonna force to say, if you’re gonna build a vision or a story to solve a problem for them, let’s start with what’s important to them.

Great news. It’s a public firm. Grab their 10 k. Do some discovery. This isn’t hard. The second thing I’m gonna do is a big deal review template, which is gonna be a slide that’s gonna tell me all the mechanics. Who are the players? What’s the solution? What’s the product? What are the needs? Who’s involved? What’s the next step? You get the point. And I can true up the right brain, artistic, industry oriented lens of how do we solve a big, scary problem, and then you true that up with the fundamentals of what they’re doing day to day in the field.

And then the third component is I want the entire team on that call. The industry team, the value team, the solution team, and the sales management. And we don’t go in picking away at this. We go in as peers saying, how do we elevate our game? And I think taking the fear out of that call and saying no one’s judging, come in with crappy ideas, like bring all of them, where people genuinely know you’re trying to help them hit their goal, you can drive criticism and provoke people in a really good, healthy, competitive way that elevates everyone’s game.

How do you do it? Think I it starts with customer obsession. If you really wanna understand what the customer needs, I think a traditional sales cycle of thoughtful discovery in a few meetings and being single threaded into, like, one buying unit or one person, that’s scary. What if someone leaves the organization? Or like you said, what if the sponsor leaves? Like, that drives problematic approaches. So if you really wanna get to know the account, you gotta be obsessed. Buy the share. If you’re selling to a cell phone organization, go buy the cell phone, go into the store, talk to the retail sales associate.

You get to really understand broadly the challenges across the organization in a multifaceted way. Number two, you wanna start threading in conversations from, like, IT to data to the line of business all the way across. The other thing you wanna do is have really good top to top alignment. And I don’t mean when it’s deal time. I mean, like, before deal time, where does a thoughtful conversation of aligning, whether it’s the CEOs together or the CIOs together or line of business executives together. If you take this customer obsessed mindset, you’re gonna have that entire organization wired top to bottom, but it’s not in your interest.

It’s in theirs. If someone’s stuck, have the bat phone to call your peer who’s my boss. That drives transparency because at all times, they know they have ultimate access to your organization. When that happens and there’s risk in the cycle, you don’t have to worry about it because you’ve got the entire place wired. And so I think if you’ve got, like, an obsessed mindset, you’re gonna have every angle covered. And when one predictably falls astray, great news. You remediate that, but everything else is gonna stay in place.

is a big part of my job is dealing with all of my parallel my peers, the extended team. Like, that’s, in some cases, the majority of my job. By the way, the first question I always ask every time I meet with those leaders, how are you measured? What do you need from me? And this is these are the three things I need from you. And do we have agreement and alignment on what those priorities are for both of us and what the expectations are? Every time we talk, I don’t wanna go through everything else.

Let’s start there, and then we’ll cover the rest of it. So I think, like, an area where it’s really hard right now is customer success, because the customer might beat them up. The sales team has very different goals than they do. And what I find is a lot of time, the sales team doesn’t understand how success is measured and paid. They don’t appreciate the challenges of how hard it is to be a success manager, because everybody wants something from you, and you’ve gotta be everywhere. If you’re measured against everything, you’re measured against nothing.

And so I think one way to kinda make that problem smaller, bring success on the sales calls with you. Make sure they’re client facing. Have them come in, and don’t do a quarterly business review. Have a success review, and elevate them, put them on a pedestal, put a spotlight on them, make them successful. The client’s gonna appreciate that because you’re not just trying to sell. You’re trying to drive value, and now their critical path in the cycle. And what otherwise would be a lagging function that’s trying to run and chase up and make everybody happy, now they’re critical path.

And if you have a big customer and they do a big buy, now you’re gonna have to otherwise go grab the success person and bring them in and say, I need you to do all this stuff. And they don’t like, I don’t even know what they bought. And so how do you make them successful? You bring them along during the process, and treat them like a teammate, and make sure they know that you’re helping them hit their metrics, and

The biggest challenge you wanna solve is alignment with how the company reports to their shareholders, whether that’s a private or a public company. How is the company measured? And then make sure there’s alignment all the way down to how the sales rep is paying. Because I think in the absence of that, there’s gonna be a tension point where what the customer wants and what the rep wants is wildly different from what leadership wants. And then you take the salespeople, whether it’s a first or second line manager, they’re in the middle getting squeezed, where the people above and below them want wildly different things, and that creates a lot of tension in the cycle.

If you’ve got full alignment, that this is how the organization’s being measured, this is how the rep’s being paid, you’re driving aligned incentives, then everything starts to work a lot better. So I think if that fundamental principle is there, the other problems start to work themselves out.

When you think about talent, bringing the right people in Okay, let me ask you a question here. Have you ever bought a house? Apartment. So you go through the process. When I bought my house, it was nice foundation, terrible color, terrible decoration. And so what happens is most people would go through this process of buying a house, and they look at it. And if they can’t see the end state, they don’t have the vision to do so, they’re not gonna buy it. So I literally told my agent when I bought my house, I was like, I’m so glad this color of this house was rust red.

She goes, No one else said that. I’m so surprised to hear you. I said, Well, if it was white, it would have been sold a year prior, and I wouldn’t have been able to afford it. So quite literally, the idea that people that can visualize the end state, that’s a very powerful tool, and it’s very rare to be able to do that. And by the way, customers have a hard time doing that. They’re busy. They’re stressed out. They’ve got a million things to do.

