👑 Keep calm, carry on
Kaylee re-lives her first-ever enterprise deal!
As an early sales hire at a growing startup, she took the reigns from a founder-led sales motion & built. Trail-blazing the next phase of the company.
Kaylee had to take an inverse multi-threaded approach to close this one & even had to overcome executive buyer turnover mid-deal. How did she do it? Hear how:
Guest Feature
Kaylee Chappelow is a Mid-Market AE at Greenhouse Software.
She has served as an enterprise AE & an Account Manager role in the past. Navigating a company acquisition along the way.
She’s also running her own side-hustle, Crash KC, where she gives a crash course on adulting for post-grads and young adults.
What problem does Greenhouse Software solve?
Greenhouse helps companies keep track of all of their recruiting efforts in one place.
Schedule candidates, send them their offer letters, and even onboard them. They’re the recruiting engine behind a lot of companies.
Deal details
What are you selling?
- Software to help product teams
Where did the prospect come from?
- Scrapped together a target account list from past closed-lost opportunities.
- Wild west in terms of territory, due to founder-led sales process.
Company type
- 700 employees, $300M in revenue. Big fish in Kansas City market.
Prospecting method
- LinkedIn outreach. Also brought her founder in to connect with the prospect founder
- We call that a ‘peer-to-peer prospecting’ play.
Barriers to Overcome
- Very technical product, a lot of lift to get up & running
- The prospect brought in a new COO (buyer) mid-deal. Threw off the timeline.
Buyer type
- Decision Maker: Chief Operating Officer
- End users: Product team
Episode Highlights
Note: timestamps correlate with the full conversation
Prospecting: ‘Inverse multi-threading’ with Kaylee’s founder (6:21)
Discovery: Always lead with WHY for more impact (10:43)
Demo: Selling to buyers & end users on the same demo (14:04)
3 Tips for Account Executives
1. Leverage internal executive relationships.
It takes vulnerability to admit you need help but pays off in the long run.
2. Always be thinking about “WIIFM” (What's in it for me).
Align the problems you solve with each buyer's business initiatives.
3. Stay calm & trust in your champion relationship.
Being creative to get a deal across the line takes guts.
Watch the full conversation
Full transcript
Taylor Dahlem
Welcome back to How I Deal, where we discuss past closed one and lost deals, how they ended up that way, and provide some real actionable sales tips that at Account Executives and really any full cycle seller can use today. My name is Taylor Dahlem, former Account Executive turned full-time content guy, and I'm joined as always by my partner in crime, Junior Lartey. How's it going, man?
Junior Lartey
Good, yeah. It's episode eight. So episode seven, as I mentioned last time, is like the death date for podcasts. They typically don't make most podcasts don't make it past episode seven. We're here at eight, so we're moving along, we're making friends and we're not going away. So that's great news.
Taylor Dahlem
Still chugging along a quick refresh each conversation that we have here on how I deal. We want to chat through a past deal, all names, places we want to anonymize fictionalize, whatever we can do to protect the people that are involved in this. But at the same time we want to dive deep. We want to understand from the first time this individual has stumbled upon may be on LinkedIn or through some prospecting tool, all the way to that close deal. At close one, where did you get the final signature? And this one's going to be a really good conversation.
Junior Lartey
Today we've got Kailey Chappelow. She's mid-market Ae at Greenhouse Software. She is also running her own side hustle. Right? A lot of negativity around the word hustle, but yes, she runs a side hustle. Sometimes you need it where she gives a crash course on adulting for postcards, postgrads and young adults. Kaylee, we can vouch for your side hustle because you're so well put together. We've been chatting for a little while and you've got this amazing deal that we're going to talk through, so we'll vouch for you throughout the podcast. Thanks for joining.
Kaylee Chappelow
Yeah, thanks so much for having me. I feel like there's this pressure to be really good for number eight to keep you guys going. So I'm ready.
Junior Lartey
Yes. If this is a success, we'll get to a number nine for sure. Kaylee, give us some insights into your role and what problems Greenhouse solves.
