How Two Best Friends Built a Signing Business and Broke Into Tech Sales

Carter (00:01.086)
Hey Erica on Andrea, give the people a quick intro. Who are you guys and what do you do?

Erica Waldron (00:07.704)
Well, I'm Erica. I am an account executive at Snapdocs located in Florida. And this is Andrea.

Andrea Castelli (00:18.427)
Hey, we're a team duo, so you'll always catch us together. I'm Andrea Castelli, also an account executive at Snapdocs. We both work on the settlement side of the team. So there's also a lending side and we're on the settlement side.

Carter (00:32.542)
Okay, and I wanted to talk about Sunny Signings. Before Sunny Signings even existed, you guys both had pretty wild paths into this industry. Take me through how each of you guys ended up in the signing world in the first place, like that initial intro.

Andrea Castelli (00:47.843)
Yes, this is actually our favorite part of the story because it's always so random. We've been best friends for over 15 years. We went to high school together. We've had the same jobs growing up. And then out of college, we moved to different towns. I was bartending and I had a regular come in and ask me if she was opening up a title company and I wanted to come work with her and I had no idea what it was. So I quit my job and I was like, yes, I'm going to come do that with you.

And so like I'm working in title and then I'll let Erica share what her background is at that time too.

Erica Waldron (01:22.432)
Yeah, so I was also a bartender and I was transitioning at that time to more of a corporate commercial real estate firm I worked at. And Andrea told me about her working in title, so it kind of went hand in hand. Like I was on the real estate side, but she was doing the title, which every real estate transaction needs title for the most part.

she was telling me all about like what she was doing with these closings and it was during COVID and she was like telling me how much extra money she was making doing the closings herself and then that's when we just put our heads together and we're like what are we doing?

Andrea Castelli (02:02.203)
Yeah, we're like, let's not sit behind a desk anymore. And like, let's get out there and start a business. And yeah, we've always had like entrepreneurial mindsets and always doing the same things growing up together. But this time, we're like, let's do this. And Erica actually quit her job, put her two weeks in before I even did before I was even ready. And I was like, wait, we're already doing this right now. And I was like, okay, so I put in my notice and then

Carter (02:07.69)
That makes sense.

Erica Waldron (02:21.358)
Thanks.

Andrea Castelli (02:29.243)
We literally just went out to it and started our business from the ground up. And then, yeah, it was all during COVID, so everyone needed a mobile notary. No one was going in the office at that time. Yeah, the demand was huge. So that's where we saw it. Yeah, we saw the huge demand for it, and we're like, this is our time. We have to do it now.

Carter (02:39.188)
so demand was huge at this time when you guys started.

Carter (02:47.284)
What was it like building Sunny Signings together and what did that experience teach you that you never would have learned working for someone else?

Erica Waldron (02:56.238)
But definitely if you have no other income, you are all in it. it was definitely like make it or break it. Like we had to go out, figure out what was working for us, what wasn't, like where our customers were, like how to get the best outreach. And that's kind of when we learned like conferences, like national conferences were a great place to like.

have higher volume clients and then also, well, how we started was going door to door actually, like just going in and.

Andrea Castelli (03:26.64)
Yeah, we were.

ride around and go to door to door and knock on title companies, doors or real estate attorneys and introduce ourselves. We would always bring them flowers because we thought flowers was, you know, bring, make some joy, bring happiness to the day when you're sitting inside an office. And we built really good relationships and we were doing all the signings ourselves at first driving around and like Prius that was actually handed down to Erica. We're like, no gas, nothing, just driving around doing signings. And then we eventually evolved. So we're like, how do we get other people to do this for us?

Carter (03:58.047)
Was that a tough sell at first? Because it seems like most of these people already have people they work with, right? And you guys kind of have to come in or is it not really like that?

Andrea Castelli (04:06.747)
Yeah, it's amazing both, I would say. Go ahead, Erica.

Erica Waldron (04:09.55)
no, I was going to say the same. Like, it's definitely a mix. A lot of people are loyal to whoever their provider is, but we seem like we were able to gain a lot of business. The flowers maybe won them over. don't know.

Andrea Castelli (04:26.477)
Also, it's a lot harder to say no to two people than it is one. So it's definitely like a unique duo. Yeah. And we just genuinely like went in and just were genuine and really built a great relationship. So it is about timing. was either they weren't happy with the current service that they were receiving or they actually just really didn't have anyone. And they were, it was just like perfect timing too.

Carter (04:30.868)
yeah.

Erica Waldron (04:32.045)
Yeah.

Carter (04:49.224)
What made you guys decide to merge Sunny's signings into first class instead of trying to keep growing it on your own?

