From rep at ADP to CRO at Houzz with Tara Di-Cristo-Schmitt

Jason Bay: The journey from rep to CRO has really a lot of mystery. I mean, if you consume sales content on LinkedIn or you're listening to podcasts like this one, there's a lot of content on rep tactics, right? On this podcast, we talk about how to do, you know, email calling, uh, meeting in person, doing all of these things to secure the first meeting. There is a ton of content, even more content on how to close the deal. But once you start to get into, well, how do I be a great sales manager or a director of sales, uh, VP of sales, a CRO? What does that look like? What should my week look like? What are some of the core skills? And a lot of people really just learn through experience, trial and fire. And hopefully they have a great mentor. And today's episode is going to focus on interviewing a CRO from a current client of ours, a company called Houzz. Uh, our guest, before we introduce her, has been a previous VP of Sales at HubSpot. She started out as a rep at ADP. So before we get to that, though, I'm really excited you're listening to the Outbound Squad podcast. My name is Jason Bay. I am the CEO of Outbound Squad and host of the Outbound Squad podcast that you're listening to. I really appreciate you spending time with me. We're all about helping you turn complete strangers into paying customers. So, um, Outbound, uh, pipeline generation Pipegen, some of you might call it, if that's something that you're focused on with your team. So Maybe you have SDRs that are doing some cold outreach to secure meetings for the account executives. Maybe you want your account executives to self source more pipeline, do some of the outbound stuff, work referrals better, and really just do a better job of building pipeline so that there's not such a roller coaster each quarter. You're definitely in the right place. And we've done that for some really cool Companies like Shopify, iHeartMedia, rippling Zoom gong, Houzz, who we're talking to today, and all of the above. So, uh, Tara de Cristo Schmidt is the guest today. I met Tara. She came to us, I want to say, maybe six or nine months ago, and they were in the process of building out an outbound motion at Houzz. And what we dissect and dig into in the interview is there's just so many great things, um, just in her career in the last 17, 20 years, how she started out at ADP, she was the, um, there was only one woman sales leader at ADP when she first met, uh, the woman that, uh, she's going to tell us a little bit more about. And she was just like, I want to be the second, you know, So I thought that was super inspiring. Um, we talk about channel sales, uh, how to be authentic, you know, as a leader. We talk about what she learned at HubSpot and transparency and showing up as your best self. She's currently the CRO at Houzz. We talk about what it's like being in her first CRO role, managing an org of hundreds of reps, um, how she prioritizes her first 90 days, how she manages the team, what her weekly rhythm looks like. Uh, so we dig into a lot of really interesting stuff. Uh, lastly, uh, this interview was done in person, which is really cool. We went to, uh, New York City, ah, a couple months ago, and I got to meet her in person, uh, film this, all of that kind of cool stuff. So before we get to the episode, there's two things that I want to let you know about. Um, if you're looking for very tactical, you know, what's working in Outbound right now. We just came out with our Outbound Masterclass. It's completely free. I sat in a studio for about six or seven hours and we walked away with three hours of solid content. It's the same stuff that we teach companies, uh, and that we customize for them. You can grab that@outboundsquad.com masterclass we already have over a thousand folks that have checked it out just in the last couple weeks. So go make sure to check that out. Outboundsquad.com masterclass it's free. And then if as you're listening to this, you're like, hey, you know, I would kind of like some help from these guys on how to implement some of this stuff with our team. Just reach out to me directly. We do a lot of great work for, you know, companies like your Shopify's and Gongs and Zooms of the world. But we work with a ton of startups as well that are just building out their outbound motion from scratch. You can email me directly. Jason, outboundsquad.com would be happy to chat with you. All right, without further ado, let's get to it. How did you find out about us? Actually, because I know you came in down through the website. How did we actually. Oh, m. My gosh.

Tara Di-Cristo-Schmitt: That's a good question. So I had seen you post something on. It had to be LinkedIn.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: And I was. It was yeah. And I was in that moment of, I need to go outbound. I need to take this team outbound. And I knew there was no one around me that had the skill to do it. They just didn't. And I knew how long it would take me. So it was. It was almost like I manifested opening LinkedIn, and there you are.

Jason Bay: That's so funny, because our mutual friend Mike Weinberg, you had asked him, hey, who should we talk to? And then, just like coincidentally, he had brought up. Cause I've gotten to know Mike well in the last year or so, too. And he had brought us up in that conversation, too. I remember.

Tara Di-Cristo-Schmitt: He did. He absolutely did.

Jason Bay: Yeah. It's funny. Um, there's so much to talk about with your career, and we've kind of outlined a few of the things. But if you could take us back to your first sales job. I'm curious. Most people don't get into sales on purpose, right? It happens on accident. How did you get into sales?