Kaylee Chappelow
Yeah, sure. So like you mentioned, I'm an account executive at Greenhouse and what Greenhouse is doing is solving a really big problem in the HR space. So if you think about the talent war right now and bringing people into your company, it's really difficult. Like seventy percent of people who are being recruited aren't actually looking for a job. So we help companies keep track of all of their recruiting efforts in one place so they can schedule candidates, talk with them, send them their offer letters, and even onboard them into their company to make sure that they are bringing in the best talent because people really are the engine behind any company. So that's what we're doing at Greenhouse. It's a lot of fun.
Taylor Dahlem
Awesome. Appreciate the quick pitch. I know it's one of those things. Nobody likes talking about their own companies and what they're solving, but it's a real problem. Like you said, there's a talent war, there's a lot of layoffs, but at the same time a lot of new hiring happens. So anyway, you can make that easier is a huge benefit to your customers and potential prospects. But yeah, awesome. Let's just dive in. Kailey, what deal are you walking us through today?
Kaylee Chappelow
Yeah, so I'm going to be walking you through my first-ever enterprise deal and some background. This actually was my first sale I closed. So I was actually thrown into enterprise sales as my first sales job at a small tech startup company here in Kansas City where I'm from. There's really lots of funds, twists and turns in this deal, so I hope that you guys will get a lot out of it today. And just some background on the company. It was a seven-hundred-person company, around three hundred million in revenue. So nice. Large fish.
Taylor Dahlem
Very large, yes. Especially being your first enterprise deal, I'm sure you learned a ton and we'll talk about that, but let's just kick things off. How did you go about initially researching this deal or maybe stumbling upon the account itself and then yeah, let's start at the start.
Kaylee Chappelow
Yeah, so because we were at a startup and we were really primarily found or selling, I didn't have a lot of to work with from a CRM perspective. So I was like scraping away and trying to figure out who we've talked to in the past and who would be a good fit, who was on my target list. And I ran across this specific company and I saw that it was a good deal. There seemed to be a need, there just seemed to be a lack of communication, frankly, on our side because our founder obviously was juggling a lot of balls at one time.
Junior Lartey
Kaylee, were you at all afraid to reach out to some of these old opportunities where there was a previous conversation and there was a no deal? Did you have any hesitation there?
Kaylee Chappelow
A little bit, especially because I was newer to the space and I didn't have all the information so I didn't know if maybe there wasn't a product market fit or maybe there was something that had happened there. But that's the beauty of sales, right? You have to put your fears aside and go for it. So I figured if I'm going to go into this not only my first sales role but my first enterprise sales role, I've got to really look at all the nooks and crannies to find all of the gold possible and really run with those deals.
Junior Lartey
I love that. And I'm sure this was not the only company in that old ops list that you reached out to. “Just for all of our listeners, did anyone respond and say no, Kaylee, screw you?”
Kaylee Chappelow
“I'm so pissed you reached out.” no one was angry. I was doing my own outreach. So of course you get the cold calls that go a little awry, and people are like, Why are you calling me? I didn't talk to you. I'm like, Wow, this is awkward. But no one was aggressive, which was good.
Junior Lartey
Yeah, I think that's so key because you have all these old opportunities that someone in your sales work has talked to somebody somewhere. Right. And we call those old goals old gold. Like, old opportunities to go through. And a lot of times there can be hesitation in reaching out there because there was a conversation that you clearly weren't a part of. But in my experience in reaching out to those people, they're very kind and nobody is ever like, what the heck? Don't ever reach out to me again because there was a conversation. So consider it. Go to the old ops if you haven't. How did you go about getting in front of this specific prospect?
Kaylee Chappelow
Yeah, I mean, it kind of goes off what you even just said. When you bring a new face to the deal, it also gives you an opportunity and that's like, normal to be reaching out. Of course they're going to be asking if they can follow up because they weren't a part of old conversations. So I did my own reach out via LinkedIn in a soft way. But what I really focused on was the executive-level relationship that had already been built from our founder and their executive member. So I actually asked our CEO, hey, can you reach out CEO to CEO and have this conversation? Let him know that we're now building a sales team and you'd like to introduce us to have a conversation. So that's how I ended up getting in front of this specific customer.
Junior Lartey
So you're like running side-by-side campaigns almost where it used to be founder-led sales, and your founder had reached out and you asked them to reach out again. Meanwhile, you're also prospecting the same person, right?