Andrea Castelli (04:57.499)
This was actually a tough decision for us. We went to a national conference as Sunny signings and we met first-class signing service there. They had a booth. There was a woman there named Velvet who changed her life. would say she did the same thing with her signing service and she merged with first-class and said it was the best thing she ever did where she took a step back from the business aspect of running and was able to actually focus on gaining business and like getting out and marketing. And she said she was able to grow exponentially.

and we're like, hmm, that is interesting. So we did have to take a step back for a short period of time, but it wasn't long. And we saw exactly what Velvet said to us and we were able to grow really quickly.

Erica Waldron (05:39.598)
Yeah, it was definitely the best decision we could have made hands down.

Andrea Castelli (05:44.251)
Yeah, we were a little hesitant at first, but it was, yeah, cause it's like letting go of your business, your name, everything you built. And it all happened really quickly too. It wasn't just like years down the road, like all of this was like boom, boom, boom.

Carter (05:46.74)
Yeah.

Erica Waldron (05:57.891)
Yeah.

Carter (05:59.307)
So you guys are at first class now, you're growing it. Snapdocs is your tech partner. When did it go from this is a tool we use or people we do business with to we should go work there? How did that all come together?

Erica Waldron (06:12.692)
So this came about from, I would say maybe being known in the industry and like Snapdocs are all these national conferences that we're at. So we knew the Snapdocs team, hands down like the best tech out there for this line of business. And so we like knew like their innovative thoughts and like how much they are known in the industry and like this is like the true inter-

enterprise solution for us and we were in talks for a while with them before fully committing because it was like letting go of your business again in a sense, but like you're going to do business. So that's where we're at today and we have Jason to thank. He flew down and met us and convinced us to make the leap and come over to Snapdocs.

Carter (06:48.095)
Right.

Andrea Castelli (06:48.699)
Yeah, it was like a second conversation.

Carter (07:06.026)
Wow, that's great. This guy flew down. So you guys were known in this whole conference world, know, title world, and you guys are doing such a good job that this guy flew down to get you guys on the team.

Erica Waldron (07:08.814)
Thanks

Andrea Castelli (07:16.731)
Yeah, he did. We actually felt very important that day. like, someone's coming all the way down. It wasn't even like 24 hours was here. flew down. We went to Disney Springs for lunch, had a conversation, and then he flew back right after our talk. Yeah.

Erica Waldron (07:17.036)
Yeah.

Yeah.

Carter (07:21.181)
Yeah.

Carter (07:31.418)
Wow, okay. What carried over from the signing services world into tech sales better than people would expect? Is the job function very similar where you're still again going out to a of conferences and doing that type of thing or was it a huge jump and a lot that really didn't cross over?

Erica Waldron (07:32.534)
Yeah.

Andrea Castelli (07:48.252)
It's really not that big of a difference because we always sold the service, right? So we know the service and coming over to the tech side, now we're able to sell both, right? And so since we were so familiar with the tech of using the platform daily to like, you know, run and operate. And so I feel like it was an easy transition to be able to sell both the tech and the service. And it's nice. And that's also part of why we really made this change, because it opened up that opportunity to have both.

and that the company is always innovative and growing and so it's leading to more opportunities as well.

Erica Waldron (08:26.764)
And I would say like to add also being in the client's shoes, like, so we have like a well versed idea of what's going on in all aspects. Like if they're using your tech, like we know like what they're running into, like if they have a question, like we can easily like jump in and help, which is really nice.

Andrea Castelli (08:44.675)
Yeah, we can share a relatable story. So like we've been on the title side, the real estate side, the notary side, the operating signing service side. So we've been on all sides of it. And so we can relate in any different way for them.

Carter (08:57.994)
That makes sense. Did a lot of the relationships cross over into that world since you guys were already pretty well-avert, you already knew a lot of people in that space? Two, like did it, I'm saying did it like lead to deals, you know, from people that you'd already known? Yeah.

Andrea Castelli (09:08.717)
Most definitely, yeah. And having the Snapdocs name behind us now led to the bigger deals that have been in conversations for some time, led them to actually come to fruition and happen. So that was super exciting. Like having such, yeah, a huge brand of Snapdocs behind you really like brought the deals to the finish line.

Erica Waldron (09:08.832)
yeah.

Erica Waldron (09:23.086)
It was.

Carter (09:29.578)
And this is what I, oh sorry, go on.

Erica Waldron (09:29.708)
Yeah, was like great. I would say it was like perfect timing, like our transition to Snapdogs to get these deals like into motion.

Carter (09:39.754)
And this is what I was really curious about. How does, like, how does this whole thing work? How does working as a pair function day to day? Do you, are you splitting territory, share accounts, tag team calls, you guys all do stuff, you know, together? Yeah. How does this whole situation work? Cause that sounds, yeah, sounds wild.

