Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20Sales: Why the Founder Should Not Be the One to Create the Sales Playbook, Why You Should Hire a Sales Leader Before Sales Reps & Why You Should Not Hire Sales Leaders From Big Companies with Matt Rosenberg, CRO @ Grammarly About this episode Matt Rosenberg is Grammarly’s Chief Revenue Officer and Head of Grammarly Business. He leads all B2B revenue, operations, and growth for Grammarly Business, Grammarly for Education, and Grammarly for Developers. Previously, as CRO of Compass, he took the company into the Fortune 500 and contributed to a more than eightfold increase in business growth. Prior to Compass, Matt served as Eventbrite’s CRO leading them to become the largest event platform in the world by event count. In Today's Episode with Matt Rosenberg We Discuss: 1. From Miserable Lawyer to World Beating Sales Leader: How did Matt make the transition from lawyer to sales leader? What does Matt know now that he wishes he had known when he started in sales? What are Matt's biggest pieces of advice for anyone who wants to make a career change and is lacking confidence? 2. The Playbook and Hiring The Team: How does Matt define the "sales playbook"? Should the founder be the one to create and execute V1 of the playbook? Should the first sales hire be a rep or a sales leader? When is the right time to make that all-important first sales hire? 3. Discounting, Champions and Urgency: What can sales team do to create urgency in deal cycles? What works? What does not? How does Matt approach discounting? When to do it vs when not to? What level is acceptable? What are the biggest secrets to creating champions within prospects? Why does Matt believe that deals are won and lost in prospecting? 4. Developing Great Sales Talent: How does Matt use sales call recordings to train teams? What is his 3x3 matrix for coaching calls? What is a good reason to lose a deal vs a bad reason? How does Matt do deal reviews? What are the single biggest elements sales leaders can do to nurture sales talent? What are the biggest mistakes sales leaders make when developing talent internally?
Transcript 10,259 words · 3 speakers
Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Speaker 00 Don't hire anybody from Google. Don't hire anybody that says on their LinkedIn, ex-Google, ex-Amazon, ex-Facebook. When they put that on their LinkedIn, they're associating themselves with the success of the business and the first sales executive. You want to hire an ex-banker, an ex-consultant, an ex-lawyer.
0:17 Harry Stebbings? I'm just going to put it out there. This is one of the best 20 sales episodes we've ever done. This guest was phenomenal. He did not hold back and there's so much goodness here. And so I'm thrilled to welcome Matt Rosenberg. Matt is Grammarly's Chief Revenue Officer and Head of Grammarly Business. Before Grammarly, Matt was CRO of Compass, where he took the company into the Fortune 500 and contributed to a more than eightfold increase in business growth. Prior to Compass, Matt served as Eventbrite's CRO, leading them to become the largest event platform in the world by event count. Get out your notebook. There are so many actionable pieces of advice here on scaling sales teams. But before we dive into the show today, Outreach is the only AI-powered sales execution platform that unlocks seller productivity to help sales teams efficiently
1:01 Harry Stebbings? create and close more pipeline. From prospecting to deal management to forecasting, their platform leverages automation and artificial intelligence to help revenue leaders increase efficiency and effectiveness of all go-to-market activities and personnel across the revenue cycle. And Outreach is the only company to offer sales engagement, revenue intelligence, and revenue operations functionalities in one unified platform. But don't just take my word for it. There are 6,000 companies, including Zoom, Siemens, Okta, DocuSign, and many more, who depend on Outreach to power their revenue organizations. To learn more, check them out at outreach.io. And then speaking of incredible products, I have to discuss ZoomInfo. I had Henry Shaw,
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2:29 Harry Stebbings? love and use them. Head over to zoominfo.com/20vc to see for yourself and sign up for a free trial of the ZoomInfo platform. You have now arrived at your destination. Matt, I am so excited for this. As I said to you just now, I had so many great things from many mutual friends. So first, thank you so much for joining me today.
2:49 Speaker 00 Well, thank you, Harry. I really appreciate you having me on. It's it's an honor.
2:52 Harry Stebbings? 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.