Kaylee Chappelow
Right, totally.
Junior Lartey
Okay, we're going to call that inverse multi-threading. Multi-threading is when, like, I reach out to the VP of Sales and the Director of sales and the CEO. This is two people from your company reaching out to the same person. We're going to call that inverse multi-threading. I created it today, so don't Google it because you won't find it.
Kaylee Chappelow
Can I start using the term at least since I was in action? Is that fine?
Junior Lartey
Yes, I think we should let's coin it.
Taylor Dahlem
We'll put together some episode eight.
Kaylee Chappelow
This is all of the good things.
Taylor Dahlem
Here, and I would even go as far Junior and tell me if maybe this tracks. But even the concept that we talk about all the time, which is like peer-to-peer prospecting, somebody on the same level as you, or maybe same background, same title, whatever it might be, but it's just that concept of, hey, we're alike in this way. I'm sure you have these problems. I'd love to start this conversation.
Junior Lartey
One thing I love about this too is a lot of times at lots of companies, the VP of Sales was a former account executive, right? So they have those old goals, those old ops that are sitting there. So you can ask your VP of Sales, hey, I know that you reached out to Google. Can you reach out to them again? I also reach out to the other two hundred and fifty thousand employees at Google and then maybe down the line there's a conversation there. But consider getting whoever previously had conversations, get them involved as well. Totally.
Kaylee Chappelow
Yes.
Taylor Dahlem
Kaylee, a lot of moving pieces. You've got the prospecting side of things down, you've got an inverse multithreaded conversation. But every department hires at some point, I'm sure discovery, it sounds like there's a lot of potential for it to be a mess or to go really well. What did that look like on your end in particular with these conversations and what did you learn?
Kaylee Chappelow
Yeah, that's a really good question. So I feel like because we've had a conversation with them in the past, it was really important for me to nail down what their real business needs were and why they didn't buy in the first place. I found out it was more of a timing issue because they hadn't started the project and they were a little bit farther out. So I'm really glad I followed up because I don't know what would have happened if we would have missed this sweet spot of a window. So what I learned was they had a really big need. They were spending hours and hours and hours doing manual work. They also had this tied directly to a business initiative within the company. So this wasn't just like a small project in this specific department. This was tied to the overall goals of the entire company. So they had the buy-in already to obviously get this problem solved. So when they are going to present software, it's like, yeah, let's do it. The other thing that I learned was just having executive buy-in. So that's really important is understanding how decision processes are made, especially in this market where decisions are going to be made slower and maybe a little bit more delicately. So that also really helps, discovering that and asking those questions to figure out, hey, who else do we need to get on board and are they on board with who we are and what we offer?
Junior Lartey
I wanted to jump back. Oh, go ahead, Taylor.
Taylor Dahlem
I was going to ask in the discovery process in Junior, I'm sure hopefully this doesn't trample on what you were going to ask, but maybe what are some favorite types of questions that pull out some of that information? Or like, how do you structure some of that in an open-ended way to kind of get the conversation where it needs to be. Are there specific maybe examples or things you use pretty consistently question-wise?
Kaylee Chappelow
Yeah, I think the first thing that's any question is I always try to have like a sort of a softening statement so they understand why I'm asking the question because sometimes people can be a little put off and you're like, what's your timeline? When are you trying to buy who needs to be involved in this process? So one of my favorite questions and ways to frame it is, hey, I really want to support you and help you get this software so it can make your life easier. Can you talk to me about a time that you bought software in the past and what that process has looked like that allowed the field to be open and it didn't feel like I was coming at my person with targeting questions and she was able to walk me through that process. I would then listen and then ask them follow-up questions like, oh, do you have any concerns or do you foresee any issues that might come up as part of this process? Or who do you feel like really on our side? Or who do you feel like might give you a little bit of trouble when you pitch this internally? So just those questions and making sure that you're positioning it in a way that you're letting them know that ultimately you're trying to get them the solution that's going to help them solve what they're looking for.
