Orange background with two circular headshots, one of the host Michelle Hawley and the second of the guest of CMO Circle, Lena Waters CMO of Grammarly
Interview

CMO Circle: Inside Grammarly’s Leap From Consumers to Enterprises

10 minute read
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How Grammarly is making the leap from consumers to enterprises with AI-powered communication and a B2B marketing strategy that keeps it human and engaging.

The Gist

  • Early Influence. When expanding into the enterprise market, it’s essential to shape audience perception early on to drive long-term demand.
  • Brand Consistency. One key to multi-audience success is maintaining a unified voice across both consumer and enterprise markets.
  • Marketing Balance. Enterprises are still run by humans. Avoid stiff B2B messaging — keep it engaging and authentic.

Grammarly isn’t just about catching typos anymore. In this episode of CMSWire’s The CMO Circle, Lena Waters, chief marketing officer at Grammarly, breaks down how the brand is making the leap from individual users to enterprise giants.

Waters shares insights into frictionless enterprise adoption, how AI-driven communication is changing the way businesses operate and why the best B2B marketing still speaks to people — not just companies. 

Table of Contents

Transcript

Michelle Hawley:  Hi Lena, how are you doing?

Lena Waters: Hi Michelle, good, thanks for having me. How are you?

Michelle: Yeah, it's great to have you here. I'm doing pretty good too. I know there are some big changes going on at Grammarly right now, so let's jump right into it. Grammarly has historically been a consumer brand. I've used it in the past, but now you're shifting towards enterprise buyers. So what inspired that pivot and why now?

Lena: Well, thanks for being a customer, Michelle. I think selling to businesses was a really obvious fit for us. We've seen users succeed professionally. I'm not sure how you used us, maybe personally, but maybe for work. But we saw this really big opportunity to expand into the enterprise. And when we started talking to organizations, we could see that the demand was really clearly there, even if they weren't necessarily looking for something like that at the time. But we know now that Grammarly really is the best solution for them.

When you look at the consumer side, we've got about 40 million daily active users who are finding Grammarly to be really indispensable. And we started hearing that we're the most requested tool at work. And so a lot of forward-looking companies are starting to realize that they need this kind of solution and they need it at scale.

And as we know and we experience every day, there are a lot of AI tools swirling around out there. New things are popping up every day, new functionality. But it makes something like Grammarly become even much more needed.

For most companies, it's really hard to incorporate all of this new AI functionality into their team's work on a day-to-day basis in a way that's realistic to adopt and that's easy and reliable. We have a cross-functional committee at Grammarly that explores how we pilot and experiment with AI tools. So we're actually seeing firsthand how overwhelming the AI landscape is for businesses. And Grammarly has really just stood out because it's such a positive and constructive tool.

And so, you know, I think the reality of work right now is that communication is happening everywhere on all different surfaces and people need tools that work across all of the surfaces. And so I think this AI future that we're evolving towards is fantastic, but we also need solutions that meet people where they're at today in tools that they already use. And that's what really led the drive towards enterprise.

Related Article: CMO Circle: The New Rules of Marketing in 2025

The Challenges of Transitioning From Consumer to Enterprise

Michelle: So you've been making that shift over to enterprise customers or incorporating both groups that you're trying to market to. What were the biggest challenges that have popped up so far?

Lena: Yeah, and it's really both. I mean, people were experiencing us, you know, sort of, you know, bottoms up as they say, so buying us for themselves through the website or buying us for a small team. The tops down was interesting and going to work in that, you know, the experience is really different.

When you buy online or buy for yourself or through a PLG motion, you try out the product and you convince yourself that you find value and then you buy it. And as you know, when you're selling to an enterprise, you're really convincing an organization and a group of decision makers that they'll find value and then the people start using it. And so it's trickier to make sure that you're really conveying that value early on to enterprises and that they understand the outcomes that they're going to achieve while not really losing that love that people have for the brand.