Tara Di-Cristo-Schmitt: It's funny. It's funny you say it that way. I got into sales on purpose. Really, I did. So I was in. I mean, I'll take you back far, but I'll go quickly through it. But in college, I knew I wanted to be in sales. My dad is a salesman, my uncle's a cousin. All my uncles, I watched it. They were more in real estate and land development, but I just got to learn what they did. But I'll tell you, I was interning at a mortgage. My dad's mortgage company, and I was sitting in the middle, I was answering phones, and, uh, I had the loan officers on one side and the processors on the other side, or loan officers are the salespeople. And every Friday, the one side of the building would come in, like, oh, it's Friday. I gotta work all day. It's so nice outside, right? Cause it's summer. And the sales people would come in and they would be telling crazy stories about the happy hour they went to last night and they were all heading down the shore and what life was like. And I was like, I would look side to side and I would say, I'm going to be on this. I want to be on this side. This looks fun. You're kind of in control of your destiny. Your days, your weekends. And so I know this is so cliche, but I really went and decided I wanted to go into sales for freedom. I wanted to have freedom in my schedule and my day. And so I continued through college, and I had a little bit of a rough time, uh, Passing calculus, believe it or not. And I said, you're not a math wizard. No, I am not. Which is weird that I'm in the role that I am, but somehow I made it. And I remember saying to the professor, listen, if you just pass, you just give me a C. I promise you I won't do anything that has anything to do with numbers. Fast forward. And my very first job is adp. Working with payroll and numbers and accountants all day, every day. Um, my parents had actually introduced me to the company. As soon as I saw the website, I said, which, who knows what it was back then, almost 20 years ago, I said, there's no way I could do this. It says payroll right on the front page. Went for my first interview. And I think that's where I, uh, just understood that sales is a culture. And you could feel that culture the minute you walk through the doors of adp.

Jason Bay: Yeah. Cause I noticed when we first met, you seemed very, like, energetic and extroverted, like definite people person.

Tara Di-Cristo-Schmitt: But I am full blown introvert.

Jason Bay: Oh, really? Me too, actually.

Tara Di-Cristo-Schmitt: Yeah.

Jason Bay: Dang.

Tara Di-Cristo-Schmitt: Yeah. Every assessment, every, do you name it, I am off the charts introvert.

Jason Bay: I think. Have you noticed a trend at all with the leaders and reps that you've worked with over the years around introversion, extroversion, anything like that?

Tara Di-Cristo-Schmitt: It's an interesting question. Yes. I think I'm less shocked nowadays finding out how many introverts are actually in sales. Because you can turn it on and off. And when you've learned that you can do that, it, uh, works. However, introverts spend a lot more time on the energy side. Think us introverts, like, we can expend the energy, but we have to go and shut it down.

Jason Bay: Definitely.

Tara Di-Cristo-Schmitt: Right. There's that moment of, I can't do this anymore, I gotta go shut it down.

Jason Bay: And I don't know what your version of shutting it down is, but mine is just like, I just want to chill with my wife. I don't want to go out to party or do it. None of that kind of stuff.

Tara Di-Cristo-Schmitt: That's exactly right.

Jason Bay: So at adp, like, you had had some experience being an intern. I'm curious, like, if you could remember, like, your first couple days or week or month on the job, like, were you good at sales? Sort of naturally. Did it take a lot of work? Like, how quickly did you pick up on, like, the thing, like the shtick?

Tara Di-Cristo-Schmitt: Yeah, I'm still picking up on, um. And I think anyone that knows me would laugh at when they, when I, they hear me Say that what I had and what I picked up on very early, like literally in my first week is. And we weren't using the word grit back then. Right. But the grit that you need it to be in sales. And what I learned back then was it is a numbers game. And if you are willing to knock at the time, knock on as many doors.

Jason Bay: Oh, were you going door to door?

Tara Di-Cristo-Schmitt: I was going door to door, building to building. I would leave my house at seven in the morning. I would come home at seven at night. I have a hundred business cards in hand. I would, you know, back then Salesforce was just coming into the market. I don't think it was called Salesforce at the time. And uh, then I would wake up the next day and I would call them all. If I didn't get an appointment, I stopped in. Can I schedule an appointment?

Jason Bay: Did you have any kind of like reluctance or anxiety around going door to door? Like, what did that feel like for you?

Tara Di-Cristo-Schmitt: So one of the things that ADP does very well is they give you mentor and they give you a very strong name.

Jason Bay: Everyone there said the training was like,

Tara Di-Cristo-Schmitt: phenomenal, phenomenal, like off the charts. So day one, you're sitting with someone that looks just like you, young, like you. Not where they're having fun. They role play with you from the minute you get into the car and to the minute you walk in to make your first knock on door. And they say, listen, just ask. Just say this one thing and I'll say the rest. And then you go to the next one. It's like, okay, now you say this plus this and then I'll say the next. And so, yeah, of course there was reluctance, but there was so much support to just go do it. And there was a lot of laughter. And they taught you early on how to kind of laugh at yourself and not take yourself so seriously. I'll tell you, I had more reluctance getting on the phone.

