The Exchanges

Q Now, I would love to start with a little bit of context. I want to start on entry into sales. How did you make your way into sales in the first place? Let's start there.

A Yeah. So I am a little bit of an accidental sales leader. You see, um, after graduating college, I didn't know what to do. So I went and backpacked through South America and along the way I decided to go to law school because I figured he could always make a living as a lawyer. That is a very bad reason to go to law school. It turns out. So after graduating law school, I became a lawyer and not a very good one at that. And it was there that I said, I need to do something else with my life. I need to actually have impact. And so this was the late 19 nineties. The first.com boom was happening out in California. I was a lawyer in Chicago, sitting in a very large office building, wearing a suit in a very large, um, office. And I was lonely and my soul was dying. And I thought to myself, boy, if I just moved out to California and join a startup, Everything will take care of itself. So I remember telling my parents, I'm moving to California. I'm going to take a pay cut of about two thirds, and I'm going to join a startup. And they said, are you out of your mind? And that's what I did. I moved to California. I joined a startup as the second employee. And along the way, um, you know, I joined them as their head of business development. They were raising money. I knew how to fundraise. I knew how to structure contracts. I knew how to structure core partnerships. So they hired me to be t…

AI assessment note: “I joined a startup as the second employee... hired me to be their head of BD”

Q I agree totally. Can I ask you, if you're a founder or a sales leader sitting above these two reps, I completely agree in terms of, ah, the transferable learnings. How do you actually make that happen? Do you have like a weekly learning review? Do you have a Slack channel with lessons from calls? Do you review calls together? How do you ensure the transfer all of those lessons?

A Yeah. I mean, early, early days we're talking like there is no reason every call shouldn't be recorded. There is no reason that every call shouldn't be listened to together. If it's sales leader and two, three in a box in a room breaking down the call, it's like any athlete breaks down tape. And you're listening and stopping and asking and probing what else could you do? And I think the three by three framework here works really well. What are the, you asked the person that did the call, what are the three things that you felt went extremely well? And what are the three things you wish you did differently? Capture that. Calls played. Ask the person listening to the call. What are the three things you went well? What are the three things that you would have done differently? And then sales leader, you go through the same process. This is why the laboratory and everybody in a room in a box is so important. You're all trying to figure it out because at the end of the day, what you're striving for is an optimal process that, um, leads to a best practice, right? And that leads to pattern recognition. So when you're starting to talk to a customer, it's like, oh, I've heard this story before. We all agree. Here's the best way to approach it. That's gonna give you a lot more scale early on than any other mechanism, because it's all about exposure and at bats, and so I think that, that …

AI assessment note: “There is no reason that every call shouldn't be listened to together.”

Q I agree totally. Can I ask you, if you're a founder or a sales leader sitting above these two reps, I completely agree in terms of, ah, the transferable learnings. How do you actually make that happen? Do you have like a weekly learning review? Do you have a Slack channel with lessons from calls? Do you review calls together? How do you ensure the transfer all of those lessons?

A Yeah. I mean, early, early days we're talking like there is no reason every call shouldn't be recorded. There is no reason that every call shouldn't be listened to together. If it's sales leader and two, three in a box in a room breaking down the call, it's like any athlete breaks down tape. And you're listening and stopping and asking and probing what else could you do? And I think the three by three framework here works really well. What are the, you asked the person that did the call, what are the three things that you felt went extremely well? And what are the three things you wish you did differently? Capture that. Calls played. Ask the person listening to the call. What are the three things you went well? What are the three things that you would have done differently? And then sales leader, you go through the same process. This is why the laboratory and everybody in a room in a box is so important. You're all trying to figure it out because at the end of the day, what you're striving for is an optimal process that, um, leads to a best practice, right? And that leads to pattern recognition. So when you're starting to talk to a customer, it's like, oh, I've heard this story before. We all agree. Here's the best way to approach it. That's gonna give you a lot more scale early on than any other mechanism, because it's all about exposure and at bats, and so I think that, that …

AI assessment note: “There is no reason that every call shouldn't be listened to together.”

Q Do you think prospecting has done well today, Matt? I love that in terms of how you broke that down. I don't see that level of thought bluntly very often.

