The Pavilion Podcast
The Pavilion Podcast

Episode · 7 months ago

Ep 143: Growth Lessons From Gabriella DeFlorio, Founder of Prelay

ABOUT THIS EPISODE

Ep 143: Growth Lessons From Gabriella DeFlorio, Founder of Prelay

Part of the TGIM (Thank God It's Monday!) series hosted by Tom Alaimo.

All right, welcome back to the Pavilion podcast. This is your host Tom Alamo. This is the show where revenue leaders can learn the tips, the tricks and tactics that they need to be successful in their roles. I'm pumped to be sharing this episode. Number 1 43. I've got Gabriella di Florio joining me, she is the co founder and Ceo of pre lay prior to that, she was in multiple growth roles at startups. Before that she was a D one cross country athlete, olympic, trial hopeful. And so we talk about a little bit about the sports journey, a lot about the entrepreneurship journey, how she's kind of put together the growth plans that go to market plans, the product and what it's like to be a first time founder at pre lay. So a super interesting conversation. I think you're really going to enjoy it before we get to that. I have a quick word from our sponsor. This episode is brought to you by Sandoz so send also. The leading sending platform is the most effective way for revenue generating teams to stand out with new ways to engage at strategic points throughout the customer journey by connecting digital physical strategies. Companies can engage, acquire and retain customers easier than ever before. Now, let's get straight into our episode. All right, Gabriella di Florio, welcome to the Pavilion podcast. How are you? Good, good, Great to be here. Yeah, excited to have you on and I'm always kicking it off during the pandemic times of seeing where people are. So it sounds like you're in san Francisco just like me, Yeah, yeah, right in the bay Area have been for some time and can't complain with the great weather recently. Yeah, and you grew up in michigan, right? You're a michigan native, Yeah, yeah, that's why I talk about the weather because it's definitely a big change coming from, from michigan. Yeah, I'm a big, well for one big michigan fan, but also I come from michigan as well, so definitely know the winters out there pretty well, but uh, it came directly out to the, to the west coast and have stayed ever since. Yeah, what's, um, because I think you had a job or two after college in somewhere in michigan and then at some point you broke out to the Bay Area, so what was the kind of catalyst to that, of wanting to get to the Bay Area was just like a deep interest in tech or a particular job that drew you out or I just got to get the hell out of these michigan winters or where was your head at? It was somewhat the latter, but I don't want to say that's the whole reason, but no, I think a lot of it was actually just, I saw the, especially during that period of time, I, I saw the passion that was happening really around building things in the Bay Area and you know, although I think there's a lot of things that are happening in michigan, I think when I started getting a taste of you know the startup world and overall kind of technology world within san Francisco it was really hard for me to say no overall like my background comes from like stems from like athletics and so it was always kind of red I guess and me that uh really wanted to surround myself with like passionate people, like I always have you know with a pretty competitive teams and everything and so for me, you know it kind of came naturally to want to move into a kind of environment where people are you know pushing themselves and building cool things and working on things they're passionate about and so for one that's one main reason I definitely came out here, I think the environment was just inspiring and empowering to be working alongside of all those people and meeting a ton of the community, but also I just you know was really interested within, I mean I already was digging into like go to market back in, back in michigan, but I really was interested in how do I make an impact of really scaling out how good a market works at companies and that was kind of my, you know to like two things that I was really interested in is like how can I work with passionate people that...

