Unlock Cloud Go-to-Market

"Internal buy-in is the hardest part – and the most important - when building a cloud marketplace strategy that lasts."

In this episode of Unlock Cloud Go-To-Market, host Patrick Riley sits down with Corey Woodburn, Head of Cloud Marketplace Alliances at Grammarly, for a behind the scenes look at what it really takes to launch and scale a marketplace motion inside a fast-moving org. Dropped into a project no one officially owned, Corey shares how she turned an initiative into a cross-functional success story.

This conversation unpacks the human side of building cloud go-to-market, navigating early-stage ambiguity, crafting internal narratives that win support, and scaling seller enablement with limited resources. With insights from Corey, as well as Tackle’s Dan Callahan, you’ll get a practical, battle-tested perspective on marketplace success.

In this episode, you’ll learn:
  • How to secure internal buy-in before you even talk tooling.
  • Why documentation—not dashboards—is the secret weapon to alignment.
  • What it takes to scale marketplace listings without scaling chaos.
Resources:
Connect with Corey on LinkedIn: https://www.linkedin.com/in/coreytw/
Connect with Dan on LinkedIn: https://www.linkedin.com/in/daniel-callahan-27692411b/
Connect with Patrick on LinkedIn: https://www.linkedin.com/in/patrickmriley/
Learn more about Tackle: https://tackle.io

Timestamps:

(00:00) Introduction
(00:59) Grammarly's marketplace journey
(02:47) The initial challenges and getting started
(04:58) Building internal buy-in and overcoming hurdles
(07:06) Creating a comprehensive plan
(10:34) The role of marketing and cross-functional collaboration
(14:57) Lessons learned and future strategies
(22:20) Connecting with other ISVs
(22:54) Executing the Plan
(23:27) Cory's approach to Tackle
(25:15) Sales enablement strategies
(27:38) Educating the sales team
(33:45) Building the business case for Tackle
(38:40) Lightning Round

What is Unlock Cloud Go-to-Market?

How do I implement my go-to-market strategy with my Cloud Partners? How do I get buy-in from my executives, sales team, and others in my organization? How can I get the right attention from the Cloud Providers?

Questions like these, and many more, arise when you’re trying to build relationships with the Cloud Providers and accelerate your revenue journey through the cloud. Welcome to ‘Unlock Cloud Go-to-Market,’ the series where hosts Erin Figer and Patrick Riley share the essential stages of the Cloud GTM maturity model to start, optimize, and grow your company’s revenue through the cloud. They’ve helped countless ISVs tackle the ins and outs of their Cloud GTM motion, and in each episode, they're sharing those success stories from the people who have put them into place. Because ultimately, this way of thinking is the future. And the future is now.

[00:00:00] Corey Woodburn: once you're set up with marketplace. A lot of things get so much easier. People wanna pay their AWS bills like You kind of have to, and so that means we don't have to own collections, which I love. Welcome to Unlock Cloud Go To Market, the podcast where we deliver actionable insights from ISVs, partners, thought leaders, and cloud providers to help you launch, scale, and succeed in your cloud go to market journey. Whether you're building your first motion, fine tuning your strategy, or aiming to maximize revenue, this show brings you the stories, strategies, and lessons learned.
From the people driving innovation in the cloud ecosystem. Each episode cuts through the noise with candid conversations and proven tactics that you can apply right away because the future of cloud B2B success is here and the time to unlock it is now.
Hey everybody, and welcome to another episode of Unlock Cloud. Go to Market with Tackle. I'm your host, Patrick Riley. Today I'm joined by some special guests, including the new Marketplace master of Grammarly. which I use in my email every day, and otherwise, uh, my language skills would be severely diminished.
[00:01:11] Patrick Riley: So, Cory Woodburn, head of Cloud Alliances, at Grammarly. Welcome, Cory. How are you?
[00:01:17] Corey Woodburn: Doing well. Thank you so much for having me here today. Very excited Patrick.
[00:01:20] Patrick Riley: Yes, we are excited as well, and you are the first guest to have a cooler background than me, so kudos to you. I think we should give out an award for that. I've also got Dan Callahan with me, our, tackles Enterprise ae Dan, welcome. I'm glad to have you on.
[00:01:35] Dan Callahan: Patrick. Excited to be here.
[00:01:36] Patrick Riley: You are the first AE on the call.
[00:01:38] Patrick Riley: So you've made a lot of folks jealous today to be on this podcast. So, uh, don't let your, your peers down.
[00:01:44] Dan Callahan: And we'll let you guys down.
[00:01:46] Patrick Riley: All right? So, for everybody listening. If this is your first time, the goal of the podcast and the aim of today is really to, uh, spotlight, uh, an ISV who is at, either the beginning stages of cloud go to market and really, figuring it out and still kind of doing some lessons learned. Folks that are kind of right in the middle. Of maturity and they've gone through the, uh, you know, early learning curves and, felt a lot of those, those initial challenges started to see some success. And then those who are really at scale. And so today we're gonna talk to Grammarly. They are kind of on the front end of this. Really going to provide some really cool context and feedback around how they got their go to market going. We'll talk about internal buy-in. Corey's gonna kind of take us on that journey on literally being dropped into a project that nobody's signed up for, to starting to see some initial success, and really, uh, looking forward to, to continuing that and going to scale. So that's what we're gonna do today. We're gonna talk to Corey and break it down. but that being said, Corey, let's start off with you. at the very beginning, you all, had marketplace as this maybe project, maybe it was a priority. Maybe it wasn't a priority. Some folks wanted to do it, other folks didn't wanna do it, and then there's you and all of a sudden somebody's like, Corey, go figure this out. Can you talk to us a little bit about what that looked like, how this fell into your lap and why that got started?
