The Pavilion Podcast
The Pavilion Podcast

Episode · 1 month 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 Pavilionpodcast. This is your host Tom Alamo. This is the show where revenue leaderscan learn the tips, the tricks and tactics that they need to be successfulin their roles. I'm pumped to be sharing this episode. Number 1 43. I'vegot Gabriella di Florio joining me, she is the co founder and Ceo of pre layprior to that, she was in multiple growth roles at startups. Before thatshe was a D one cross country athlete, olympic, trial hopeful. And so we talkabout a little bit about the sports journey, a lot about theentrepreneurship journey, how she's kind of put together the growth plansthat go to market plans, the product and what it's like to be a first timefounder at pre lay. So a super interesting conversation. I thinkyou're really going to enjoy it before we get to that. I have a quick wordfrom our sponsor. This episode is brought to you by Sandoz so send also.The leading sending platform is the most effective way for revenuegenerating teams to stand out with new ways to engage at strategic pointsthroughout the customer journey by connecting digital physical strategies.Companies can engage, acquire and retain customers easier than everbefore. Now, let's get straight into our episode. All right, Gabriella diFlorio, welcome to the Pavilion podcast. How are you? Good, good, Great to behere. Yeah, excited to have you on and I'm always kicking it off during thepandemic times of seeing where people are. So it sounds like you're in sanFrancisco just like me, Yeah, yeah, right in the bay Area have been forsome time and can't complain with the great weather recently. Yeah, and yougrew up in michigan, right? You're a michigan native, Yeah, yeah, that's whyI 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 Icome from michigan as well, so definitely know the winters out therepretty well, but uh, it came directly out to the, to the west coast and havestayed ever since. Yeah, what's, um, because I think you had a job or twoafter college in somewhere in michigan and then at some point you broke out tothe Bay Area, so what was the kind of catalyst to that, of wanting to get tothe Bay Area was just like a deep interest in tech or a particular jobthat drew you out or I just got to get the hell out of these michigan wintersor where was your head at? It was somewhat the latter, but I don't wantto 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 passionthat was happening really around building things in the Bay Area and youknow, 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 andoverall kind of technology world within san Francisco it was really hard for meto say no overall like my background comes from like stems from likeathletics and so it was always kind of red I guess and me that uh reallywanted to surround myself with like passionate people, like I always haveyou know with a pretty competitive teams and everything and so for me, youknow it kind of came naturally to want to move into a kind of environmentwhere people are you know pushing themselves and building cool things andworking on things they're passionate about and so for one that's one mainreason I definitely came out here, I think the environment was justinspiring and empowering to be working alongside of all those people andmeeting a ton of the community, but also I just you know was reallyinterested 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 impactof really scaling out how good a market works at companies and that was kind ofmy, you know to like two things that I was really interested in is like howcan I work with passionate people that...

