🏆 FOMO for the win!
Spencer walks us through the most mentally challenging deal of his career.
This mid-market deal came from an old opportunity that went with a competitor a year prior.
But returned after falling victim to over-promising & under-delivering tactics.
Featuring webinar prospecting perfection, lockstep his sales engineer & weaponized FOMO.
Hear how this sale played out!
Guest Feature
Spencer Wuthrich started began the sales grind in door-to-door pest control.
Since then he’s sold at a few notable Utah tech companies as an Account Executive.
Namely Divvy, Entrata, & currently Clozd.
Whose mission is to help companies understand win-loss analysis & where the pipeline goes.
Deal details
What are you selling?
- Software product for the multi-family housing industry
Where did the prospect come from?
- A target territory account list
Company type
- A mid-market multi-family housing management firm
- 13 properties. 2,000 units (apartments)
Prospecting method
- Invited them to a webinar & followed up post-event to meet.
Barriers to Overcome
- They originally went with a competitor who over-promised, under-delivered
- Spencer had to build their trust back in a solution & show them the better alternative
- Preemptive high cost expectations that he had to walk back with a cost-benefit analysis
Buyer type
- Decision Maker: CEO
- Users: Marketing team
Deal length
- 5 months (expected to be a year)
Episode Highlights
Note: timestamps correlate with the full conversation
Demo: Out of 4 different demos, which one did you hate the most? (17:27)
Team selling: Account Executive & Sales Engineer Relationship (19:30)
Barriers: Addressing pre-conceived pricing objections (21:22)
3 Tips for Account Executives
1. Prioritize empathy in all deal stages.
Walk a mile in their shoes.
2. Avoid needing to sell a prospect more than they want to buy.
Don’t have ‘Commission Breath’.
3. Big deals take time to close.
Create multiple paths to quota by consistent prospecting.
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 played out that way, and hopefully provide some very actionable sales. Sales tips that everyone, in particular account executives, the full cycle variety, could use in their deals today. My name is Taylor Dahlem, full cycle account executive, turned content guy. And I'm joined as always by my co-host, Junior Lartey, the sales superhero here at Pickle. How are we doing, June?
Junior Lartey
Good. It's episode fifteen. I'm stoked for today in particular because it comes from Entrada. We're going to talk about an Entrada deal, property management software company. I worked there for three years, so I know how long and bumpy these conversations can be. I'm really excited.
Taylor Dahlem
We don't always get inside baseball deals, but this one is certainly going to be exciting. At least junior is going to try not to spoil things ahead of time, but I know he's pumped to talk about this one. But before we dive in, as always, I want to give a quick refresh for anybody who hasn't listened to us for a while. Or maybe you might be listening for the first time. Each conversation we chat through a past deal. We want to keep all names, places and details as fictionalized as possible, but that way we can really dive deep from the first time the individual saw this prospect. Whether it's in their CRM, on an account list, a specific region, anything like that, all the way to getting that final approval. Whether it's a DocuSign, PDF, completed fax machine, whatever it takes. But we want to get all the way through and essentially have a ton of details to work with.
Junior Lartey
Today. We've got Spencer Wuthrich. He's a good friend. I had the pleasure of selling with him at Entrada. He is now an AE at Clozd, which is a pretty hot Utah startup. Spencer, tell us about your role at Clozd and what problems they solve.
Spencer Wuthrich
Hey guys, thanks for having me. In short, Clozd helps companies understand why they're winning and losing deals that go through their pipeline from the prospect perspective.
Taylor Dahlem
Spencer, what deal are you walking us through today?
Spencer Wuthrich
Yeah, so I'm walking you through one of my mid-market size deals at Entrada. We're talking roughly two thousand units, which are doors within an apartment community. Thirteen properties selling to a C-suite. Different levels of leadership within the organization. This deal in particular happens to be my most mentally challenging and probably most emotional deal that I have ever gone through.
Junior Lartey
No spoilers, but it can get pretty bumpy, right? Mentally challenging. We're going to tackle that towards the end of the pot episode, so keep listening. But the multifamily industry, it's very relationship heavy. A lot of in-person events and conventions. I'm not making assumptions about how you met this person or became aware about them. So you tell us, how did you become aware about this company and what research did you conduct before reaching out?