...will learn from and then also how can I be able to like drive impact on how people are like for one working together and then to how they're kind of scaling out even growth at their company. So it was definitely a, you know, a big jump from michigan. I definitely haven't looked back since as I mentioned and I love it definitely felt very natural for me. Yeah, yeah. And this is you spoke about your competitive nature but you were an olympic hopeful at one time, is that right? Like in cross country or track? Yeah, yeah. Watching the olympics right now, it's actually a lot of good friends that are in the olympics right now. So it's uh it's hard to watch from so far, far away. But yeah, it was definitely a really intense time during college and even prep school and everything having to compete at a high level and I think it goes back, it's like that's why I think founding companies sales honestly super similar to of athletics and having to achieve this like high level and trying to push the mark every time. But yeah, I I learned a ton during that period of time of how do you work with like elite team also, how are you pushing yourself individually but bringing your team along too. Our coach there was at michigan was coach of money olympians and he really taught us like the overall, I would say motive around not, you know, overthinking things and really thinking through your training and your overall motives around why you're doing this sport super holistically and not. Um, you know, I think there's a lot of times with running and sales you can over index on the numbers and not really going to flow of really what makes sense what type of goals you should be setting for yourself. So it's definitely a period of time where I really learned that of, you know, how can you be pushing yourself, put pushing the limit and not over indexing on those key numbers, but rather how are you making sure you're focusing on yourself and kind of keep on moving that goal post like further and further. So yeah, I think I think with a coach, it reminded me of coach and also similar to now, like for me, right as a founder investors as well as also for any like salesperson? It's very, very much similar of somebody kind of pushing you to that next level for yourself, but also obviously it brings the team along too. So it's a very unique experience of, you know, working alongside of pretty elite athletes and also coach that has just seen so much right in the past. So yeah, it was definitely a pretty cool experience, you know, don't recommend people running as much as I did, but uh, definitely, uh, couldn't ask for more there. That's great. And I'm just curious before we move on to you, no more business topics. Was there anything that stood out to you from the other elite performers that you were with at michigan and and you know through your years they're of high performance training. Like were there any significant characteristics that stood out like outside of maybe the the things that people might expect like Yeah, they worked hard or they ate well or something like that was there. I'm just curious whether it's physical or mental that stood out to you as a key characteristic. Yeah, yeah, yeah. You hit on this for sure. This is a topic of mine that I actually a super opinion on from athletics to also just like life in general and I think also performance of any sort of work or job you're doing, you know, from my perspective, the I mean it kind of goes back to you know, simone biles and a lot of people recently where they've had a lot of mental, you know, problems with being able to hop in this performance and balanced mental, mental and physical and although I think athletics is like a very much a stream of that where it all comes together and if you're off mentally it's very hard to be physically there. I think that's the same for anything that might be like sales related even to is um what I've really found is the best athletes were able to focus their able to if anything blind out anything around them, any sort of crazy pressure, anything...

...that might be a goal that's in front of them at that point in time, all they had to do is be able to perform and execute and what I found is like I had, you know, housemate, she now runs for Nike and unfortunately this olympics by like very small inch, I always found she was very strong at being able to hop on the line and no, she was going to put her best foot forward, didn't matter like what goals she had in front of her, she knew that she prepped and prepared and trained for that moment in time to make sure that she can achieve the goal she wanted and not to like really overthink that right and that mentally she had to be prepared and ready and knew that she was ready as well physically, so typically I feel like this is actually something that I coach, you know, my team as well, and I also really, if anything push anybody that I'm entering to is not overthinking things and really being mentally ready and confident that you've prepared for that moment or you've prepared as much as possible as, as you can, at least with time you have and that you kind of have to happen and just trust yourself and I think that mental kind of confidence that comes with that pushes you to never like next levels because you're not overthinking where your limits are at and I think that's, you know, running anything else that's mentally taxing from athletic standpoint, but I also think it's a huge thing with sales and everything, right, your baby with 5, 10 different stakeholders in front of you, you're doing a large pitch to be able to close up on a massive deal potentially, and that's a lot of pressure, right? You have your manager, you have your sales leaders behind you and somehow you have to achieve this goal. But typically again, it's the preparation, you have knowing you've already trained yourself to be able to know all these things, talk to these people really understand what you're talking about and be that expert and I think again again, people just get mentally off because they feel like they're not ready, but typically most people, I feel like are really ready, they're just not really trusting the process and trusting themselves that they can be able to inevitably like execute on the plan and just be able to run with it when they have that focus time that they really have to be executing. So yeah, it's definitely, uh I think that mental focus and confidence in one very short period of time is super important and I think personally, I, you know, even growing up when I was much younger and I was prior to any sort of collegiate running, I would definitely like very high pressure races, you know large championships, I would just not do very well because my mental state wasn't there, I wasn't trusting myself and it really is that shift of mentality that you have to trust yourself, you have to trust the process and not overthink that your performance is enough and your performance will get there and um you know, you have the capability to to be able to achieve the goal. So it's definitely a thing that I think sales athletics, competing in general, I mean obviously is a founder, it's very similar to athletics as well of having goals and growth and everything, but I think it's uh super interesting such as more of a life mentality you have to have of just like pure focus and like confidence and grit and everything. Yeah, absolutely. So you were one of the first handful of hires, you know, at a few startups, you know, in the go to market space, successful in your role. So I'm curious your first time founder here with relay, I believe you started about two years ago. So I'm curious like what was the, what was that like tipping point that made you say like, I want to I want to go at it on my own. Obviously we know how challenging it is. Sure you have plenty of battle stories from the last few years, but I'm curious like what was that inflection point that made you want to start relay? Yeah, and I well I think there's a couple of things that came into play, I think for one, I I saw the pain and the problem, like, you know, it was something that I wanted to solve and it wasn't necessarily something that I was like, You know, I feel this pain and let me go be a founder and commit to this for the next 10 plus years, you know, it's not...

