25 years of EdTech sales lessons and an $835M exit | Sean Gannon, GTMppl

Carter (00:01.487)
Hey Sean, so introduce yourself. Who are you? What do you do now? A little, a little background about yourself.

Sean Gannon (00:07.822)
So Sean Gannon, I'm an EdTech alum. I've been in EdTech for Gaffs for probably about 25 years, which is weird to say. And I was most recently at Instructure after they acquired the company I worked for, Parchment, which I was there for overall about 13 years. And I left there and started my own advisory firm called GTM PPL or GTM People.

where we focus on working with mostly ed tech companies, but just SaaS companies that need help with go to market and with a focus on sort of data generally. And so that's what I do today. And the website is gtmpeopleppl.com.

Carter (00:57.155)
Okay, perfect. And yeah, I wanted to talk about your time at Parchment slash Instructure. What over those 13 years, what were the like two or three biggest lessons you learned about scaling revenue in EdTech?

Sean Gannon (01:10.542)
It's a good question. would say, think most of all, and this also informs the work I do now, it really starts with data. For me, is any sort of competent sort of revenue organization needs to start with the data points. And the good thing about EdTech is if you think about it, it's a relatively finite market. There aren't new universities popping up every day.

I mean, there are charter schools on the K-12 side that come about, but for the most part, it's relatively static. And if you're in that market, you can really get a good look at the schools that you're going after and really target and using sort of signals in 10. I know that you recently interviewed Matt Stinson, who was a colleague of mine, and he and I built Parchment together for a time before he went over to Starbridge.

Carter (02:05.455)
Mm.

Sean Gannon (02:05.486)
And like one of the things that you know, we would talk about is like intent signals and that's really what starbridge kind of does now with like on a level that you know back when 12 years ago none of that stuff existed when we were building it so I really think that the biggest lesson at least in EdTech that I take away is data and then I think experimentation

I'm very much a proponent of bottoms up kind of organizations because I do believe that, you know, the best ideas don't necessarily come from sort of the executive team. No offense to the executive team. I was a part of it, but in many cases it comes from individuals that are trying things out. And I think it's really important for organizations to encourage that type of experimentation because that's really where, you know,

The most fun is I think people get a lot of value out of it when they come up with something that works for them. And when the company gets behind them versus like slapping them on the hand or scolding them for going outside the bounds of whatever, I think that's sort of a negative environment that you don't want to be in.

Carter (03:20.163)
Did you want people reaching out to you? Because I remember our executives at Rocket Mortgage, they would always say, yeah, send us stuff and yeah, recommend, you know, just different things. Yeah, if you're finding something new, basically anything, but no one really ever did. But so you wanted people to reach out to you if they found out something new or along the, were experimenting with things or not really.

Sean Gannon (03:39.662)
Yeah, absolutely. mean, usually it would come up in sort of discussions with sort of sales reps and stuff like, I want to try this angle. Awesome. Let's try it. And if it took, but like, here's the thing, if it doesn't work, we're going to pivot into maybe something that does or something that we established. But if it does work, you know, we're going to double down on it or we're going to expand it out to the team. We're going to share that success and share your experimentation with the broader team.

I think it's also one of the reasons why I'm insanely proud of this and Matt Stinson was a big part of it as well. The ability to keep sales reps on board for an extended period of time, we were really able to increase that. Usually 18 to 24 months is the rough average and we were around 36 months, which was really an incredible experience. It's people that are building careers and you're showing them.

sort of the trajectory and the steps that they can take to move up in an organization. And I think that's really like a key part of it as well, because you want good people to stay around. you know, I tend to think that type of experimentation as well as, and I've talked about this sort of with other folks that know me, is, you know, I want to be an invisible manager. And what I mean by that is, is like,

it's, this is going to sound like odd, but I have a theory that the best managers are individuals that want to make themselves sort of obsolete to management. Like I want to set up operational structures within the org that make my involvement in your day to day Carter. For example, if you were a sales rep working under me, like I trust you, we have these processes we follow. We don't need to talk and I don't need to check in on you on every little thing that you're doing.

So it's basically like anti-micro management. And sort of has like, you know, it has pros and cons to it, of course, but it's kind of that thing. I think the best managers are ones that almost don't want to be managers or want to make themselves obsolete, as odd as that sounds.