3:01 Speaker 00 Yeah, so I am a little bit of an accidental sales leader. 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 you 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 nineteen nineties. The first dot com boom was happening out in California. I was a lawyer in Chicago, sitting at a very large office building, wearing a suit in a very large office. And I was lonely and my soul was dying.
3:45 Speaker 00 And I thought to myself, boy, if I just move 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, 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 their head of BD. And along the way, we had multiple pivots. The business, like most startups, failed a number of times and we kept pivoting our way into. A new market and I was the one that helped the company figure it out and sell the first
4:28 Speaker 00 big solution. And then I fell in love with sales, the intellectual aspect of it, the emotional aspect of it, all of it. And that's how I ended up in in sales and as a sales leader.
4:37 Harry Stebbings? Can I ask a really personal question? I didn't expect to go here. Actually, I actually did law as well, because I thought you could always earn a living as a lawyer. And I always wanted that security. I wanted something to fall back on. 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?
5:03 Speaker 00 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. 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,
5:45 Speaker 00 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.
5:52 Harry Stebbings? I mean, I don't think it comported with your personality, because I think you had a personality. The lesson I have from law school is the ones that succeed don't have one. But there's a reason 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 quite seismic pivots from lawyer and then to sales leader? What would you say some of those reflections or lessons are?
6:23 Speaker 00 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. 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 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 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.
7:04 Speaker 00 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.
7:11 Harry Stebbings? How do you build momentum in a sales team in the early days when you join as a sales leader?
7:16 Speaker 00 When you think about early, early days, 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 it to the next thing. 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
8:00 Speaker 00 having to build and go out and win and place and all that stuff. But those little wins actually add up to the ultimate win, which is you can win your first customer.
8:09 Harry Stebbings? I totally agree. I always think it with new hires as well. I say you have to manufacture hype around new wins, which is like you get that second call. I'm gonna like buy a cupcake to celebrate with you because I want you to feel it's almost more than it is. Just to give you that confidence.
8:24 Speaker 00 Absolutely. And confidence is is really everything because it's such a hard job. You're listening and you're processing and you're trying to figure it out. And there is this actual overwhelming pressure if you let it overwhelm you. Because the company rests on your shoulders. You're brought in to figure all this out and the the reality is nothing's been figured out. And as much as the founder who sells you into the job says, there's product market fit, we figured it out, it's going to be glorious. All you have to do is walk into the market and it'll sell itself. Well, it never does. It just never does.
8:56 Harry Stebbings? You said there about kind of walking into the market, selling itself. It reminds me of the wonderful term of sales playbook. How do you define the term sales playbook?
9:05 Speaker 00 Yeah, I mean, a playbook is simply a set of repeatable processes that lead to the best possible outcome.
9:11 Harry Stebbings? Do you believe that there is like a sales playbook? Because I find there's a sales playbook for each stage of a company.
9:17 Speaker 00 Yeah, I've had a lot of debates with my colleagues around playbooks. 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 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%
10:01 Speaker 00 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. You can come with a set of ideas about how to run something based on stage, based on product, but it will all be offset 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 develop your playbook because you have to figure out how to get around the punches, how to move through and navigate the process. And that navigation, the nuance of it, when you start to start to crystallize that into a playbook, that's where winning happens. That's the difference between building a high performing team and a team that may win once or twice, but it's not going to
10:46 Speaker 00 win repeatedly because that's the magic is in that 20%.
10:49 Harry Stebbings? Speaking of that magic being in the 20%, can I ask, are there elements? Which are continuous throughout. Like, how, as a sales leader, can you know what things you should be rigid on? And yes, it worked at last company, and so it will work at this company versus that worked at last company, but it may not work. How do you know the things you can be rigid on and take versus the things you need to be plastic on?
11:13 Speaker 00 Yeah, I would encourage a lot more flexibility than rigidity. The great sales leader is able to deeply and uniquely understand the market they're in, what they're positioning, what the process needs to be to maximize the success to the team, and they're able to build that. And I've kind of lived this, right? I've never worked in the same industry twice. I very rarely work in the same sales motion twice because I believe part of the the challenge and the joy is figuring out hard problems. And what I bring to companies is the unique perspective that is formed from lots of different experiences. Because you're seeing sales models start to merge. You're seeing, it used to be enterprise, then it's SaaS.