Spencer Wuthrich
Yeah, so around the time that I received this new geographic area, we happen to be going through a global pandemic, so there wasn't anything in person that was going on. But in Entrata, being at the forefront of the multifamily industry, they decided to put on a virtual event for the industry to kind of keep those relationships strong. One of the things that they did with this virtual event is they allowed us to use it as a prospecting effort. So I had seen this particular company in my area, had had some conversations with some previous reps, didn't seem to have gone anywhere, so I decided to send them an invite to our virtual event.
Junior Lartey
When you say previous conversations, you're talking about conversations with the former Entrata rep and where they like because, right. Everyone takes notes, they're in the CRM. Was this like, hey, I met so and so. I had a phone call with so and so. What type of conversations had previously been.
Spencer Wuthrich
Yes, this was a good old fashioned, I'm going to do a couple of demos and then never talk to you again.
Junior Lartey
Nice. Just beautifully ghosted.
Spencer Wuthrich
Yeah. Every sales reps nightmare.
Taylor Dahlem
That's not enough values created.
Spencer Wuthrich
Right?
Taylor Dahlem
Or maybe there was, and the timing was right. All kinds of ways that goes wrong, but it's always the worst feeling as a sales rep to get ghosted like that. But yes. Junior tells me that when you joined and Trotted at this moment, there's kind of a big momentum shift in prospecting. Right. Like a different strategy, a different course was taken, of which you were a really big part of curious. How did you go about getting in front of this prospect? Give us some details and maybe some insights on that process.
Spencer Wuthrich
Yeah, as Junior knows, it was very much old-fashioned. It was hop on a plane, get out to your area and go shake some hands, drop some cookies off. We don't need to get into the Utah cookie wars. But yeah, essentially because the world stopped traveling, we had to find new ways to prospect and to get in front of these people because it is so relationship based. I felt like they had some conversation with Intra in the past, so I'm going to invite them to our virtual event. No surprise, they didn't respond, and the event came and went, and I was actually shocked to see that they had RSVP on the attendee list and they had attended both of the virtual sessions. So naturally, I went about sending them an email saying, hey, I saw you attended our virtual event. I would love to gather your thoughts just to hear what you thought. And she responded back to my surprise and was like, yeah, call me on Friday. And we scheduled a time, and we spoke there, which she had actually come clean and said, hey. When I was evaluated in Entrata at that time, we ended up making a decision, and we aren't very happy with our decision. So that definitely transitioned to, okay, discovery, what are you not happy about? She told me a few things, and frankly, the conversation was getting way too long. We decided to schedule a more formal discovery at that point to dive in into discovery conversation.
Junior Lartey
I think it's really cool to be able to do that. Where you have this one was a bit more scheduled, but it's like a pre-discovery call before. It's like, let's get into this formal momentum, formal sales process. But just a quick, hey, I saw that you were at this thing that we hosted. Let's chat and just see what your thoughts were about it. And obviously she joined for a very specific reason. At this point. She tells you that it wasn't the best decision. No brainer there, and Charles the best. She should have made the right decision first time, but we'll get to that point. Did you have a backup plan or other? You invited her to the webinar via email. She never responded. Were you, like, following up? Did you have a backup plan in trying to get in front of her initially?
Spencer Wuthrich
Honestly, no. You know how it is. It's so relationship based that I was just kind of shooting my shot. If she was going to respond, that was great. But where I saw that she had attended the event, I was like, okay, I've got to talk to her, even if it's just casual, because it's a marathon, not a sprint in that industry.
Junior Lartey
Was she the only person that you invited to the event?
Spencer Wuthrich
Yeah, basically she was like the COO of the company, so I was like, okay, C suite. She spoke with us about a year ago, not knowing really anything else about the industry being new to the lead list and everything. I just kind of sent it and hope for the best.
Junior Lartey
Very cool. And at this point, it landed. So I think maybe now is as good of ever time to talk about discovery. We used to at and try to have these extensive documentation for Discovery where it's an account plan, because ultimately you're trying to learn all this information that you then hand off. And the sales engineer, someone who actually demos the platform, helps pick it up from there, and keeping them informed is really important, but they do the bulk of the demoing while you navigate the conversation. So here you need to find out and uncover a ton of information. So what did discovery look like and what did you ultimately learn?