[00:03:08] Corey Woodburn: We had kind of a weird start to this and, and we've kind of had to figure out how to get on the track, so to speak. Grammarly is a very strong AWS customer. Our infrastructure is hosted there.
[00:03:17] Corey Woodburn: so in light of some conversations with them, it came up to our CRO, that we probably should be on the marketplace and Amazon kind of had approached us about that. and at the time we didn't have. Anyone that it should really sit with. It kind of is this weird in-between. and our CRO was talking to, head of channel resellers at the time and was like, Hey, if somebody from your team wants to take this on, like vet it, find out about it.
[00:03:41] Corey Woodburn: It's kind of interesting. and my manager at the time, we were just getting started. We had started with the channel motion, and that's. You know, where we were starting, so to speak. and I was kind of a little bit of an oddball on my team. I come from a solutions partners background, customer success partner, success, really program building, not so much reseller.
[00:03:59] Corey Woodburn: And he is like, Hey, your partner's not doing great. Here's this weird thing that we were kind of offered. Do you want it? I did a little bit of research, and I said, yes, please, like I am, I am so tired of difficult resellers. I would much rather bite off a massive project. And so that's kind of how it came to me.
[00:04:18] Corey Woodburn: I didn't know what I didn't know. I did a little bit of research into like the broader market. I knew marketplaces were important. I've done some work with marketplaces, but really didn't understand what it took to go live on AWS, Which is for the better. I don't know if I would've jumped in quite the way I did if I had known how hard it would be.
[00:04:37] Corey Woodburn: but yeah, that's kind of how we got started. I definitely didn't have support from leadership and there was nobody being like, yes, we have to get live by this state. We didn't have a customer pushing us. It was just kind of like this side thing that happened to line up with, things that were going on with my partners.
[00:04:54] Corey Woodburn: And like, if they hadn't struggled, I probably wouldn't be doing marketplace.
[00:04:58] Patrick Riley: Well, I wanna get into the internal buy-in in a minute, but I, I do wanna ask Dan, because I think that he's gonna have an interesting perspective. We've never had. On the podcast, Dan, you're looking at Grammarly, they're a prospect account. what were you hearing maybe from AWS, was there any indication that this was a priority?
[00:05:14] Patrick Riley: That, could you validate that they really didn't have any buy-in? Like what did this level of effort look like for you on the outside?
[00:05:21] Dan Callahan: I think anytime it's a category creator. AWS is super excited about the company and I think all of us know Grammarly, even if we don't even know what they do, we know the name. I was like, man, that is a logo. That one needs to be selling with AWS two. I personally wanna make sure we land.
[00:05:40] Dan Callahan: Right. And so In the sense of like, yes, we knew AWS was leaned in there. Absolutely. And I was hearing that just from conversations I'd had with AWS, but I was unaware that Grammarly didn't have top-down buy-in around it until obviously with with co team.
[00:05:56] Patrick Riley: So I totally sympathize Corey with where you're at. We've got AWS who really wants you to do something. You've got internal teams who have no idea what this is maybe, or maybe they do and it's not a priority because there's no clear value. ROI like there's not a if this then that. there's you. Who's already doing another job and then is told, Hey, go figure this out and this is what we're gonna go work on. that was me five years ago at Dell. totally sympathize with, with what you're seeing. Exact same scenario, but, I kind of failed to, to get the bigger internal buy-in you know, there's a number of challenges with that, every org or every ISV that wants to come into marketplace, really needs to have internal buy-in.
[00:06:41] Patrick Riley: I think everybody knows that, that's listening to this. you had to go focus on this maybe part-time with all your other duties. How did you start to. Figure out, Hey, I need to build a plan to go get this internal buy-in. I need to start to do some things. Like, what did that look like for you? Was there a plan or was it kind of like, I'm figuring that this out as I go?
[00:07:00] Patrick Riley: And, and how did you handle getting the CRO and leadership involved in that?
[00:07:06] Corey Woodburn: we'll talk about all the things that worked, but it's funny looking back on the first couple months, 'cause to your point Patrick, I'd actually say we had some touch and go moments and like almost. Early failures early on and things where I'm like, oh yeah, I totally did it.
[00:07:17] Corey Woodburn: And then you're like, oh no, like that integration, it's gonna require 25 people, 50 hours of work. Like I didn't know what I didn't know. and so I think almost thinking we had things done and then realizing, I don't know a lot of what's going on here, really made me step back and realize like, okay, this is gonna involve.
[00:07:36] Corey Woodburn: A lot of people, a lot of time and people kind of think they understand what's going on, but they don't actually know that much about marketplaces. And so I need to figure out a really, really easy way to educate people, on the marketplace, on how we fit in the marketplace, why we're doing this. and so something that happened that,
[00:07:57] Corey Woodburn: I'm in partnerships and so like building a coalition and like getting people to want to do things for with you and, and showing them the value to them is like, comes very naturally to me. and is something that, you know, I was actively thinking about and prioritizing. but ultimately one of the resources that like really took off, and kind of is one of the things I wanna talk about today was we actually.