11:55 Speaker 00 And now you're seeing a lot of different motions all come together in unique ways. And I think sales leaders need to be flexible and understand that and be able to pick up different signals from different parts of the market and pull it together. Otherwise, you end up at a playbook that's probably 80% right, but you need it to be 100% right to actually build a motion that wins repeatedly.
12:16 Harry Stebbings? 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?
12:33 Speaker 00 Yeah, so, Harry, let's call this our first point of divergence. I think founders, 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. Like I've been, I've worked with some amazing founders and their language, their narrative is always a little bit different than the customer.
13:18 Speaker 00 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. And I think sales leaders can hear things differently than the founder. Now, the founder will be great at positioning and they should be in the meeting because they understand the product deeply.
14:03 Speaker 00 But I think in terms of building that process, that abstraction actually is a benefit to the business. So I think we diverge a little bit in points of view there.
14:11 Harry Stebbings? I am fascinated. How do you then know what type of leader to hire if you don't have a playbook in place? So my, my pushback to you is if you don't have a playbook, you have no idea who is the right person to hire. A PLG motion versus a heavy enterprise motion, you have no idea on your channels. You have no idea on your messaging, your positioning, your ICP. Well, geez, Matt, you know, there's so many different types of sales leaders. It varies so much. You could hire totally the wrong type of leader if you don't have a playbook. So the founder should be the one to identify the playbook to a certain extent, to have clarity around it. Because that will hugely inform the type of leader they hire. What do you think about that?
14:53 Speaker 00 Yeah, so I agree with you there. I think founders have a point of view around the type of leader they want to hire based on the model they're selling in, right? That, to me, is very different than a playbook, which I'm defining as a process by which to win an account. Now, what I will tell you in terms of your question around sales hire, this is again, one where I may have a slightly different view than most, which is the mistake that I see founders make all the time is the hire for pedigree, where they try to match perfectly someone from the sales motion that they're selling in. So I have seen time and time again. I'm hiring someone from Google. Harry, don't hire anybody from Google. Okay, don't hire anybody that says on their LinkedIn, ex-Google, ex-Amazon, ex-Facebook.
15:38 Speaker 00 Okay, when they put that on their LinkedIn, they're associating themselves with the success of the business and it is almost impossible to tell what contributions they actually made to the success of that business. But the founder sees it and says, wow, I'm hiring an executive from Google. They must know. The reality is they don't. What you're looking for when hiring that sales executive is something very different. The first sales executive, you want to hire an ex-banker, an ex-consultant, an ex-lawyer. You don't even necessarily want to hire an ex-sales leader, right? Or a sales leader. You want to hire someone that can radically listen, that can actively listen, that can ask probing questions, that is able to think critically, analytically,
16:23 Speaker 00 and is able to figure out patterns based on a set of conversations to quickly hone in on, here's actually where the market is, here's actually where the ICP is, here's the kind of things that the buyer is actually asking for. Those types of folks are great active listeners. They ask incredible questions to get at the essence, the root of things. That is where you're going to build your playbook.
16:46 Harry Stebbings? 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?
17:02 Speaker 00 Yeah, 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 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 for scale. The problem is that junior rep then will ultimately be replaced and it creates a whole bunch of challenge internally. I just think you could avoid that because someone that has been there and seen that and has a little bit of maturity, you're going to be able to build around that person and scale that team a lot faster. 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.
17:41 Speaker 00 They'll bring that junior rep along and train and develop them so that perhaps they could 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 next level. You may have another decision to make, like that person you brought in, you have to scale above them, but I would start higher.
18:15 Harry Stebbings? 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?
18:29 Speaker 00 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. 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?
18:41 Harry Stebbings? Yes.
18:42 Speaker 00 How do you sell it? How do you build it? How do you ask the questions? How do you build discovery? And 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, but 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.
19:23 Harry Stebbings? Do you hire them both at the same time?
19:25 Speaker 00 So that would be ideal. Very hard to do because most companies at the very, very startup stage don't have the capital budget to do it. And typically, sales ops will want to have a little bit more certainty around what it is they're building to. So it's a hard thing to hire initially, but a fast follow for sure. If he can, I think that's the way to do it.