...something that you necessarily wanna commit to right away, but it was something I was passionate about and I was trying to solve internally for one. Additionally, I just built up that confidence, so you know, I know how to scale, go to market, I know how to scale it from scratch, I know how to scale out like, you know, the earliest stages of companies because I've done it before and then also I have worked with Ceos in the past and I've seen steps, missteps, anything in between of knowing how we can, you know, best scale at least at the earliest stages and beyond that as well as we find more scale more people, etcetera. So it's like, you know, obviously the confidence in being surrounded by things that have gone well, things have not gone well and being able to learn from those, and then also, obviously just the guy that goes back to what I mentioned earlier around the passion is, you know, I was passionate around the space, I was passionate about helping our sales team, be able to execute, help our team be able to grow and it was something that I wanted to be able to bring more of a macro level, not as micro, and it's been honestly, pretty awesome to be able to do it now at this macro level where we're impacting organizations across the, you know, board of S and B S to enterprises and yeah, I think it's just pairing passion with confidence that you can be able to execute, which goes back to what I just mentioned is I think a good pairing of, you know, why you'd want to do it now, certainly, you know, it's a thoughtful process of, am I the right person to be building this and am I willing to put the work in to do this? Because like you said, founding is not, I think there's a lot of times it seems really glamorous, it's probably one of the hardest things jobs you can commit to, especially if you want to do the job right and exceed any sort of goals. So it definitely hasn't been easy, there's a lot of long days, but that's why it's super important to have that passion behind you because you don't wake up every day and you're excited to be working on what you work on and speaking with the people every day, especially, you know, you don't have to talk to people. Um it becomes too laborious at that point. So yeah, I've definitely been able to find that balance of, you know, passion and confidence at that, like Inflection point and that's what really made me want to want to build it and honestly test myself and see how far I could take it as well. Yeah. And you have just a great list of investors that you've been able to nail down from, from Y C two has to be angel to executives at box, dropbox Microsoft, etcetera. So I'm curious again as a first time founder, like what was that experience like throughout the fundraising rounds? It was, it was interesting. So we raised, we raised during the middle of the pandemic. It was our, yeah, it was, it was a blast. You know, we had my main investor called me, let me know that we would have the check coming through and then san Francisco is shutting down the next day. So it was a lot of highs and lows for sure. It's very quick 24 hour span. Um, but uh, yeah, I mean it was a really interesting time of really pitching is an interesting motion where it's not always the same as like a sales motion. You're pitching a market, you're pitching an idea, You're pitching how this can be differentiated over multiple years that software have been, has been around right and typically not every single person has dug into it as much as you have, right. Like I took months to be able to get to this point of feeling confident that this was the right way that we wanted to go about pre lay and I think that's the biggest thing. That was hard because there was so much information you want to share and so many things that you're excited about, but you have to shorten it and be able to really build it up into this more of a story. And it's a really great storytelling exercise and, you know, I think it honestly is very similar to sales and a lot of ways, but it's more general and like market based versus it's just a...

