Matt Rosenberg
Chief Revenue Officer, Grammarly. On 1 show, 1 appearance. The Shows tab opens the full record on each.
executiveoperatorgrammarly.com ↗
Matt Rosenberg is the Chief Revenue Officer and Head of Grammarly Business, overseeing enterprise growth and go-to-market strategy. He previously served as Chief Revenue Officer at Compass and Eventbrite following an early career in corporate law.
1shows
1appearances
25statements
1resolved
1supported
0contradicted
100%fully supported
Everything Matt Rosenberg said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Rosenberg: Never hire early sales leaders with big tech pedigree
“Harry, don't hire anybody from Google. Okay. Don't hire anybody that says on their LinkedIn, ex Google, ex Amazon, ex Facebook. Okay. When they put that on their LinkedIn, they're associating themselves with the success of the business. And it is almost imposs…”
Rosenberg: Hire ex-bankers or ex-consultants as your first sales leaders
“What you're looking for when hiring that sales executive is something very different. The first sales executive. And here's my point of view. You want to hire. An ex banker, an ex-consultant, an ex-lawyer. You don't even necessarily want to hire an ex-sales le…”
Rosenberg: Startup founders are too close to product to build sales playbooks
“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'…”
Rosenberg: Early sales hires should collaborate rather than compete
“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 is the response I get, what do you think? This worked for me, does it work for you? You…”
Rosenberg: Early-stage startup products never sell themselves despite founder claims
“And as much as the founder who sells you into the job says, there's product market fit, we figured it out, it's gonna be glorious, all you have to do is work, walk into the market and it'll sell itself. Well, it never does. It just never does.”
Rosenberg: Custom 20% of a Sales Playbook Determines Success
“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, th…”
Rosenberg: Early Startups Should Hire Sales Leaders Before Junior Reps
“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 buil…”
Rosenberg: Blaming a CFO for a stalled sale means you failed
“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.”
Rosenberg: Software sales discounts over 10 percent signal underlying pricing issues
“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. But I would say like, you know, 10 to 15%…”
Rosenberg: Cold calling is dead because no one answers unknown numbers
“Yeah, cold call. Who picks up their phone? Like literally, who picks up their phone?”
Matt Rosenberg: Sales is translation between buyer language and product strategy
“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 …”
Rosenberg: A startup's second sales hire must be in sales operations
“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. Th…”
Rosenberg: Early-Stage Startups Must Record and Collectively Review Every Sales Call
“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.”
Matt Rosenberg: Sales deals are won or lost during customer discovery
“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 l…”
Rosenberg: Asking payoff questions reduces discounting and speeds deal closing
“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 the value is of sol…”
Rosenberg: Reference Stories Reduce Sales Discounting by Building Urgency and Conviction
“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, You essentially create the urgency…”
Rosenberg: Enterprise sales and PLG are fundamentally different business models
“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.”
Rosenberg: Launch enterprise sales when PLG is controlled, not perfected
“There's 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 life cycle motio…”
Rosenberg: Cannibalization is the hardest issue in PLG-to-enterprise transitions
“It's a very hard one because cannibalization is the trickiest of all issues that you have to wrestle through.”
Rosenberg: Enterprise expansion stages require specialized compensation structures
“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 …”
Rosenberg: Gong executed an exceptional strategy in defining its market
“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 t…”
Rosenberg: Sales Is One of the Least Secure Performance-Driven Careers
“When you get into sales, you're probably in the least secure profession, because it really is a performance-oriented profession”
Matt Rosenberg: Grammarly's CEO recruited me via a cold email
“I actually came to Grammarly in the most unusual ways. I got a email, a cold email from the CEO of Grammarly, and the CEO of Grammarly reached out to me with a very precise message. His interest in talking to me Because of a number of different reasons based o…”
One line per show, most statements first. The link opens Matt's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
 20VCLEDGER | Chief Revenue Officer, Grammarly | 1 | 25 | 100% 1/1 | full record on 20VC → |