How to Win Deals That Take a Year to Close | Zac Basile (Account Director, Polly)

Carter (00:01.298)
Hey Zach, give the people a quick intro. Who are you and what do do now?

Zac Basile (00:05.592)
Yeah, for sure, Carter. My name is Zach Basile. I'm head of sales at Poly. Once upon a time, I was our founding AE. My five-year anniversary was yesterday, so I just celebrated five years. But yeah, excited to be on today, and I appreciate you taking the time.

Carter (00:23.146)
Nice, yeah of course. Do they, for the five year reunion, or for the five year, do they do any, like do they make you a cake or anything or not?

Zac Basile (00:29.102)
no, we're a remote company, so there's no indictment behind that. But I did have a nice Slack message post, which was nice, but you know, it's all good. I'm an easy guy.

Carter (00:33.218)
Okay, yeah.

Carter (00:37.716)
Yeah. And you said you were the first AE at Poly when there's no real playbook yet. How do you figure out how to sell the product and build the process from scratch? And was it heavily influenced by what you did at Oracle or just completely different?

Zac Basile (00:52.654)
I think, that's a question. I think first and foremost, like just being resilient and like, things are gonna change. Things are gonna change every day. Sometimes things are gonna change five times in the same day. And just like being willing to just kind of roll with the punches for lack of a better way of putting it, I think was huge. A lot of it was influenced by Oracle. I think just like the building blocks, the foundation of like process, being meticulous about like.

Why are we here? What are we buying? Why are we buying it? What is it solving? What does it help achieve for our organization? And what does that mean based on my role in the or like all that that Oracle taught us, like us, me was great for sure. Just from like a, you know, having a process perspective, but like, you know, building the plane while you're flying it or just like building something from scratch is not necessarily easy. And so I think it was really just trying to figure out like, Hey, look, do we have a product that resonates? Yes or no.

Carter (01:33.26)
Yeah.

Zac Basile (01:49.396)
Once we started to like hypothesize that that answer was yes, it was like, okay, why does it resonate? And then really just like, you know, fleshing out like, okay, great. Like, yes, we have a product that resonates. Now we're starting to learn why it resonates, building a sales motion around that. And then just kind of, again, like being, being willing to pivot and just like not being tied to any one thing, school of thinking, motion, whatever that looks like to just understand like, Hey, look, like

Carter (02:16.183)
Yeah.

Zac Basile (02:18.464)
we're getting XYZ feedback or pushback at this point in the sales cycle. So like, what is something that we can institute that addresses like, whether it's like early stage feedback or objections or like middle or late stage, and then just kind of like, again, building out a process around really the feedback that we're getting at any given point in time throughout the sales cycle. And that was fun, but that's really kind of what it, you know, it's what it's like really.

Carter (02:43.234)
So just what a lot of iterating as time goes on, like just little by little.

Zac Basile (02:47.202)
Yeah, like think of you push out a new software product, right? You roll out MVP. So it turns out you, five features to your MVP. Two of them work great and people love it. The other three may be just like not as important. So you pivot and then you get feedback and you crowdsource and you iterate and that's really what it was. It was just an iterative process to get to like the sales process we have today.

Carter (03:07.542)
I'm curious, not to go too off topic, but I'm curious what brought you to Poly because it seems quite different from a massive company like Oracle to go to a startup is a pretty big, pretty big difference.

Zac Basile (03:18.35)
Yeah, so both my parents were entrepreneurs are they're still alive are entrepreneurs and retired that is but so I just was always around like we had a family business restaurant industry. My mom was a you know started her own consulting company. So I just like always was in around sort of the startup life for lack of a better way of putting it and I always knew that that's the direction that I wanted to go. I was always fairly passionate about real estate and just generally like development.

Carter (03:23.682)
Yeah

Zac Basile (03:48.096)
Mortgage was tan is tangentially related is certainly part of like the larger sort of real estate real estate housing market obviously like Mortgage is the backbone of our economy largest private debt market in the world So all those things and then really poly phone my lap So, you know take all of those cool things aside and then here's this opportunity to go join this startup that kind of came out of nowhere it Seemed to sort of all check out for lack of a better way

Carter (04:15.296)
Yeah, yeah, that makes sense. To go more multi-threading deal process type stuff, you on LinkedIn, you said your deals can take six to 12 months. What is the first 30 days of a deal look like versus month six versus that final push to get everything closed?

Zac Basile (04:24.472)
Mm-hmm.

Zac Basile (04:30.606)
Good question. I mean, first 30 days is a lot of discovery, just like deal architecture. Like what does the process look, what does the buying process look like? Who are we going to be involved with? Who needs to sign off on this? We generally have a pretty good understanding of that now. Right. And especially if we've been through a past cycle with them, but like out the gate, a lot of this was again, just like iterating on figuring out like, who do we need to be engaged with? Who ultimately is going to sign off on this? What does that influence structure look like at the organization? You know,

Carter (04:44.577)
Yeah.