Spencer Wuthrich
Yeah, the discovery process was interesting because, as you know, in Toronto is a full ERP, so it's a huge sale that really touches the entire every aspect of the business there. So she being over operations. I was able to have a discovery with her. Understand that they had just recently finished the migration onto this new software. They were still under contract with this new vendor and they were having so many issues with their day-to-day operations that she was starting to have second thoughts. And I think I was able to build a lot of trust and build a good relationship by listening to those problems and knowing that they're under contract and knowing that, hey, it's a pretty slim probability that any movement, if any, is going to happen at this point of time. Again, thinking more of the marathon mentality, but, hey, I'll be a shoulder to listen on and I'll take good notes and when they're in a better position to buy, I'll be able to bring up all these past pain points that she talked to me about and really drive home when she is in an evaluation process. She's she explained that she was feeling a lot of pain, but the most pain was being felt by their accounting team, their controller side, and that there was a lot of emotional barrier built up because of this last transition.
Junior Lartey
Yeah. And part of the struggle here is how often are people changing this type of software after purchase? How long do they keep it?
Spencer Wuthrich
Yeah, I would say on average they're keeping it five to ten years. It's not a switch that just happens every year. It's not something that happens overnight either. Typically, these people would rather just go along with the issues and then change software, frankly, because it is so painful and it does disrupt the business so much. So for them to be feeling that much pain in less than a year, to potentially want to see what could have been, have the FOMO there and want to see what else is out there, was pretty incredible. And really, I think it only happened because we were there to list them first.
Taylor Dahlem
Spencer, I got a two-part question. First one for us layman that aren't in the industry, what is an ERP?
Spencer Wuthrich
So, ERP, essentially it's a full platform sell. It's a piece of software that touches the entire part, every part of the business.
Taylor Dahlem
Got you. No worries. I was like, maybe there's some specific jargon that most would know listening to this, but second part and this kind of backs up to the prospecting question. But as a marketing guy, I'm always fascinated with the funnel that somebody goes down through. A conversion funnel.
Spencer Wuthrich
Right.
Taylor Dahlem
So a virtual event they attended, maybe there's a specific kind of pain or something they want to learn and do from there. You're capitalizing on that conversation, maybe just trying to see what triggered a sense of urgency or maybe a sense to start looking at this. And as you mentioned, most people don't change within five to ten years, and this is after one year. They're sensing some large pain, so it's probably pretty rare. But I'm curious, is there more, I guess a little more specific maybe you can share with us on, like, what are some very specific pain that they were feeling or maybe things that you might have dug up in discovery that you specifically started kind of piecing together team by team. Just kind of curious about that.
Spencer Wuthrich
Yeah, I think the biggest pain point that they were feeling was ultimately there were parts of their operations that weren't sinking back to their main point of reference when it comes to their data center, their day-to-day operations, which causes a huge issue within a business like this because it makes their data become invalid. There's no data integrity, so they can't make the decisions that they need to based off of the data that is supposed to support everything. So when the integrations are failing, their data is failing. Really, their business is failing. So it's a huge pain point for these companies.
Junior Lartey
And the data that we're talking about here is like the move-ins and the move-outs, right? How many move in and move-outs happened? What is the Occupancy rate of all these different properties? And if you can imagine, these property management companies are trying to keep Occupancy up to ninety-eight percent. Maybe Strike Zone is like ninety-seven percent, ninety-eight percent. And their data says, well you're ninety-nine percent, but the revenue numbers are off. There's like a huge gap between what is happening on the property and what is happening with the revenue. So trying to figure that out could take a really long time. And before software, they're doing it pen and paper. So you could imagine the type of pain that someone is feeling when they come back and they don't have accurate data. But ultimately, having sold these type of deals, we know that these can be like longer deal cycles. It's not just your typical thirty-minute demo. So what does that time frame actually look like and how did the demo process go for you?
Spencer Wuthrich
Yeah, I think overall we did four demos, about ninety minutes each demo. The first one tailored to the operations team, so it was a lot of the issues that they were seeing as far as lead source attribution from a revenue standpoint, like you said, Junior, the second one was after a pretty intense discovery call where we had to convince the accounting team to just take a look because those barriers were so big. And she wanted to make sure from the accounting standpoint that really we could check all the boxes, that we wouldn't disrupt any of their day-to-day workflows, that there wouldn't be any changes to how they would need to do things. And so we were able to check off the boxes, but again, just listen on that. And then the other two demos we had to pass off with the CEO and owner of the company. So this man, very successful man, owns a plethora of real estate, so very wealthy, but just a great guy and he listened. And after that we brought in some additional people from their other teams who would be end users, day-to-day users, to show them kind of, hey, we are really thinking about making this switch. This is what your life is going to be like. If we make the switch, how would it improve your life? Would you be able to sleep better at night? Typical questions like that. And ultimately, we were able to build enough momentum in those and the relationship as well with the accounting team to be able to break down those barriers and for them to trust us to say, hey, a software change, especially another one this year, is going to be just the absolute worst. But it's what's necessary for our business to improve, so we're going to bite the bullet, and we're going to go through with it.