A No, it is not done well. If you just check my LinkedIn messages, um, it is done very, very poorly. A quick aside where it's done really well, so this will give all prospectors out there hope. I actually came to Grammarly in the most unusual ways. Um, I got a email, a cold email from the CEO of Grammarly, and the CEO of Grammarly, um, reached out to me with a very precise message. His interest in talking to me Because of a number of different reasons based on my background. And it was a cold outreach. And I read the email and I was like, wow, like that's a very interesting approach. I understand what they're looking for. I believe there's a good conversation to be had. So I picked up the phone and here I am as CRO of Grammarly. But so I think that kind of prospecting is incredibly effective, but really understand your message, understand the person in the other end. Do your homework and it works. Where it doesn't work is what's happening today. Proliferation of AI, prospecting, proliferation of, I know you, you may have a problem with pipeline. Do I? How do you know I have a problem with pipeline? I'm insulted now. Don't, don't tell me I have a problem because I don't. You know, it's like all these things that go wrong today, people are just putting back at you.

AI assessment note: “No, it is not done well. If you just check my LinkedIn messages”

Q the chief product officer, whoever in the company wants to buy the solution, the CFO is just not open for business. Not open for business. I don't know what I'm going to do. What do I do? If you were asked that by a friend who's a head of sales, who's just facing a brick wall because the CFO is not buying new Products. What do you say to them?

A I started a discovery process, frankly, and try to understand what is it they're selling and what is it they're solving? Because here's what I found with CFOs. CFOs start oftentimes from a place of I'm not buying because I'm controlling the budget. The reality of CFOs are they are very rational actors. In fact, they're some of the most rational actors within a business. They can be very objective. And if you have something that adds demonstrable value, Then they will buy it. I think it's a falsism to say my CFO is going to block. What that says is you haven't done a good enough job of showing the value and you haven't made it a priority for the organization. It also says you haven't brought the CFO along in the process. And that's a huge exposure point. And so one of the things I always tell my team is you keep your eye on the CFO. You have to get this to their desk in front of them and understand what they care about.

AI assessment note: “What that says is you haven't done a good enough job of showing the value”

Q no lawyers listen to this show. Don't worry, I haven't offended anyone. My question to you is, a lot of people go through career pivots or transitions, and it's quite a difficult and unnerving thing to go through. What are some of your big lessons, having been through really quite seismic pivots from lawyer and then to sales leader? What would you say some of those reflections or lessons are?

A Yeah, well, I think as you heard in my narrative of going from lawyer to sales leader, it Just takes a lot of courage and conviction, right? And so one of the big lessons is when you make that pivot, just remember why you made it, like, remember what drove you to make it in the first place. And that is an anchor for you because there are all sorts of moments of insecurity and doubt and fear. And I think the more you have that, uh, reminder of the conviction of why you made it, I think ultimately the more successful you'll be. And then along the way, it really is about Momentum. I think as you move into something new, there are little wins along the way. There are lots of defeats, but it's those little wins that you have to focus on and celebrate because win begets win. And I just think that momentum really helps you get through all the inevitable challenge that you have as you, as you make that pivot.

AI assessment note: “remember why you made it, like, remember what drove you to make it”

Q Do you believe that there is like a sales playbook? Because I find there's a sales playbook for each stage of a company.

A I've had a lot of debates with my colleagues around playbooks, and, um, I, I tend to fall in a little bit of a different, um, place than a lot of my peers. A lot of my peers have their playbooks, and they come into their business, they get a new job, they bring their playbooks, And that will somehow manifest victory. I am not a subscriber into, here is my playbook, hire me and I'll run my play. Because I think every company is actually unique, and hopefully people agree with that, because every company has a different product, sells into a different market, has a different position, has a different way of pricing, has a different way of thinking about it, has a different culture. All of these things ultimately are unique for a company. While Certain processes may be repeatable. There's 80% of commonality. It's that 20% that actually is the difference between winning and losing, and that 20% of the playbook that you really have to build only once you get there, and you understand the business deeply, and you understand the process, that's where the win happens. So you can come with a set of ideas about how to run something based on stage, based on product, But it'll all be upset once you get into the market. It's a little bit like the Tyson quote, everybody has a plan until they get punched in the face. Well, when you get into the market and you start to get punched, you then de…

AI assessment note: “I am not a subscriber into, here is my playbook, hire me”

Q and I, I always wanted that security. I wanted something to fall back on. Um, I saw my grandparents lose all of our money when I was younger, and it really just instilled this fear of having nothing, and so I wanted that security of, I could always have that. Why do you think you had that need for safety of, oh, I can always make money as a lawyer?