Jason Bay: Oh, really?

Tara Di-Cristo-Schmitt: Than I did knocking on doors. Yes.

Jason Bay: Dang. I guess in person, was it that you could just smile? Smile, make eye contact?

Tara Di-Cristo-Schmitt: Yeah. And they'd smile back and I'd ask questions.

Jason Bay: Dang. Okay, so, um, at what point did you decide that, you know what, like, being a rep is really great, but this whole leadership thing sounds, sounds kind of cool.

Tara Di-Cristo-Schmitt: Yeah. I think the impact my first leader had on me was pretty impressive. And, uh, she took an opportunity where she went to be what we called at the time a corporate sales trainer. And I thought that was so cool. I thought, I want to do that. But they only took three people every 18 months out of thousands of sales reps. So I waited my time, and, uh, I had moved to Fort Lauderdale in that. In that timeframe still with adp, and I had posted for the job, and I ended up getting it. And what that job did is it allowed me to see how. How valuable training is and how process works and why a company asks a sales professional to do something a certain way. Yeah, there's. There's outcome behind it. There's a result that's anticipated. And I really liked seeing the behind the scenes. And I realized that I liked training. I liked taking someone from this level, even just in the two weeks I had them in that training course and seeing them leave with a totally different level of confidence. And then there was someone else that I had met. Uh, there was a leader sitting in a glass room. Ah, at adp, with her feet on the desk and a leather jacket on. Now, I say it that way because to this day, ADP probably doesn't have any glass door, glass offices. Um, she would never put her feet on her desk, and she definitely wouldn't wear a leather jacket to adp. Right. But in my mind, I saw this. Like, what is this?

Jason Bay: She sounds like a rock star.

Tara Di-Cristo-Schmitt: It was like a rock star experience. And I said, who is that? Because I just moved to Florida. And they said, oh, uh, that's a division, uh, vice president. She's the only female division vice president in the company.

Jason Bay: Nice.

Tara Di-Cristo-Schmitt: And I said, well, can I talk to her? And they said, no, you just got here. Go do something first and then we'll introduce you to her. And I remember waiting like any good salesperson until everybody left the. And I went. I knocked on the door and I had said, hey, here's who I am. I'm from New Jersey. Anyway, can you tell me about your job? And she said, yeah, I can. And she said, but I'm going away for a month. When I get back, I'll take you to lunch. Between that moment she said that to me and the 30 days that passed, I met with everybody and anybody that had a job between me and her to understand what I needed to do, the roles I needed to take to get that job, to be the number two. I mean, you know, had big dreams, right? To be the number two female division vice president there. When I met with her, I turned my paper around. She said, tell me what you want to do with your career. I took out my paper, I turned around, I said, well, I did some research. I want your role. I want to be In a role like you. And here are the jobs I think I need in order to get the skills. And she became a sponsor and a mentor from that day on. And I was not number two. I was, like, five or six in the company.

Jason Bay: Okay. So many questions. So I'm just thinking you're, like, in your early 20s at this point, or, like, 23 maybe. Okay. M. Yeah. Where did that. Like, I want this. I'm going to talk to every single person, like, advocating for yourself in that way and, like, building the relationships. And where does that come from for you?

Tara Di-Cristo-Schmitt: It comes from, I mean, your childhood. I mean, my childhood and my upbringing. I had, uh. I had a dad that I just watched him from the ground up, like, build. We just kept building and moving into different homes, and I just watched our life continuously get better and better and better. I watched him lose it all, too, not give up and rebuild again and again. My mom owned, uh, her own hair salon. And I remember living in a town where we were up and coming. Right. My parents were young, and so we were up and coming. And I went to a private school, and they were not super kind, um, because I didn't live in the right town right at the time of going to that school. And so there were a lot of things.

Jason Bay: Education on the east coast, for those that are not from the east coast, is, like, a really big thing. Like, where you're from, where you went to school, where your parents go to school, where you went to college.

Tara Di-Cristo-Schmitt: I remember being on the outside a lot, uh, until we weren't. And then I remember that feeling of not being on the outside and being like, whoa. Right? Like, that's not how, um, I'm gonna roll. But so it just taught me that if you want something, go get it. I remember being 16 years old, sitting in my room, looking up at a Michael Jordan poster. I love basketball. And it said, someone somewhere is practicing, and when they meet you, they will beat you. And that just, like, I just absorbed that. And when I was sitting in my room, I was writing out my Life goals at 16, and one of them was to be an executive. Big executive in corporate America. I didn't know what that meant at the time, but, uh, I knew I wanted that.

Jason Bay: Uh, if you're comfortable sharing, I'm curious, what was this experience like for you as a woman in the workplace at that time? You said that there were very few sales execs. You wanted to be the second. I did want to be the second female sales exec. I'm just division, obviously. It's hard for me to put myself in those shoes. But I'm just imagining there weren't a lot of examples of women in leadership positions. What was that like then?

