Why You Should Never Hire a VP Sales First, How To Create Urgency in a Sales Process, How…

Harry, my man, it is so good to be here. Thanks so much for having me on the show.

I came to the world of enterprise sales from the world of wine. I recognize that’s not the typical journey one makes. So I was working in Massachusetts as a salesperson for a wine distributorship while I was going to business school. And upon graduating, was the Great Recession, not a great time to leave a good paying job for an unpaid internship somewhere. So I actually founded my own company. I bootstrapped the SaaS business back then, knowing nothing about SaaS, mind you, but built a cloud based company with tools in the cloud specifically for the wine industry.

Bootstrapped it. We had paying customers. It was a wild, incredible experience. After a few years, ultimately, I did decide to wind down that business. My wife and I moved out to Silicon Valley when she took a role with a little startup in Mountain View called Google. And so I found myself out here in Silicon Valley and I said, okay, I’m to be an account executive now again for SaaS companies. And I sent my resume out to about a hundred companies and the response was there was no response.

Literally could not get an interview. More than a hundred resumes sent out. I had founded my own company that was a SaaS company. I had always been a top performer in sales, and yet no one was interested in even interviewing me. It was a frustrating experience. It was a humbling experience. But ultimately, as someone who has already had a giant chip on my shoulder, it drove me to go out there and perform.

There’s fault on both sides. I think there’s a challenge from software companies and sales leaders thinking too small inside of a box in terms of the profile of who they’re looking for. And there was also a challenge on my approach not having lived in this world. It was a world that was foreign to me and I needed to find my way in. Ultimately, after a couple of months, I connected with a terrific recruiter and ultimately taking a position with a video conferencing company called Highfive. It was backed by General Catalyst and Lightspeed. was competing against Zoom, and this was before the pandemic when selling video conferencing was maybe a little bit harder.

Ultimately ended up getting recruited by TripActions, now called Navan, and was their first enterprise account executive and really built the enterprise go to market there.

The first lesson that I really took away, and this comes from when I was an IC, an enterprise account executive there. I built up a massive amount of pipeline the first six to nine months. I had 87 opportunities in my name, Harry. And if you know anything about enterprise sales, that’s way too many opportunities. But I started to close deals about month six. And what I recognized was you don’t need product market fit in order to sell an enterprise, especially as that first seller. What you need to find is product customer fit.

And so when you have a huge amount of pipeline like that, you can really prioritize it and focus on the accounts that match best with the vision that you’re building toward and where their required capabilities match with your core competencies. So when you focus on that 20% that’s gonna drive 80% of your outcome, amazing things happen. And I closed about million of revenue that first year.

Yeah. So it it goes down to something that I built later on, a qualification methodology called lean pivot walk. And essentially what you’re trying to do is understand, hey. if the boxes that they’re looking to check are the boxes that we check really well, you should lean in. You should be going after that opportunity full force. If what they’re looking for is something that is not even on your roadmap and wouldn’t be on your roadmap for the next five years, you need to be honest with yourself.

So many reps out there have happy ears and just because someone wants to meet with them, they think, hey, they’ve got an opportunity. You need to be honest and be able to walk away and qualify that deal out. And then there are other opportunities where maybe you check some of the boxes and not others. And is there a world where they’re willing to have two different solutions, one for the rest of the world and maybe one for North America. And so you start to understand these dynamics and you can play off of them and ultimately close a lot of business that way.

Yeah, for product market fit, I think that is driven more by the founder being out in the field talking to customers, talking to prospects, really understanding their pain points and being able to dive in at that level. But when you think about sales and a sales playbook, I think that’s originating from the salesperson. And in some businesses, the founder is that first seller. In other businesses, you to hire a junior salesperson to go out there and figure things out. But in no circumstances do you really want to bring in a VP of sales before you have a seller because they’re gonna come in with the preconceived notions that ultimately might not mesh with your particular business model.