Zac Basile (04:57.294)
our decision makers sometimes are the economic buyer, most of time they're not, right? So just like generally understanding all those different things. But the first 30 days, a lot of learning, middle of the cycle is a lot of validating. Like we don't do proof of concepts, right? So like we have to sell through demos, through, you know, there's some things we can do around like test drives and stuff, but really it is like understanding what the pains are and the goals are of whatever prospect we're talking to and whatever, like within that organization.

making sure that we're aligning like, look, this is how we solve either paying or provide value and doing that through series of demos for different stakeholders versus then like negotiating and closing. And toward the end of the cycle, it's a lot of, I it's a lot of back and forth. Like we're selling to financial institutions. Like there's gonna be red lines. There's gonna be negotiations. Like terms are gonna change throughout, like depending on what you do or don't give as part of the negotiation. So, you know, it's really like learning.

discovery, deal mapping, validating that we are the right solution, negotiating and closing, right? So.

Carter (06:04.322)
And how many people are on these deals usually? Like 40? Like 10? 40? How many generally?

Zac Basile (06:09.04)
honestly, it could be as few as like five and it could be, you know, if you're talking to a depository bank, yeah, it could be 40, 50 people. Now they're not necessarily all going to have like a say, but you know, they will evaluate some might be end users. Some might be technical counterparts. Some might be product owners. Some might be business, like line of business owners. Like some might be C level executives, sales, you know, sort of all these different things kind of manifest themselves throughout.

Carter (06:11.596)
Yeah.

Carter (06:20.556)
Right.

Zac Basile (06:36.514)
you know, with what our solution does, like within the context of these, you know, lenders, we see all those different sort of lines of business.

Carter (06:43.946)
What would kill a deal at month nine that looked great at month three? Like what things usually come up midway through the process?

Zac Basile (06:49.966)
That's a really good question. Time. I mean, I don't say that to be cheeky, but like rarely do we lose a deal because we can't come to terms. Like rarely. That's not generally something that happens. We're usually able to sort of see the negotiation process through successfully. Atrophy. Just like time kills all deals. And that is very true in our industry. And if you can't accelerate through the cycle,

Carter (07:14.113)
Right.

Zac Basile (07:20.844)
with a compelling event, a reason to make a decision, many reasons not to make no decision, because at the end of the day, indecision is a decision. It's just not a yes, right? But like, sure, they didn't say no, and it's better not to hear no, but like, is the result of indecision not the same as a no? It is. So like, time. And the more that deals drag, the more that...

questions go unanswered, follow ups go unfollowed up on, like questions linger, things don't get sort of tied off like with a neat bow and you're not sort of constantly reminding prospects like, you know, our prospects all have like day jobs that keep them very busy, specifically the people we need to champion our deal, right? So if we're not accelerating through the cycle with urgency at every sort of step and opportunity that we get, indecision becomes

the main reason we don't close deals, honestly.

Carter (08:19.392)
What do you do to speed things along? Like just go through the process as quick as possible, set very clear expectations, just calling these people all day or not, maybe not all day, hitting them up a lot or what? Yeah, what do you do?

Zac Basile (08:29.102)
I would say it's like a combination of a compelling event, having the right access at the organization and yes, operating with urgency, but really through like clear expectation settings of just like, Hey, Carter, look, like, I understand that I cold called you. I understand we're having this meeting because we reached out. You seem interested. That's great. Like at any point throughout this entire process, like I'm going to lead you through a sales process. Here's what it looks like.

Here's who we ultimately need to talk to based on like what I know to be true about your organization if at any point you're not willing to Get us access move us through this process continue. Just tell me just use your words. It's okay. Like you're an adult I'm an adult it's all good But if we don't hear anything from you then then yeah Like I'm gonna keep following up because it's my job and like that's anything stall now All of a sudden deals are off track and that's all good and fine But like we could avoid this whole song and dance if you just like tell me where you're at

Carter (09:18.484)
Right.

Zac Basile (09:27.906)
constantly throughout every point in the cycle. I just think that that goes a long way. It's also not intrusive. Like, I have a job to do the same way you have a job to do. Like, it's all good. Like, we don't have to fight about it. But, you know, like, if you're not, I think having, like, I like to give people an out as often as I can.

Like a no, like a low stakes, no pressure. Like, hey, look, if at any point this isn't working anymore, we'll just call it off. We'll throw time on the calendar. We'll catch up once a quarter until you're ready to like actually evaluate. But like my time is valuable too, right? And I think sometimes in sales, we forget that. think we're like afraid to hear no. So we do anything we can to keep the deal moving. But the reality is like you would just do yourself so much. You'd save yourself so much aggravation and you'd free up so much time to go find other deals and prospects that might actually

be buying right now if we stop chasing deals that we know like aren't really moving anymore. Right, for the sake of keeping an opportunity in our pipeline that isn't a real opportunity by all, you know, intents.