19:43 Harry Stebbings? Okay, so we've got RevOps there. But when we're hiring underneath, should we hire two by two? Jason Lampkin at Saster says we should hire two at the same time and do this kind of competitive mechanism. Should we do that?
19:56 Speaker 00 Yes, but did you say like a comparison mechanism?
19:59 Harry Stebbings? Yeah, to understand if you get one and they're crap, you could just think that it's your product that's not selling, or it could just be that they're not very good. But if you get two, you'll clearly understand, oh, the product sells, but this one's not very good. Or if both fail, maybe it's the product. But you actually get a much more holistic picture by having two at the same time.
20:18 Speaker 00 I definitely like the idea of two and support that. And I understand the value of comparison for sure. But I think it's the collaboration value that actually outweighs the comparison value because, one, you're doubling your conversations. Two, if you have two in a box that are really working together and not competing with each other, the challenge with two is you end up with two people competing. And they're kind of racing and it's like, who's better than the other? Even the way you set up the question, it felt like one's going to do better than the other and that's going to say something. I actually think.
20:47 Harry Stebbings? Is that not good? Do you not want to create that competition between team members?
20:52 Speaker 00 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 and you want scientists collaborating, you want people working together. 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 it to.
21:34 Speaker 00 That's going to give you, I think, a more positive outcome than any chaos. Because like you could have a great salesperson and a bad salesperson and bad product market fit. And the great salesperson is, he can sell anything either. And then what are you really told?
21:45 Harry Stebbings? Can I ask you, if you were a founder or a sales leader sitting above these two reps, I completely agree in terms of 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 transferal of those lessons?
22:05 Speaker 00 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 a 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. You ask 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.
22:47 Speaker 00 You typically will have some pretty good alignment at the end of what's good and what you need to tweak. 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 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 going to 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 really does help.
23:24 Harry Stebbings? Does the learning become much more challenging when you are remote?
23:28 Speaker 00 Yes, it does. It becomes more challenging because the level of conversation amongst your peers is just different.
23:36 Harry Stebbings? You mentioned the word discovery there and you mentioned like what could be done better. I think discovery universally could be done better bluntly. And you 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? Identify their three biggest problems.
23:57 Speaker 00 Yeah, I mean, I've always, if anyone that's ever worked for me that happens to be listening to this will know. I say it always comes down to discovery and deals are won and lost in discovery, right? I mean, it's very simple. You win a deal in discovery or you lose your deal in discovery. Now, you may not realize you've lost it because bad discovery leads to very long losses. Good discovery leads to very quick wins. It's a truism in my world, right? 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. If you understand what their boss cares about, you probably understand what they care about. Now, what does their boss care about?
24:42 Speaker 00 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. You 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 priorities are? Generally, you find some pretty good alignment. The next set of questions is, how is your success measured? Like, what do you care most about? And how do you know whether you're being successful or not? Next set of questions, what are you doing very well? Always start with what's going well, because people will open up and they'll talk about it. And then what could you improve? And if it's nothing, that's fine.
25:27 Speaker 00 What are things that aren't going so well and why? They'll tell you that. And then that's where you're really listening. If you were to fix those things that aren't going well, what impact would it have for you, for your business, or how you're measured? That's the question that's always missed by salespeople. They're just so happy to hear something that they think they can sell against that they move too fast. Slow it down and ask that payoff question. Because if you truly understand what their value is of solving it, then you'll have a business case. Then you'll reduce discounting in the end. Then you'll be able to build close plans and you'll actually be able to close that customer quickly. And then at the end of it, you repeat back what you heard. How would you prioritize those issues? Because you need to know what they care most about, one, two, three. And then you have the map to winning the account.
26:12 Speaker 00 You understand how to win it. If you don't have that information, if you don't understand their biggest pain points, what it means to solve them, you're probably going to be on a slow road to a closed loss in the end.
26:23 Harry Stebbings? 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 is actually their boss's priorities? How do you get the truth?
26:42 Speaker 00 Well, people will feel comfortable expressing themselves more openly if they believe that you're 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 customers, 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. If that resonates with them, you're on the track to issue identification.