I think about it a lot, but where I come from, ultimately, if you have a sales leader who’s coming in, they have a playbook in mind. They have processes in mind. They have sales tools in mind. And that playbook might not mesh with the product that they’re actually selling. It might not mesh with the people in that organization. And so when you try to jam that square peg in the round hole, you ultimately create thrash. And for an early startup, you can waste a lot of cycles and a lot of time having the wrong people in the wrong position.

I think they should make that first hire as soon as they have a product that they really want to be testing out in the market. I think it’s a lot sooner than a million ARR, to be honest. Those first sales, I don’t think about revenue as being important. The revenue or the currency that matters in those first sales are the logos. You you need to be acquiring logos. You need to be able to say, hey, this company works with us. That gives you credibility when you’re trying to make that sale for revenue.

You want their feedback. You want the case study. You want them to be a reference for you. That matters a lot more than revenue in those early days.

The way that I think about it is I’m looking for salespeople who can provide 10x growth, not one x or 1.5 When When you find someone who can provide that 10x level of growth, they’re a rare find. To find two at the exact same time and to be able to recruit them and have them join at the same time is an exceptionally rare opportunity. If you do find them, by all means, you should hire them. You should hire them as fast as you can whenever you can.

But ultimately, if you are at scale, it’s easier to hire, hey, two salespeople at a time. You’re going from 20 reps to 30 reps to 40 reps. Great. Hire an incoming class. But in those early days where each additional player is going to have so much impact, you need to be grabbing the best talent when you can.

There is only one way to know if they really are a champion for you. you. have to test them. And the way that you test them is asking them to take you to the executive buyer. Now, that can result in two things. One, they have the power and influence to be able to take you to the EB. Typically, that’s a CFO, especially today. If they have the power and influence to do it, and they’re willing to take you there, help present with you, you, need to be in that meeting on your behalf, they’re selling internally, you’ve got a champion.

If they say no to you for whatever reason, it means one of two things. Either they don’t have the power and influence to take you to the executive buyer, in which case you’re dealing with a coach or just a stakeholder in the organization who really is not going to be meaningfully important for you, or you haven’t earned the right yet to have them take you to that CFO or to that EB, in which case you have more selling to do.

You need to set that expectation from the start. Literally, in the first meeting where I walk through a pitch deck, I share with them why we exist, we’re solving for, and what it’s like to be working with us. And Everything from implementation and onboarding to, hey, part of our sales process is we’re going to want to have an open dialogue between your executive team and our executive team. This is not a typical vendor customer relationship, but it’s a partnership. And so we to make sure there’s that open dialogue so that what your CFO cares about, our CEO

You need to be able to get to the executive buyer. There’s a lot of different ways you can get there too. It’s not just through a champion. You can leverage your network. You can leverage your board members. You can leverage your executive team to back channel into that executive. Typically, you want be able to get some kind of a business value assessment where you’re agreeing on what the value is that we can provide for an organization. And at that point, you’re going to go with your champion and present those findings to the CFO or to the executive buyer.

of that question scares the shit out of me, Harry. And the reason why is that you need to be in that meeting. There is not a world that I would ever be comfortable living in where I to outsource my job to a champion and a prospect that is living very dangerously on the edge. I know a lot of salespeople who will take completely wholesale what a champion says. Hey, my CFO doesn’t meet with anybody. My CFO is too busy. I will be the one to talk to them on your behalf.

We can’t have that. Because what happens when the CFO asks you that question, Or and Mrs. Champion, that you don’t know the answer to? What happens when they question these numbers or they ask about implementation or have you talked to these different stakeholders and you don’t know the answer? We have to be in that room with you.

people tend to wear rose colored glasses. They get happy ears, as I mentioned before. People are meeting with them. They’re excited. Rose colored glasses people are great fun at parties, but they make for shit sellers. You need someone who is a lot more skeptical, who questions everything. The way that you see around corners is you ask the hard questions. You run toward the danger and what scares you, not away from it. So Harry, what are the reasons why you’re going to lose this deal? What happens if your champion leaves?

What happens if the CFO says this, that, or the other? If you ask yourself all of these questions and any possible way you could potentially lose this deal, now you have a map of all of the things that you potentially need to overcome. And in a worst case, you’re overcoming objections that might not actually take place. And in the best case, you’re really prepared for when that punch inevitably comes.