...different audience that's looking at it compared to, you know, a sales you're typically selling to the experts, right? They understand exactly the pain points you're mentioning hopefully about the, about the product and solution. And so for, you know, investing, it was interesting, you know, obviously you're, you're pitching this, you know, product or uh, just an eventual, like company and in the early stages it's, you know, whether it's a product or a full, um, just like an idea at that point we are a product and you're asking for money for it. So it's, it's a commitment, it's weird cause it's like a commitment to you for the upcoming 10 years, you're gonna be partnering with this person for the upcoming 10 years and you have to make that decision so fast. So you have to kind of think through a lot of attributes of these different investors, like, you know, each person like Jeff or a box, you know, Quintin over at Dropbox, plenty of others, like Gt over at Red Canary, all these people, they were excited about pre lay, but they all brought value to us to make sure that we could also be continuously growing. And I think that's always like the thing I kept, even though it was such a short period of time to be Raising or also like picking a partner that would be with you for 10 years what is the value that, you know, our team can be getting and also we can be providing to you as well, honestly, not too far off of sales on that end too. But yeah, it definitely was exciting time interesting pitching some of the experts and top investors in Silicon Valley and obviously was really exciting to be able to also garner a lot of investment from them as well. Yeah, I love that. Did you get, was it do you find that it was more challenging as a first time founder that to get people's commitment or that people were questioning you or did you not really feel like that was that was an issue that you ran into? I mean, I think that, you know, it depends right, if there's a repeat founder and they've had a successful company before then, you know, it's honestly typically like automatic funding at that point, if not a successful company than kind of questionable there I think is the first time founder, you have kind of a different kind of characteristics, you can drive for yourself and how to stand out against the crowd and really, um, yeah, really kind of pinpoint how you want to be conveyed to these investors and for me, you know, again, I always drive with passion and I always drive with like excitement around what I'm doing. And so I think for me that's what allowed me to kind of stand out in a lot of ways I think. And additionally, I think it was definitely more difficult potentially where I had to prove the market and you know, they probably asked me more questions than a serial founder they would, but I know I enjoyed it. I loved the challenge where they like cost a ton of questions about the market that you already kind of really dug into and it was like a fun problem kind of solving exercise. But um, yeah, definitely asked lots of questions but not something that I felt like was too much. I think it was plenty enough where they should educate themselves in the market and understand how much we've dug into it and validated and everything. That's what you mentioned a little bit ago that part of the reason that you're so confident was you have proven to yourself and to others that you can scale go to market organizations from scratch. I'm curious like what do you do differently than others or where do you, where some of the common mistakes that folks make when they're trying to scale the go to market efforts like in the early days of a business. Yeah, good question. So I think it's two things. I think one is not all sales and deals are equal and products are equal. So I think one playbook from one place won't always work for another in another place whether or not there even at the same stage. Right? So I think that's a big portion. I think obviously that's something that we do solve for it really is like how do you really think through from your product, the people involved, types of people you're selling to, that you can be really pulling together the best process for you and your team. And I think that's the kind of latter half I was going to...