...will learn from and then also how can Ibe able to like drive impact on how people are like for one workingtogether and then to how they're kind of scaling out even growth at theircompany. So it was definitely a, you know, a big jump from michigan. Idefinitely haven't looked back since as I mentioned and I love it definitelyfelt very natural for me. Yeah, yeah. And this is you spoke about yourcompetitive nature but you were an olympic hopeful at one time, is thatright? Like in cross country or track? Yeah, yeah. Watching the olympics rightnow, it's actually a lot of good friends that are in the olympics rightnow. So it's uh it's hard to watch from so far, far away. But yeah, it wasdefinitely a really intense time during college and even prep school andeverything having to compete at a high level and I think it goes back, it'slike that's why I think founding companies sales honestly super similarto of athletics and having to achieve this like high level and trying to pushthe mark every time. But yeah, I I learned a ton during that period oftime of how do you work with like elite team also, how are you pushing yourselfindividually but bringing your team along too. Our coach there was atmichigan was coach of money olympians and he really taught us like theoverall, I would say motive around not, you know, overthinking things andreally thinking through your training and your overall motives around whyyou're doing this sport super holistically and not. Um, you know, Ithink there's a lot of times with running and sales you can over index onthe numbers and not really going to flow of really what makes sense whattype of goals you should be setting for yourself. So it's definitely a periodof time where I really learned that of, you know, how can you be pushingyourself, put pushing the limit and not over indexing on those key numbers, butrather how are you making sure you're focusing on yourself and kind of keepon moving that goal post like further and further. So yeah, I think I thinkwith 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'svery, very much similar of somebody kind of pushing you to that next levelfor yourself, but also obviously it brings the team along too. So it's avery unique experience of, you know, working alongside of pretty eliteathletes 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 recommendpeople running as much as I did, but uh, definitely, uh, couldn't ask for morethere. That's great. And I'm just curious before we move on to you, nomore business topics. Was there anything that stood out to you from theother elite performers that you were with at michigan and and you knowthrough your years they're of high performance training. Like were thereany significant characteristics that stood out like outside of maybe the thethings that people might expect like Yeah, they worked hard or they ate wellor something like that was there. I'm just curious whether it's physical ormental that stood out to you as a key characteristic. Yeah, yeah, yeah. Youhit on this for sure. This is a topic of mine that I actually a super opinionon from athletics to also just like life in general and I think alsoperformance of any sort of work or job you're doing, you know, from myperspective, the I mean it kind of goes back to you know, simone biles and alot of people recently where they've had a lot of mental, you know, problemswith being able to hop in this performance and balanced mental, mentaland physical and although I think athletics is like a very much a streamof that where it all comes together and if you're off mentally it's very hardto be physically there. I think that's the same for anything that might belike sales related even to is um what I've really found is the best athleteswere 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 ofthem at that point in time, all they had to do is be able to perform andexecute and what I found is like I had, you know, housemate, she now runs forNike and unfortunately this olympics by like very small inch, I always foundshe was very strong at being able to hop on the line and no, she was goingto put her best foot forward, didn't matter like what goals she had in frontof her, she knew that she prepped and prepared and trained for that moment intime to make sure that she can achieve the goal she wanted and not to likereally overthink that right and that mentally she had to be prepared andready and knew that she was ready as well physically, so typically I feellike this is actually something that I coach, you know, my team as well, and Ialso really, if anything push anybody that I'm entering to is notoverthinking things and really being mentally ready and confident thatyou'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 andjust trust yourself and I think that mental kind of confidence that comeswith that pushes you to never like next levels because you're not overthinkingwhere your limits are at and I think that's, you know, running anything elsethat's mentally taxing from athletic standpoint, but I also think it's ahuge thing with sales and everything, right, your baby with 5, 10 differentstakeholders in front of you, you're doing a large pitch to be able to closeup on a massive deal potentially, and that's a lot of pressure, right? Youhave your manager, you have your sales leaders behind you and somehow you haveto achieve this goal. But typically again, it's the preparation, you haveknowing 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 thatexpert and I think again again, people just get mentally off because they feellike they're not ready, but typically most people, I feel like are reallyready, they're just not really trusting the process and trusting themselvesthat they can be able to inevitably like execute on the plan and just beable to run with it when they have that focus time that they really have to beexecuting. So yeah, it's definitely, uh I think that mental focus andconfidence in one very short period of time is super important and I thinkpersonally, I, you know, even growing up when I was much younger and I wasprior to any sort of collegiate running, I would definitely like very highpressure races, you know large championships, I would just not do verywell because my mental state wasn't there, I wasn't trusting myself and itreally is that shift of mentality that you have to trust yourself, you have totrust the process and not overthink that your performance is enough andyour performance will get there and um you know, you have the capability to tobe able to achieve the goal. So it's definitely a thing that I think salesathletics, competing in general, I mean obviously is a founder, it's verysimilar to athletics as well of having goals and growth and everything, but Ithink it's uh super interesting such as more of a life mentality you have tohave 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 yourrole. So I'm curious your first time founder here with relay, I believe youstarted about two years ago. So I'm curious like what was the, what wasthat like tipping point that made you say like, I want to I want to go at iton my own. Obviously we know how challenging it is. Sure you have plentyof battle stories from the last few years, but I'm curious like what wasthat inflection point that made you want to start relay? Yeah, and I well Ithink there's a couple of things that came into play, I think for one, I Isaw the pain and the problem, like, you know, it was something that I wanted tosolve and it wasn't necessarily something that I was like, You know, Ifeel this pain and let me go be a founder and commit to this for the next10 plus years, you know, it's not...

