Sam Hillestad
Product Marketing at SetSail
Table of contents:

Join Gabriella DeFlorio, CEO of Prelay, for a discussion on the keys to selling a new category. Learn about consultative sales, picking the right segment, finding early adopters, overcoming objections, and most of all, team selling.

The following transcript has been roughly edited for clarity. Please excuse any errors.

Peter: Hi everybody, this is Peter Mollins with SetSail and we're here with another episode of The Hot Seat. Today I'm very excited, today I'm joined by Gabriella DeFlorio who's the CEO and founder of Prelay. Gabriella, welcome to The Hot Seat.

Gabriella: Hey, Peter. Thanks for having me. Excited to chat.

P: Absolutely. Well, first off, I'd love to hear a little bit more about your background. So maybe you can tell me the story of how you got to the position of founding Prelay and your background and story. I'd love to hear it.

G: Yeah, and I can do a kind of a brief version of it, but it's been past, I guess, four and a half years that I've been working and really diving into the team selling market. You know, prior to that, I was in more, kind of go-to-market strategy and operations at fast scaling startups in Silicon Valley, more HR tech, fintech realm at that point. But those had very complex deals. So that was kind of my first experience. really diving in head first and figuring out ways of simplifying complex deals from a systems, people and process standpoint. So that's been living the dream since then and doing that more at a macro level now over at Prelay.

P: That's great. And so that experience with working with complex deals must have really informed the launch of Prelay and the ideation behind Prelay since you're really helping to simplify sales processes, particularly at enterprise deals. But so maybe you can tell me a bit more about Prelay and how it can help sales organizations.

G: Yeah, and I, you know, as mentioned kind of the approach I've always taken within even, you know, past roles within operations is how do you really stand and think through systems, process and people combined and really making sure that we can, you know, drive that as efficiently as possible, especially as companies are agile and scaling all the time. So that's really the first thing that we started with is how do we start to really pair all three together when we started building out Prelay. So Prelay ultimately is a team selling the software. It helps to drive people and process together, especially when it pertains to more complex deals. Think very technical products maybe, or multiple product lines that you're having to sell, multiple market segments could be all the above. We really help to build out those playbooks, have the right roles and responsibilities involved from, you know, solutions engineers to account executives to even some post sales teams that have to get involved to make sure that everyone's working as efficiently as possible internally, but also externally as well. So we do have like an external buyer side of the product too

P: Yeah, it's amazing how much, you know, I think you and I were chatting about this on LinkedIn the other day was around how much of a team sport sales has become. So you mentioned about the coordination between all these various roles. I love your thoughts on, on sort of that, that team sport element to selling.

G: Yeah, and you know, it's very near and dear. That's why I named Prelay. Prelay in the beginning, actually, was a proactive relay of information, you know, really having those handoffs and really making sure you're as succinct as possible across the team. That's not only selling presales, but also post sales is there's, you know, more models coming into play, like consumption-based models that are becoming even more complex over time. It's really critical that you have. It's really critical that you have all hands on deck and make sure that everyone's on the same page and knowledge is shared thoughtfully. And that's not only, again, internally, but also externally with the buyer, really making sure that customer journey is mapped out correctly. So the team part of sales is critical to making sure that you can really execute upon the revenue that you're shooting for.

P: So a question for you about, since as a CEO and co-founder, you've obviously started with a hypothesis about what your sales strategy would be going into the launch of Prelay. So I'm curious if that's adapted over time, or have you seen changes to your sales strategy? And how have you formulated those changes as you've built out, gone from zero to where you are now?