Andrea Castelli (09:55.952)
So you'll never find us apart. Our parents used to joke with us when we were younger all the time, because we're always together. We are considered one AE, I guess, technically. And we have accounts assigned to us, because there's another AE on the team, too. So there's split accounts.

We pretty much are the same when we go to conferences. We genuinely interact and meet with whoever comes our way.

Yeah, we split everything. So everything would be between both of us. We hop on calls together from day to day. We don't really have like a set structure. We just naturally work really well together. We'll be on the phone with each other all day long. Also, while we're in between calls and working, like saying, Hey, did you do this? And she'll hop on something and then remind me of something. And then I'll hop on and go do that. So we'll like tag team everything, but also like know what our strengths are. And we'll go do that individually.

Erica Waldron (10:54.326)
And it's also really easy working with someone in sales as far as like following up so you don't feel like so redundant.

Andrea Castelli (11:03.15)
Yeah, so like, I don't have to follow up. I'll send the original email, for example, and then she'll follow up like a week or two later, whatever we need to follow up on our cadence.

Carter (11:03.43)
Yeah.

Carter (11:14.012)
What's something Erika is better at than you, Andre, and vice versa? Like, are you guys pretty similar, or is there a lot of yin and yang going on?

Andrea Castelli (11:22.778)
We're both, we're very similar, but there is some yin and yang. Like she's great at picking up the phone. Like I love being on a call, like having like interactions in person. She's great at picking up the phone. Like she has no problem with it right away, she'll do it. And if I forget something, she remembers right away exactly what it was and vice versa too. Like we help each other with our memory. So between the both of us, we never forget anything.

Erica Waldron (11:48.407)
Yeah, it's really nice. And then Andrea's like really good on the fly, like quick with it, like whatever someone asks. I have to like sit there and maybe think about it. She's like already answering it. And I'm like, this is perfect. And I also call her my personal IT because she's really good with the computer.

Carter (12:07.674)
Neither of you guys took the traditional SDR to AE route. Do you have any advice for someone trying to break into mortgage tech sales? Should they try to follow your path with creating this whole company and doing that? Or yeah, any advice you guys have, I'm curious.

Andrea Castelli (12:21.902)
I would say just never put yourself in a box and feel like you have to go down the traditional route. Like you can get creative with it. Like Eric and I never in a million years thought we would be doing this.

And we've had other opportunities that people have come to like pull me separately or Erica separately. And we're like, well, we're kind of like a package deal and they say no. And then it's like, okay, well then it wasn't the right fit for us. And then, you know, it just led to here and this is like the best and most perfect opportunity for us.

Erica Waldron (12:53.717)
Yeah, so I would definitely also add, forever's trying to do this, like keep your options open and like, cause you'll never know where it'll lead you. As long as you have like a longterm goal of envision of what you want to do, or maybe you don't and it just will lead you here, but definitely just keep it open.

Andrea Castelli (13:16.068)
Yeah, you don't have to have everything figured out. Most people, when they think of opening a business, they think, have to have this plan, everything's set. And we honestly did not do that. And I mean, it could have went either way, right? But I mean, it really was successful for us. And you don't have to have everything exactly planned and thought out as like, it needs to go perfect. You can figure things out along the way too.

Carter (13:40.33)
That makes a lot of sense. And I'm curious, so people will come to you guys and try to say, we want to hire you, Erica, or we want to hire you, Andrea, as one person. And you're just like, can't do that. We're a package deal.

Andrea Castelli (13:52.686)
Yes. We're about to go.

Erica Waldron (13:53.527)
Yes.

Carter (13:54.514)
Wow, that's crazy because that really seems to have worked. But in my mind, I would think that would never work. Like especially going to some tech sales place, I would think, yeah, two people working together, like that would never, that would never work. But that seems to really have worked well for you guys.

Erica Waldron (14:07.729)
Yeah, doubles the power.

Andrea Castelli (14:08.058)
Just some people things like really unheard of. And then we had went all the way through the interview process and then they decided that like two wasn't gonna work out. So we're like, okay, well, there's always still gonna be two. And Snapdocs sees like the vision and the bigger picture of it. And they see what actually we've done in the industry and all the relationships we've built. And it's nice that someone will always see it in you if that's what someone else wants to do.

Carter (14:26.344)
Yeah.

Carter (14:38.568)
And is there anything else, I'm good on my questions, is there anything else that you guys wanna share or anything about your story or anything that we didn't get to that you really wanted to say?

Andrea Castelli (14:50.068)
Erica Waldron (14:51.745)
I think we covered a lot. I don't know.

Carter (14:57.192)
Okay, well good. No, think we're... I think we got some pretty good stuff here. I will end it here.

Andrea Castelli (14:59.484)
No

Erica Waldron (15:03.788)
All right.