I think the biggest mistake that people make from sales qualification standpoint is really not going deep enough. They’ll ask discovery questions and then that first level of discovery question has been completed and they’re already selling their solution. You need to go deep. You need to do some significant discovery where you get to secondary, third level pain and really let someone stew in that pain. I’ll give you an example, Harry. You’re on a run this weekend and you scratched your arm, right? So I ask you about that and find out, hey, you know, yeah, it of stings.

Maybe you need a band aid. I don’t know. Is there blood there We start to dig in and find out, hey, you’ve got some serious pain. What happens if you don’t address that pain right now? Maybe it’ll get infected. And now instead of a band aid, maybe you need antibiotics. And if you don’t do that, what’s the risk to you? Shit, maybe my arm’s gonna fall off or I’m gonna have to get it amputated. Well, now this little scratch that you weren’t really thinking about is a painful festering wound that you really need to address.

Hey, turns out I’ve got a band aid, Harry, and I can solve this for you right now. You have to be able to go deep on that pain and qualify what is it that this person or this organization needs from a solution standpoint to solve their pain. And if what they need is what you have, great. You’ve got that match. You should lean in. But if what they’re looking for is something that’s completely different than what you provide, you need to be able to walk away.

Again, it comes down to that lean pivot walk. You can do med pick. Med pick is incredibly enlightening from a qualification standpoint. It’s me and my team. I don’t want a MEDPC filled out. I actually want you to come in, and we’re gonna do an active discovery together. And I’m gonna ask you about your deal. I’ll ask you about this opportunity. What’s going well? What’s MEDPC? What’s MEDPC? Are you kidding me? MEDDPIC is is an incredibly important qualification methodology. It’s really how you understand the deal dynamics.

You can look up the definition afterward, but basically, it’s an acronym. And what we to find out are what are the metrics that are important? The economic buyer, the decision criteria, the decision process, paper process, implicated pain, not just pain. We wanna understand the implications of it your competition as well as your champion. That’s what MEDPICK pick stands for. Ultimately, it’s an act of discovery. Harry, what do you like about this deal? What gives you pause? Are there any red flags you’ve encountered? Okay, if I could give you a magic wand, Harry, what are the five things you would want to know or see happen here that that you don’t know or haven’t happened yet?

Great. Now we’ve got an action plan for what to do.

It comes down to pain, Harry. If you don’t have enough pain, there’s not a world where I can get you to have the urgency you need short of discounting, and that of cheapens what we all do. What I would suggest is you got go back to first principles. You to go back to discovery. And if you, Harry, don’t have enough pain, I need to find someone else in the organization who has that burning pain. I need to find other people and build groundswell. Again, this comes down to multi threading and pipeline generation.

You to get as high and as wide as you can in an organization because the only thing better than having a champion is having multiple champions.

I think that discounting is an expectation that’s built into procurement teams. It’s built into the way that sales operates today. I think some organizations lean on it very heavily, whereas others are able to sell the value and really hold the line more. The more pain that you find and the more your solution matches with the pain that you’re solving for, the less you need to discount.

Yeah. So one, I don’t ask for assumed close there is really important. As part of working with us, we to support our customers. We love to show off the great companies that are working with us. And so we’re going to have your logo on our sales materials, on our website. That’s part of what we do. Oh, we don’t allow companies to do that. Okay. It was great chatting with you. Good luck finding a solution that is going to solve for the pain that that you have today.

You have to have confidence around it, Harry.

No, not at all. Why is that? It’s a great question. I think when you’re a junior sales rep, when you don’t have as many bats, you see things all the time that are new to you. And that’s scary. As a junior salesperson, hey, I’m encountering something I’ve never seen before. I don’t know where this path will take me. When you’ve done hundreds of deals like I have and you don’t have that much hair left on on on your head and what is there is graying quickly, have what one of my mentors Carlos Torre, he had a great colorful phrase for it.