...mention is typically at an earlier stage, like the process won't really work the same for you versus, you know, a massive enterprise company now, I think you can certainly try to follow it as much as possible, but there's different quirks and um kind of, I would say since your resources constraint things that you have to really tighten up and be able to optimize as much as possible at the earliest stages where you don't have as many resources that you have to end up kind of be a little bit more creative with. And I think that that's the problem sometimes with early stages, people aren't creative enough, they're not thinking through the nuances of their product and how it may be should be sold a little bit differently than others. You know, whether it's defining use cases or it's being able to ensure that you're doing some sort of land and expand model or how you're pricing it. These are all things that I think people have to piece together and be able to really defined for themselves in the earliest stages and obviously pulling inspiration from others. But unfortunately think sometimes there's a downfall when people think that they can, you know copy and paste like a like a playbook from a large company over to like a pretty small like you know, scaling start up as well. Mm I'd love for you to talk a little bit about relay and and some of the problems that you're solving just as it relates to team selling and um yeah, I mean what you're the problems that you're solving for your customers now. Yeah, for sure. Um so what I already mentioned, some of what a second ago was around just like the people that are involved in the process as well. And so really what we saw for is overall kind of complexity of the sale. Typically we work with companies that have more high touch type of um engagement. So they're selling to more, maybe enterprise companies, they might have more technical product. Additionally, maybe even honestly just more of a customer complex product that they have to build out inevitably. So we typically work with companies that have pretty large deal team getting involved. So we have, you know, e s hopping in our platform, we have solutions engineers hopping in our platform, we have legal sometimes hopping in our platform deal desk. A lot of people that are typically, you know, maybe collaborating on slack to date or ad hoc systems where we allow for them to be able to better orchestrate the deal and communicate and coordinate pretty seamlessly and really have real time updates throughout as well. So a lot of our core use cases are like proof of concepts, proof of value, things that get more complex from a process standpoint. Also we do core kind of like how do we involve people in the deal? How do we make sure that as a rep, I can get a hold of any where anyone from anywhere and provide up from context of what I need. So we really make it so how can the people really be working for the process and make sure that vice versa as well as money? No, especially people that be listening here is like on uh, you know, sales process, these engagements can run for, you know, multi year, sometimes a year and to keep track of all this, it's quite difficult. So we try to make sure that for one, how do they collaborate as easily as possible, but also how do you scale it out? How do you start to think through what works best for your organization from a data perspective, we can track like he, how your team is being utilized. Um, additionally, how your processes can be potentially scaled out more effectively. So these are all things that we really try to think through pre lay for best practices for one. But obviously from our system standpoint, really allowing the teams to be able to work together in one place and having those key workflow integrations as well that they can work off of Well as a sales rep that's, that's worked in several different, you know, startups. Like there's so many issues when it comes to team selling, right? You could have one where I've been on a team where there's 10 days to one solutions engineer. Right? So everyone is fighting for their time and you know, they don't have enough bandwidth or you know, somewhere it's just an absolute cluster of who do I involved in this situation or who not to or obviously when you, when you loop in an executive, you know, you may be a Ceo or C R O into a deal, they have a million things going on and so it's hard to maybe keep them...