Tara Di-Cristo-Schmitt: Yeah, there were not a ton of examples, for sure. Um, the ones that were, Aside from the. The two that I just described, who were everything I think a great female leader should be. Um, either took on, um, the Persona of a male figure, um, either weren't married or didn't have children, and that was okay. And they were still wonderful, and they were still female. But I wanted to be married, and I wanted to have children, and there was nowhere to really look at that point in time. Um, and I also wanted to be authentic. And there's a lot of that not being shared and shown. I mean, I remember being taught how to not cry.

Jason Bay: Oh, wow.

Tara Di-Cristo-Schmitt: Right? If you look up and you drink water out of a water bottle, you cannot cry. So if you're ever in a meeting and you get upset about something as a woman, grab your water, always have water, look up and start drinking.

Jason Bay: This was taught to you?

Tara Di-Cristo-Schmitt: That was taught to me, yes. Now, I don't. Yes. By people there. I wouldn't say that was the ADP way, by any means.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: Um, but that was taught to me during that time in my life, um, through different people there. But I think it was hard. It was really hard. And I feel privileged to have gone through that with adp. And I remember sitting with HR one day, and they were trying to do so much because they wanted. I mean, there's a female CEO right now. She's fantastic. Right. Maria Black. But, um, I remember being in rooms with her as she was just a frontline leader at the time.

Jason Bay: Oh, wow.

Tara Di-Cristo-Schmitt: Yeah. And so we really put the work. And I remember sitting with HR and saying, like, well, I don't know how you're gonna change this. Do you have a list? So think about my outbound sales experience. Do you have a list of talent that you've identified? Do you have a top 10 list that you want to get into this DVP role?

Jason Bay: Dang.

Tara Di-Cristo-Schmitt: And I remember her looking at me, and her name was Jill. And she looked at me and she's like, we do not have that list, but we will have that list. And, uh, you know what? They built that list, and it took off one after another after another after another, started getting promoted. And not because they were women, because they were talented and they had the skill set, and now people were paying attention.

Jason Bay: Dude, that's inspiring. I love that.

Tara Di-Cristo-Schmitt: It was pretty cool.

Jason Bay: So you learned so many lessons. I don't know if we have time to get into all of them, but you highlighted a few that I definitely want to talk about. Personal, um, brand.

Tara Di-Cristo-Schmitt: Yes.

Jason Bay: This is something that I sort of learned the hard way. I was. You know, I grew up in a town of 5,000 people. My dad taught me to be, like, super humble. So his whole thing is like, keep your head down, work hard, things will eventually work out. That's not really how it works in the corporate environment, especially in sales. And I remember, um, after I was a VP of sales, I actually worked down at this large construction company. I used to work for their corporate office to create their marketing department from scratch. And one of the things that Spencer, my boss at the time, he was one of the partners at the company, was like, hey, you know the reason why I bug you to send these, like, update emails to me and the other three partners every Monday is like, you're advocating on behalf of your department. This is your personal brand. And it just clicked for me. I was like, oh, shit. Yeah, I need to be thinking about the perception of what I'm doing. Um, was this taught to you? Is this something that you had to sort of learn yourself? It sounds like you had some great mentors, too.

Tara Di-Cristo-Schmitt: It was taught to us. Uh, I mean, when you were interviewing or you were in a mentor relationship or just a conversation with someone at a different level, the question would be asked, what's your brand?

Jason Bay: Oh, dang.

Tara Di-Cristo-Schmitt: Okay. What's your brand? And then after you answered, they would say, well, I'm gonna go. You know, if I walk down the hallway and I start asking people in sales that you directly report to, what will they say?

Jason Bay: Because that's your brand.

Tara Di-Cristo-Schmitt: That's your brand. What will the service partners say? What will the finance team say? That's your brand. And so what are you doing to build that brand?

Jason Bay: Wow. What's your brand now? How would you describe your brand now? Not to put you on the spot.

Tara Di-Cristo-Schmitt: Wow, you are putting me on the spot. Uh, you know, I would listen the way that I would describe my brand, and I think if anybody hears it, they'll sit there and be like, mm, yeah, that's probably her brand. That's right. Uh, you know, I am, um. I wanna say. What's the word? Like, I'm the. I don't wanna say Spark. Spark, isn't it? But, like, I am. Like, I'm the spark that fuels the fire.

Jason Bay: Yeah, for sure.

Tara Di-Cristo-Schmitt: Uh, if you spend enough time with me, you will be doing things that you didn't know you were capable of doing, nor did you think you could. And you actually won't really realize in the moment that it was me that sparked it. But then you'll look back and be like, how did she do that? She get me to do that?

Jason Bay: That was the immediate thing I noticed in interacting with you during the sales process that we went through. And then definitely working with you as a client was like the energy and you know, there's just certain leaders you've worked around where whatever it is that they have is just very contagious and you want to be around it. You definitely have that, uh, like, it is just like, there's just no. Like when you see how people interact with you and how like lit up they get. Like when you are trying to get them excited about something, can that be taught or is that just something you feel like is just kind of a natural, like a personality trait or what?