A Yeah, well, I grew up in a family of professionals, right? When you grow up in the middle of the country, you do a job, and you typically do it for life. Like, that is what you are, and that is what you do. My father, I think, has had one job his whole career, so for me, it was always about you have to earn a living, and so being a lawyer, you could always earn a living. The irony of all of that is when you get into sales, you're probably in the least secure profession, because it really is a performance-oriented profession, but I found that Much more suited to my temperament and personality. I loved the competition, the challenge, the striving, and so it sort of struck me in ways that, that law didn't, but I think that was the original thesis was you just have to earn a living, and then I found by trying to earn a living being a lawyer, it just didn't comport with my personality, with my sense of what I wanted to do, and that led me in a very different direction.

AI assessment note: “I grew up in a family of professionals... My father, I think, has had one job”

Q with this. I want to start on, you know, when you say about kind of the sales leader building out and taking those from company to company, often the founders are tasked with, you should build the sales playbook. I have a strong feeling that it is the founder that should build the sales playbook. Do you agree with me or should it be created by the first sales hire?

A Harry, let's call this our first point of divergence. Um, I think, I think founders are They have superpowers in lots of areas, but my point of view is building a playbook ain't one of them. And let me explain. I think you need a level or a layer of abstraction to be great at building a playbook. Now founders are so close to their business. They're so close to their product. Their language is the language of going out and talking to investors, of talking to pilot customers, and they hear things through that lens. That's not actually the lens through which I think you ought to build a playbook. I worked with some amazing founders and their language, their narrative is always a little bit different than the customer. The challenge of sales is translation, right? You have to translate what you do in a way that the buyer can hear it. And you need to take the buyer's language and translate it back to the company in a way that company could hear it. That translation is what's going to ultimately lead. I think the company to build to product market fit. And founders sometimes hear things very differently based on the universe and world in which they live, because they've been told certain things from the investor community, from early employees, and it doesn't really matter. What matters is how the customer hears them. And so I think that layer of abstraction actually is important. An…

AI assessment note: “Harry, let's call this our first point of divergence.”

Q You said there about banker, lawyer, consultant. You don't want that to be your first hire though, do you? Because they won't know how to create sales process, structure, the foundations of a sales team. Or do you actually want them as your first hire?

A You know, that's how I started. So I have a particular bias. It's not recency bias because I'm old. But they figure it out. Like the first thing you're doing for that first hire is you're trying to figure out how you're going to sell this thing, right? Like how do you sell it? How do you build it? How do you ask the questions? How do you build discovery? Now they may not think about it in terms of the traditional, well, here's the discovery process. We're going to move from stage to stage to stage to stage. But this is why I would say the second most important hire is get a great, great sales operations lead to partner with that person. Everyone always neglects sales ops. The sales ops is sitting in the background, figuring out the process, the motion, the stages. They're very different skill sets, by the way. And if you separate the two skill sets, I think you end up with the best of both worlds. You end up with a documented process that's following along with someone that understands how to actually figure out what the customer needs, what questions to ask, what product to build. And then you end up in a pretty good spot. I think.

AI assessment note: “that's how I started. So I have a particular bias. But they figure it out.”

Q always quite open to sharing the challenges of my life. So I totally agree with you there. The hard thing is also just urgency. You said there about kind of, um, good discovery can lead to actually good sales cycles. I'm kind of bastardizing what you said, but relatively. How do you create urgency in a sales process? Cause it is fricking hard to move the ball down the field.

A To me, that's what I said early on, like if you run really great discovery, you actually create urgency because great discovery points to a business outcome for solving the problem. If you understand the pain and it's quantified in a way where you know if you could solve it, your prospect agrees there's this economic benefit that they will realize every unit of delay is equal to some value. So you could actually start to work with them to say, look, let's agree, we'll get this done by the end of the quarter, as an example. If it doesn't hit by the end of the quarter and extends a month, you know what a month's worth of lost revenue, lost time, lost economic value unit equates to, and you start framing it that way. That does create urgency, if, only if, you understand what that unit is worth to them. If you don't, You're basically playing their game. There's no reason for them to try to jump over the procurement queue to get their deal done faster because you haven't created the urgency and you haven't aligned on it. So to me, if you can create and understand that unit of benefit or economic measure, it creates a level of urgency already that wouldn't otherwise be there.