It’s called scar tissue. And scar tissue is also known as pattern recognition. And the more pattern recognition you have, the better you’re able to combat that. Because instead of living in your head and having to analyze every single decision and every single thing you do, you can actually live by instinct. You’ve seen it before, what the proper response is.

I think the key to mentorship is helping people see their blind spots. So I’ll give you an example. I know you spoke to a founder of a YC company who I mentor. He actually reached out to me in a cold LinkedIn message, and it cut through the noise, and I responded to him. And I’ve been excited to to work with him and his team, but he’s not a sales professional. And so he’s going through this deal cycle and I shared with him what are his blind spots?

He thinks he’s got an opportunity here. What happens if it doesn’t work out? Does he to have all of his eggs in that basket? No, you to build more pipeline. Right? So I’m helping him, as an example, to see around his blind spots and ultimately to be able to close more opportunities with other reps, with other people, the dynamics can change. The buttons you need to push will change, but ultimately, you’re helping to make them more well rounded.

The four H’s is something that I came up with that really is about saying the intangibles matter more than the tangibles. First H, hunger. You need to want it more than anyone else. If you don’t have that burning desire to succeed, that deep need to win, that insatiable yearning to compete, you probably won’t win or compete or succeed. Hunger is an incredible motivator to get you through the inevitable challenges. It’s not enough to just be hungrier than everyone else, you need to be prepared to outwork them too.

There’s a great quote from John McMahon, who was a tremendous sales leader, and it sums it up well. The difference between winners and losers is that losers practice until they get it right. Winners practice until they never get it wrong. And also applies to sports. I always think about Tom Brady when I hear that. Someone who was not the most gifted athlete of all time, but certainly the greatest professional athlete of all time because he outworked everyone else. Watched more film than everyone. Was in the gym earlier than everyone.

No one would outwork him. And so he was able to rise when it mattered the most. Third H, humility. This is one that I will grant you a lot of salespeople don’t have. They come in with bravado, but I actually think humility is the approach. You need to know that no matter how much success you’ve achieved, there’s always someone who’s done more, and there are always areas you can improve. None of us are perfect, certainly not me. You need to recognize and embrace that. You need to use that to fuel your growth.

The last h is heart. It should be table stakes, but instead it’s more like special sauce. Think of it like grit, what it takes to be a champion, to be able to take a punch and keep fighting. There’s a great book by Reed Hastings called No Rules where he talks about talent density. I actually think as important or potentially more important than talent density is grit density. To have a team that just has an massive amount of grit.

It’s a little bit of a mixed metaphor, but let me tell you. So from a product standpoint at Ramp, we think of the legacy state as a horse and buggy. And do we want build a faster horse and buggy, or are we to build an automobile? On a slightly different vein, I’ve heard guests of yours talk about the expression in sales recruiting that fast horses run together, right? A players attract a players. But if you want 10x productivity, you need to think outside the horse. You need a race car, not a race horse.

Let me give you an example here. If you have a 10x better product, and I hope you’re investing in companies with 10x better products because they’re amazing. But if you have a 10x better product and a good traditional sales rep, the best you can achieve is a 10x outcome. It’s a pretty good outcome. But if you have a 10x better product and a 10x better sales rep, you can achieve a 100x outcome. And the best salespeople in my experience rarely fit the mold of what great salespeople should look like.

And I’m not even talking about myself and my challenge getting into Silicon Valley. The best salespeople I’ve seen in the last several companies I’ve been in, none of them would be hired today based on the rubric that sales leaders have. You need to think outside the horse.

For one thing, didn’t come from the right companies or they didn’t have the right LinkedIn profile or something about them would have canceled them out from even getting into the funnel from a hiring standpoint. But the best salespeople will have those four h’s, but they’re also going to have creativity. Can you take duct tape, chewing gum and a Zoom link and MacGyver a seven-figure figure closed one deal? Right? That takes creativity. I’ve seen people do it. It’s extraordinary. Not everyone has that. Are they adaptable? The two first salespeople at Ramp.