Tara Di-Cristo-Schmitt: It's a very good question. So if you were to call people that worked with me at AEDP very early on, they would call me, what is it? A wallflower? Uh, is that what it is? Where you like, sink in and you don't talk? Yeah, that's how I was. The senior leaders would call on me on purpose and I would get red faced and I couldn't speak and I wouldn't answer. And, uh, and they just kept pushing on me because they would get me one on one and they would see a different person one on one. So can it be taught? Yes. I mean, I actually have an executive coach that I remember being in Charlotte. It was the first time I was a vp and one of the sales reps came in and she slid a CD across the desk at me and she goes, this is a new customer of ours. He's a culture, Ah, coach, you need him. And she slid, uh, it over. And I worked with. His name is, um, Eric Hoffberg, out of Charlotte. And he taught me how to do it. I remember he would spend hours with me. Tell me a story, tell me more, tell me more. And then he would show me how to connect that story to work. And the very first time I had this big meeting, uh, as like the leader.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: And I wasn't in someone else's meeting, it was mine. And he came to the office to make sure I was okay in that meeting. And I remember he's like, are you ready? And I said, I'm ready. And I stood up and I looked at him and I go, I called him Hoff. I go, Hoff. And he's like, yes. And I go, I can't hear my legs. And like, we still, like, we still laugh about that because he looked at me like, oh, no, how am I gonna get her to pull this off? She's saying she can't hear her legs. Like, that's how. Right. That's how nervous I would get. Um, but, yeah, he taught me. You walk in, you have a one minute story that you tell, and you don't care how people are reacting to that story. That story is for you. And then that will calm you. And then you go. And, uh, it worked really well with me for a lot of years.

Jason Bay: So the one minute story is like just a personal story that you share that kind of tells a little bit more about yourself. Or what's the.

Tara Di-Cristo-Schmitt: It could be something like. So I was driving in this morning.

Jason Bay: Oh, so you're just having something in there to kind of break the ice

Tara Di-Cristo-Schmitt: a little bit without being an icebreaker. Yeah.

Jason Bay: This is interesting because, uh, and I noticed not to stereotype too much. I noticed that male executive leaders tend to be very serious. Like at Houzz, it's like, is Alex, Is he the only.

Tara Di-Cristo-Schmitt: He is, yeah.

Jason Bay: Male leader on the.

Tara Di-Cristo-Schmitt: Senior leader. Yes, Senior leader on the team right now.

Jason Bay: And, um, it was so refreshing. When I first met the rest of your leadership team, I was like, this is cool. I've never seen this before. Um, and I noticed that, like that one minute story, um, you do it for you and it helps kind of break the ice a bit, but it also for other people too. It humanizes you a bit.

Tara Di-Cristo-Schmitt: Can't wait to hear it. They start to know that you're going to do it.

Jason Bay: Yeah. So, um, one thing I want to ask you about, sort of related to this is executive presence. So we have, uh, our head of training, Clara. So we brought her in. She, uh, used to work at outreach, so she was a top rep manager. She leads all of our training engagements. Now we have another trainer, Amanda, and then we have Brittany on our team who kind of does a lot of, like, the ops and stuff, um, in the client interactions. And around Christmas time, right before Christmas break, we were going into our yearly planning and I was like, there's like, there's this thing, I feel like we really need to elevate in our company. And that's like, how we show up with the executives that we work with. It's the executive presence. And when it's not there, it's really easy to see and to talk about. What I found, though, is it's really freaking hard to explain what executive presence is and, like, break it down into, like, actual digestible skills that someone could work on. And there was a couple videos. Um, there was a Google talk on it. There's a woman, I'm forgetting her name, she's written books on it, and she really broke it down. And I was like, oh, this is perfect. And a lot of it was like your tonality, the language that you use, avoiding really unsure tones, and all of these things that I think if you've been doing, if you've been leading for a while, you kind of take for granted because you probably learned how to do it the hard way. How do you think about executive presence either for yourself or when you're mentoring others where you're like, you have the skills, but the way you're showing up in those executive meetings or with your team or wherever, it's missing a little bit of polish or whatever it might be. Um, what are your thoughts just on executive presence?

Tara Di-Cristo-Schmitt: Yeah, it's a crazy important topic. For example, crazy important is probably not super executive, like. Right. Um, but I will tell you, it was interesting. Adp, it was like drilled into us. Executive presence, executive presence. The way that you walked, the way that you talked, what you wore, like, it was, you need to display this. Do you understand your data? Are you able to speak your data with confidence? Are you making the right eye contact? Do you know when to stop talking? Do you know when you're not over talking? Um, I don't think I ever got it right. Although I continued to get promoted at adp, I don't ever felt that I've reached this level of I have executive presence. I would argue. I still don't think I have.

