The Pavilion Podcast
The Pavilion Podcast

Episode · 2 months ago

Ep 240: Growth Lessons From A First-Time Founder, Gabriella DeFlorio of Prelay (Throwback)

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Ep 240: Growth Lessons From A First-Time Founder, Gabriella DeFlorio of Prelay (Throwback)

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

Book. All right, this episode is brought to you by contract book. Raise your hand if you love managing contracts. We didn't think so. Contract book created an all in one contract automation platform with data at the heart of everything. To help organizations automate mundane tasks that waste your valuable time, energy and resources. Visit Contract Bookcom to excess contract books complete set of automation tools for free. Now let's get into the show. All right, Gabriella de Florio, welcome to the pavilion podcast. How are you good? Good, a great to be here. Yeah, excited to have you on, and I'm always kicking it off during the pandemic times of see more 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 from in Michigan, right, you're a michignate of Yep. Yeah, that's why I talked about the weather, because it's definitely a big change coming from from Michigan. Yeah, I'm a big well, for one, a big Michigan Fan, but also I come from Michigan as well, so definitely know the winters out there pretty well. But yeah, came directly out to the to the west coast, and have state ever since. Yeah, what's 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 catalysts 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 ladder, 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 well, especially during that period of time, 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 somems from my athletics, and so it was always kind of read, I guess, in me that I really wanted to surround myself with like passionate people, like I always have, you know, with pretty competitive teams and everything, and so for me, you know, it kind of came naturally to want to move into kind of environment where people are, you know, pushing themselves and building cool things and working on things they are 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 you know, back in Michigan, but I really was interested in how do I make an impact of really scaling out how go to 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 I'll 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, but I definitely haven't looked back since, as I mentioned, and I love it. It's 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. If actually a lot of good friends that are in the Olympics right...

...now. So it's it's 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 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 to our coach there was at Michigan was coach of money a Libyans 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, I guess, motives around why you're doing the sport super holistically and not, 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 with the flow of really what makes sense, what type of goals you should be setting for yourself. So it is 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 like key numbers, but rather how are you making sure you're focusing on yourself and kind of keep on moving that goal posts like further and further? So yeah, I think, I think with a coach. You remind me of coach and also similar to it now, like for 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 Ely athletes and also a coach that has just seen so much right in the past. So yeah, I was definitely are pretty cool experience. You know, don't recommend people running as much as I did, but you know, definitely couldn't, you know, ask for more there. That's great and I'm just curious before we move on to you know, more business topics, was there anything that stood out to you from the other elite performers that you were with at Michigan and, you know, through your years there of high performance training, like where there any significant characteristics that stood out, like outside of maybe the things that people might expect like yeah, they worked hard or, you know, they ate well or something like that? was there any I'm just curious whether it's physical or mental that stood out to you as a key characteristic? Yeah, yeah, and you yeah, you hit on this for sure. This is a topic of mine that I actually 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, someone biles and a lot of people recently where they've had a lot of mental, you know, problems with being able to hop in his performance and balance mental, mental and physical. And although I think athletics is like a very much of 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. What I've really found is the best athletes were able to focus, they are 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 when all they had to do is be able to perform and execute. And what I found is like I had, you know, a housemate. She now runs for Nike and fortunately Miss Olmpis by like very small inch. I always found she was very strong at being able to hop on the line and know she was going to put her best foot forward. Didn't matter, like what goal...

...she had in front of her. She knew that she prepped and prepared and trained to 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 mentoring 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 hop in 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, you know, sales and everything right, your baby, with five ten different sequels ors 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 enoughably, 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 a 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 clegit 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 you know you have the ability to to be able to like achieve the goal. So it's definitely a thing that I think sales, athletics competing in general. I mean obviously, as a founder it's very similar to athletics as well, having goals and growth and everything, but I think it's a 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, 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 prelay. I believe you started about two years ago. I'm some curious like what was the what was that like tipping point that made you say, Hey, like I want to I want to go at it on my own. Obviously we know how challenging it is. I'm 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 prelay? Yeah, and I well, I think there's a couple things that came into play. I think, for one, I saw the pain in 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 paid and let me go be a founder and commit to this for the next ten plus years. You know, it's not something that you necessarily want to commit to right away, but it was something that was passionate about and I was trying to solve internally for one, you know. Additionally, I just built up that confidence...