The first one now leads half the sales and SDR teams. The second one is chief of staff to our CEO. Right? They’re adaptable. You’re hiring people not for what they can do today, but people who have enormous growth potential. That’s how you get a 10x outcome.

Yeah, you need to get really intimate. You need to go deep in your interview questions. Get at the why, not just the what. So many interview questions are, what did you do next? What were you doing at that company? What deals did you close? I to know the why. I to know the how. I to know them and get really deep to understand what makes them tick. What was the reasoning behind decisions they made, not just the performance? And a great way to test this is with a challenge.

So I know different organizations think about this differently. I want them to sell to me, not what they’re selling today, but I want them to sell my solution back to me because it shows if they can do research. It shows if they can synthesize that information. I know if what they’re saying is correct or not. I can see all of the gears turning and I can test them as well in that setting and say, hey, I’m a CFO. We scheduled this for 45 minutes. I actually only have 10.

Go. Are you adaptable? Can you take a punch? Can you pivot really quickly? God, that’s harsh, Mark. It happens in real life, though. I’d much rather it happen in an interview than with a real prospect.

I don’t want you to be comfortable in that interview process selling me something that you could talk about with your eyes closed while you’re sleeping. I want you to have to think. I want to challenge you. It’s called a challenge for a reason. I want to see if you can rise to that occasion. Enterprise sales is hard. I want to see if you have what it takes to rise up and be able

For me, I think it’s about selling enterprise deals, so that value, to selling to organizations that size. because the scale is so different. I’ve seen mid market account executives get promoted into enterprise in my past and flame out pretty quickly. And the reason is usually they’re used to a certain level of multithreading. Hey, I need three or four people in the deal. Now all of a sudden, everything is magnified by an order of magnitude. Can you play 20 simultaneous games of chess? It’s great that you can play chess, but can you play 20 games at the same time?

It’s much harder.

for them to fail when the stakes are low so they can succeed when the stakes are high. You have to be in the boat with them. First of all, as a sales leader, my quota, I’ve got a quota, and my quota is a roll up of my reps. So number one, I’m in the boat with you because your performance is going to matter for my performance. Putting that aside, I want to see everyone on my team succeed, but I can’t do the job for them. Right?

I can’t be in every deal, in every place, in every call at the same time. So I need to give you the tools to succeed when I’m not there, and I need to be in the boat with you and teach you, mentor you throughout that process. But what I’ve also found, no matter how much you say the stove is hot, people still want to touch it in order to find out that it’s really hot. And so it’s my job to make sure the burner’s on simmer and not on high.

So it’s not a catastrophic wound.

So for me, I want to be able to qualify quickly. Is this person of the right caliber? Have they closed the right level of deals? Do they have the right experience? Do they have the right gravitas to be able to hold themselves in an executive meeting? That is usually like a 30 minute getting to know you call. Assuming that goes well, you to go deeper. You to spend an hour with them. You want really go deep. You to ask those why questions, those how questions, really get to understand what makes them tick.

You to have other stakeholders meet with them as well. Typically in enterprise, you’re a quarterback. You’re working with other people internally and externally. So how do those relationships form? Are you able to play off those dynamics? And then ultimately, yeah, you want to do a challenge with a panel of interviewees all the way up to your c suite leadership.

I’ve certainly made mistakes. I think sometimes when you assume their experience, if you assume their fit based on where they’ve been or what they’ve accomplished in their career, you put yourself in a very risky situation where when they come in, if you haven’t tested for that, they may fail. I’ve seen people who are extremely accomplished join organizations I’ve been a part of, and within six months, they’re no longer in the company because they weren’t able to cut it. The fit was wrong. And so you really need to test for that because the last thing you want is to waste six months of their career, of their time, and six months of your runway and six months of your time on someone who isn’t a fit.

to early sales hires, there’s not enough emphasis placed on equity in sales. They give out equity for other roles. And I think equity is often something that founders don’t really think of when it comes to salespeople. They really only think about cash compensation. That’s the wrong approach. If you’re hiring a 10x salesperson, someone who’s going to be with you for a long time and drive an inordinate amount of impact in the organization, you should want to keep them for a long time. And they’re going to be able to see the impact of their revenue generating activities on the company, all the way up to raising funds.