Taylor Dahlem
Spencer. What? I guess this is a left-field question that we haven't asked before, but I'm always curious when there's multiple demos involved. Specifically, you mentioned four with four different teams. Which one do you feel like you really crushed when you walked out of it and which one you're like, shit, I got to go back and do some more work, clean up on something. I'm just always curious what teams that kind of gave you, what feedback.
Spencer Wuthrich
Yeah, great question. I can tell you which one I didn't feel comfortable going out of, and that was the accounting demo. I do not understand accounting at all. I always make the jokes. I don't do numbers. I do sales. And they always laugh. But I think that the accounting demos are typically a little bit more they just want to see it. They just see what their day-to-day would look like. They want to make sure they're checking off boxes, and they're typically a little bit more quiet on the demo, too. So there's always that awkward silence where you're like, hey, this resonating. And even when they're still like, yeah or no, right?
Taylor Dahlem
When you do a pulse check, they're like, yeah, sure.
Spencer Wuthrich
That was probably my least confident one. Once I was able to get to the owner, I was like, okay, if I can nail this, then he can give us the green light. Depending on the decision of the next level down, then we're good to go.
Junior Lartey
So here's another out-of-left-field question as well, one that we haven't tackled yet. But in your sale, you've got a sales engineer who handles the actual demo. Handles the actual I'm clicking the buttons, navigating the screen, and showing the platform. Maybe some of our listeners have one of those, maybe some of our listeners don't. But your sales engineer is a sales engineer for four reps, so they can't join every discovery meeting that you have. They're not hopping onto the phone calls in between the deal. So how do you keep them informed? What is the relationship like between you as the seller and the sales engineer who's trying to demo the platform and still needs to understand the core problems that your prospect has.
Spencer Wuthrich
Yeah, I think that's twofold, Junior. It's a being able to take good notes in the account plan that you mentioned. As you mentioned, they are doing the blue of the work in the demo. So it's your job to really be listening to ask good questions during pauses, ask good questions, take those notes and continue to push the conversation forward and be in between those demos. When the sales engineer can't be present, you need to be meeting with them fairly regularly to keep them up to date on the health of the deal, what potential roadblocks were seeing, but also to follow up on any deliverables that you may have promised. In this case, they always want report packets, what the financial reports will look like coming out of the system, potentially some follow-up questions that we need to talk to products about, but yeah, it's really just getting those answers and serving them back to the prospect in a timely manner.
Junior Lartey
So imagine you've got all these pieces, you've got the SDR handing off to the Ae, the Ae handing off to the sales engineer. Sometimes the VP of sales joins the conversation and then if you win, it's going to implementation a lot of moving pieces. So you've got to keep good notes, you got to keep everything documented and at the end of the day be able to present a business case. And a lot of times the business case is what helps you overcome some of these barriers or bumps in the road. So what were some of the major barriers that you had to overcome through this deal?
Spencer Wuthrich
Yeah, so during the process we were able to discover ultimately they went with price because they saw how innovative our solution would be and just automatically assume that we were going to be way more expensive than they wanted to pay. So they ended up going with a solution that had less bells and whistles, but they would require more integrated third-party shops to hook onto it. So one of the biggest challenges that we ran into was going through an actual cost-benefit analysis with comparing apples to apples with their full software landscape compared to our single-stack solution. And as we were able to add it up, we were able to show them how we could actually save them some money. It wasn't super significant, but it was interesting for them to actually see that. The second barrier I've mentioned a couple of times on the call, it was just the mental and emotional scar tissue that had been built up from the last transition, ultimately caused by some over promises and under deliver, which unfortunately happens all too often in sales. So it's not uncommon in sales to having that be one of the biggest barriers that we run into.
Junior Lartey
I'm going to pull you back to the cost-benefit analysis really quick because it seems like the reason they're doing this or having to do this you mentioned Apples to Apples is because they have one system and they think, I'll just go buy the best tools and integrate it into the system. Whereas you're saying you don't need to do that. We already have all the functionality. And so you're trying to balance what the buyer sees versus what you understand about the industry and the product. Can you give us a little bit more any specifics or details into how you conducted that or did you keep it on a spreadsheet? I don't even know. I'm trying to wrap my head around what this thing would look like.