Carter (05:27.778)
Right.

Carter (05:46.283)
No, that makes sense. And you know, when it comes to the selling aspect, I know EdTech and higher ed is a complex sale. What's the most common deal killer reps and leaders underestimate? And then how do the best teams or your teams at Parchment Instructure, like get ahead of that and prevent those issues.

Sean Gannon (06:05.196)
Yeah, I mean, think deal killers are not listening. You know, I think, and I think going in with like preconceived notions, like I need to close this deal. Like commission breath is a real thing, which I think you've probably experienced as well. If you really want something, that people tend to be able to read that and things like that. If you go in where it's, think, you know, we're two business people trying to maybe get something done, we may have a solution that you need.

Carter (06:17.379)
Yeah.

Sean Gannon (06:34.744)
We also might not and that is okay. And I think that is, think the key, some of the best sales reps that I know go in with that sort of just general curiosity. And then like there isn't that pressure that I need to close you or I'm not gonna make my number. Like you move away from that. It also, I think enables folks to come to better deals in the end because, know, Carter, if you're like hungry for a deal, you're gonna sort of discount.

I as the prospect might be like, yeah, I know Carter needs this deal, so I'm gonna rake him over the coals on price. Versus pivoting to value, pivoting to sort of the relationship build and stepping away from it. That I think is some of the best sales reps that I've worked with have that mentality. And then there was a second part of your question which I missed. It was about what they don't do.

Carter (07:09.154)
Right.

Carter (07:28.919)
Well, no, I mean, you kind of answered it. I was just saying, are your teams preventing those issues? But I guess it would just be listening more and not being so hungry for the deal. Is that it or is there other ways that you guys would go in and prevent that from happening?

Sean Gannon (07:40.782)
Yeah, I mean, I think it's like it's so cliche. It's like Hopium, if you've heard that, like don't go into deals with kind of Hopium where you're hoping for something to come about, like go into them with and Sandler, the Sandler sales methodology. I'm a big fan of talks about this a lot. You go in with equal business stature. We're just two people. We have sort of maybe something that you want from me. I have something that maybe I want from you. Let's talk about it as equal partners.

to see if we can come to some sort of agreement. And I think it takes out sort of that being seen as a vendor is especially, I think, important in EdTech because you don't want to just be there to be like, like Sean's calling again and he wants to sell me this blah, blah, blah solution or whatever. It's like, no, I have this solution. It may be a need for you. It may not be, but that's okay. Would you like to have a meeting to discuss it? That changes it versus like,

being a vendor, like it's a death knell for a sales rep if you're thought of as a vendor. Absolute death knell with prospects because then they're going to treat you poorly, they're going to treat you negatively and I try to get sales reps to come away from that and that equal business stature mentality I think goes along.

Carter (08:58.649)
What do mean by vendor? Is that like an order taker? Is that what you're saying? Like selling some sort of commodity or coming across that way or am I not? Or not really?

Sean Gannon (09:04.621)
Equal business. Yeah, no, it's a little bit different. Equal business that you're just is like we're two business people. That's all that we are. I have a bunch of solutions that may be helpful to you. They may not be. But like what I don't want to be is like, oh, I'm going to call Sean and abuse him over the phone because I view him as a vendor, not someone who is at my level, which is which is really tough to do. And I think with young sales reps that are sort of earlier in their career,

Carter (09:25.173)
Right, right, okay.

Sean Gannon (09:33.686)
I think it's often hard to sort of get out of that mentality that like, cause you, you, technically you are a vendor, you're calling someone, you're trying to sell them, you're a vendor, but you want to approach it. Some of the best sales reps approach it as I'm a partner. Like we're going to have this type of discussion and equal business relationship. It's not going to be sort of like one way. This is going to be gives and takes on both sides.

And I think that's the key. And it's often hard to do, especially when you're dealing with like C-level, CIO level folks or, you know, provost level individuals in ed tech who are very well educated to have sort of been with these universities for, you know, possibly decades and have, you know, reputations and other things like that. But I think the best sales reps kind of, you know, push that aside and then just go, here's what our solution does. And, you know, does this meet a need? Does it not? And you go into it.