[00:08:19] Corey Woodburn: Built, and by we, I mean me with a little bit of feedback from my marketing counterpart, built this document, that was massive. But I listed everyone I was working with and every team shared every link, explained what marketplace was, and then had a section of considerations and things that we've done.
[00:08:37] Corey Woodburn: because what we figured out is like. People, once they heard it and understood it and understood how it fit with them, were like, oh, I'm happy to help, but you need to talk to tax first. You need to talk to finance first, you to work with billing. there's all these legal questions, and tax questions and finance questions that come up before you can even begin to think about selling on AWS.
[00:08:58] Corey Woodburn: And so what we did was actually like, list out here's why we should be on Marketplace and here's some of the conversations we've already had. And then if you go back to the top of that document, here's specifically the people I talk to so you can feel comfortable like, okay, actually somebody very senior and legal has signed off.
[00:09:13] Corey Woodburn: I'm allowed to look at just my slice of the pie and be really excited to help Corey with just this and not worry about all these other things. 'cause I trust that she's got it on lock, that worked really, really well for us. And what was interesting with that plan, my marketing manager and I, especially towards the end, it was a lot of marketing folks that really helped make a big difference for us.
[00:09:35] Corey Woodburn: and we'd go to a stakeholder and we'd send this over in advance, give it kind of as a pre-read, and they'd read through it and be like, okay, actually this is so cool. I'm so excited. We're doing this campaign, we're doing that campaign. What I found out later is that people I was working with, as soon as we got them bought in, would actually send this document to other teams.
[00:09:54] Corey Woodburn: And so by the end I actually had like product marketing coming to me and being like, Hey, I see that your launch date is on this day. I think it's gonna cause problems with insert product launch. Like can we work together to make sure that the moment we go live on AWS you have the latest, greatest brand new products?
[00:10:11] Corey Woodburn: and so it was really cool to kind of see this very. Odd, very stripped down document, end up being effective enough that it kind of expanded, like even beyond my immediate reach. it was really, really helpful in helping people understand and also helping get people excited and trusting that we were doing our due diligence across all of these different components, if that makes sense.
[00:10:34] Patrick Riley: It's so cool that you had marketing, as the. Champion, if you will. I'll use like Dan, uh, sales speak. Like they, they were the champions for marketplace. They were helping you drive this across the other parts of the org, it's usually just the alliances person, or in some cases companies have to hire. A third party, they use tackle a lot of times to help try and do that. Or they have an internal, like we had a transformation team that we had to pay internally to try and figure that out. So it's neat to hear marketing was the person who had your back. when you approach these other teams with, Hey, we've already talked to, legal or trade or whoever, how did you get them to see. Marketplace as a win. Like aside from the hey, we're prepped and ready to go. How did you convince them that this was going to be worth its effort, for their time? Like what was the ROI statement?
[00:11:28] Corey Woodburn: I always try to adjust that ROI statement to whatever the stakeholder cares about. and honestly for us, the engineering justification, I did have to get leadership buy-in for that. And that was a little bit of a different process and like. Writing out financial justification to be honest, but with tax and legal and finance, it was a lot of education for them, both about like what is the upfront investment and making sure we were really clear on what we were asking for them, as well as the benefits.
[00:11:58] Corey Woodburn: Because really once you're set up with marketplace. A lot of things get so much easier. People wanna pay their AWS bills like You kind of have to, and so that means we don't have to own collections, which I love. We're not gonna get pressured to do super custom MSAs and some of these things like, Hey, I've already gone through this process to get us.
[00:12:20] Corey Woodburn: technically security and financially cleared with Amazon, that's gonna help us like jump over some of these barriers that you're generally facing that become an absolute nightmare at the end of the quarter. And so we had like our big. Rocks of big benefits for marketplaces. And then whenever we'd go in and meet with someone, we'd have like benefits to their team more specifically.
[00:12:42] Corey Woodburn: And again, we usually had already done something that would make their life a little bit easier if marketplace were to be turned on effectively. and so they were trusting that we were good stewards of the business. We wanted to collaborate, we were coming to them before anything was urgent. And I'd also say.
[00:12:58] Corey Woodburn: Even if I didn't know exactly what the project would be, I'd start talking to people really, really early to be like, Hey, just so you know, this is coming down the pike next quarter, we're gonna have to align on these things. Here's what we're gonna ask. Can't wait to talk to you next month. and so people felt like this was a much bigger project than it really was.
[00:13:17] Corey Woodburn: 'cause again, a lot of people touched it, but at the end of the day, like. It's, what does Corey Woodburn think? the project felt bigger than I think it really was. and that was a PR strategy on my part.
[00:13:27] Patrick Riley: It's kinda like you were starting your own business. I feel like you have the, a very good sales methodology, mindset, I mean, you took it internally like you were selling externally. I have to have a different message for each stakeholder. I have to make sure I've outlined kind of that clear ROI and what I've already done just to, you know, get them to buy in. Dan, how often do you see that kind of mindset, that self-starter Does that make or break the success of this route to market in your opinion?