Jason Bay: Really.

Tara Di-Cristo-Schmitt: Yeah. Executive presence. I mean, maybe the way that it was drilled into me and there was a certain look and feel, but I would tell you, when I went to, um, when I went to HubSpot.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: Uh, someone that I think exudes executive presence is Yamini.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: But I have to tell you, she is the most authentic human I have ever met in my life.

Jason Bay: Really.

Tara Di-Cristo-Schmitt: So what became for me, executive presence after working with her is being 100% fully who you are. And if you can do that, if you can really do that, uh, you will exude executive presence. And then the other little, like, asterisks there is prepare for the conversations and the meetings that you're going into. And if you take that minute or hours to prepare, uh, you'll show up the way you need to show up. And what I mean by that is on stage, you see the executive presence. In conversation with her at a table, you see executive presence, but you also see a real person the entire time. So you're seeing both. And to me, that's what executive presence is.

Jason Bay: Yeah. Let's talk real quick about. And we're going to kind of jump around your career just a little bit. Um, you spent 17 years at ADP. You spent four or five years at HubSpot, and that was one of the things you called out was, like, authenticity. Can we break that down a little bit? Like, if you were mentoring, ah, you know, a director of sales or a sales manager that you just brought in, you wanted them to be more authentic. Like, how would you even go about, like, helping them. Them do that? Is this an exercise that you do with them? Is it a conversation? Is it a series of conversations? How. How do you help someone be more authentic?

Tara Di-Cristo-Schmitt: You have to be authentic. You have to model the behavior.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: Remember I just told you a story about being taught how not to cry? My very first meeting at HubSpot. I remember two executives crying on the call, and it was.

Jason Bay: Oh, wow. Really?

Tara Di-Cristo-Schmitt: It was wildly accepted. They were telling personal stories. Right. To inspire and motivate. Um, and I don't. No, I don't think you teach it. I think you accept it. You accept people for who they are, and when you can accept them for who they are, they can bring their whole self to work. You create a psychologically safe environment, and you, too, show up as you are, because people can see right. When you're not who you really want to be. And HubSpot did a fantastic job of that.

Jason Bay: Yeah. I think you mentioned something that is such a critical part of leadership, and it's like, leading by example.

Tara Di-Cristo-Schmitt: Yeah.

Jason Bay: It's really easy to give a lot of things lip service, but to really put your money where your mouth is and, like, live the thing. It's, um, it's so refreshing and doesn't call into question anything that you're doing when someone can just see it. Um, and you mentioned psychological safety, I think is. I know people say, like, safe space and judgment free zone, and they use those words a lot. But when I interact with a lot of these teams, I'm like, this doesn't feel like a safe space, actually. Um, is there anything that you've picked up, uh, over the years, uh, or do you, with the team now to. Especially when you're a new leader, is there anything that you do to create that psychological safety so that people do feel comfortable giving you Feedback or bringing something to you or just being their authentic selves.

Tara Di-Cristo-Schmitt: Yeah. One of the things I learned at HubSpot, I mean, I guess I learned it all the way through, but where really I really acknowledged that I learned at HubSpot was, um, bringing a sense of curiosity m to every conversation that you're having. Like, I'm really curious about you and who you are and what you want to do and why you want to do that and how you got here. And I think sales leaders, you're always like, oh yeah, I gotta ask questions, I gotta ask questions. But there was a point in my career where I wasn't just asking to get to the answer I wanted. I was asking because I was genuinely curious. And that allows people to open up. And then what happens is that builds trust. And when there's trust, you can say whatever you wanna say, no matter the level that the individual is in the commandment. I remember being scared to death, uh, in the hallway of seeing a senior leader and I was like, I gotta, how do I get, how do I make a turn so I don't have to walk past that senior leader? Because you were afraid to say the wrong thing.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: To fast forward several years later and you're welcoming any thought that anyone has because ultimately the wisdom is in the room. And if you're shutting people down, that wisdom is never going to get to you. And the people closest to the work, they know the answers well before anybody else. So you want to constantly invite that in.

Jason Bay: Yeah. Again, it sounds like such an obvious thing to do that I don't think gets executed often.

Tara Di-Cristo-Schmitt: No, it's not.

Jason Bay: It's pretty freaking wild. Um, because we move so fast. Yeah, yeah, absolutely. Um, yeah, we can take the conversation in a bunch of different ways. Um, I want to talk about something a little bit more tactical in the sense of like, everyone's got pipeline on their mind. And I think right now, especially if you look at the state of buying, at least for software, um, there are fewer people buying, uh, people want to get started with smaller projects. Like average deal sizes are down. People don't want to commit to stuff that's as long, um, there's a gartner stat that 56% of B2B buyers have experienced buyer's regret when it comes to software. It's like, it's a very different buying environment in the last three or four years than, you know, the record breaking bull market run that we had in America, at least from like 2009 to 2022. So pipeline. Yes, let's talk about that. And this is some stuff that you started to pick up at Paychex, it sound like. And feel free to segue that into what you're doing now at Houzz. But how do you think about the different parts of Pipegen and balancing, like, inbound versus outbound versus channel versus let's kind of start there, like, with the mix. Like, how do you look at that and determine what the right mix is? And then maybe we do, um, a dive into some of the channels and some things that you've learned.