AI assessment note: “if you run really great discovery, you actually create urgency”

Q I totally agree. How do you bring in the CFO? Without making the other side feel a bit of a second-class citizen. You know, Matt, it's great to get to know you, but can we bring in your CFO, because I know who the real boss is. How do you get around that?

A Well, you don't say it like that because that's going to get you in trouble. You're very clear up front. Look, as part of our process for you to be successful, we found that we collectively need to engage the CFO because the CFO at the end of the day is the person that's like, approve the process or not. And so being very clear about your process upfront and giving them a roadmap to how the deal's going to progress is exactly how you bring the CFO. And then sometimes say, look, we're not going to continue. The lesson until the CFO is engaged, because we've seen all too often that these deals will fall apart if the CFO isn't involved. And I don't want to waste your time. I don't want to waste my time. It's a very hard position to take. I always call it the power position. But if you know the CFO is going to be there and you don't take it, you're just going down a long path to lead to a very unfortunate outcome. Pull it forward, be clear, be transparent, bring the CFO in, and you'll have a lot more success. But if you know it's out there and you avoid it, You're really not serving yourself, your investors, your founder, your business. You're not doing them any good.

AI assessment note: “being very clear about your process upfront and giving them a roadmap”

Q I love it. My one challenge. People aren't always open, and so they won't always reveal that in the most transparent way. How do you make sure that people are open and honest in revealing what's not going so well? What, what is actually their boss's priorities? How do you get the truth bluntly?

A Well, people will feel comfortable expressing themselves more openly if they believe that you are a trusted partner and have some insight To share, right? Like, are you worthy of getting the truth? And that's just human nature. So if you're doing that research in advance of the discovery call, and you have a pretty good idea of what their strategic goals and priorities are, you know, you start with some insight, bring it back to them. You know, in our experience, we found through talking to cus to potential customers like yours, that people are struggling with the following issue. And we also find that with people struggling with that issue, they can solve it through whatever. Does that resonate with you? And just get them talking. Once it, if that resonates with them, you're on the track to issue identification and it gets them to open up because they don't feel alone. They don't feel isolated. Yeah. Someone else has that problem too. Well, that's interesting. So do I, oh, you do to tell me more about that. Yeah. It's like what you said. And then all of a sudden you're off and, and, and, and on your way. So those things called insight discovery openers is give them something that shows Connection. Understanding. Empathy. And people do open up.

AI assessment note: “give them something that shows Connection. Understanding. Empathy. And people do open up.”

Q Tell me, discounting. Often CFOs come in and say, hey Matt, love it, but I'm adding a thousand seats. It's a relatively big customer. I want some discounts. How do you advise heads of sales on discounting, when to do it, when not to do it, and lessons from your experience?

A So let's start with the utopian state and then we'll work down to the realistic state. Okay. The utopian state is, well, I've done such a fantastic job doing discovery, uncovering pain, demoing perfectly against the pain point, quantifying value, putting out pricing that has a huge ROI. I don't need to discount and I'm going to hold firm. Sure. That's great. Like let's, let's call that the utopian state. Let's say you run a perfect process. Some percentage of deals. You just don't have to, right? The reality though is oftentimes, um, even the company you're working for has a tradition and habit of discounting at the end of quarter. So you sort of set the market up for the discounting conversation. That's a hard one to overcome because everybody's waiting. You're under pressure. You'd have to hit your number and inevitably you're faced with, should I discount to close or not discount to close? That's a very personal decision for this, the, the, the sales management team. And whether to do it or not, I have discounted in the past. This is true. Um, and it will be because there will be something that is so important to the business that I need to do it. And that's the reality of it. Like there are times when you will be forced down a discounting path and you have to make the tough calls. You may not like it, but at the end of the day, if you're going to do it, just do it with prin…

AI assessment note: “if you're going to do it, just do it with principle, do it with guideposts”

Q Matt, your CRO at Grammarly, obviously one of the most unbelievable products I think that is the machine behind so many of us, customer expansion. How do you think about really getting the juice and the value out of every customer most efficiently today?