...something that you necessarily wannacommit to right away, but it was something I was passionate about and Iwas trying to solve internally for one. Additionally, I just built up thatconfidence, so you know, I know how to scale, go to market, I know how toscale it from scratch, I know how to scale out like, you know, the earlieststages of companies because I've done it before and then also I have workedwith Ceos in the past and I've seen steps, missteps, anything in between ofknowing how we can, you know, best scale at least at the earliest stagesand beyond that as well as we find more scale more people, etcetera. So it'slike, you know, obviously the confidence in being surrounded bythings that have gone well, things have not gone well and being able to learnfrom those, and then also, obviously just the guy that goes back to what Imentioned earlier around the passion is, you know, I was passionate around thespace, 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 ableto bring more of a macro level, not as micro, and it's been honestly, prettyawesome to be able to do it now at this macro level where we're impactingorganizations across the, you know, board of S and B S to enterprises andyeah, I think it's just pairing passion with confidence that you can be able toexecute, 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 thoughtfulprocess of, am I the right person to be building this and am I willing to putthe work in to do this? Because like you said, founding is not, I thinkthere's a lot of times it seems really glamorous, it's probably one of thehardest things jobs you can commit to, especially if you want to do the jobright and exceed any sort of goals. So it definitely hasn't been easy, there'sa lot of long days, but that's why it's super important to have that passionbehind you because you don't wake up every day and you're excited to beworking 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 toolaborious at that point. So yeah, I've definitely been able to find thatbalance of, you know, passion and confidence at that, like Inflectionpoint and that's what really made me want to want to build it and honestlytest myself and see how far I could take it as well. Yeah. And you havejust 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 thatexperience like throughout the fundraising rounds? It was, it wasinteresting. So we raised, we raised during the middle of the pandemic. Itwas our, yeah, it was, it was a blast. You know, we had my main investorcalled me, let me know that we would have the check coming through and thensan Francisco is shutting down the next day. So it was a lot of highs and lowsfor sure. It's very quick 24 hour span. Um, but uh, yeah, I mean it was areally interesting time of really pitching is an interesting motion whereit'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 differentiatedover multiple years that software have been, has been around right andtypically 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 thatthis was the right way that we wanted to go about pre lay and I think that'sthe biggest thing. That was hard because there was so much informationyou want to share and so many things that you're excited about, but you haveto 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 ithonestly is very similar to sales and a lot of ways, but it's more general andlike market based versus it's just a...