Junior Lartey
I love that, like the one question in there and this is just you talking off the top of your head, right? I love where you said, who is on our side? Let's really map this out and figure out who have we talked to that is in favor of this project, in favor of this technology and not that everyone else is against us, but now you can start to build more than one champion and you can really pull more information from additional parties. I also noticed where you mentioned the biggest find that you found was there are hours of manual work. But you realize that's obviously not enough for any company to be like, hey, we're just going to buy tech because it's going to save us time. But you're able to find here's this technical problem that they're facing and then pull more and more out of this until you are able to get to the real problem, the real business problem, and find how do we get the impact from this technical thing that is going on across the organization. It's not an easy thing at all to do.
Kaylee Chappelow
Yeah. And I think sometimes people are our prospects aren't thinking in the sales process mindset. So they're not thinking about how is this impacting me and my business like we are. So it was like, okay, what is having all these hours taken away by this project actually causing your team. Then she was able to say, oh, we're not able to meet deadlines, and now we're getting a lot of heat from executives because we're going to be behind on this project. So, yeah, to your point, we got to the root of the problem and the impact in a way that wasn't threatening.
Taylor Dahlem
You start putting real numbers to it.
Junior Lartey
Right.
Taylor Dahlem
Like, all right, here's the problem. But what does that cost you or how much time does that take? Just like you said, the hours of manual work.
Junior Lartey
Yeah, we can go deep into this. Right? Okay, well, how many hours additional does that cost? And what happens when the project pushes back and are you having to pull in other parties to complete it sooner? And now I'm just talking about discovery because we get so tied into this.
Kaylee Chappelow
Foundation because we're salespeople.
Junior Lartey
Okay, so post-discovery, right, you're going into demo time. You got to show the workflows. You're hoping nothing breaks along the way. Tell us about the demo experience and anything unique to anything you did to make that unique.
Kaylee Chappelow
So, first off, being at a startup is so real when you're hoping things don't break. Like, literally, I was sweating going into every demo, but yes, that was number one. The second thing was I kind of got caught off guard with this demo because we were supposed to do one for the end users, the product team, and then one for two executives. And then I get on the call and the two executives decided to be free spirits and join our end-user demo. So I was like, okay, it looks a lot different, right? They care about how is this going to help me with my high-level goals? Whereas the product people are like, I want to see every single button and filter. So it's like, okay, in my head, I'm panicking. How am I going to cater to both of these audiences? So what I did was I asked each of them as a group, hey, what's one quick thing that you're looking to see today that's going to help you in your job and get to your goals? I was able to get that information and then remember those things and then tie those into the demo. So, hey, Tim, I know you're really excited about saving the hours of work so you can do XYZ and have more time and back in your day. I think you're really going to like this feature and same thing with the executives as well. So that really helped make the demo flow more smoothly and really just make sure that everyone was involved and not bored and not feeling like I was getting way too much in the weeds. And when I did get it in the weeds question, I was quick to say that's such a great question. Let's table that. We'll set up a follow-up and we'll really get into the nitty gritty with some of our product specialists.
Junior Lartey
It's got to be so hard selling to two different mindsets. One, that is, I'm going to use this every day, so I want this product to do everything that I imagine it can do. And the other thinking, like, are my people going to be supported? And is this going to cause me no additional pain? Right? If I buy this, can I just stop talking to people and my business runs smoothly? So being able to tie that in sounds like you're trying to be super adaptable on the fly, different personalities that you're tying in. It's not an easy task asking, what can I do or not, what can I do? But what from you would you like to see? I think that was a really great way to position the conversation. In hindsight, do you think that helped or hurt? Not your question, but the fact that the executives jumped into that meeting.
Kaylee Chappelow
That's a really good question. I think it helped. I wish executives had more time in the day to sit on those demos because they were able to see firsthand and hear the frustration and the pain that their product team is experiencing. And I think that almost just deepened the wound a little bit. I think sometimes what happens is if we're on calls only with champions and end users, they're expressing all this pain to us. Then there's this risk that that's not going to get communicated when they then pitch that internally because they're not selling the product. So I think it was a beautiful mix of we still got to address everyone's questions and concerns and how this related to their goals. But we also were able to give the executive insight into what their product team was really experiencing on a day-to-day basis from a paying perspective.
Junior Lartey
Awesome.
Taylor Dahlem
And I think just to move to the next step here, in my humble opinion, and I'm sure Junior, I know you agree with Kate, I'm sure you do, but discovery is the most important part of the sales process.