...organized or be able to collaborate effectively with them. So I feel like part of your job as an A is to be the, you know, the quarterback quote unquote of, of the deal and be able to, you know, not only kind of direct the prospect on, on the process and run that effectively, but just as important, you know, direct the internal team to get the resources that you need. So I feel like the team selling dynamic, Especially for more complex, complicated six Figure 7 figure sale, you need to, we need a lot of help. So I'm glad that you are trying to solve the problem. Yeah, absolutely. And I think that's the exciting thing here that, you know, a lot of people are excited about like the different aspects of it as well. It's not only reps, it's a lot of solutions engineers that are wanting to have more process around their P O V S and P O C. S and wanting to collaborate more closely with those teams were typically again, you find that a lot of these teams are kind of siloed and not as empowered to partner with sales quite as much. So we really try to like bring that alignment together in a lot of ways for sure. So I'm glad you're excited about it too. Yeah, I love it. So one of the last questions I've got for you here, um, pavilion, it's all about the community and trying to add value to others and networking things like that. I'm curious like what are one or any networking tips that you found to be particularly helpful either as a founder or even in some of your previous roles and go to market just throughout your career. Yeah, no, uh so what I really like to say is you need to be genuine I think, um you know, especially moving out to san Francisco, you know, during that period of time, it was like a networking frenzy, Everyone was trying to meet people, everyone was a transplant and really where I found that it was just really helpful to connect with people was just being genuine. I think everyone has their own agenda, everyone wants their, you know, own things. And I think in the end if you're genuine and really truly trying to build a connection or relationship that really makes you stand out and allows you to also start to gain relationships network everything of that sort, but I think there's often times, you know, I think it's just, it's super similar sales. Obviously it's like you're, you have this uh, you know, goal in front of you, you need to close this deal, you need to build this relationship and yet so many people get just like hop over the process, especially with networking, they just like hop directly to, hey, I need this and it starts to become transactional. And so from my perspective it's how do you be genuine, how do you build this relationship over time? You can help them vice versa. And I think that's where typically there's kind of missteps there and I think you kind of stand out in that sense if you do that. Yeah, absolutely. It's, it's kind of playing the long game and you know, trying to add value just like you would, like you said in a sale cycle, right, you're not just like trying to close someone on the first cold call and you're not just asking for stuff and not trying to, you know, offer value and give something in return. So I love that, I love that as a tip last question. Any resources, whether it's like books or podcasts or anything that you found particularly helpful either throughout your career or anything that you're getting into right now that, you know, has been taken up a little bit of your mind space. Yeah, let me think what would be the most useful. I mean, honestly, what I, what I love doing is following communities like Pavilion, you know, I think a lot of it is very pointed to now. I think my, my way of consuming things is real time. Like how can I get the most relevant information to myself as much as possible. I think I'll read some books here and there. But I love just like in general, you know, obviously that comes with like twitter, you will soak up and follow people that are relevant there, especially in the sales world and then additionally, you know, events and everything that I can be, you know, hopping into and learning more about because again, it's all relevant information for now rather than kind of looking at books that might have been back in the day now, there's certainly fundamental things that come with that. Um if you kind of read things that a little bit older,...

...but I always like to stay kind of more in the now and what's really relevant that I can be listening into, so love the communities that are popping up right now. I think there's lots coming up that are providing a ton of value for the space and community in general, but also things like real time things like twitter and everything. I love soaking up those like bits of insights information, always any good follows on twitter recommendations, so many uh, I feel like my twitter is filled with uh, successful founders in the past vcs, I love like, I think nick but always pushed his out good stuff with um, with gain site and everything of that sort. I think he's been able to build an awesome brand for himself and he has some great tweets out there as well and yeah, I think, you know, following a lot of like successful founders that have built great go to market companies in the past and then also, um, some great investors that have been been around at least building amazing companies as well. I always like to look out for, Yeah, that's great. He is a great fall, he's funny as well as puts out actual good content about the business. It's a good combo. So Gabrielle, I appreciate you coming on any last words that you have, that that we didn't get to And then where's the best place for folks to connect with you if it's linked in or email or some other form, what's the best place that folks want to reach out? Yeah, no, again, I appreciate the time today and you know, happy to chat with anyone around like team selling. Always just love jamming on any of the topics on that end and then you can reach out to me. I'm always on linkedin. I love linkedin right at Gabriella Di Florio but then also as I mentioned, love my twitter. So you can also help on at Gabriella di flow as well. I love it Gabrielle, thanks for coming on, I appreciate your time. Yeah, I appreciate it. All right, thanks for checking out that episode. All podcasts in october are going to be brought to you by the lovely people at Sandoz. So they deliver modern direct mail, personalized gifts and other physical impressions that make your outreach more personal. I'll be back next monday with another episode until then feel free to hit me up on linkedin. My name is tom Alamo and go out and get after it peace. Say something Mhm.

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