A Specifically at Grammarly, you know, we, a third of the fortune 500 use and deploy Grammarly today. There's over 50,000 teams using Grammarly today across businesses. What's interesting about that is typically the deployments will start in a particular function. So marketing as an example, or CS as an example. The reality of Grammarly is we work across 500,000 applications across the enterprise. So the issue is the average company is deploying hundreds of apps in their environment, and each of those apps, as an example, is bringing AI to the party. So all this content's being generated. Grammarly is the only one that works across all the applications within an enterprise. And so what ends up happening is You want a broad-based deployment because we're able to solve communication issues across the business because every department is trying to be effective communicators. That's how business works. It's essentially the operating system of the business. And so when you're talking to a customer, you're able to really help them understand and ask for the introductions to other departments who see the value, but they don't know how to buy it. And so this is where we then get into these conversations with IT, Around enterprise license agreements, and that's where expansion happens. Once we become part of that ecosystem, then we can expand quite quickly. But we have to do a lot of work…

AI assessment note: “that's where expansion happens. Once we become part of that ecosystem, then we can expand”

Q Is there a way to test it without committing a huge amount of resources? Like Stevie at Vanta said it's, she'd like to wait to kind of dip your toe in the water, so to speak. Is there a way to do that? Or do you have to fully commit full scale? We're going to be going enterprise.

A The testing happens organically. Like the testing's already there. It's in the data. Because like, so for example, you know, at Eventbrite, you started to see very large organizations adopting Eventbrite and deploying it in enterprise-like ways. At Grammarly, you see the proliferation. I think at Compass, my alma mater, 30,000 employees, there were 3000 people using Grammarly. It's there. It's in the enterprise. If I were to look at almost any enterprise, Grammarly's there. And in a lot of product-led motions, it already sits in the enterprise. People are bringing their applications to work more and more, and so the signal's already there. It's already sort of being proven out that it can be used in that environment. Now, should it always be used in that environment? No. Is it optimized for the environment? No, but there's enough signal that you don't really have to tip your toe in because your toe is already in the water. You just got to see it and understand it for what it is.

AI assessment note: “you don't really have to tip your toe in because your toe is already in”

Q and I, I always wanted that security. I wanted something to fall back on. Um, I saw my grandparents lose all of our money when I was younger, and it really just instilled this fear of having nothing, and so I wanted that security of, I could always have that. Why do you think you had that need for safety of, oh, I can always make money as a lawyer?

A Yeah, well, I grew up in a family of professionals, right? When you grow up in the middle of the country, you do a job, and you typically do it for life. Like, that is what you are, and that is what you do. My father, I think, has had one job his whole career, so for me, it was always about you have to earn a living, and so being a lawyer, you could always earn a living. The irony of all of that is when you get into sales, you're probably in the least secure profession, because it really is a performance-oriented profession, but I found that Much more suited to my temperament and personality. I loved the competition, the challenge, the striving, and so it sort of struck me in ways that, that law didn't, but I think that was the original thesis was you just have to earn a living, and then I found by trying to earn a living being a lawyer, it just didn't comport with my personality, with my sense of what I wanted to do, and that led me in a very different direction.

AI assessment note: “I grew up in a family of professionals... My father, I think, has had one job”

Q Do you believe that there is like a sales playbook? Because I find there's a sales playbook for each stage of a company.

A I've had a lot of debates with my colleagues around playbooks, and, um, I, I tend to fall in a little bit of a different, um, place than a lot of my peers. A lot of my peers have their playbooks, and they come into their business, they get a new job, they bring their playbooks, And that will somehow manifest victory. I am not a subscriber into, here is my playbook, hire me and I'll run my play. Because I think every company is actually unique, and hopefully people agree with that, because every company has a different product, sells into a different market, has a different position, has a different way of pricing, has a different way of thinking about it, has a different culture. All of these things ultimately are unique for a company. While Certain processes may be repeatable. There's 80% of commonality. It's that 20% that actually is the difference between winning and losing, and that 20% of the playbook that you really have to build only once you get there, and you understand the business deeply, and you understand the process, that's where the win happens. So you can come with a set of ideas about how to run something based on stage, based on product, But it'll all be upset once you get into the market. It's a little bit like the Tyson quote, everybody has a plan until they get punched in the face. Well, when you get into the market and you start to get punched, you then de…

AI assessment note: “I am not a subscriber into, here is my playbook, hire me”

Q there in terms of kind of the processes and the type. Can I ask you, When we think about seniority level, I know it's hard because it is generalizations, but broadly speaking, what would you advise me if I was an early stage founder hiring my first sales hire? Should it be sales rep or should it be sales leader where they then can build out the junior team themselves?