...of, 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, etc. So it is, like, you know, obviously the confidence and 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 get it 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 with, 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 us and BS 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 get 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 if you don't wake up every day and you're excited to work, be working on what you work on and speaking with the people every day, especially you know amount I have to talk to people, it becomes too laborious at that point. So yeah, I've definitely have been able to find that balance of, you know, passion and you know, 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, you know, how far I could take it as well. Yeah, and you have, you know, it just a great list of investors that you've been able to nail down, from from why see to s be angeled to executives that box, dropbox Microsoft, etc. So I'm curious again as a first time founder, like what was that experience like in like throughout the fund raising rounds? It was 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'd have the chuck coming through and then San Francisco is shutting down the next day. So it was a lot of highs and lows, for sure, and it's very quick, Tony, for our span. But 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 prelay, 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 really great storytelling exercise. And you know, I think it honestly is very similar to sales have 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 the products and solution. And so for you know, investing, it was interesting. You know, obviously you're you're pitching this you know, product or just in eventual like company, in the early stages it's you know, whether it's a product or a full just like a 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 because it's like a commitment to you for the upcoming ten years and you're going to be partnering with this person for the upcoming ten years, and I 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. You know plenty of others like gt over at Red Canary, all these people. You know, they were excited about prelay, 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 ten years, is 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, definitely was an exciting time, interesting pitching some of the experts and top investors and 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 it. Did you get was it defined 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 all, honestly, typically like automatic funding at that point. If not a successful cost company, then kind of questionable. There, I think is a first time founder, you have kind of different kind of characteristics. You can drive for yourself and how to stand out against the crowd and really, 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 you know the market, and you know, they probably ask me more questions than a serial founder they would, but I don't know, I enjoyed it. I loved the challenge where they like tossed 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 yeah, definitely has 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 about sort. Yeah, you mentioned a little bit ago that you are part of the reason that you're so confident was that you've been you have proven to yourself and to others that you can scale go to market organizations from scratch. I'm curious, like what what do you do differently than others or where do where are 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 and another place, whether or not they're 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. prelay 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 ladder half I was going to mention. Is Typically at earlier stage, like the same 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 kind of, I would say, since your resource 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, is people aren't creative enough. They're not thinking through the nuances of their product and how it maybe 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 early stages and obviously pollen 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. HMM, I'd love for you to talk a little bit about prelay in some of the problems that you're solving, just as relates to team selling. And Yeah, I mean what you're the problems that you're solving for your customers. Now, yeah, for sure. So what I already mentioned some of what a second ago is around, just like the people that are involved in the process as well. And so really what we solve for is overall kind of complexity of the sale. Typically we work with companies that have more high touch type of engagement. So they're selling two 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, as hopping our platform, we have solutions engineers hopping in our platform, we have legal sometimes hopping in our platform. Deal to ask 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 wrap, I can get a hold of anywhere, anyone from anywhere and provide up from context of what I need? So we really make it so how can the you know, people really be working for the process and make sure that vice versa as well as you know, as many know, especially people that'd be listening here, is like on you know, sales process. These can run, 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 key, how your team is being utilized additionally, how your processes can be potentially scaled out more effectively. So these are all things that we really try to think through. Prelay for Best Practices for one, but obviously, from our systems standpoint, really allowing the teams to be able to work together in one place and having those, you know, key workflow integations as well, that they can work off of. Well, be as a sales rip that 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 it's I've been on a team where there's ten a's 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 involve in this situation or who not to? Or, obviously, when you when you loop in an executive, you know, you loop a maybe a CEO or cro 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 AE is to be the you know, the quarterback, quote unquote, of the deal and be able to, you know, not only kind of direct the prospect 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 a more complex, complicated six figure, seven figure sale, you know, needs a lot. 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 wraps, it's a lot of solutions engineers that are wanting to have more process around their Pov's and POC's and wanting to collaborate more closely with those teams where 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 and a lot of ways, for sure. So glad you're excited about it too. Yeah, I love it. So that one of the last questions I've got for you here, 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, so what I really like to say is you need to be genuine. I think, 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, you know, relationships, network everything of that sort. But I think there's oftentimes, you know, I think it's just it's super similar sales. Honestly, it's like your you have this, you know, goal on 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 meet 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 kind of playing the long game and, you know, trying to add value, just like you would, like you said, in a sales cycle. Right. You're not just like trying to close someone on the first gold 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 podcast 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, being a 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 formation for now, rather than kind of looking at books that might have been back in the day. Now there's a certainly fundamental things that come with that if you kind of read things are 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 in comedity 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, any good follows on twitter, recommendations, so many. I feel like my twitter is filled with successful founders in the past. You know, VC's I love, like I think nick mud always pushes out and stuff with with gainsight 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 some great investors that have been built, been around at least building amazing companies as well. 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, 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 linkedin or email or some other form, what's the best place that folks want to reach out? Yeah, I know. 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 topics on that end, and then you can reach out to me. I'm always on Linkedin. I love Linkedin right at Gabriella de Florio, but then also, as I mentioned, love by twitter, so you can also hop on at Gabriella do flow as well. I love it. Gabrielle, thanks for coming on. Appreciate your time. Yeah, appreciate it all right. Thanks for checking that episode out. This was brought to you by contract book. Contract Books Digital Contract Management Platform allows scaling businesses to automate and manage the entire contract life cycle in one flow. Get started for free at contract bookcom. Will be back next week with another episode piece.

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