Spencer Wuthrich
Yeah, that is part of the account plan. Part of the spreadsheet is to uncover their entire software landscape. Who are they using on the front end? There could be three or four different solutions that they're tying in from their front-end into their back-end accounting software, which I know seems very complex and it really is. They can end up creating this entire spider web of solutions all tied back to this main database and going back to some of the issues. If those integrations are broken or janky, then it can ruin their operations. So what we did is created the spreadsheet they were able to pull invoices from each of those software solutions, create that, show them against our pricing proposal, and stack it up to show them the cost.
Junior Lartey
So at the end of the day, they're looking at fifteen services in a final price versus intrada and a final price. And throughout the journey you've been able to help them understand functionality-wise. We can still have you covered, right?
Spencer Wuthrich
Yeah.
Taylor Dahlem
Spencer, let's kind of recap quickly the entire timeline of the deal because at this point we've gotten demos, barriers. The timeline itself always is curious or fascinating to me of how long did this take? Start to finish, but also behind the scenes, like the deal management aspect of keeping everything together from your perspective, from the sales engineer perspective, from the prospect side, just always fascinated with that. So tell me a little bit about the deal management and how you kept kind of everything straight and how long the timeline was.
Spencer Wuthrich
Yeah, so I believe we started conversations in what was probably late April, early May of that year, had our first discovery call probably mid to early May, and had a demo towards the end of May. I think we signed contracts towards the end of August of that year, which was insanely quick given the circumstances. I think their contract with that specific vendor wasn't even up until November of that year, so they were already planning to make a move before their contract was ended. Overall, probably one hundred emails. Between the internal emails and external going to them, we probably met with them a dozen, maybe even fifteen times. Four demos, as I mentioned, and then probably another dozen internal meetings to make sure we were all in the same page.
Junior Lartey
Awesome. Throughout this deal at intrada and even at your time of close, we won't keep it. What am I trying to say? Okay, Spencer, what are three things any sales program can do today to inch closer to a closed one on some of the deals they're working?
Spencer Wuthrich
Yeah, I think the first one that has always been really important to me is just learn how to put yourself in the person you're talking to shoes. No matter what stage you are in the sales process, if it's prospecting, you're thinking, what is going to resonate to this person? If it's discovery, wow, that pain point really sucks. How would I feel going through with that? How would that affect my day-to-day or even in the demos? What I'm saying is the solution that I'm proposing resonating with them. So first things first, put yourself in the other person's shoes. Second piece of advice that I think has always been great is you can't want to sell to somebody who doesn't want to buy, or I guess better said, you can't want to sell to someone more than they want to buy. Aka you've heard it other times more informally. Don't get desperate, don't have sales breath. Ultimately, everybody has their own timeline. Always make sure that you're solving the problems and that there's communication on both sides so that you're in line with their timeline. The third tip, I would say would be to try and create as many pathways to your number as possible. Everybody wants to close that big mammoth of a deal. That one deal. The fact of the matter is, they take a long time to close. There's a lot of stakeholders and they're very complex. While you're working that deal, you should be eyeing out smaller deals to supplement as you work that bigger deal. And on top of that, a lot of us have expansion opportunities, renewal opportunities that also go to our sales quotas. So being able to use all of those different ways to attain your number, it's really important to find as many streams as possible to be able to hit your goals.
Junior Lartey
Spencer, it's been great chatting with a good friend, walking through this epic deal, pulling me back to my time at Entrada, which is always nostalgic. It's great to do in your sales career. I love the tips to put yourself in your audience's shoes and to match your selling to their buying and ultimately, like open pathways to quota, because the more you're able to do that, the better off you're going to be. Not just short-term quota, but long-term sales experience. So thanks again for joining us.
Spencer Wuthrich
It was fun, guys. Thanks for having me.
Taylor Dahlem
And just like that, another episode of How I Deal is in the books. Thanks again for tuning in. If you enjoy what we're putting out, please le us know in the comments on Spotify, Apple, wherever you listen to your podcast. And if you feel so inclined, deliver us three, four, five stars maybe. But all of this is an effort to drop as much sales tips and sales knowledge as possible. For all of you AE's listening out there and Spencer is one of the pros. Again, we appreciate them for joining and you all for listening. We will see you next time.