[00:13:56] Dan Callahan: I think our approach to this was unique and it's, it's why they've been able to be so successful.
[00:14:02] Patrick Riley: Excuse.
[00:14:03] Dan Callahan: and set up correctly. we call it a champion, like you said, Patrick, there's a difference between a coach and a champion. a coach is the person that maybe tells you what to go do.
[00:14:12] Dan Callahan: The champion's the one that goes and gets stuff done. I think that Corey just really kind of exemplified that it's not as common as you'd like it to be for sure.
[00:14:21] Patrick Riley: maybe speaking too much here, but a lot of times we're having to build, build those champions and then go deliver. maybe it's more we're building up coaches and then we have to champion for them internally. So having somebody I. is inside the organization. Actually trying to do that actively for their company is huge. it's definitely necessary at, at some point everybody gets there, but it's a matter of do I have the time to dedicate to this and do I actually get it? And it sounds like that you actually understood, Corey, what you were getting into from a value perspective. Maybe not the, all the activities I have to go check off this list. it's cool perspective.
[00:14:58] Corey Woodburn: Yeah. I'd also say too, to your earlier point, like I kind of halfway understood and we kind of halfway did it and it failed. And that's when it was like, okay, smarter or not harder, like this document sounds like it was super hard to put together. It wasn't. And by having it, everything else got easier.
[00:15:15] Corey Woodburn: And so I realized with Amazon, like it was a wound that was never gonna heal and like the bleeding would never be staunch or like we were gonna sit down and just do it. Right. and I saw the opportunity for me, I saw the value for Grammarly and so I was really excited to be like, okay, buckle up, we're doing it.
[00:15:32] Corey Woodburn: And it really took me deciding that to make it happen. you can do that. You can just decide. now it's a thing that I own and I'm responsible for marketplace strategy.
[00:15:41] Patrick Riley: for those listening, they've heard you, that you created a doc, it's got FAQs, you had cross-functional contacts, you had your information on the marketplace. it was shareable in your org. You used it for advocacy, you used it for buy-in. people would come to you as the subject matter expert. we talked about already that like your internal sales piece, it was more of like, this is the guiding document for us to get started. what do you envision the future of that tracker?
[00:16:10] Patrick Riley: That piece being.
[00:16:11] Corey Woodburn: I will spoil the secret. We have templatized this. so again, if you wanna see this, you can see it. We've, I've done what I can to anonymize some things. And again, some of it's outta date now. and it's funny, there's like an enshrined version of the document that was like when we launched what it looked like.
[00:16:25] Corey Woodburn: there's kind of a new version of it, and we're, we're updating and I'm getting closer to, what do we'd call a partner plan, which is how Grammarly, like consistently across our organization, showcases our partnerships and how those work. I have fit into that. Now again, like I'm not doing the same level of advocacy.
[00:16:41] Corey Woodburn: but I do think that once we start probably doing a couple more technical integrations and I'm, doing the road show, I will absolutely be going back to this template and using it again. It helped a lot.
[00:16:53] Dan Callahan: one of the blockers we typically see on the sales side is that there's not a lot of cross-functional buy-in. You know, usually there's a couple teams like, like you called out earlier, tax or finance, that just don't quite get it. so I think just how proactive you were here really helped solve that.
[00:17:08] Patrick Riley: Corey, uh, you wouldn't believe the amount of times Dan him and the other sellers are asking for, you know, tacklers to come have a conversation with tax teams, finance teams, legal teams, because our internal coaches, the ISVs who were selling to just haven't got to that step yet.
[00:17:24] Patrick Riley: And that sounds like something you did almost first. what made you. get to those folks early. Like was there, was it just like happenstance or was there a, a plan on like, this is probably where I need to start.
[00:17:36] Corey Woodburn: Yeah, so again, I would say I got humbled really quickly by the process of going live and I, I really did think I had things together and I realized like. We are so very far away. and I think that like splash of cold water made me like really sit down and kind of figure things out. again, I have a success background.
[00:17:54] Corey Woodburn: I've worked with customers, I've worked on big, big, big platform implementations, and so realizing I was out of my water and like, okay, what are the big buckets of things I need to get done? What are people that are successful? What have they done? What are the weird edge cases with Grammarly and what's going on in our business that slow down deals?
[00:18:12] Corey Woodburn: I did sit down and kind of map out all of the big things we were gonna need to do in order to actually go live. it's funny, where I spent the most time and what was the hardest for me was actually engineering. And it was just 'cause those resources are really difficult to get allotted and.
[00:18:27] Corey Woodburn: I think I'm pretty technical for a non-technical person. we were so far above my head it was hard versus like, I'm not a tax expert, but I can understand different countries have different laws and I become prepared with what I knew. Here's what we have from Amazon, and so I.
[00:18:45] Corey Woodburn: Again, I didn't wanna look unprepared, I didn't want to get caught off guard by anything. by putting together the teams that we needed early, even if it was just a, Hey, just so you know, once we've talked to finance, we're gonna come back to you tax. Get on the same page, but you're gonna be my contact and I'm gonna put you on the sheet.
[00:19:04] Corey Woodburn: Are you cool with that? that really helped. And so, yeah, it really was systematic and again, giving people notice early and controlling what I could control, was really, really essential and being successful for this.