I think it really helps that Grammarly is so easy to try and to adopt and that when we deploy it within an enterprise, it just turns on. So you literally have a one-day implementation timeframe. And so it was easier, I think, for us to be able to position the brand to enterprises because they were able to try it for themselves right away. You don't have to go through this huge enterprise implementation, which sometimes creates that gap between your consumer and your enterprise experience.

Crafting Messages That Capture Two Different Audiences

Michelle: So when it comes to creating campaigns or messaging for these enterprise buyers, how do you still craft messaging that resonates with your individual users?

Lena:  Yeah, it's a great question. And I know a lot of companies find this tricky to appeal to both. I think when you look at a company's business model, it's easy to talk about the consumer business and the enterprise business and the fact that they are different. You usually have a growth team and a sales team and you support them differently. The ads and content are different.

But I think the reality is that a lot of these people that we bucket into consumers are actually taking us with them to work or to school. So they're using us within an organization. I mean, people are not using Grammarly because it's entertainment. You don't go in there to use it. You use it to write or to communicate better. And they're using it because they want to accomplish outcomes and companies also need to accomplish outcomes. So it's really just two sides of the same coin.

And so the way we like to think of it here is that, you know, we don't try not to separate out too much the consumer and the enterprise funnel. I think on the contrary, we're really trying to join them. It has to be based around the customer and their journey. Because some people are starting with us in school or college, some of them at work. So it's not just that they're different businesses, but the customers are at different spots of their journey.

And so our job is to really meet them where they are. And at the end of the day, people are people no matter what, and they want to get that same value out of it. So you're trying to appeal to the outcomes and make sure that it makes sense if they're going to get it for their entire department or their company.

So you take a company, say like Databricks, who invested in scaling across marketing, sales, CX, support, finance, IT, engineering, legal. They've gotten almost to like a 2000% ROI because they're really ensuring that on-brand communication and cutting out that cost of miscommunication.

And so this journey from individual to a widespread enterprise use case like that sometimes can flow naturally, but sometimes it might be an individual use case, an individual or the whole company. Really people are getting the same sort of positive outcomes from that. So what we found is that as long as we are being clear on the outcomes, the value proposition really translates well across both.

Related Article: CMO Circle: From Classroom to C-Suite With Jonathan Copulsky

Applying Old Lessons to New Markets 

Michelle: So you mentioned these groups are pretty closely related, how you market to them because of the nature of the tool. But with your success in the consumer space, what lessons have you learned there that you've taken over to the enterprise side?

Lena: I think that the importance of thinking about how we focus on brand has been really important. It's really critical to create the market and drive that perception that Grammarly is for work, no matter how you're using us.

Learning Opportunities

People can use us as an individual user. Sometimes it's for work, for school. Sometimes we're capturing that demand just a little bit later down the funnel, which is true no matter how we're marketing too. You know, when you think about the funnel, the top is the biggest, it's where most of your audience is. So it's really important to be shaping the audience's perception and getting on their radar from day one and helping them understand how they're going to find value.

And so I think sometimes the difference is that people will look at the wide part of the funnel and go widespread for consumer. And then when they go to enterprise, they start thinking about leads and only going further down in the funnel. But it's important even in enterprise marketing to keep that consumer hat on. Make sure that you're thinking about shaping the market and the audience perception not missing that chance to create real buying intent early on and really be part of that day one consideration set.

Standing Out in the Crowded AI Space

Michelle: You had mentioned about all the AI tools that are out there in the space now. There's a lot of noise, especially for enterprise users. Vendors are promising everything under the sun. So with that in mind, how do you stand out then in the enterprise space?

Lena: Well, we've got this sort of winning combination of product market fit and brand affinity and fortunately, customer love. There's a lot of trust and a personal feeling in the brand that really carries through no matter how customers are using us. I think that's really critical.