And we just need to get more creative, and we need to find a path forward. And so when you have people who can drive an impact like that and put an entire team or company on their back, you want to reward them. Cash is great. We all like cash. Sales reps are coin operated. I get it. But you want them to be bought into the long term vision as well. And it needs to be aligned with what the company cares about.

You need to, in the early days, figure out what is the goal that the board is setting for you or that you’re sharing with the board, number one. Is it realistic? Is it achievable? Work backward from that goal. Working backward is something that I often teach to my teams. Okay, here’s the goal that we’re trying to get to. If we’re just driving toward it in a forward direction, we may drive off a cliff. And if you don’t to end up like Thelma and Louise, then what you need to do is work backwards so you know where the cliffs are, you know where the landmines are, you know where the traps are, and you can find, hey, is there one path?

Is there no path? Are there multiple paths to get there? And then you can move forward. So if you work backward from that goal, regardless of how lofty it is, you can figure out the way to achieve it. The other thing that’s really critical here is pipeline generation. If you have a massive amount of pipeline, you are able to qualify deeply and make sure that you’re going to hit the goals that you’ve set for yourself. This is something that I instill in my teams, and I’m proud to say that this quarter, the enterprise team at Ramp is trending to hit more than 300% of their quota, which is pretty insane.

Traditional outbound is the most important thing, Harry. And if you’re not doing it, you are doing sales wrong. And the reason why is because pipeline is the most important thing if you to hit your quota, as we just established. And the way that you build pipeline is through outreach. The founder that I mentor, he PG’d into me. He cold messaged me. Without that, I wouldn’t be mentoring him. We have so many opportunities that are in our pipeline because we did the hard thing. We picked up the phone.

We sent out an email. We were persistent with it because usually it takes about five messages before someone is going to respond. And ultimately, we feel good about it because we’re providing a solution for them that helps them. We’re not trying to sell them something that they don’t need. And so if you think of it from that standpoint, what you’re doing when you’re picking up the phone is something that’s good for you and good for the people that you’re calling.

I think it needs to be a mix of structured learning and unstructured learning, so asynchronous learning. I think there needs to be a fair amount where they’re going to be shadowing the best reps on calls. I think you need to dig in with them and go deep on a daily and weekly basis, so one on one coaching as well. And you need to make them drink from the fire hose. I know we try to limit that as companies get larger where, hey, we’re going to give them this nice cushy ramp up period, but you’re going to find out a lot those first few weeks about their ability to run at pace if they can drink from the fire hose and start to synthesize that information.

So I’m a big believer that the training wheels need to come off quickly. I do think there’s benefit as well to giving them what I’d call t ball opportunities. So if you’re an enterprise, you don’t to risk some massive deal by giving it to the guy who just or the woman who just started. You need to be able to give them a smaller opportunity that’s safe, that’s a safe place for them to iterate and figure out the motion before they’re getting into these really large, complex deals.

I recognize that not everyone is a type a personality and gregarious, even in sales. But if someone is not asking a lot of questions, if they’re not vocal in that first month or two, to me, that’s a red flag that I want to at least dig into. It’s not a sign, hey, we need to fire them because they didn’t ask questions. It’s, hey, are they not asking questions because they understand everything? Bravo, Brilliant. Go forth and prosper. Or are they not asking questions because they don’t actually even know what questions to ask?

And is it an aptitude issue or an attitude issue? You need to understand that if you want to try to fix it. And in some cases, you’re right. It’s hire slow and fire fast. If someone can’t make it, the merciful thing to do is to let them go so that they can go to a place where they can be powerful, efficient and grow their career.

It’s why you need to ask those why questions, Harry. Some companies are great at product led growth, and they’re selling to an organization when it’s an SMB. At what point did you sell to that organization? Was it a 10 person company that grew to a 10,000 person company, or did you sell to them net new when they were 10,000 people? Did you sell wall to wall across the entire organization, or was it a land and expand motion? Who else was involved with you in selling that deal?