[00:19:18] Patrick Riley: we talked about the internal buy-in and you just talked about the listing and kind of those lessons learned on how to get there. What we didn't talk about was how long it took to get your first listing up, and then your second one. Do you remember how long it took you to get your first listing up and running?
[00:19:32] Corey Woodburn: I'm painfully aware. and I'd say we had multiple failed attempts. Like, there were several times where I really thought we had everything ready and we didn't. so in total, from like me actually starting the project and like trying to work towards listing our first list listing took us 10 months.
[00:19:47] Corey Woodburn: and I would say it was a very full 10 months to make that happen. and it's interesting talking to people. I've, I've heard that's actually not. That long of a timeline, especially considering it was me and a little bit of help from somebody on the marketing team. there's so much that we learned, that actually a couple months ago I was approached by my leadership.
[00:20:06] Corey Woodburn: They were like, Grammarly for education time is now, sorry. Strategies changed. We gotta get it listed. so I called my BFF Dan and was like, Hey. We're doing it. and between the lessons we'd learned and the help of tackle and specifically the platform, like the tackle platform saved me from just the day that we decided we were going to try to go live to going live or submitting everything to Amazon to go live was 18 days.
[00:20:35] Corey Woodburn: versus 10 months. And I will tell you that 18 days was busy, I knew what I needed to do and it was all within my skillset. So, it's shocking the difference between those two listings.
[00:20:45] Patrick Riley: And a lot of that had to do with one, the experience you had from that first go around all the failed attempt sites. So like I think a lot of people, when they start out, they wanna skip over a lot of those pains, which, uh, absolutely you should. But if you have already tried it and now you don't wanna make another attempt at it because of all those failures, I think that's a good story on, hey, actually use that experience, but also use this new education.
[00:21:10] Patrick Riley: Then you can go get help. You don't have to go do this on your own. and that help can speed that process up by and a half months. But you had great documentation. So like, it's not like, we did it all on our own. You were the ones who put all that together and what that looks like. you had the systems kind of, and the learning on that first go around and obviously it's a huge time difference. Somebody listening, they're trying to figure out, Hey, maybe I just did this once and now my CROs or, or my product team's, like, Hey, I gotta put this other product up. scratching my head, or maybe I haven't done this at all yet. What's one or two things you think are the most important for them to take away from, from your lessons?
[00:21:51] Corey Woodburn: first I would say figure out. What has changed since the last time you listed? So things change on marketplace constantly.
[00:22:02] Corey Woodburn: And so like there's new processes, like things that I did that were terrible now are really easy. There's new things like just kind of do a little bit of research to understand what's changed and under that category, I'm gonna cheat and like shoehorn something else in there, talk to other people that have done it.
[00:22:20] Corey Woodburn: There's so much value in talking to other ISVs, other alliance managers just talk to some people and like a little bit of it is commiseration, but it's also like, no, you really can do this. And the second thing I do is like when it was my time to do this, I sat down and I wrote same thing. We went through the whole document.
[00:22:39] Corey Woodburn: I wrote down, okay, what do I actually need to do? And I will tell you that actually was kind of a useless exercise because like if you have tackled the answer is like, open up your app and like look at all the fields you have to fill in. which is great. And so regardless, whatever tool, platform, whatever you're doing, just make a list of all the things you think you need to do and see what's missing and like what, over the course of a week.
[00:23:04] Corey Woodburn: And as you start socializing with people, you realize you're missing. Then just execute on that plan and do your best to not get distracted by all of the other random stuff that comes up or is really distracting
[00:23:17] Corey Woodburn: during that process. And like, you just gotta keep going. You just gotta keep going. but trust that that second time is gonna be so much easier, like night and day difference for us.
[00:23:27] Patrick Riley: Dan, what was the difference for you when Cory approached you with, Hey, this is what I've done already. Here's how long it took me. now I need tackle's help. I'm sure that was exciting, from a, a sales perspective, but like what did you see as a true differentiator in how Cory approached tackle, from a readiness perspective versus how, you know, somebody else might come with background?
[00:23:51] Dan Callahan: I think a lot of is the experience she'd already had. So we, we weren't or starting to build internal biome. We already had it. I mean, even on our first couple calls, we had Corey, we had leadership, we had everyone going, do this, let's do it better. how do we maximize this strategy rather than how do we get started? and I think that was obviously. groundwork that she laid. And I think originally Corey came to me about how do we automate this? just like, let's get another listing up. It was more about, this is cool and everything, I'm in the weeds now. I'm in the trenches doing data entry and these things I don't want to do, how, how can tackle come and help us automate this?
[00:24:33] Dan Callahan: So that was kind of the genesis of the discussion. And then we were like, well, it's also pretty easy to throw up some listings too, so let's get some more products up.
[00:24:40] Patrick Riley: Nice. So value realization was top of mind. You're forward thinking on, we already need to start to scale this. but when you look at, and you break out like successful ISVs in the marketplace, the internal buy-in and getting, all the internal teams. Aligned, getting your tooling quote to cash, everything ready for that transformative to market, route. is step number one then comes, okay, now I've got people that have to sell this and I have to change how they think about this, and I need to make sure my sellers actually understand what we're doing. So when you start to think step number two, which is. How do we optimize our listing for buyers?