Carter (10:06.575)
Hmm.

Sean Gannon (10:30.124)
more open-minded.

Carter (10:32.719)
Yeah, that makes sense. I wanted to talk about this $835 million deal, because you said you were on the executive team, so you were a pretty big part of it, right? Like, how did that go down? Was it very secretive until the end? Anything, like what did due diligence focus on? Anything that surprised you about that, where buyers were maybe cared about something that you thought, oh, maybe this isn't as big of a deal?

Sean Gannon (10:55.982)
Yeah, so the sale to win structure, I mean, it obviously involved bankers and sort of other firms that were assisting in that process. A lot of the due diligence when you get to that stage involves around financials and then like sales velocity and things like that, just to make sure that the asset that they're buying is sort of, you know, accurate to the numbers that they have and that

It's not all of a sudden they're going to close on the deal and then all of a sudden all the pipeline disappears type of thing. So they want to, you know, basically pressure test everything to make sure that it's real. And then it involves a ton of calls and due diligence and reporting requests and other things like that. They have to go through multiple levels. And especially at a company like Parchment where, you know, we had sort of a data team that would compile it.

you know, there would be certain reports that sort of the sales or the CSM side would have to pull on a pipeline going out usually about two years in order to sort of be accurate. And there'd be like renewal pipeline and then new sales pipeline. And then that would get sort of combined with institutional level data. So they could actually like in instructors case, they wanted to compare sort of footprints between the two companies like

are we all working with BYU or in what capacity and what is their spend? Are we all working with Ohio State? You know, what is the spend and how's that spread look? And so I think that that's the other part that gets really, really complex. You usually interface with associates at like, you know, companies and banks like Goldman Sachs who are then crunching the numbers and turning them into like these crazy spreadsheets and

pivot tables and all this really fun financial stuff that I'm glad I didn't have to do and just provide the reports. But it's to make sure that all the revenue and other stuff is real and there's a full understanding to it. And then I think the more fun things is getting to meet sort of your counterparts on the other side and hear the types of questions that they ask and other things like that. And I think that can be nerve wracking as well, like, you know,

Carter (13:02.486)
okay, yeah.

Sean Gannon (13:09.996)
Most, if you think about it, any time like two executive teams come together and there's a big dog and the little dog, usually the little dog is the one where the team is kind of departing after a period of time. But I do think it's interesting to hear the people's questions, realize that they don't understand your business like someone who's been there a decade and that that's okay. And you're just coming to the table to try and make sure that you understand sort of the level of questions that they have and.

And I think that was valuable for me is in working with all these people, we all had kind of like a shorthand for like describing and everyone understood the business and how it worked. But then like you explain it to someone who's in a completely different industry, not completely different, still ed tech, like an instructor, really smart people. Um, and then I'm realizing, Ooh, yeah, no, I need to work on my, my explanations aren't like the shorthand does not translate. And I need to like take a step back and do like a 10,000 foot view.

Carter (13:49.111)
right, yeah.

Sean Gannon (14:08.95)
when talking with these folks so that they have a full understanding of our business. Because we were very different businesses. Instructure is very much a standard SaaS type business. You sign a contract, you implement, you pay them, you cut them a check. Parchment was a very different business. We still had that regular SaaS subscription type stuff, but we also had what we called a student pay model where we would sign a zero dollar contract with the university.

And then we would make money once they were live because students would order transcripts, order diplomas or things like that. And so if you think about it, for someone that's used to just like our platform costs 100K, you're going to pay us 100K versus like our platform costs zero. But then by the end of the year, we're going to make 100K because of your student orders. So a very different kind of process that was like, you know, had to be explained to them so that they had a full understanding of what they were purchasing.

Carter (15:07.917)
Yeah. And then now to fast forward to your GTM strategy consultant job at GTMP. You call it GTMPPL or GTMP people. How do you usually refer to it at GTMP people? Okay.

Sean Gannon (15:17.474)
Just GTM people, but I obviously do not own GTM P-E-O-P-L-E, so it's PPL is the name of the advisory practice, yeah.

Carter (15:23.16)
yeah.

Carter (15:29.913)
So when a company comes in and they say, need predictable pipeline, what are the first three things you diagnose and what does a big win usually look like for them?