...different audience that's looking at itcompared 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 wasinteresting, you know, obviously you're, you're pitching this, you know, productor 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 area 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 andyou have to make that decision so fast. So you have to kind of think through alot of attributes of these different investors, like, you know, each personlike Jeff or a box, you know, Quintin over at Dropbox, plenty of others, likeGt over at Red Canary, all these people, they were excited about pre lay, butthey all brought value to us to make sure that we could also be continuouslygrowing. And I think that's always like the thing I kept, even though it wassuch a short period of time to be Raising or also like picking a partnerthat would be with you for 10 years what is the value that, you know, ourteam can be getting and also we can be providing to you as well, honestly, nottoo far off of sales on that end too. But yeah, it definitely was excitingtime interesting pitching some of the experts and top investors in SiliconValley and obviously was really exciting to be able to also garner alot of investment from them as well. Yeah, I love that. Did you get, was itdo you find that it was more challenging as a first time founderthat to get people's commitment or that people were questioning you or did younot really feel like that was that was an issue that you ran into? I mean, Ithink that, you know, it depends right, if there's a repeat founder and they'vehad a successful company before then, you know, it's honestly typically likeautomatic funding at that point, if not a successful company than kind ofquestionable there I think is the first time founder, you have kind of adifferent kind of characteristics, you can drive for yourself and how to standout against the crowd and really, um, yeah, really kind of pinpoint how youwant to be conveyed to these investors and for me, you know, again, I alwaysdrive with passion and I always drive with like excitement around what I'mdoing. And so I think for me that's what allowed me to kind of stand out ina lot of ways I think. And additionally, I think it was definitely moredifficult potentially where I had to prove the market and you know, theyprobably asked me more questions than a serial founder they would, but I know Ienjoyed it. I loved the challenge where they like cost a ton of questions aboutthe market that you already kind of really dug into and it was like a funproblem kind of solving exercise. But um, yeah, definitely asked lots ofquestions but not something that I felt like was too much. I think it wasplenty enough where they should educate themselves in the market and understandhow much we've dug into it and validated and everything. That's whatyou mentioned a little bit ago that part of the reason that you're soconfident was you have proven to yourself and to others that you canscale go to market organizations from scratch. I'm curious like what do youdo differently than others or where do you, where some of the common mistakesthat folks make when they're trying to scale the go to market efforts like inthe early days of a business. Yeah, good question. So I think it's twothings. I think one is not all sales and deals are equal and products areequal. So I think one playbook from one place won't always work for another inanother place whether or not there even at the same stage. Right? So I thinkthat's a big portion. I think obviously that's something that we do solve forit really is like how do you really think through from your product, thepeople involved, types of people you're selling to, that you can be reallypulling together the best process for you and your team. And I think that'sthe kind of latter half I was going to...

...mention is typically at an earlierstage, 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 followit as much as possible, but there's different quirks and um kind of, Iwould say since your resources constraint things that you have toreally tighten up and be able to optimize as much as possible at theearliest stages where you don't have as many resources that you have to end upkind of be a little bit more creative with. And I think that that's theproblem sometimes with early stages, people aren't creative enough, they'renot thinking through the nuances of their product and how it may be shouldbe sold a little bit differently than others. You know, whether it's defininguse cases or it's being able to ensure that you're doing some sort of land andexpand model or how you're pricing it. These are all things that I thinkpeople have to piece together and be able to really defined for themselvesin the earliest stages and obviously pulling inspiration from others. Butunfortunately think sometimes there's a downfall when people think that theycan, you know copy and paste like a like a playbook from a large companyover to like a pretty small like you know, scaling start up as well. Mm I'dlove for you to talk a little bit about relay and and some of the problems thatyou're solving just as it relates to team selling and um yeah, I mean whatyou'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 likethe people that are involved in the process as well. And so really what wesaw for is overall kind of complexity of the sale. Typically we work withcompanies that have more high touch type of um engagement. So they'reselling to more, maybe enterprise companies, they might have moretechnical product. Additionally, maybe even honestly just more of a customercomplex product that they have to build out inevitably. So we typically workwith 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 inour platform, we have legal sometimes hopping in our platform deal desk. Alot of people that are typically, you know, maybe collaborating on slack todate or ad hoc systems where we allow for them to be able to betterorchestrate the deal and communicate and coordinate pretty seamlessly andreally have real time updates throughout as well. So a lot of ourcore use cases are like proof of concepts, proof of value, things thatget more complex from a process standpoint. Also we do core kind oflike 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 fromcontext of what I need. So we really make it so how can the people really beworking 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, salesprocess, these engagements can run for, you know, multi year, sometimes a yearand to keep track of all this, it's quite difficult. So we try to make surethat for one, how do they collaborate as easily as possible, but also how doyou scale it out? How do you start to think through what works best for yourorganization from a data perspective, we can track like he, how your team isbeing utilized. Um, additionally, how your processes can be potentiallyscaled out more effectively. So these are all things that we really try tothink through pre lay for best practices for one. But obviously fromour system standpoint, really allowing the teams to be able to work togetherin one place and having those key workflow integrations as well that theycan work off of Well as a sales rep that's, that's worked in severaldifferent, you know, startups. Like there's so many issues when it comes toteam selling, right? You could have one where I've been on a team where there's10 days to one solutions engineer. Right? So everyone is fighting fortheir 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 situationor 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 andso it's hard to maybe keep them...