27:25 Speaker 00 And it gets them to open up because they feel, 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? Tell me more about that. And then all of a sudden, you're off and on your way. Those things called insight discovery openers is give them something that shows connection, understanding, empathy, and people do open up.
27:45 Harry Stebbings? I agree with you in terms of empathy and people opening up. I always think kind of vulnerability breeds vulnerability. I'm always quite open to sharing the challenges of my life. The hard thing is also just urgency. You said there about kind of good discovery can lead to actually good sales cycles. How do you create urgency in a sales process? Because it is fricking hard to move the ball down the field.
28:06 Speaker 00 It's really hard. I mean, yeah, like 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, 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.
28:48 Speaker 00 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.
29:14 Harry Stebbings? Does that mean you can only create urgency if you sell a painkiller and not a vitamin?
29:18 Speaker 00 It's a lot harder when you're selling vitamins. You could do it and then it comes down to really understanding what their goals are and what achievement of whatever it is you're giving them helps them achieve as opposed to pain reduction. But at the end of the day, it is going to be a lot harder. Then it comes down to budget, it comes down to process, it becomes down to really understanding how they move the deal forward and holding them accountable to a timeline that they set out early on. You don't have the economics behind you, but you have a timeline and a process and an agreed upon process. And that's hard because that slips all the time.
29:50 Harry Stebbings? Matt, you're a mentor to so many. I get a lot of heads of sales calling me and they just say, Harry, just every CFO is running budget today. And regardless of whether 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?
30:18 Speaker 00 Yeah, well, I'd start 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. So I think it's a falsehood to say my CFO is gonna 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.
31:02 Speaker 00 One of the things I always tell my team is keep your eye on the CFO. You have to get this to their desk in front of them and understand what they care about.
31:09 Harry Stebbings? 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?
31:23 Speaker 00 Well, you don't say it like that because that's gonna get you in trouble.
31:28 Speaker 00 They're upfront. 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 like approved the process or not. Okay? Being very clear about your process upfront and giving them a roadmap to how the deal's gonna progress is exactly how you bring the CFO. And then sometimes say, look, we're not gonna 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 gonna be there and you don't take it, you're just going down a long path to lead to a very unfortunate outcome.
32:11 Speaker 00 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.
32:24 Harry Stebbings? Discounting. Often CFOs come in and say, hey, Matt, love it, but I'm adding a thousand seats to 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?
32:40 Speaker 00 Yeah. 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 a hold firm. Sure, that's great. 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 even the company you're working for has a tradition and habit of discounting at the end of a 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 have to hit your number.
33:24 Speaker 00 Inevitably, you're faced with, should I discount to close or not discount to close? That's a very personal decision for the sales management team on whether to do it or not. I have discounted in the past. This is true. 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 principle, do it with guideposts, do it so it doesn't get out of control. Make sure the customer understands exactly why you're doing it. So it's defensible and you try to ring, ring it, right? Like put fence posts around it. Otherwise, it does get out of control and it's a big problem.
34:04 Harry Stebbings? Out of control is like more than 50%, more than 10%. What's like, oh, if it goes above X, they're really asking for too much.
34:13 Speaker 00 Yeah, I mean, a discount is a concession. So you could start from a place of any discount you want to contain. Because you really shouldn't discount your product if you're solving customer issues and you're pricing it appropriately, right? You know, 10 to 15% discount or more is a problem. Like, I think 10% discount is really where you want to be at all. And from there, you're looking at a slippery slope. Because 10, 15, all of a sudden becomes 30, it becomes 50, and then you're in a really bad spot. You may look at the root causes for why you're discounting in the first place. It's usually a process issue. It's usually a product issue or a pricing issue.
34:49 Harry Stebbings? In terms of process that you mentioned there, you said a brilliant thing to me earlier. You said, "Let the data speak and guide your process." It was a bit of a cliffhanger, honestly, Matt. I was wondering what you meant by that. Can you unpack that for me and how it? It's your thinking.