Sean Gannon (15:39.822)
So I'd say, I mean, the first thing is usually I ask them about, and especially if it's EdTech, I usually ask them about their sort of revenue ops infrastructure and their data. Great. How do you have like institutions in your system? our sales reps enter them in as they come in as leads. Okay, that's flag number one. You you should be going to iPads and downloading that data and getting access to it. iPads is run by the National Center for Education Statistics.

which is a department in the Department of Education for the US. And then, or, you know, there's K-12, they have K-12 data there as well, which is in a separate data set called the Common Core Data. But that's really where I like to start is in like, what is the data foundation that you have? The reason for that is, and I talk about this a lot, Sixth Sense came out with, you know, a report on how people buy.

And what they found was 70 % of teams of companies today are all the way through their sales process before they even engage with sales. So what that means, what that says to me is, is people are no longer getting informed about your solutions by talking to a sales rep. They're doing their own research. They're asking, you know, chat GPT, give me all the transcript providers that are out there and a list of benefits for each. You don't see any of

But if I have a really good data foundation where I am doing nurture campaigns and I'm targeting all these different institutions, well, then I'm going to be on likely, more likely to be on that short list. And then as well, like Starbridge, think is a really great tool for intent signals. For example, that if we talked about how our LMS sucks and we hate it and we want to replace it in a board meeting. Well, then that's something that any vendor should, that is an LMS vendor.

should likely pounce on because it's showing that they're having a pain that your company could potentially solve. So I think the first thing I like to do is look at the data and then it's like the processes on top of that data and the tools on top of that data to make sure that you have a really seamless like lead to SDR, to sales, to opportunity flow, depending on sort of the size of your team. I know not all companies.

Sean Gannon (18:05.474)
have sort of a sales development rep team and then a separate sales team, but like the lead to opportunity flow and then auditing that to make sure that it is as optimized as possible is a big part of it. And then I also then will dig into, your comp plans aligned with how your sales reps are selling with your marketplace? know, do you have the right tools in place? Are you using a chat tool?

You know, is that optimized? A lot of that stuff is really like a part of it, but the core is really about the data foundation because most companies do not get that.

Carter (18:43.649)
And you're saying a lot of times with deals that close, you're saying the client or the customer, they've already, by the time a salesperson reaches out, they've already heard of the company or they kind of know like what the solutions are.

Sean Gannon (18:56.75)
Yeah, usually like what their study showed was that there's 70 % through the sale by the time they engage with vendors. So what that means to me is like previously, if I was selling a solution, I would be cold calling you, cold emailing you, I'm informing you about what we do. But for the most part, there's, you know, there's a general lack of trust with sort of sales reps, unfortunately, and it's just the nature of human psychology.

Carter (19:14.712)
Yeah.

Sean Gannon (19:26.286)
So it tells me that the way people are buying and the way companies are buying is changing, that they are doing their research way upfront. are getting a short list of companies. And in order for you to be sort of on that short list, you need to be, for lack of a better term, noise. You need to be like, hey, Carter, we have this solution or boom, this thing. And then you get on that short list. become like answer engine optimization. If you've heard that term is a big thing in AI.

where if I ask and Parchment was a sort of transcript provider, for example, but we also did diplomas and other things like that. If I said, you know, give me the top three credentialing or transcript companies out there, you know, it might pull up credly because they do badges and other things like that or are credible. And it hopefully is pulling up Parchment in there. Like you have to be on that short list is what the sort of industry trends in that study.

is telling me or you're going to be left by the wayside. It means, it also I think means for those companies that do not have their data model really well dialed in, and I think even larger companies don't have this in place, they risk being overtaken by more agile, smaller companies that do. Because now with like generA.I and agentic.ai and what you can do with LLMs and ClaudeBot and everything else that's out there,

There's some really exciting things that if you have a ton of tech debt because your sales force is 20 years old, oof, yeah, you better get that in line because your competitors are coming to eat your lunch.

Carter (21:05.335)
And I know this is at the company level, but is there any way sellers should think about? Obviously they're not, you know, they can't, they don't own the company or whatever, so they're limited in what they can do for some of this stuff. But the concept you're talking about, is there some way sellers should think about that and bring that in? I don't know, like some way to get on the short list or something like that, or not, not really.