Finding people that can be visionary, that can imagine the end state, and then creatively reverse back, engineer through the lens of the customer the challenges that they’re gonna see, and then how to remediate that, and then bring that to life and take the customer on the journey, and inspire them, and excite them, and then get them to the state mentally where they believe you, and they see what the outcomes can be. That is an art that is extremely difficult to find. And when you can find someone who has it, you grab them, you bring them over, and you just give them all the resources possible, and you try to retain them as long as possible.

That is a skill and a value that’s very difficult to find. That, and teaching people to communicate with senior executives, hard to find skills, and so I appreciate that when I see it.

And here’s the deal, Harry. That’s a competitive advantage. Right? And so you recognize that, like, very few people do that. What they want do is just hire more people. The ability to, I think, to capitalize on that is rare. If you get really good at something other people don’t pay attention to, I think that’s

Listening, discovery, personal relationships, face to face. COVID? That changed a little bit, mate. Well, it changed, but the need for it didn’t change. So now that we’re cycling back to face, what I’m finding is it’s really difficult to build relationships when you’re remote. It’s easier to retain them over time, But I think what I’m finding is the absence of face to face, something is missing from the cycle. You’ve gotta find a way to recreate that, acknowledging that it wasn’t there for a while. We’ve gotta bring that back.

I’d say there’s two things that I learned during COVID. One is if you’re a hunter rep, if you’re like an SMB, it’s really hard. You’re trying to build a relationship from scratch. Fortunately, we were in the enterprise space, so we didn’t have that. But in the Enterprise space, I think one thing that we would do is we build, like, a big executive briefing, and we would send Uber Eats gift cards to everyone who would be a part of that briefing, and we would have, like, a really nice digital experience.

And we were trying to bring in the events team and get really kinda clever and crafty and make it fun and exciting for the customer. And then on the internal side, we would do a lot of virtual happy hours at the very beginning when people were scared. How do you kinda bring morale up, get people connected? But I think now that we’re on the back end of COVID, the value of face to face when you can do it and it’s safe, we need to bring that back.

Tell me, what sales time ticks have died a death, Frank? Hiding information, the idea of solution selling, which is I have information, you don’t, and I’m gonna go tell you what people have wild access to information on your firm and the organization and the product. I think recognizing that and being super transparent and coming in saying, tell me what you know about it, and being really authentic with that, I think hiding information and trying to be protective, that’s twenty years ago. Love that little body motion.

I think there’s a maturity curve of an organization going from a few customers to really big and scale, and I think as you start to hire the sales team, you’re gonna get to a maturity point where you wanna move upmarket. Customers have a different expectation. And I think trying to train folks that don’t have the enterprise experience and convert them over, I don’t think it’s setting them up for success. I think you need to be able to find folks that have done this before that bring in the top end of the game, and then having really good segmentation, SMB, commercial, enterprise, and then alignment by industry.

You need to hire the proven team that’s got experience doing that. Your customers expect it, but you still want the other team to be able to manage the lower end of the business because they really know the organization and the product. So I think it’s

I think everything starts and ends with the customer. If you understand their needs, I think everything else is gonna work better. I do think in some particularly large deal cycles, you don’t wanna give someone an at bat where they’ve never really been in the beginning before. That’s not really fair. But if I had to stack rank that industry experience and driving client trust and relevancy, you can reverse engineer everything a lot easier than having big experience on a deal, but not understanding what’s gonna make your customer successful.

It’s not about you. It’s about your team. So I always think that you wanna put the customer first. I think you gotta put the employee first before the customer. It’s always been kinda wild to me that folks would be self focused as a sales manager, because by definition, you’re as successful as your team is. And so, like, I was just reading the book, The Go Giver. I want my team to be more successful than I ever have been. I want them to be able to create wealth for their families.

And so I think the more that I work for them, I serve them, and they know that, and I’ll do anything they need for me to do. So I think just running a very flat organization, being very selfless, and driving their success, what I found is not only do they end up producing, it creates a level of incredible loyalty that you really weren’t planning on. Sometimes they don’t wanna leave the nest even when they need to. So it’s kinda simple, but I don’t see it enough.

What would you most like to

Empathy. I think we need to really remember how hard it is for our team. Go look at the last two years. How hard is it to be a sales rep who might have joined an organization, and after two years never actually went into an office? To be able to, like, get in the mindset of a sales rep who’s never actually been in, they haven’t met their comrades, they haven’t met the customer face to face, and remembering just how hard that is. And as you go farther up in the organization, more and more of our job as sales leaders is internal.

But if you get too far away from the customer, you get too far away from the rep, you forget how dang hard it is to do their jobs. And so being empathetic and spending quality time with them keeps you humble, keeps you relevant. So that’s probably the one thing I’d change.

For me, it’s Miro. Now that everything’s been remote, of course, we’re trying to, like, ramp that back. I’m super right brain brain, super creative. I like to grab a whiteboard at an office and work through stuff. I’m super visual. It’s really hard to do remote. I put, like, a whiteboard up in my office. My wife throws it away. And so Miro’s, like, the technology that enables the ability to feel connected as a team, have a connected sort of set of tools that bring all these disparate ideas together, and allow the team to rally when you’re remote.

And then that’s now a digital format that you can bring into the office and extend it when you’re in person. So that’s really been something that’s helped us in the last couple

Yeah. Well, listen, I’ve never done this before. I’ve been, like, not anxious, but I’m excited to see what the outtakes. What what?