Carter (10:24.01)
Right, that are just going nowhere, yeah.

Carter (10:33.58)
So you've sold through an awesome real estate cycle and now in these last few years, a bad real estate cycle. How did your sales approach change once budgets got tighter and the market turned?

Zac Basile (10:44.952)
Good question. Well, fortunately by that time I'd like gained a lot of mortgage knowledge that I didn't previously have. So I just felt a lot more comfortable operating like autonomously without air cover on calls or what have you. And I think that it really just kind of honestly what changed is I became sort of even more direct than I already was and kind of goes feedback to the point we just made about just like the expectation setting.

Really going so there's two things that change primarily one like I really focused on a more top-down approach of like hey Let's go to the highest levels of the organization and start there Because I don't want to spend seven months of my life trying to get this deal to the finish line only to find out that the CEO or see whoever Was never gonna sign off on the project anyway, right? And so like doing ourselves a favor there So I really leaned into a more top-down approach, which I just generally feel is the right

It's never a wrong approach in my mind, guess is really all I'm trying to say. Capital markets, like capital VP of capital markets, head of secondary, whoever, whoever was running secondary for the organization, because that's generally who oversees the software we sell. but then taking that either a step or two higher to really go right to the, like, you know, in many cases, economic buyer to be like, Hey, look, like is, you know, here's the value we're creating. Here's why your peers are doing this. Here's.

Carter (11:46.604)
Who were you guys reaching out to before? Like, wet wet roll.

Okay.

Yeah.

Okay.

Zac Basile (12:13.834)
An example of a peer who did this does that all resonate with you? Do you see the same, you know, either pain points in your organization and or do think you would find this interesting? If yes, like can I go validate this with your team and come back to you at the end of the process? And if the answer is yes, like we then agree that you'll take a, you know, you can't force anyone to sign a contract, right? But like more effective way of going about it, particularly when I mean,

Carter (12:33.633)
Right.

Zac Basile (12:38.924)
Within our industry, people were going out of business left and right. People were either selling their company, emerging. Yeah, we saw mass consolidation of our TAM. So it was just like, also same thing, if you go to the top down, it's like, hey, Carter, I'm hoping to X, Y, Z. It's like, hey, man.

Carter (12:42.519)
I'm bright.

Zac Basile (12:55.646)
not a good time for the organization and you can kind of read between the lines like okay like maybe these guys aren't going to be around that much longer right but if you're not having those executive conversations at the highest level like it's information you just might never learn right so

That would be like the biggest thing, but then really anchoring every deal to a compelling event with a strong like ROI embedded business case because it just like wasn't enough to sell based on like, I like your guys' software and I like you and I'm sick and tired of the incumbent in the industry. And so yeah, let's make a move. Let's try it out. We don't got a lot to lose. yeah, that sort of, mean, never did I think that was the best approach, but that certainly wasn't getting it done anymore to say the least.

Carter (13:41.578)
Were some people buying more and trying to get more market share or not really things were kind of down across the board. Cause I've heard some companies really try to go over at least with me at rocket mortgage. I know every downturn they try to go overboard with marketing and you know, buying different things like that.

Zac Basile (13:55.202)
Yeah, think it, mean, honestly, I saw both and it really just kind of depends on your company strategy, like how you were trying to employ that. But I mean, like, you know, for like a recession, for people who have money, like a recession is a great time to build wealth for your future self, right? Like that's not necessarily true for every person because you need access to that capital to do it. But it's the same idea in the mortgage industry, right? Like the companies who knew that they were going to weather the storm definitely doubled down on like, this is the time to like lean up.

Carter (14:14.624)
Yeah.

Zac Basile (14:25.136)
clean up, invest in software. We just made billions of dollars over the last however many years. We've got cash to spend and we want to make sure that we operate more efficiently during the next boom so that we can make more money than we made during the last boom. But the only way you can do that is if you are like operationally set up to see volume rise and fall like as is just like cyclical in the mortgage industry, right? And if you're not

I mean, if you're not leveraging software now, AI and whatever that looks like to run a leaner, more efficient business, like then how are you going to scale up? You're going to hire people that you're just going to have to lay off one day when volume comes back down and then sort of rinse and repeat. And that's, you know, one of the huge problems I see just generally in the mortgage industry or industries generally speaking. But, but yeah, I mean, it goes both ways, but then some people didn't have any cash to spend, right? So it's tough.

To say the least.