Tara Di-Cristo-Schmitt: Yeah, sure. Uh, so let me just start here. I grew up only knowing outbound.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: Right.

Jason Bay: For years, like, inbound, there's people that come to us.

Tara Di-Cristo-Schmitt: Yeah. For 12 years, all we did.

Jason Bay: Right.

Tara Di-Cristo-Schmitt: Is if someone called and left you a voicemail, you were like, oh, it's must be because I left my card. And then they called me back. Right. That's what I knew inbound as. So that's what I knew. And then I had the opportunity to go and run an inbound team, which was mind blowing to see the leads and the customers come, um, into us. But I'll start with breaking out how I think about pipeline in general. And then we can go into the different ways of building the pipeline. So something that I learned very early on was results is. Is primary. So you're constantly looking for results, and then if the results aren't there, then you're having conversation and you're jumping into, okay, well, what did you advance? What's the opportunity? Um, and then if the pipeline, per se, is not there, you're diving into activity. So it's activity, pipeline results, results, activity, or pipeline activity. So we get to this point where you're now in a world. So when you're. When I think about inbound, inbound is, um, you're capturing demand, and outbound, you're creating demand. And so I grew up in a sales world of creating demand. So now I'm leading sales teams that capture demand. Well, we went through, as you just said, those years of good and plenty. Right. There's plenty of opportunity, and it slowed down. But what we had is a generation of salespeople that just went from company to company, learning inbound skills over and over and over again. So now that we didn't have that inbound to capture, how are we gonna create the demand? We have to teach them outbound. We have to bring outbound. What was cool is I was at HubSpot through the evolution, where they went from inbound to all bound.

Jason Bay: Right.

Tara Di-Cristo-Schmitt: And I was hired in. I'm like, we're going Outbound. Right. So. And to come over to Houzz, we have a very strong inbound team. But guess what? I'm building Outbound. Outbound, Yep. And. And then on. So. But then you think about Outbound, and Outbound could be a very expensive way to grow the business. The. The time to, uh, value could be sometimes 48 plus months when you're getting started. Right. If you don't have the right ICP and everything isn't aligned.

Jason Bay: So 48 months is wild.

Tara Di-Cristo-Schmitt: It's insane.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: It's too long.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: Yeah. That's like, it should be six to 12 months.

Jason Bay: I know. Figuring out the Outbound Motion, I think is. I mean, it's interesting talking to you about it because you did bring us in to help kickstart this. Right. There are organizations that have 0 reps and leaders on the team with Outbound, and they try to fix it through enablement and doing trainings and a couple workshops here and there, and it just never works. And then they just assume that Outbound doesn't work because of that.

Tara Di-Cristo-Schmitt: So.

Jason Bay: Right. Which is crazy. Um, so with. What have you seen over the years with Inbound in terms of like. And I'm curious what you guys are seeing at Houzz too. Has the cost of Inbound, like, gone up significantly at all for you guys?

Tara Di-Cristo-Schmitt: I mean, our organic is our. Is our best, um, Inbound flow. And you know what that is? That's word of mouth.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: That's Outbound getting out there and telling the story. And that's partnerships and creating community. And that's really what I think we lost. I don't mean we house. I mean we as a sales profession lost. Is that Outbound motion and the impact that Outbound can truly bring to the bottom line.

Jason Bay: Yeah, it's crazy. Um, if we could speak on Outbound for a bit. So you mentioned there's this generation of salespeople that only know Inbound. And that's been like my thesis too, where you have managers that didn't have to Outbound now holding reps to accountable to doing something that they don't really know how to do or never had to do.

Tara Di-Cristo-Schmitt: That's right.

Jason Bay: And in your experience with Outbound. So we're working on right now, we're building like, a formal, like, methodology, like Challenger, but for Outbound, there isn't like an actual Outbound methodology, which is crazy.

Tara Di-Cristo-Schmitt: Insane.

Jason Bay: Um, so I'm trying to formalize this and really look at what are the core components of a great outbound motion and what do you need? And a big part of that is. I'll just kind of go through the framework, maybe just get your feedback on it, actually. So the core thesis is around like three parts. Um, if you look at what's really needed to make Outbound work right now, there's a pillar around disqualification that doesn't get talked about a lot. And Outbound is a herculean effort. It's 12 to 15 touches via email, phone and social to even get in contact with a prospect. So the very first thing you must do if it's houzzed, let's say, is here's the three quarters of the market that I don't want the reps to reach out to. That's right, because they're not big enough. It doesn't fit the profile, whatever it might be. The whole TAM thing that people talk about so much in software, uh, we're not going to do that. We're going to over index on where we, where we have the highest propensity to win.