35:04 Speaker 00 Yeah, I mean, there's a lot of ways to use data. My job as a sales leader is to make everybody wildly successful. Like what I will tell my teams when they join me is like, my job is to get you set up for the next best job. So my job is to develop your talent and make you incredible at what you do. To be incredible at what you do, you have to understand the data of every single person in your organization. Because if you're understanding what that process is and where the gaps are in their process, the data will tell you that. It will tell you, for example, a sales rep is really struggling with discovery. They're losing at a much higher rate in the discovery motion than another rep. Boom, I'm in there, I'm helping them, I'm diagnosing the issue, I'm getting them out of that hole onto success.
35:50 Speaker 00 The average time to close, win rate, loss rate, average transaction. Like data is telling you a million stories about your team. Your job then is to figure out, how do I coach and develop talents? They could overcome those roadblocks to become wildly successful. Data will also tell you your sales process as a whole. Is it working? Is it not working? Where do we slow down? Where can we speed up? What's happening on pricing? Am I discounting? Am I not discounting? Am I up-selling, cross-selling, expanding? Data will tell you all of that. It'll even tell you your sales motion. Where do I invest my time? For example, I'm a big believer in connecting dots on data to be able to prospect efficiently and effectively. An example, at Compass, a company I was at prior to coming to Grammarly, all real estate data is public.
36:33 Speaker 00 So you could see every real estate agent, when they did a transaction on the other side, who the other person was on the other side. I could understand the person on their side who was a prospect. I could see into their data and understand their volume. Was their business increasing? Was it decreasing? I could then ask my customer, did they enjoy working with this prospect? And were they willing to make an introduction to that prospect? I could do that all the background with data. If the answer was yes, in Salesforce, those operatives would be surface to my sales team. So they would know exactly who to go after. So these are all different varying degrees of how to use data. But at the end of the day, data, if you're a great CRO or
37:15 Speaker 00 a great revenue leader, use it. It's your friend. It'll guide your team, your process, and your individuals to success.
37:22 Harry Stebbings? 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.
37:29 Speaker 00 No, it has not done well. If you just check my LinkedIn messages, 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. I got a cold email from the CEO of Grammarly, and the CEO of Grammarly reached out to me with a very precise message around 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, that's a very interesting approach. I understand what they're looking for. I believe there's a good conversation to be had. I picked up the phone and here
38:11 Speaker 00 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 on the other end, do your homework at works. Where it doesn't work is what's happening today. Proliferation, 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 with, because I don't. You know, it's like, all these things that go wrong today, people are just putting back at you.
38:39 Harry Stebbings? I love that in terms of the email from the CEO. I had no idea about that. So that is like fantastic. And what also like what humility respectfully. I don't know many CEOs that will do that, quite frankly, especially not at Grammarly's scale.
38:53 Speaker 00 I loved it for so many reasons, not the least of which is the humility and the non-alpha nature of that leader to be able to be like, hey, I'm looking for assistance here. I think you're an interesting person to talk to. Well, let's have that conversation. I just loved it.
39:07 Harry Stebbings? You mentioned data and also kind of identifying upsell and expansion. Customer expansion is hot again. How do you view this? How do you think about this? And what do you think you see that others aren't mad?
39:18 Speaker 00 Yes. First of all, isn't it crazy that it wasn't TOT? Can you imagine a world where it wasn't the thing? It's always so much easier to expand and retain a customer than go get net new. But everybody, all the glory is on net new, which is fine. But anyway.
39:33 Harry Stebbings? 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.
39:48 Speaker 00 Yeah, I think that was a huge part of it. It was also how investors thought about the value of the business and was there a product market fit? And all of those things sort of led to this emphasis on net new. When you have this unbelievable opportunity with your installed 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 it all the opportunities to continue to expand it, you're missing the huge opportunity because it is all there in front of you. And by the way, those reference customers 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,
40:32 Speaker 00 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 have your discount, it ends up dissipating. That's natural, that's human, right? You want the solution more, so you'll do more to get it.
40:47 Harry Stebbings? Matt, your CRO at Grammarly. Grammarly was the ultimate PLG. It was the ultimate consumer product led, amazing wow moment scaling into enterprise. Moving from a consumer grade product to an enterprise sales led product in many respects is really hard, making that transition. What do founders not know about moving from consumer to enterprise? That you just really think they should?