Carter (15:24.214)
Yeah, that makes sense. You sell into a tight knit market. A lot of people, the top lenders tend to know each other. How much does your reputation carry from one deal to the next?

Zac Basile (15:34.55)
a lot. I think it makes or breaks some deals, quite frankly. Look, I don't believe reputations alone close deals for you. Like, competence closes deals. Showing up and impressing people shows, like, that closes deals. Teaching them something they didn't know about their own business and why it matters, like, that closes deals. However,

If your reputation precedes you in a not so hot fashion, like that's also not gonna, I mean that might block you from even getting in the No, it might block you from even getting in the door, right? So it goes both ways and your reputation particularly in this industry. mean, for some people, you know, I'm a big believer of like your word is all you have at the end of the day and if you're not a man of your word or a woman of your word, then like.

Carter (16:08.386)
That's not good, yeah.

Zac Basile (16:26.094)
It's not going get you very far in life, quite frankly. I just am a big believer in doing what you say you're going to do, following through, speaking with intention. That is how I was raised. It's what's been ingrained in me. I think it's what's helped me build a strong reputation in the industry. But again, that alone won't close your deals. Competence and showing well and showing up every time you get the opportunity to do so, that helps advance deals, in my opinion.

Carter (16:55.464)
Now that you manage a team of AEs, when a rep needs help on a deal that's not moving forward, what's the most common thing they're getting wrong? Like what issues are they running into and how do you fix that? What do you tell them?

Zac Basile (17:08.28)
question. There's, I'll give you two answers. Like the low-hanging fruit answer would be like multi-threading, but that's just true. I see that a lot. Like, you know, it's very easy to cling on to one champion who you really like, who you get along with, you have a great rapport with. They get you access to the organization. They help you coach. Like, you know, sometimes they might even look more like a coach, but it's just very easy to cling on to one person who's doing and saying all the right things. And

Carter (17:31.724)
For sure, yeah.

Zac Basile (17:32.62)
The second that I identify that with any of my reps in any one of their deals, like I try to just point out, you know, hey, look, this is risk. But I think the larger thing that's a little harder to understand is like navigating influence structure at an organization. I think the biggest problem I see

just generally speaking, this isn't even just, I'm just saying across like SaaS in general, quite frankly, and with AI, but just technology sales is like misinterpreting.

Who might actually be making the decision versus who's actually signing the check? What influence do they all have on each other? Does my champion have any juice? Does my champion not? Is there really someone who doesn't care at all about the evaluation but trusts like Carter to make the right decision but is ultimately the like just generally navigating the sort of heat map for an organization and understanding like who really has influence versus who really has authority

What is the difference between those two things and how do they play on each other in any one organization? Like that's where I see the biggest just like opportunity for coaching and or improvement, you know across any given deal

Carter (18:52.706)
How do you figure those things out? Like what do tell people to do to figure that out?

Zac Basile (18:56.622)
That's a good question. mean, first and foremost, just like testing people. And there's so many different ways you can test people. But look, the bottom line is at the end of the day is if you aren't prepared to walk away from a deal, you don't really have any leverage, right? And so the reality is that it's like, something simple, can we get access? No.

Like, are they gonna give us access to XYZ person or ABC person at the organization? Like, are they blocking us? Are they just coaching us, but they're unwilling to go do anything about it internally? They're just giving us their two cents and feedback, but then when asked, like, well, can you make an intro or, no, like, you know, I'm just trying to help you out. Like, or whatever that looks like. You know, playing good cop, bad cop, you know, hilariously effective strategy, like in...

Carter (19:39.713)
Right.

Zac Basile (19:48.578)
you know, with like a rep and a sales leader, right? You know, asking them to do homework for us, that's a huge one. Like, how often do we ask people that, and they'll tell you on the call, they will commit to doing something on the call, and then you never get it, ever. They won't do it. They won't go find out how much their invoice is, or they won't go find out, like, you know.

They won't even help you validate ROI. They don't wanna put their skin on. So there's a bunch of different things you can do to figure out, like, does someone have influence or not, and are they willing to use it? And then from an authority perspective, I generally find that that's, you know.

Kind how you get the T, right? Just like through asking the right questions and the right sort of who's been at the company a long time, how long have they been there? Look at the roles they've moved through, see if you can get an org chart, who reports to who, who's closest to the C-suite, who's like CEO, delegate, right-hand man or woman. Like all of these different things can kind of inform you on like, all right, like now you start to paint this picture of what the company looks like and you start to understand like how these different players all fit together.

And generally I find that coaches are the best. Someone who can't really champion the project for you but is rooting for you and wants you to succeed, I generally find that they're willing to share the most information about the company and influence structure.

Carter (21:15.234)
Okay, well that makes a lot of sense. I think this is pretty good. I will end it here.

Zac Basile (21:21.742)
Perfect.