Sean Gannon (21:26.734)
I think it's just a matter of like there's a couple of different strategies out there like it used to be a trend and I'm sure you've seen this like You see someone advertising like a white paper or company and it's like hey, here's my white paper on blah blah blah blah blah like Fill out this form and give me your email address in order to get access to it. That is an example of gated content

I think gated content with agentic AI and like you want the LLMs to all be sort of going over your website to get access to that unique data or that unique information or perspective that you have. Like scarcity used to be a play. I don't think it's a play anymore because you're just getting left out of being considered by these sites that are sort of combing the internet and looking at information and I may be going on there and

Carter (22:08.526)
Right.

Sean Gannon (22:16.162)
Like you may not know that I'm asking ChatGPT for the top transcript companies, but I am. And if ChatGPT doesn't have you down as the top transcript company, that's going to be a problem. And that means that ChatGPT has to be, you know, combing over your website, getting access to interesting content, all that other stuff so that, you know, you are properly at the top of the list when, when sort of that request comes in.

Carter (22:43.631)
Okay, yeah, that makes sense. And then final question, if you were advising a 5 to 20 million AR CEO or VP of sales, what are the top three GTM priorities for the next 90 days that you would tell them to focus on? I know you mentioned some, think, already.

Sean Gannon (22:59.16)
So I would say, I mean, again, I go back to the data thing, get your data house in order, 100%. And then, you know, make sure, I would say number two is make sure it isn't convoluted or difficult to reach out to you. It should be easy. It should be, I can fill out a form, I can chat with someone right away. Like the amount of tools that are available now that can alert someone immediately, immediacy is really key.

And especially if you're sort of a young kind of lean startup type of thing or in that five to twenty million range like you can really Response tip, but would be the word not responsivity. I don't think it's word But like the ability to be like immediately available to them for when they have an issue I think goes a long way and sort of building a solid relationship with sort of a company or someone

potentially that you're going to do business with. And so I think those two items are really key. And then as well, I would say experimentation is really, you know, I take that a lot of the tools that are available today, 10 years ago, we were writing emails on our own and then that would get filtered throughout the team. Now you can have ChatGPT write,

you know, six different versions of the same email and try them out in your outreach instance to do A-B testing, when I say A-B-C-D-E-F-G testing and see which one sort of resonates the most. And it's encourage your team members to experiment as much as possible in getting the word out there, especially if you're a younger company, because you will be surprised what works and what doesn't. And management isn't always correct in what works and what doesn't.

go back to our original sort of topic of conversation, some of the best ideas come from, you know, folks that are on the ground floor and in the trenches doing hard work.

Carter (25:01.839)
I'm curious, do you find that to be common or is it usually a company will use one email template and then it's working and they just keep doing that over and over and over again and don't change it very much?

Sean Gannon (25:11.822)
Um, I think it's people are changing it. I think a lot now because of like chat GPT and Claude and all the different tools that are available out there where you can get different versions of that email. I think the key is, is to sort of, know, it's still person to person. Like, you know, no one likes getting that email where it's like, Sean, I saw you were here five years ago and you did this.

Carter (25:37.807)
Right

Sean Gannon (25:38.826)
Or like they take something that you posted on LinkedIn, which is super common, like, I saw that you did this or that you posted about this recently. Like that feels kind of contrived and fake and to a certain extent. I do really think it's about sort of using psychology and then obviously not writing gigantic long emails, but really being to the point about, I have a solution that could work for you. This is what we do. Boom, boom, boom. Would you like to meet or discuss? Does this resonate?

Etc and then you know move on to the next one next one and try different variations of it I think it's really about the experimentation and there are clearly like Templates or styles that that work that are that are sort of built on psychology that should be sort of adopted by sales teams I feel so but that's what I would say

Carter (26:31.929)
Alright, well good. Well, I'll end it here. I think this turned out pretty good. I think the people got some good info here.

Sean Gannon (26:38.999)
Good, hope so. was a Carter was super nice talking to you and I appreciate you reaching out and talking to me about this. It was fun.

Carter (26:48.173)
Most definitely. Well yeah, thank you. And do you mind actually?