41:13 Speaker 00 Everything. Like, so I've done it twice. I was at Eventbrite. Eventbrite was a Thirty million dollar product led growth company. I was brought to come in and build out enterprise motion on top of it. Granually the same. Everything about enterprise versus product led is different. Language is different. Messaging is different. Positioning is different. Customers are different. Product is different. Pricing is different. It really is a very different business. The differences have to be reconciled against the strengths of product led growth because they have to work together. There can't be cannibalization. There can't be conflict. But founders need to understand it's a very different business. It deserves different levels of staffing, different types of staffing, different capabilities from
41:56 Speaker 00 the marketing team, from the product team, from the security teams. And it's a very hard thing to do to build on top of the very successful motion. Because again, the data will guide your enterprise motion because you have a lot of data coming out of product led growth. How you use that data to build a brand new enterprise motion is going to be unique and different. How you position and market is going to be different than what you've done on the individual or consumer side. But it all again, has to work together. And so it is a very complex but achievable thing. But it is hard and founders know it's all different.
42:33 Harry Stebbings? Given the scale of just everything is different, how do you think about advising founders on when's the right time? You don't want to go too early, distract resources, distract team. But you also don't want to go too late, potentially let competitors in, leave money on the table. How do you think about the right time?
42:49 Speaker 00 Yeah, there is a point where you really understand your product led motion, where it is measured, it is calibrated, you know what dials to turn to be able to optimize spend against acquisition. You understand how to optimize retention. Your retention lifecycle motion is going to the point where you feel like you have some control. When you feel like you have some control, you'll never feel great. When you feel like you have some, that's the time. I wouldn't encourage you to wait till it's perfected, but I would encourage you to wait till you feel like you have control and visibility into the motion of the business. And then I start on the other side.
43:27 Harry Stebbings? Is there a way to test it without committing a huge amount of resources? 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.
43:42 Speaker 00 The testing happens organically, like the testing's already there. It's in the data because like, so for example, 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 3,000 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. 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 to the environment?
44:26 Speaker 00 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've just got to see it and understand her for what it is.
44:34 Harry Stebbings? I find incentive mechanisms foundational, but also really challenging. When we look at a product like Grammarly, incentives, especially in comp structure, where do they go? Because you've got a PLG motion in a lot of ways that can get it into the hands of the end user, which gets it into the enterprise in the first place. Is the sales leader can really turn that from a customer into an enterprise customer? But then CS can also do a lot in terms of upselling and expansion. How do you think about, especially in this new world of PLG to enterprise and that transition, where comp structures and incentive mechanisms should be placed?
45:10 Speaker 00 Yeah, it's a very hard one because cannibalization is the trickiest of all issues that you have to wrestle through. But remember, selling an enterprise license is very difficult and it's very different. And the product-led motion into an enterprise is very different than selling an enterprise agreement where the enterprise sanctions, supports and budgets for your solution. That deserves compensation separately. Just getting an enterprise license in an agreement and then expanding it across the whole business is difficult as well, and that deserves compensation. There are unique aspects of the same value chain start all the way Through expanding to a whole enterprise, but each of those things are different in and of themselves,
45:51 Speaker 00 complex in and of themselves, and do require a degree of specialization that warrants that kind of compensation. Does that make sense?
45:58 Harry Stebbings? No, it totally does. Why don't we do a quick fire and we can rock and roll from that? Sound good? So what sales tactics have not changed over the last five years?
46:06 Speaker 00 Uh, well, great discovery. Never changes. It's always important. That would be number one.
46:10 Harry Stebbings? What sales tactics have died a death?
46:13 Speaker 00 Yeah, cool call. Who picks up their phone? Like literally, who picks up their phone?
46:17 Harry Stebbings? What one piece of advice would you give a new sales leader today, starting a new role?
46:21 Speaker 00 My piece of advice would be, and I do this for every role, I create a very detailed list of questions. It's a question rubric for individuals, every line of leadership within the business, every function within the business, same set of 20 questions. I go and I ask the same questions over and over again to every person in the business that I can. Because what happens is it speeds up your rate of learning. There's pattern recognition that emerges. You understand strengths and weaknesses. And I think spending that time, it's painful, asking the same questions over and over again. But if you just map it out, you'll see the organization in ways that it would take probably six to nine months to see, but you can do it within 30 days.