G: Yeah, I really like how you frame it as a sales strategy. I think that a lot of founders tend to start with product strategy, like just as a baseline and they're not thinking through distribution at all and making sure that they're really pairing, go to market, and how they're going to be going to market, getting in front of the right personas, the right ICPs and solving clear problems for them alongside of obviously building out the right product to those problems. So that was really the starting point is how do we think through what problem is in the market today that we can clearly solve with a solution in general and then build to that and really make sure that we're solving the pains of very clearly defined ICPs and personas. So since we were very thoughtful in the beginning, there's been things that have maybe shifted. You can't build everything at once, right? So we started initially more on how we have engagement requests between maybe AE to SE or... to overlay or other teams that are having to get involved. It's more internally facing where you want to share and engage them throughout the process and you don't have any formal process around that. That was kind of our initial phase of the product and that didn't actually shift the sales strategy by any means, but we did start kind of shifting our product even further from that and starting to really build out playbooks from there. Honestly, a lot of it has been just making sure we're as focused as possible. and getting in front of the personas. We haven't thankfully had to pivot anything too wildly. I think the only thing that we've really shifted on like a sales strategy front is going more kind of mid market. So when we defined the problem upfront and what I really wanted to solve for in the market was a problem that hasn't been solved for some time and something that is not easy to necessarily build, right? There's a lot of, you know, sales force overlays and things that can be kind of quick products to build out, but don't really have any clear moats around them that can be long lasting products. So we really started from scratch in building out this full platform play. And it's been, you know, we have to be very thoughtful of who we approach then, right? Because if we're creating a category and creating a new product, we need to find mobilizers within organizations. We need to find early adopters, people that are getting excited about what we're bringing to the market. and hasn't really existed before. So if anything, the biggest shift we've had is more, not going towards like enterprise and fully targeting enterprise, but letting those enterprises come to us and then really targeting those mid-market commercial mobilizers that are super excited about what we're bringing to market and really see the value at the organization, especially as it's rapidly changing as they're growing. So not too much on the persona. been going after a lot of the team sales, like account executives, solutions engineers, deal desk and rev ops, but a large part of it is, what is that segment you ultimately go after first? Certainly you always wanna win the full market, but how do you really focus on those people that are going to mobilize for you and really bring you into the organization and help ultimately help Prelay and the products grow?

P: Yeah, I think that's, that's really something that a lot of founders trip up on is not, not being willing to focus their attention on precisely the right kinds of potential customers that are going to be a good fit and good fit for your growth. I guess maybe that, that brings me to a sort of a question, how do you differentiate between an objection? Like someone just simply that is objecting to, you know, the value prop or whatever. versus a bad fit. Like what do you see in there that's gonna identify, well, this is an objection we Like what do you see in there that's gonna identify, well, this is an objection we can overcome and they are a good fit and we just got to get there versus an objection that really highlights that maybe they're not a good fit for this moment in your life cycle.

G: Yeah, I mean, I think, especially when we define good or bad fit, I think a lot of it comes down to a mixture of obviously the company and then it also comes down like the business model and everything. And then also the persona we're speaking with and if it makes sense from a timing standpoint from priorities and initiatives and, you know, the maturity of the organization and maturity can mean a lot of things, right? Maybe too mature, you know, they're just early on in their journey, they're shifting CRMs and there's just like too much going on, right? So I think a mixture of is just going to be like discovery that we do ultimately to really dive in and be very solution oriented So we try to be very consultative in the way that we approach problems And I mean ultimately, you know not a great fit is if someone's not open to that consultative sale, right? So if we can't be speaking with a persona that's really excited to open up and be clear on you know What their needs are and where they stand is like from an organizational perspective. Then that's going to be tough for us to really land there and doesn't really make sense for us to spend the time. It's not a great fit from that perspective. Now if we can dig in, there are going to be times where obviously if we can't find a good fit from a company standpoint, maybe it's more product led growth, like not super complex deals, very edge case kind of sale, maybe there are more services or something. That's where it just doesn't make sense for us to spend the time. But again, it ultimately comes down to like... doing that consultative sale and really digging into the initiatives and what potential use cases that Prelay can provide back to them. But again, that comes down to the prospect and the buyer really being open and direct with us and their needs, their problems today, and so we can bring a solution to them.