People recognize big enterprise names, but you can't just rely on being aware of the brand. Getting genuine user affection almost is a huge growth driver for us. People like the way the product works, how it makes them feel. It's sort of a trusted advisor and partner, even if you're using it in an enterprise setting, you still get this very individual experience.

A Grammarly customer is going to feel like the platform really understands them and helps them show up as the best version of themselves. And they really love that personalization. It's really sitting on their shoulder, understanding the nuances of communicating with different audiences and waiting to provide useful advice.

And so it's really had this multiplier effect across organizations where, you know, if we can make sure that the product continuously delivers on helping people feel good about their experience and their accomplishing outcomes, it really, it really helps us stand out amongst other tools that may be useful, may solve a problem, may even accomplish an actual outcome, but it doesn't have that persona of being that trusted advisor.

Future Opportunities for Enterprise Marketing 


Michelle: So as you move forward with the strategy and you continue to market to enterprise customers, are there any opportunities that you can think of that you're really excited about?

Lena: Well, recently you may have heard that Grammarly acquired the company Coda. So we're really excited about that.

You know, I think that the two companies have approached productivity from different but really complementary angles. Grammarly of course built this AI assistant that helps you communicate everywhere you work across all of your surfaces. But Coda's really defined what a modern workspace looks like. And you know, as we got together, we found that we were both seeing the future the same, that AI and humans are really going to need to work together.

And so you think about this 15 years of AI experience that Grammarly brings, this infrastructure at a really massive scale and we process 200 billion words daily. And we've got this trust from all of these daily users that we have. And Coda is now bringing these really cutting-edge AI features like access to reliable real-time company insights.

And so, you know, I'm excited in the future that it's going to enable us to really build this productivity platform that brings this vision to life, that there'll be smarter assistance everywhere that's powered by your immediate context, but also your broader company knowledge. So it's really AI assistance that works wherever you work. And it's enhanced by that deep context and the understanding of your actual workflow.

Related Article: CMO Circle: Personalization as the Ultimate Business Game-Changer

Advice for Marketers Making the Same Transition


Michelle: I want to ask one more question before we go. And I wanted to know if you have any advice for marketers that are on a similar journey where they're moving from the consumer space to the enterprise plus consumer space.

Lena: Well, you know, I'd say that I think we all recognize that a lot of B2B marketing can be a little stiff and formal. And honestly, sometimes it can be a little boring. I think we tend to load up enterprise and B2B communications with a lot of formal language.

You know, somehow we have this belief that you have to become very official when you're talking to the company. But I think it's important that we keep in mind that the people who use our product and make the decisions are still human. And your brand needs to connect with them and appeal to them on a human level. So it doesn't mean you have to go too hard on the other side of the scale and be unprofessional, but you do have to stay authentic and creative.

So I would say remember that you're building connections with people. You're not building connections with personas or functions or account names. So that brand trust and affinity are still really important. And I think sometimes this is difficult because marketing leaders often face internal resistance to brand investment because it's viewed as being harder to measure the immediate ROI.

So I think it's really incumbent on us as marketing leaders to understand that that hesitance, making sure that you're paying attention to how a brand is perceived and that you're really shaping that in the market that that needs resources and time and attention because we all know that strong brands lift companies over time.

Michelle: Yeah, I think that's great advice. Well, thank you so much for being here today, Lena. It was great talking with you.

Lena: Thanks so much, Michelle. I appreciate it.

About the Author
Michelle Hawley

Michelle Hawley is an experienced journalist who specializes in reporting on the impact of technology on society. As editorial director at Simpler Media Group, she oversees the day-to-day operations of VKTR, covering the world of enterprise AI and managing a network of contributing writers. She's also the host of CMSWire's CMO Circle and co-host of CMSWire's CX Decoded. With an MFA in creative writing and background in both news and marketing, she offers unique insights on the topics of tech disruption, corporate responsibility, changing AI legislation and more. She currently resides in Pennsylvania with her husband and two dogs. Connect with Michelle Hawley:

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