[00:25:23] Patrick Riley: How do we optimize our sales team to understand marketplace? what was the plan of attack you had for getting sales involved in this process? thinking about not only the, how to get opportunities through the marketplace, but also co-sell. What did that look like in the beginning when you started that?
[00:25:40] Corey Woodburn: I think it's. you've never arrived with this. And I, I knew that from the start. And so it was, how do we start small? Like what is the MVP version of this, and then how do we grow it to. We can help you with every single deal. and so from the very beginning it's been really helpful to have Dan, 'cause he is like, Corey, sales enablement so important.
[00:26:01] Corey Woodburn: And I was like, dude, I couldn't agree more. Let me show you what we're doing and please add to it. And so what I would say is even before we were live on Amazon, like at least six weeks out. We have a meeting called Launchpad at Grammarly with our full sales teams every week.
[00:26:16] Corey Woodburn: And like I would show up and start talking. And so as soon as we could technically co-sell with a WSI was beginning to do like bite-size education snippets. I'll also say we did a co-selling with AWS session right before we launched. and we brought Amazon in to co-sell with us and like kind of teach my sales team a little bit.
[00:26:34] Corey Woodburn: That was a 20 minute session and like it was super helpful. We recorded it. Those resources, like I still get very frequent replay on it. It was like. 2% of my team paid attention and like retention was very low. So like one training's not gonna solve the problem. and I'd say we've kind of just done bite-sized pieces since then.
[00:26:54] Corey Woodburn: So we actually launched with like our main primary tackle integration this week, live in our sales force, like. It's the best week of my life. I'm so excited. but even with that, like I started working with our enablement team in February to say, Hey, this is coming. Like this is an implementation we're doing.
[00:27:11] Corey Woodburn: This should change our sales. Cycles and our sales processes. So I need to be working with the people that control our sales cycles and our sales processes and fit into what they're doing. and so that influenced, okay, how do we set up the Salesforce pages? How do we, when do we slide this information in?
[00:27:28] Corey Woodburn: And so, I just presented this week and I think, again, really keeping front of mind. Who are you talking to and what do they care about is really helpful. My sellers are not experts on Amazon and they're not even experts on cloud marketplaces. And so the first thing I do with those sessions before, it's like, here's how to cement an NACE opportunity with tackle.
[00:27:48] Corey Woodburn: Like that's what I need to teach them. But the real thing is, is like cloud marketplaces are coming and they're here to stay and they're not going away. And so our first two slides were like. Hey, here's what cloud commitments look like over the last five years. We're crossing that 500 billion line this year.
[00:28:05] Corey Woodburn: If you haven't sold a marketplace deal, it is coming. It is coming. This is what your customers are doing. And so giving them the business context of like, oh, okay. What's going on? Where does this fit? How does this help my deals? And then we can get to the tactical, Hey, go submit your five opportunities with tackle and like co-sell with Corey and then use all the junk that we've shared over the last six months.
[00:28:31] Corey Woodburn: Like we have to show them why do you care? How do I make your life easier? and starting from that place has really helped the adoption of the resources that I've actually built, if that makes sense.
[00:28:42] Dan Callahan: I gotta add something there. Prior to tackle, I heard the word SaaS, but I didn't really know what it meant. that's the case for a lot of sellers is they know their product that they're selling, but they don't really know that their product is built somewhere or hosted in a specific cloud, not even know what that means. so I think Corey, just how you approached your seller enablement, just to give them the understanding of the. Really, the ecosystem builds the right foundation.
[00:29:12] Corey Woodburn: Yeah, we, before we can get to how do we sell with AWS, I think just doing education on what are cloud marketplaces, because again, I didn't know. And even once I started learning, I didn't even fully understand. and it's interesting. I think so many people also are like cloud commitments.
[00:29:30] Corey Woodburn: It's these PPAs EDPs free money. And like, yeah, that is true, but that's not really why we're gonna see this big shift. And so it's this, education piece. Again, our sales teams are like, free money. Free money. They love that. That's not gonna be most of your deals. We're gonna have a couple of those. And so explaining like that, that spectrum of, hey, this is really helpful for your absolutely biggest monster clients that are spending hundreds of millions.
[00:29:59] Corey Woodburn: But on the other end, like we've automated procurement, security, billing, this is really helpful for SMBs. and so we've actually found a lot of success in, in transacting and helping and working with small to mid-market businesses. On the marketplace. Like that's where I've seen a change in how I'm doing business or like where I'm focusing on deals.
[00:30:21] Corey Woodburn: and of course we're looking at PPAs, of course we're collaborating on these monster deals, but it's a lot of these small ones that I think are gonna end up being the difference. And like Amazon has a serious value prop. For businesses at all stages of development and that are making, you know, all different sizes of revenue.
[00:30:39] Corey Woodburn: so yeah, like there's the education piece. It's not the seller's fault. They don't know, but how do I invite them and get them excited about learning more has been a big part of my job, I feel like.
[00:30:49] Patrick Riley: you can't tell a seller something once that's, how is that true? sales has so much stuff on their plate, right? Because every quarter operations makes changes to something that they're doing. How they're supposed to file contracts, what documents they need to use, what tools they need to use for that within Salesforce, what buttons do I have to change?