You need to dig in to understand, did they do all of the work? Did they generate that deal themselves? Was it self sourced, or did an SDR make a cold call and that’s how it happened? Or did marketing generate the lead and it came inbound?

I think you should do a deal review for any deal that is going to be impactful toward you hitting your goal for that quarter or that year, period. And that means that you’re probably doing more deal reviews than you’re typically anticipating. You need to give time for that. If you’re not digging in with your rep and understanding the deal dynamics, what could go wrong, what needs to happen, the various stakeholders, have you mapped the organization, and getting really into the details, then you’re putting yourself at risk because that deal could slip. that deal could end up as a closed lost.

And if you were counting on that, if you were committing that opportunity, man, that is an unpleasant place to be. I can tell you it has happened in my career a long time ago when you commit a big deal then and it doesn’t come through. That’s a painful experience for everyone. You don’t to be living like that. What are the

In my experience, when you do lose to competition, you can lose for a variety of reasons. One, it could be price. And if you’re selling something to someone who’s really price sensitive and you haven’t sold the value and articulated it, you can have someone come in and offer a product for free or offer it for a really low price, and that company may grow to regret that decision, but ultimately, they might make that decision. You could get outflanked. You have a champion, but you know what?

They’ve got a champion that’s more senior. And so the more senior person who’s got more influence in the organization is potentially going to win. There are a variety of reasons you could lose, but you need to map the organization. You need to understand the dynamics at play.

Yeah. If you’re doing it badly, it’s, hey, I’m handing you off over here. See ya. That’s not the way it should go. You need to be introducing that implementation and that CS team before the deal is ever closed. Implementation, onboarding, how we’re going to make you successful as a customer is part of the sales process. And so you want to bring them in to be able to walk them through what the implementation plan looks like, what does success look like, what are you trying to solve for, where are you at today, and what does good look like, what are your goals?

And once we’re aligned on all of that, and there’s some overlap here between the sales team and and CS, now you feel more comfortable moving forward with us. And when you do, you already have this relationship formed with the team you’re to be working with to make you

That’s a great question. Typically, they end up being compensated in a slightly different way, which is that CS often in most organizations are going to be compensated based on adoption, at least in companies that are based on usage. Are you seeing that adoption curve? Are you seeing full adoption? So that’s how they’re going to get paid. So ultimately, by helping to bring in a deal and seeing that adoption happen, they are going to be compensated for it.

The fundamentals. Cold calling, cold emailing, that pipeline generation, qualification, champion building, getting to the EB. It’ll never change.

It pains me to say it, but I think in person meetings, it’s not that it’s died. I think it’s on life support. Video conferencing, digital whiteboarding, sales intelligence tools, they’re all built so we can collaborate and be productive in a remote first world, but it can sometimes create this soul crushing reality where human interaction becomes transactional instead of deep.

It hasn’t been required the last few years. I miss it. I love it. I will take every opportunity to meet clients where they are, but I think it’s a dying art.

I think so. I think with any kind of really large company trajectory changing deal, you want not just the CEO, but you want the entire executive team to be involved.

I think, again, it’s about trying to hire people who fit inside a box with their preconceived notions. Every time that’s going to end up biting you in the butt.

Always look to raise the bar. Don’t settle for B players. I’ve made that mistake myself. I now have a rule which is that each subsequent hire has to raise the bar for the entire team. If don’t they have the potential to be as good or meaningfully better than everyone else in seat, why are you hiring them?

The perception of it. There’s science behind great sales. It’s not some parlor trick. Sales is often deeply misunderstood by those in other roles. And I think if you step back and look at all of the process behind it, there’s real science.

You have to start with understanding why it happened. Who’s responsible? How do you ensure it never happens again? And the answer inevitably is pipeline coverage. And whose responsibility is that, Harry? Everyone’s.

I think anyone who’s executing right now and exceeding their goals outside of generative AI, which I think has a very unique tailwind, they’re doing something right. Starlink’s performance has been especially impressive given they fly under the radar, which is odd for a company that dots the skies.

My pleasure, Harry. Thanks so much.