Junior Lartey
Right.
Taylor Dahlem
It's where you figure out the pain. It's where you figure out what they're trying to solve, and that guides the rest of the conversation. But where I think reps and in particular full cycle account executives, like, where we learn the most is through the barriers and objections is where I asked such good questions. There's something that came up that I wasn't even thinking about that that could lead to a problem. Let's address that now. And I think that stems from great discovery, but at some point, barriers, objections, things like that always come up. So what were some of those major roadblocks that may be potentially lost? The deal that came up throughout this conversation.
Kaylee Chappelow
Yeah. So I feel like the biggest objection that we got was it's a very technical product, right? So it's like they were like, okay, how can we actually integrate this and implement this in the time frame that we have in terms of getting this implemented? So that was a big one as well as we actually had a fun twist where our CEO, CEO actually switched out. So the piece we're out, we're at the ninety-yard line and we're like, oh crap, what are we going to do? I had leadership being like, this deal is over. And I'm like, oh my gosh, let's chill out for a second, let's figure out what's going to happen here. But what we did was we realized that this was in a very unique position. They were starting a new role. They had things that they wanted to accomplish as well. So we got on the phone with them right away. We were also feeding our champion encouragement to ask for time with that COO and talk about this to make sure that we were aligning with this particular individuals objective. So we were saying, what are your goals in the next thirty, sixty, ninety days? One of them, AHA, was this big project. So we let him, we asked him all these questions and then we were like, okay. When he asked us permission, we shared how we might be able to help him. Now all of a sudden, buying our solution was his idea and he was all on board and ready to champion us to the finish line.
Junior Lartey
I think that type of switch where a COO leads the company and a new one comes in and you've already had the bulk of the conversation that's probably like the death date for most deals. Sounds like one of my most dreaded experiences. I'd freak out. How did you stay calm? What reassurances did you give yourself to make sure you can still orchestrate this thing through?
Kaylee Chappelow
I think it goes back to what Taylor said about discovery being so important. We had done such good discovery and we figured out this is a true business problem and a need that they have, that I had all confidence that we were going to be actually be able to help them. And I think that is what kept me cool was if they don't have us, they're not going to get this project done point blank. We're a very unique system that it's not like we were going up against three other competitors anyway, so it wasn't like we had that aspect. I think that's where it gets a little bit more hairy when you have a CLO coming in with a prior relationship with another vendor where things can even go worse. So I think we have that to our advantage. But yeah, really just staying true to the fact that we are really helping them. And there was a way to again, make the COO look good as well in it. So it was really a win-win for all parties.
Junior Lartey
Yeah. I love that you come full circle back to Discovery because there are pieces in there where it was like this when understood, when everybody understands what is happening, like, you need to have the software that we offer, and obviously that relationship that you're able to build quickly with the champion to get the COO and help him recognize that as well, I think was really key too. So we love to ask, where did the final yes come from?
Kaylee Chappelow
Oh, it didn't close. No, I'm just kidding. But what happened was another twist and turn. So what happened is our software was around three hundred grand, and they had tied us in with a larger initiative that was one point five million. It was another big core system. So we were experiencing some delays with the board getting approval for this specific piece of software, and they needed it by January one. St we had worked backwards from their end date of their goal, and they were stressed about not getting it in place. So we actually suggested and said, hey, I called my champion. I was like, what do you think about this? Just off the cuff. What if we asked your COO contact to pull this out of the bigger initiative? You've already got board approval that they want you to have this solution. We're literally just waiting on logistics because of how much is tied into this budget and this piece of approval. So she was like, Wait, that's actually a really good idea. So she went up to the CEO and then we got it done, we got it pulled out, and we were able to get the deal closed before the end of the year. So that way they could start on January one.
Junior Lartey
St this is a task, I've seen this in my own deals where I'm working with the company and they say, hey, we're going to hire rev ops or sales apps. So we want to hold off on your type of tech until that person is here so it can be fully utilized. Right? And what you're doing is you're trying to help them understand. If we do this now, here are the benefits. And being able to do that with this project. This project, while it seems it needs to be part of this much bigger picture, you can still be more efficient and get the initial needs done. And the other stuff is things that can be put on pause or carry over to the end of the year. Being able to convince someone of doing that is not easy. So kudos to that. I mean, creating you urgency is essentially what we're talking about. You created so much urgency around the value of what you bring around the value of the project that they're doing that they're like, all right, let's move faster than that. You had mentioned the deal closed over Zoom. What did you do to celebrate?