[00:31:07] Patrick Riley: And then you've got the whole sales side of things where they're talking through. Now we're changing our sales methodologies, or we should be asking this question. And you've got product coming to them with, these are our new product feature updates. And like, there's so much coming in, it's uh, you made a good point earlier. This has to be repeated and recycled. Dan mentioned, it's, it's important to also make sure you not only talk about the operational activities that they need to do, but yes. What is this space that we're in? and it's funny, even a, a lot of other companies that just do co-sell or just do marketplace listings. There's not a lot, there's a education gap in like, if I only do co-sell, like what is marketplace and listings, or if I only do listings, like what is co-sell. So this whole space, this cloud go to market ecosystem space is still so new. There's really not a ton of subject matter experts out there to, to help go through that.
[00:32:00] Patrick Riley: So it's, it's a good thing to bring up. Dan, I had a follow up for you. You've been spending a lot of time, obviously, with Corey and Grammarly this over the last year. from your perspective outside of just the sales enablement, what stands out most to you on, how they've approached go to market differently and been successful with it?
[00:32:23] Patrick Riley: Is there any other keys to success that you wanna share that you've seen, that might be different from other ISVs?
[00:32:28] Dan Callahan: I think kind of how we started off just getting internal buy-in the way that Corey did for sure. But I think how she's really approached. enablement of sellers is gonna be absolutely key to their success. I wanna flesh that out 'cause I know Patrick, you said outside of that, but I think there's components of that that have made it different. And it's because Corey's focus has been, make it easy for them. ask them to do too much and remind them about it often as a seller. Great. I heard a great, cool presentation about a new thing. Well, I get that every week and I have tons of calls on my calendar all the time. Right. And so being reminded about is super important.
[00:33:07] Dan Callahan: And then don't make me do too much. Don't add a ton of med pick fields to my sales force and then make me fill em out. You know what I mean? Like, these are things that we just don't want to have to do. And so think Corey's just done a great job of, of simplifying it making the actual process of doing marketplace easy for her sellers.
[00:33:27] Patrick Riley: So Corey, you,you all are still kind of in your beginning stages. There's a ton more we could talk about operationally, but I want to talk about kind of what's next on your cloud, go-to-market journey, maybe public sector, some competencies, et cetera. But before I do that selfish kind of shameless plug. useful for me to understand. How did you build that internal business case for tackle? what was your message to leadership on, hey, this Dan Callahan fellow is someone we should trust. Uh, he's got something we need. Like what was that business case and how did you approach it? I.
[00:33:58] Corey Woodburn: it was interesting, what I'd say is like, once I kind of got educated on how uneducated I was, I sat down with teams and was like, okay, what do I need?
[00:34:05] Corey Woodburn: Like, what do I need? In 18 months to be running a successful practice and like a CRM integration is a non-negotiable. and so as soon as I really understood that, I went to my leadership and was like, Hey, if we don't have this. Here's what is not going to happen. Like all these exciting things that we want, we can't do any of that without these things.
[00:34:28] Corey Woodburn: and I gave them some examples and kind of some feedback that I've gotten from other ISVs. I also talked to Amazon, so okay, if this is required. How would you advise I go about this? What have you seen work? and I had a really good relationship with my PDM and they gave me some great advice on building your own connection.
[00:34:45] Corey Woodburn: Some, some vendors that I should work with. different things like that. And I, from the very beginning, I was fortunate that our, our executive sponsor, Matt Rosenberg, he's our CRO, he's great, kind of who started this project too, actually came to a team offsite and we had the opportunity to present our partnerships and, you know, what our needs were.
[00:35:03] Corey Woodburn: And so I was very far ahead of when we potentially needed this. I did our initial launch by myself, I would advise. Getting help earlier. I wanna be very clear on that. But I was kind of where I was at and I knew that I would be making this ask at a very specific time. I highlighted to Rosenberg the pain I was feeling today because we didn't have an integration.
[00:35:26] Corey Woodburn: the opportunities we were going to miss out on and the scale, that we'd miss out on without. You know, this an integration and I put a dollar amount on what I thought it would cost. and I'd already done a little bit of research. and so again, I talked to a number of vendors, but it's really, really interesting.
[00:35:43] Corey Woodburn: I would say from day one, tackle was our preferred vendor. And there's a few reasons for that, but my favorite one, I don't even think I've told you this, Dan. I talked to my like vp, my manager, like three or four different people, and I was like, Hey, here's the vendors I wanna connect with and, you know, I'm gonna reach out to their sales teams this week.
[00:36:05] Corey Woodburn: Here's how I'm gonna go about vetting them, getting, pricing, all these different things. And everyone I talked to said, oh, we're connected with the taco seller on LinkedIn. Like he pings me once a month. Like, I'll introduce you to Dan. Everyone knew Tackle. Everyone knew Dan.
[00:36:20] Corey Woodburn: Everyone was excited to introduce me to Dan. and as someone who gets a lot of follow up. I can think of like one or two salespeople's emails. So Dan, you did a great job of connecting with folks. It was super easy for me we had a very good trusting relationship from the beginning and I was able to meet with Dan, talk about where I was at, and we figured out a plan, from a sales cycle perspective and an implementation schedule that like really did work for both of us.