A I think you should be a sales leader. I really do. I mean, I think that the junior rep has a lot of success because they're, they're figuring it out. They're the first one on the ground. And so you want to invest behind that person. The reality is you're trying to build a, you're trying to build for scale. Right. And the, the problem is that junior rep then will ultimately be replaced and it creates a whole bunch of challenge internally. And I, I just think you could avoid that because someone that has been there and seen that and has a little bit of maturity, um, you're going to be able to build around that person and scale that, that team a lot faster. And so my point of view is why not just start there, just start with someone that can see the patterns that could ask the questions that understand it. They'll bring that junior rep along and train and develop them so that perhaps they can become a director of sales or run a team. You're not going to lose the junior person if you bring the right senior person in over them. You're going to give them actually a lot of headroom in which to grow their career, but junior folks will hit the ceiling and then they'll burn out and fall apart, and it just doesn't end well for the business or the culture of the business. My bias, if you're a founder, is shoot above the junior mark because you want someone that you can scale with to the ne…

AI assessment note: “I think you should be a sales leader. I really do.”

Q You said there about banker, lawyer, consultant. You don't want that to be your first hire though, do you? Because they won't know how to create sales process, structure, the foundations of a sales team. Or do you actually want them as your first hire?

A You know, that's how I started. So I have a particular bias. It's not recency bias because I'm old. But they figure it out. Like the first thing you're doing for that first hire is you're trying to figure out how you're going to sell this thing, right? Like how do you sell it? How do you build it? How do you ask the questions? How do you build discovery? Now they may not think about it in terms of the traditional, well, here's the discovery process. We're going to move from stage to stage to stage to stage. But this is why I would say the second most important hire is get a great, great sales operations lead to partner with that person. Everyone always neglects sales ops. The sales ops is sitting in the background, figuring out the process, the motion, the stages. They're very different skill sets, by the way. And if you separate the two skill sets, I think you end up with the best of both worlds. You end up with a documented process that's following along with someone that understands how to actually figure out what the customer needs, what questions to ask, what product to build. And then you end up in a pretty good spot. I think.

AI assessment note: “You know, that's how I started... But they figure it out.”

Q Is that not good? Do you not want to create that competition between team members?

A Not with your first two sales hires, not that early. You want collaboration, not competition. You want people to be able to experiment with each other and say, I asked this, this is the response I get, what do you think? This worked for me, does it work for you? You're essentially in a laboratory, right? And you want scientists collaborating, You want people working together. I think that collaboration of idea and idea, what works, what doesn't work is much more valuable than person against person. The market, it's too small a sample size to be able to draw real conclusions from two people. What you want to do is you want to draw conclusions of what's working and what's not working. Two different styles. You want to figure out your styles that are working and marry the two. I think for me, That's gonna give you, I think, a more positive outcome at the end of the day than anything else. Because look, you could have a great salesperson and a bad salesperson and bad product market fit, and the great salesperson can sell anything either, and then what are you really told?

AI assessment note: “Not with your first two sales hires, not that early. You want collaboration, not competition.”

Q the word discovery there, and you mentioned, like, what could Be done better. I think discovery universally could be done better bluntly. And you've said before, if you can't identify a customer's three biggest challenges that they want to solve, and can't map your solution to it, move on. Can you just unpack this for me in terms of what questions do you ask to identify their three biggest problems?

A Yeah, I mean, I've always, if anyone that's ever worked for me that happens to be listening to this, um, will know, I say, uh, it always comes down to discovery and deals are won and lost. In discovery, right? I mean, it's just, it's very simple. You win a deal in discovery, or you lose your deal in discovery. Now, you may not realize you lost it, because bad discovery leads to very long losses. Good discovery leads to very quick wins. It's just, it's in my, it's a truism in my world, right? So, to your question, how do you do it? What questions do you ask? Well, great discovery starts way in front of that conversation with great research. Now, the person you're talking to cares about certain things. They typically care about what their boss cares about, right? So if you understand what their boss cares about, you probably understand what they care about. Now, what does their boss care about? If you do the research on the company, you could understand a lot about what the boss cares about. What are the core strategic objectives for the business? What are their priorities? And a lot of this is very readily available. If it's a public company, it's all out there. Just read the filings. It'll give you a pretty clear roadmap into what the business is trying to achieve. Once you understand that, And then you ask, what is that person's priorities? How does it map to what the business…

AI assessment note: “The next set of questions is, how do you, how is your success measured?”

Q always quite open to sharing the challenges of my life. So I totally agree with you there. The hard thing is also just urgency. You said there about kind of, um, good discovery can lead to actually good sales cycles. I'm kind of bastardizing what you said, but relatively. How do you create urgency in a sales process? Cause it is fricking hard to move the ball down the field.