P: That's great. So maybe shifting gears to more personally for yourself. Thinking about it again, objections there. What would you think, what would you say is the toughest objection that you've ever encountered yourself and how did you, how did you handle it?

G: Yeah, I think for in Prelay, like in particular, I think the toughest thing, and we honestly, it's not just one objection. This happens all the time, right? When we're creating a category, creating a new space, budget is always a problem. And it's not budget like, oh, we, uh, you know, have our budget full or there's another competitor in the space that is using our budget. Oftentimes we have zero budget. We've never heard of Prelay before, you know, why should we even be purchasing a solution like this? And so that's difficult, right? Because you're creating space, you're educating the market, and you're having, again, to be very consultative then. And so that's a very difficult objection to handle. Obviously, over time, we've really been able to hone in on that and learn and figure out ways of really breaking in from that perspective. And I would really say like a few things there is like being direct to the buyer, making sure that we're really clear that this is a very common process we're running, right? Like it's very common, all of the companies typically never have budget built out for Prelay And so we're more than happy to be supportive, work directly alongside of them to develop ROI potentially, develop any sort of value case so that they can have that business case back to like the internal team of why it's critical. But again, that consultative and guided approach is going to be critical there. making sure that we can solution out what's valuable to them based upon the discovery that we've really done to date from a use case standpoint, what they'd be using in a Prelay all tied back to clear initiatives and priorities and things that truly matter to the business. It ultimately comes down to value selling them. I think it can get very complex when you don't have that budget already nailed down. If you already have it nailed down and you have direct... competition, you can just be feature for feature and really focus on that where, um, you know, you definitely have to be more organized and, uh, do a lot more of like homework in the end to make sure that you can get that budget across the line. So, it's honestly very common for us, just like I said, but it's, uh, you know, something that we knew we were signing up for, but I think it's really exciting when we then do gain that budget that's brand new, um, for these companies.

P: That's great. So a theme that I keep pulling out from your responses here is about learning. It seems like really learning quickly, taking feedback from the market, from your customers and prospects, and iterating on it. And so again, a personal question to you is from a quality or a skill perspective, when you think of your own sales experience, what would you say is the one thing that you've had to work on, I guess, to, to learn about improving, uh, in order to make yourself a better salesperson for, for a Prelay, I mean, as CEO, you're the ultimate salesperson for Prelay, but, um, so what, what would be an attribute that you think is critical to focus on?

G: I think that's the hardest part about being a founder and CEO and having to sell. You're going to have to sell at any stage, but even in the earliest stages, you know so much about the product, right? You're an expert around the product. You know every little inch. It makes it a lot harder to slow down and understand that not everyone understands the product like you do. You really have to educate the person in front of you and really understand. where they stand from an educational standpoint. What I mean by that is like, what's the context they have coming in? Are they asking questions? Are they just sitting there? Are they confused? Really reading the room and making sure that you can ask the right questions to get them up to speed, I think is the hardest piece. And I think that's hard for a lot of people. And I think it's honestly one of the most critical pieces of sales is, how do you read the room? How do you get everyone up to speed? Especially if you have multiple stakeholders. You know, it's hard when you know a lot about the product and you have to take a step back and be like, hmm, the other person in the room, their perspective might be vastly different from mine. So I think that's something that's been a huge learning, you know, on my end. I think in addition to that, you know, I really like preparation in the end, I typically like to prepare, but I think even just thinking through the small things within each meeting from a sales perspective. is huge, especially when you are going to have to do a lot of reading of the room, really be agile during the meeting. The more you can prepare, it'll really set you up for success in the end. But yeah, I definitely think being thoughtful around educating the room and getting everyone at that same playing field is very critical.

P: That's great. Well, Gabriella, this has been a terrific conversation. Very much enjoyed the chance to meet you, hear more about the great success at Prelay and congratulations on that success. So thank you again for joining.

G: Yeah, thanks again for having me.