47:02 Harry Stebbings? Penultimate one, what would you most like to change about the world of sales?
47:05 Speaker 00 I'd like to see more women in sales leadership roles. If you really want to find a great sales executive, hire a mom. Hire a mom because they know how to multitask, they know how to drive behavior, they listen, they have empathy, all of these things. I think it's very hard for women, particularly younger mothers, to be successful in this field because there is a level of alpha, there's a level of you gotta grind, you gotta put the work in. If you want to find efficiency, find a mom. They will be the most efficient people on the planet. Or dad. I don't mean to be discriminatory with moms versus dads, but find a parent, particularly a parent of young children. More stuff will get done in an eight hour block than you could imagine. That's what I'd like to see.
47:50 Harry Stebbings? Final one for you. What one company sales strategy have you most been impressed by recently?
47:55 Speaker 00 Yeah, I'm always impressed. By companies that make markets that sort of take something and make it into something that they then own. I think you'd have to look at Gong. I'm just amazed at what Gong's done. Now it's very common in my profession. Everybody records calls, everybody breaks down the calls. Every sales leader leverages the application. So kudos to them for not only creating the technology, but then creating the market, the brand, all of it. I think they've done an exceptional job.
48:21 Harry Stebbings? Matt, this has been such a joy. Thank you so much for being so flexible with my questions and I've absolutely loved it.
48:27 Speaker 00 Thank you. I am as well and it's an honor and privilege to be here. So thank you, Harry.
48:33 Harry Stebbings? You know, sometimes I can't believe podcasts are free and sometimes I just rate my own. Matt was incredible. That was such a good discussion. If you want to see more from us, of course you can on YouTube by searching for 20VC. But before we leave you today, Outreach is the only AI-powered sales execution platform that unlocks seller productivity to help sales teams efficiently create and close more pipeline. From prospecting to deal management to forecasting, their platform leverages automation and artificial intelligence to help revenue leaders increase efficiency and effectiveness of all go-to-market activities and personnel across the revenue cycle. And Outreach is the only company to offer sales engagement, revenue intelligence,
49:15 Harry Stebbings? and revenue operations functionalities in one unified platform. But don't just take my word for it. There are 6,000 companies, including Zoom, Siemens, Okta, DocuSign, and many more, who depend on Outreach to power their revenue organizations. To learn more, check them out at outreach.io. And then speaking of incredible products, I have to discuss ZoomInfo. I had Henry Shaw, the founder and CEO, on 20VC recently and ZoomInfo helps companies supercharge their revenue potential. Landing your next customer, it's really freaking hard, but it doesn't have to be. You can be more efficient. So get more efficient, close more deals with ZoomInfo's all-in-one tech stack and the world's best B2B data. Their quality data delivers the insights you need to identify the right prospects at the right time.
50:00 Harry Stebbings? Their software helps you engage those people and convert them into customers. You know the saying, people Buy from people, but people sell best when they have the best data at their fingertips. Don't just take my word for it, check them out and see why 30,000 customers and growing, including the likes of Snowflake, PayPal, Dropbox and thousands of startup and growth companies, love and use them. Head over to zoominfo.com/20vc to see for yourself and sign up for a free trial of the ZoomInfo platform.
50:30 Harry Stebbings? As always, I so appreciate all your support. I so love doing the show. Let me know what you think on Twitter at Harry Stebbings and we have an incredible episode with Guillermo Vassal on Friday.
Previous 20VC: The Services Model of Venture Capital is Broken, The Best Founders Do Need Help, The Most Important Signals to Assess When Meeting Founders & Why Kids Bring Less Happiness and More Joy with Phin Barnes @ TheGP Next 20VC: Why Great Companies are Defined by How Many Things They Say No To, Why Being First Does Not Matter & Why Market Over Traction or Team is the Most Important Thing with Guillermo Rauch, Founder & CEO @ Vercel Page updated September 29, 2026 · transcript and summary are machine-generated