...organized or be able to collaborateeffectively 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, youknow, not only kind of direct the prospect on, on the process and runthat effectively, but just as important, you know, direct the internal team toget 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 solvethe problem. Yeah, absolutely. And I think that's the exciting thing herethat, you know, a lot of people are excited about like the differentaspects of it as well. It's not only reps, it's a lot of solutions engineersthat are wanting to have more process around their P O V S and P O C. S andwanting 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 topartner with sales quite as much. So we really try to like bring that alignmenttogether 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 andnetworking things like that. I'm curious like what are one or anynetworking tips that you found to be particularly helpful either as afounder or even in some of your previous roles and go to market justthroughout your career. Yeah, no, uh so what I really like to say is you needto 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 reallywhere I found that it was just really helpful to connect with people was justbeing 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 reallytruly trying to build a connection or relationship that really makes youstand out and allows you to also start to gain relationships networkeverything of that sort, but I think there's often times, you know, I thinkit's just, it's super similar sales. Obviously it's like you're, you havethis uh, you know, goal in front of you, you need to close this deal, you needto build this relationship and yet so many people get just like hop over theprocess, especially with networking, they just like hop directly to, hey, Ineed this and it starts to become transactional. And so from myperspective it's how do you be genuine, how do you build this relationship overtime? You can help them vice versa. And I think that's where typically there'skind of missteps there and I think you kind of stand out in that sense if youdo that. Yeah, absolutely. It's, it's kind of playing the long game and youknow, 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 calland you're not just asking for stuff and not trying to, you know, offervalue and give something in return. So I love that, I love that as a tip lastquestion. Any resources, whether it's like books or podcasts or anything thatyou found particularly helpful either throughout your career or anything thatyou're getting into right now that, you know, has been taken up a little bit ofyour mind space. Yeah, let me think what would be themost useful. I mean, honestly, what I, what I love doing is followingcommunities like Pavilion, you know, I think a lot of it is very pointed tonow. I think my, my way of consuming things is real time. Like how can I getthe most relevant information to myself as much as possible. I think I'll readsome 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 thatare relevant there, especially in the sales world and then additionally, youknow, events and everything that I can be, you know, hopping into and learningmore about because again, it's all relevant information for now ratherthan 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 ofread things that a little bit older,...

...but I always like to stay kind of morein the now and what's really relevant that I can be listening into, so lovethe communities that are popping up right now. I think there's lots comingup 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 lovesoaking up those like bits of insights information, always any good follows ontwitter 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 alwayspushed 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 hassome great tweets out there as well and yeah, I think, you know, following alot of like successful founders that have built great go to market companiesin the past and then also, um, some great investors that have been beenaround at least building amazing companies as well. I always like tolook out for, Yeah, that's great. He is a great fall, he's funny as well asputs out actual good content about the business. It's a good combo. SoGabrielle, I appreciate you coming on any last words that you have, that thatwe didn't get to And then where's the best place for folks to connect withyou if it's linked in or email or some other form, what's the best place thatfolks want to reach out? Yeah, no, again, I appreciate the time today andyou know, happy to chat with anyone around like team selling. Always justlove jamming on any of the topics on that end and then you can reach out tome. I'm always on linkedin. I love linkedin right at Gabriella Di Floriobut then also as I mentioned, love my twitter. So you can also help on atGabriella di flow as well. I love it Gabrielle, thanks for coming on, Iappreciate your time. Yeah, I appreciate it. All right, thanks forchecking out that episode. All podcasts in october are going to be brought toyou by the lovely people at Sandoz. So they deliver modern direct mail,personalized gifts and other physical impressions that make your outreachmore personal. I'll be back next monday with another episode until then feelfree to hit me up on linkedin. My name is tom Alamo and go out and get afterit peace. Say something Mhm.

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