[00:36:47] Corey Woodburn: And it's not just t and i, it's, it's Tackle and Grammarly. And I really felt like I had a partner. From our first meeting,
[00:36:53] Corey Woodburn: great kept secret, the amount of money that Tackle has helped us get pays largely for this program. And so it's interesting. I actually got new leadership. I received new leadership after.
[00:37:07] Corey Woodburn: We had purchased tackle, and I laid out like what we were doing, how much it costs, the funding, like all of these different things. And the person I was with was like, wait, wait, wait. You're telling me you get 10 K when you go live with this and then you get 10 K again when you list it? And that alone makes up x percent of our annual commitment with them.
[00:37:26] Corey Woodburn: And I was like, yeah, most of this funds itself. I look like a genius at that point, which helps. And again, it's like, no, like you guys did a good job educating me. I have a great partner development manager at Amazon and I really try to stay on top of the programs. So between like Dan and I, we got it figured out.
[00:37:44] Corey Woodburn: I'm already thinking about justifying the budget for next year. 'cause like, I can't live without this tool or we're not gonna have a scaling Amazon partnership without the support of tackle. It's just not gonna happen.
[00:37:57] Patrick Riley: Corey Grammarly is obviously not stopping here. So what's next on your your go to market journey?
[00:38:02] Corey Woodburn: So much. Grammarly actually bought another product, uh, and we are making some big changes on the product side, As we figure out, go to market, figuring out cloud go to market at that same time is really exciting. So that overarches everything. but we're learning to work with the AWS public sector team, continuing to evaluate other marketplaces.
[00:38:22] Corey Woodburn: We are working on competencies right now as well. and yeah, really just excited to figure out how to work with our sales team to help, you know, marketplaces help all of their sales, and then also generate new business. So kind of what you would expect.
[00:38:35] Patrick Riley: Awesome. we've never done this one before, so you're gonna be our first guest. A
[00:38:39] Corey Woodburn: Okay.
[00:38:39] Patrick Riley: today. we're gonna do a quick lightning round. I've got some pre-filled out questions. I'm gonna skip, well, I'm not gonna skip one of them 'cause we already know the answer to it, but everybody will get a chuckle when they hear it. so Corey, I'm gonna set you up for five questions
[00:38:51] Corey Woodburn: Yep.
[00:38:51] Patrick Riley: wrap it up and get you outta here.
[00:38:53] Patrick Riley: Okay. So what has been your favorite use case somebody's told you about for Grammarly?
[00:38:59] Corey Woodburn: People love Grammarly, which always makes it fun to talk about. My favorite, though is when somebody who's dyslexic tells me how much grammarly means to them, because as someone who is a really good writer. And struggles with dyslexia like Grammarly saved my life. Like it makes things so much better. So that one's always my favorite and I'm always excited to get to talk to folks, about what a life-changing tool it is.
[00:39:25] Patrick Riley: Cool. That's a great use case. If you could automate one part of this cloud go to market process forever, what would it be?
[00:39:32] Corey Woodburn: I hate submitting opportunities in Ace. Like I have spent hours every week. so that is my number one, which is why we bought tackle. So,
[00:39:41] Patrick Riley: who's your favorite tackle teammate to Bug when you need help?
[00:39:44] Corey Woodburn: Oh man, Dan's the man. Uh, calm sometimes gets pings from me, but, when I have a question that I don't wanna ask or I feel dumb, always Dan.
[00:39:53] Dan Callahan: Fill in the blank. Cloud, go to market. Is
[00:39:56] Corey Woodburn: here to stay
[00:39:57] Corey Woodburn: Okay. And then last question, one thing you wish you knew when you started this journey. That's a hard, short lightning question.
[00:40:03] Corey Woodburn: No one knows what they're doing. I just took a cloud marketplace class, and I was shocked how much. Better we were doing than other people. Like, not to sound rude, but everyone's figuring it out live. Everyone's testing templates, everyone's testing different strategies. So, even if you're at the very beginning, you're not that far behind other people, and it's a really exciting opportunity.
[00:40:26] Corey Woodburn: So no one has it all figured out at this point.
[00:40:30] Patrick Riley: Corey, you've been incredible. Thanks for, uh, doing that with us, Dan. Awesome to have you first AE on the call on the podcast. if you wanna know more about Grammarly, uh, go to grammarly.com. You can also look up Corey Woodburn LinkedIn, head of Cloud Marketplace Alliances at Grammarly. Follow her and her journey on there. Uh, if you wanna learn more about Marketplace Journeys, email Dan Callahan or go to the, tackle.io website and subscribe, to our Unlocked Cloud Go To Market podcast. Thank you, Corey. Thank you Dan. Uh, really appreciate you making time to do this.
[00:41:06] Dan Callahan: Of course use Grammarly and take it through the marketplace.
[00:41:09] Corey Woodburn: Yeah, go buy Grammarly on Marketplace.
[00:41:12] Patrick Riley: Thanks everybody. Thanks for watching another episode of Unlock Cloud Go To Market. I'm your host, Patrick Riley. Until next time.
[00:41:17] Corey Woodburn:
Thanks for listening to this episode of unlock cloud go to market.
For more resources on executing your cloud go to market strategy, you can visit our website at tackle. io.