Kaylee Chappelow
I just wanted to realize we did send a nice bottle of wine and so that got sent out. My boss also sent me a bottle of wine for it being my first Enterprise deal. And I still actually haven't opened the bottle of wine because I'm kind of scenty sentimental. You know, I said that word the other day to my team and they're like, what is Cinti? And I was like, is that like a Denzee term? I don't know if you knew that. But anyways, yeah, so I haven't opened my bottle of wine yet. I'm waiting for I don't know if I'll ever open it. Maybe it'll just be like a keep stake.
Junior Lartey
I do love the appreciation gift, though, letting them know, like, hey, it's been a long journey. We've had a lot of conversations. Yes, we love the business. We're grateful that we could do business, but we're passionate about you and your company and we want to show appreciation. So I think that's a great touch, something that we haven't touched on in the podcast. So you're the first. Kudos.
Kaylee Chappelow
Awesome. Absolutely. I told you it's going to be strong.
Junior Lartey
Yeah, first.
Taylor Dahlem
It's the first, and I think it starts the relationship on a great foot. What's funny is especially our perspective as salespeople, it's like, oh, this is the natural conclusion of the sales cycle. And realistically, and we don't talk about this a ton, this is one of our last questions, typically. But sending that bottom line, the onboarding experience, those next steps, I mean, that's really where it comes to play because you can sell all you want, but if they have a rough onboarding, a rough customer success experience, or at least not successful, a lot of that effort that you just described and everything you went through doesn't really matter in the long term. So that's an awesome way to kick things off, really.
Junior Lartey
So, Kaylee, hit us with your three sales tips that you learned from this deal that reps can use today to inch closer to closed one.
Kaylee Chappelow
Yeah, let's talk about it. So the first is leveraging executive relationships. This has changed a little bit because now I'm in the mid-market space, so it wouldn't be likely for my CEO to hit up the CEO of some of the companies that I'm working with. So what instead I've done is I've really leveraged my manager to help open the lines of communication, even if it's just VP director level to director level. That opens up a ton of just vulnerability and saying, hey, whatever I can do, let me know. And also just I don't think a lot of your competitors are maybe doing that same thing. So it just puts you in the ear of the decision maker a little bit sooner before they get in, brought in by the champion. And it's not overstepping the champion because I don't want to be the one to go over my champion's head sometimes and reach out to that decision-maker. So it's nice to have that second person in command to help you do that. The second is aligning your problems that you're solving with the business initiatives that they're having as a company. So saying, okay, champion, you're going to have to pitch us internally. What does your boss care about and how can we relate what our software will do for you and for them to help hit their goals? Because right now, decision-makers are in this place where they're having to pick and choose what software they're going to allow people to buy. And so if you can pitch yours to match up with what they want to do, we're all a little bit selfish. We're going to go with that option. And then the second, the last thing is staying calm and trusting your relationships that you build with your champions. So I could have called this person and said, hey, do you think this is a good idea to try to pull us out? And they could have said no, and that's fine, but we have that trust and that vulnerability to test out those things and get a little bit creative on how we could get the deal across the finish line.
Junior Lartey
Perfect. Implement those three things. I think a lot of value in what you've said. Kaylee - it's great to have you. So, listeners, if you've tuned in today, go connect with Kaylee on LinkedIn. We'll post about it. We'll drop the links so that you can catch the show. Go search your CRM for some old gold. Do some inverse multi-threading, which we've created today. Also look for some more blog posts on that. Taylor that's an initiative I think we should strive for at this point. But again, Kaylee, great to have you.
Kaylee Chappelow
Awesome. Thanks so much, guys.
Taylor Dahlem
And just like that, another episode of How I Deal in the books. Episode eight. Junior, we did it. Hopefully, after this one airs, we've got a few more coming that are just as good. But thanks again as always for tuning in. If you enjoy what we discussed, please give us feedback in the comments. Throw us a couple of stars, maybe four or five, if you really like it, and we will see you next time.