A To me, that's what I said early on, like if you run really great discovery, you actually create urgency because great discovery points to a business outcome for solving the problem. If you understand the pain and it's quantified in a way where you know if you could solve it, your prospect agrees there's this economic benefit that they will realize every unit of delay is equal to some value. So you could actually start to work with them to say, look, let's agree, we'll get this done by the end of the quarter, as an example. If it doesn't hit by the end of the quarter and extends a month, you know what a month's worth of lost revenue, lost time, lost economic value unit equates to, and you start framing it that way. That does create urgency, if, only if, you understand what that unit is worth to them. If you don't, You're basically playing their game. There's no reason for them to try to jump over the procurement queue to get their deal done faster because you haven't created the urgency and you haven't aligned on it. So to me, if you can create and understand that unit of benefit or economic measure, it creates a level of urgency already that wouldn't otherwise be there.

AI assessment note: “if you run really great discovery, you actually create urgency”

Q the chief product officer, whoever in the company wants to buy the solution, the CFO is just not open for business. Not open for business. I don't know what I'm going to do. What do I do? If you were asked that by a friend who's a head of sales, who's just facing a brick wall because the CFO is not buying new Products. What do you say to them?

A I started a discovery process, frankly, and try to understand what is it they're selling and what is it they're solving? Because here's what I found with CFOs. CFOs start oftentimes from a place of I'm not buying because I'm controlling the budget. The reality of CFOs are they are very rational actors. In fact, they're some of the most rational actors within a business. They can be very objective. And if you have something that adds demonstrable value, Then they will buy it. I think it's a falsism to say my CFO is going to block. What that says is you haven't done a good enough job of showing the value and you haven't made it a priority for the organization. It also says you haven't brought the CFO along in the process. And that's a huge exposure point. And so one of the things I always tell my team is you keep your eye on the CFO. You have to get this to their desk in front of them and understand what they care about.

AI assessment note: “I started a discovery process, frankly, and try to understand what is it they're selling”

Q I totally agree. How do you bring in the CFO? Without making the other side feel a bit of a second-class citizen. You know, Matt, it's great to get to know you, but can we bring in your CFO, because I know who the real boss is. How do you get around that?

A Well, you don't say it like that because that's going to get you in trouble. You're very clear up front. Look, as part of our process for you to be successful, we found that we collectively need to engage the CFO because the CFO at the end of the day is the person that's like, approve the process or not. And so being very clear about your process upfront and giving them a roadmap to how the deal's going to progress is exactly how you bring the CFO. And then sometimes say, look, we're not going to continue. The lesson until the CFO is engaged, because we've seen all too often that these deals will fall apart if the CFO isn't involved. And I don't want to waste your time. I don't want to waste my time. It's a very hard position to take. I always call it the power position. But if you know the CFO is going to be there and you don't take it, you're just going down a long path to lead to a very unfortunate outcome. Pull it forward, be clear, be transparent, bring the CFO in, and you'll have a lot more success. But if you know it's out there and you avoid it, You're really not serving yourself, your investors, your founder, your business. You're not doing them any good.

AI assessment note: “You're very clear up front. Look, as part of our process”

Q Tell me, discounting. Often CFOs come in and say, hey Matt, love it, but I'm adding a thousand seats. It's a relatively big customer. I want some discounts. How do you advise heads of sales on discounting, when to do it, when not to do it, and lessons from your experience?

A So let's start with the utopian state and then we'll work down to the realistic state. Okay. The utopian state is, well, I've done such a fantastic job doing discovery, uncovering pain, demoing perfectly against the pain point, quantifying value, putting out pricing that has a huge ROI. I don't need to discount and I'm going to hold firm. Sure. That's great. Like let's, let's call that the utopian state. Let's say you run a perfect process. Some percentage of deals. You just don't have to, right? The reality though is oftentimes, um, even the company you're working for has a tradition and habit of discounting at the end of quarter. So you sort of set the market up for the discounting conversation. That's a hard one to overcome because everybody's waiting. You're under pressure. You'd have to hit your number and inevitably you're faced with, should I discount to close or not discount to close? That's a very personal decision for this, the, the, the sales management team. And whether to do it or not, I have discounted in the past. This is true. Um, and it will be because there will be something that is so important to the business that I need to do it. And that's the reality of it. Like there are times when you will be forced down a discounting path and you have to make the tough calls. You may not like it, but at the end of the day, if you're going to do it, just do it with prin…

AI assessment note: “if you're going to do it, just do it with principle, do it with guideposts”

Q Why do you think that was? Do you not think it was just because it was easier? There were so much people with new budgets and there was so much free money going around that actually just a net new customer Was a win for the person. Show me the incentive. I'll show you the outcome. The incentive mechanism was set up to reward that.

