The Exchanges

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: “one of the big lessons is when you make that pivot, just remember why you made it”

Q Penultimate one. What would you most like to change about the world of sales?

A I'd like to see more women in sales leadership roles. If you really want to find a great sales executive, um, 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's a level of alpha, there's a level of, you got to grind, you got to 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.

AI assessment note: “I'd like to see more women in sales leadership roles.”

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 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 Does that mean you can only create urgency if you sell a painkiller and not a vitamin?

A It's a lot harder. When you're selling vitamins. 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, what achievement, and whatever it is you're giving them helps them achieve, as opposed to, you know, 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 comes 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.

AI assessment note: “It's a lot harder. When you're selling vitamins... You could do it”

Q 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?

A Um, everything. 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. Grammarly 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 be cannibalization. There can 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 the marketing team, from the product team, um, 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 do you use that data to build a brand new enterprise motion is going to be unique and different. How you position in 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, you…

AI assessment note: “Everything about enterprise versus product led is different. Language is different. Messaging is different.”

Q 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, well, 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?

A I would encourage, and again, this is why I fall probably on the other side from a lot of my peers, I would encourage a lot more flexibility than rigidity. You know, 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 of the team, and they're able to build that in a way. 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 I think what I bring to companies is a 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. 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 with a playbook that's probably 80% right, but you need it to be a hundred percent right to actually build a motion that wins repeatedly.

AI assessment note: “I would encourage a lot more flexibility than rigidity.”

Q 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, well, 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?

A I would encourage, and again, this is why I fall probably on the other side from a lot of my peers, I would encourage a lot more flexibility than rigidity. You know, 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 of the team, and they're able to build that in a way. 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 I think what I bring to companies is a 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. 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 with a playbook that's probably 80% right, but you need it to be a hundred percent right to actually build a motion that wins repeatedly.

AI assessment note: “I would encourage a lot more flexibility than rigidity.”

Q 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 upsell 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?

A 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, you know, 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, right, which is start all the way through expanding to the whole enterprise, but each of those things are different in and of themselves, complex in and of themselves, and do require A degree of specialization that warrants that kind of compensation.

AI assessment note: “each of those things are different... and do require A degree of specialization that warrants”

Q 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 upsell 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?

A 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, you know, 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, right, which is start all the way through expanding to the whole enterprise, but each of those things are different in and of themselves, complex in and of themselves, and do require A degree of specialization that warrants that kind of compensation.

AI assessment note: “require A degree of specialization that warrants that kind of compensation.”