A I think that was a huge part of it was also how investors thought about the value of the business and was their product market fit and all of those things sort of led to this, um, emphasis on that new when you have this unbelievable opportunity with your install base of customers who have already raised their hand. They said, I like the product. I want to use the product. And if you're not paying a lot of attention to how that all the opportunities to continue to expand it, you're missing the huge opportunity because it is, it is all there in front of you. And by the way, those reference customers, um, make your net new acquisition a lot easier. And by the way, help you dramatically reduce discounting because when people hear the reference stories of all the benefit that they get from the solution, You essentially create the urgency around the solution, the need around the solution, the conviction, it's the business case you've laid out, and therefore their motivation to hold you to a heavier discount is, it ends up dissipating. And that's natural, that's human, right? You want the solution more, so you'll do more to get it.

AI assessment note: “I think that was a huge part of it was also how investors thought”

Q Matt, your CRO at Grammarly, obviously one of the most unbelievable products I think that is the machine behind so many of us, customer expansion. How do you think about really getting the juice and the value out of every customer most efficiently today?

A Specifically at Grammarly, you know, we, a third of the fortune 500 use and deploy Grammarly today. There's over 50,000 teams using Grammarly today across businesses. What's interesting about that is typically the deployments will start in a particular function. So marketing as an example, or CS as an example. The reality of Grammarly is we work across 500,000 applications across the enterprise. So the issue is the average company is deploying hundreds of apps in their environment, and each of those apps, as an example, is bringing AI to the party. So all this content's being generated. Grammarly is the only one that works across all the applications within an enterprise. And so what ends up happening is You want a broad-based deployment because we're able to solve communication issues across the business because every department is trying to be effective communicators. That's how business works. It's essentially the operating system of the business. And so when you're talking to a customer, you're able to really help them understand and ask for the introductions to other departments who see the value, but they don't know how to buy it. And so this is where we then get into these conversations with IT, Around enterprise license agreements, and that's where expansion happens. Once we become part of that ecosystem, then we can expand quite quickly. But we have to do a lot of work…

AI assessment note: “ask for the introductions to other departments... conversations with IT, Around enterprise license agreements”

Q Is that not good? Do you not want to create that competition between team members?

A Not with your first two sales hires, not that early. You want collaboration, not competition. You want people to be able to experiment with each other and say, I asked this, this is the response I get, what do you think? This worked for me, does it work for you? You're essentially in a laboratory, right? And you want scientists collaborating, You want people working together. I think that collaboration of idea and idea, what works, what doesn't work is much more valuable than person against person. The market, it's too small a sample size to be able to draw real conclusions from two people. What you want to do is you want to draw conclusions of what's working and what's not working. Two different styles. You want to figure out your styles that are working and marry the two. I think for me, That's gonna give you, I think, a more positive outcome at the end of the day than anything else. Because look, you could have a great salesperson and a bad salesperson and bad product market fit, and the great salesperson can sell anything either, and then what are you really told?

AI assessment note: “Not with your first two sales hires, not that early. You want collaboration, not competition.”

Q Can I ask a weird one? And I I'm just so jumping around here. How do you build momentum in a sales team in the early days when you join as a sales leader?

A When you think about early, early days, it could be momentum could be the first time you pick up the phone. Momentum could be the first meeting that you're able to secure. Momentum could be you have a first meeting, you actually get a second meeting. Momentum could be you have a first meeting and you're able to translate that meeting back to the product team to help them understand what it is you heard. There are lots of little ways to do it in sales that doesn't have to manifest in the win. Because the win is a byproduct of lots of little things that you do along the way, and you sort of have to study each one of those things that got you to the next thing, that then gets you to the next thing, that gets you to the next thing, and each one of those things, it's actually a win along the way. It may not feel like it because you feel the overwhelming stress of the organization, having to build and go out and win and place it, all that stuff, but those little wins actually add up to, in the end, the ultimate win, which is you can win your first customer.

AI assessment note: “Momentum could be the first meeting that you're able to secure.”