Tara Di-Cristo-Schmitt: That's right.

Jason Bay: That's step number one. Step number two, um, offer. So the offer. We did a really big study with Gong on email, uh, 85 million cold emails. And what we found is that the Reply rate is 28% higher if you have something to give them. And it's 40% lower, 44% less likely to get a reply if you just simply ask them for time. So again, if we use Houzz as an example, that's uh. Hey, I took a look at your website and noticed xyz. I took a look at your Google Reviews page and I noticed that it's 3.2 stars. And a few people were complaining about this. It's like I'm giving you something like a value right there. And then the last one really is around, um, I'm calling it Provoke right now. Okay, so Provoke is around like the message. So instead of here's what we do and how our solution works and why we're so great, it's trigger. The reason I'm reaching out to you is because I noticed this thing. It's tension. A lot of people tend to have this problem and then trust. Oh, by the way, we've worked with every other house painter in the Seattle area, right? So it's like having those core components. It's like these are the things that I need to disqualify. So I need to think very differently from how everyone else is doing outbound. It's less is more. Um, I need to make an offer. So instead of asking, I'm going to offer. And then the third thing is, instead of talking about product, I'm really going to make sure that I can create tension in this message by talking about a problem and showing them that I've helped other people with it. Those are the core components. I've noticed that if you don't have these things, you're just like putting AI slop out into the ether. You're just dialing for dollars, all of that kind of stuff. But that's my thesis right now. What do you think?

Tara Di-Cristo-Schmitt: So I'm having this flashback of the first conversation I had with Mike Weinberg and we were talking about leadership and he did exactly what you just did to me. I had that exact same feeling. So what was happening when I was talking to Mike at the time is I was thinking, this is how I was taught. Where did this all go? And as you were talking, I was thinking, this is exactly how I was taught. And I often said, why isn't someone over at ADP writing a book about this? Because they have. And you're exactly right. That is the exact way to go outbound and to be successful at it. And we're not teaching it that way today.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: And it's not hard.

Jason Bay: It really isn't.

Tara Di-Cristo-Schmitt: It's not.

Jason Bay: Yeah, it really isn't. I think what it requires is.

Tara Di-Cristo-Schmitt: Or it's not difficult. Maybe it's hard, but it's not difficult.

Jason Bay: Exactly. Yeah, it's. I think it requires this top down buy in around it because I can't tell you how many teams we'll work with where. What they've tried before bringing us in is like, oh, yeah, we're doing mandatory prospecting days where AES just sit on the phone for six hours and we don't give them any kind of guidance around who they should call or what they should say, or we don't really equip them with any kind of, uh, value that they could give.

Tara Di-Cristo-Schmitt: No, that's the initial benefit statement. You need to give them that.

Jason Bay: Yeah, it's just none of that kind of stuff. Um, so with outbound, though, I am curious around your experience and what you've seen with it is no easy feat to convert an inbound culture into more of an outbound culture. What's your guidance on that? Because that's in the last couple years, I would probably say if there was a pie chart of the reasons why, uh, leaders come to us, that's probably 2/3 of it right there is like, we need to change the culture on the team.

Tara Di-Cristo-Schmitt: Yeah. I have a pretty strong opinion about this. And my opinion is this. If you have an uh, inbound team, you know where your break even is. So build the, keep that team intact.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: And have that team produce that and that becomes revenue that you can depend on year over year over year over year. Right. And if we get another wave where we have to add more heads, uh, or to keep up with the demand. Excellent. Right. That's not a hard thing to do. We've learned that that's not super hard. We can add the heads or we can add sdr. So we could add AI now and we could capture that demand, build a team. Uh, the converting inbound to outbound in my opinion is hard and it takes so much time and energy. And the truth is if you can't find willing people like will and skill, you could give them all the skill. But if they're not willing, they're not gonna do it. And that's why I talk meant when I said generation of people, of sales professionals, they don't want to do it and so they're not going to. No matter how good you are as a leader and how passionate you are about it. Um, unless it's you shut off inbound. So I am a big believer in invest, bring in new talent, determine what you need and then change your profile and go bring out, start to build your outbound arm and you will drive productivity just like you're seeing TOAST doing. Right. Like TOAST is taking off with the outbound momentum. They're now building field teams.

Jason Bay: Yeah. It makes a lot of sense.

Tara Di-Cristo-Schmitt: Yeah.

Jason Bay: The resistance of trying to take people that are used to being spoon fed leads and honestly to their defense, they probably joined the company and were promised by the people that recruited them that they wouldn't have to do outbound or very much of it.

Tara Di-Cristo-Schmitt: That's right. That's right. Because the outbound can be scary. You're calling someone that doesn't know you're calling and you're offering something you don't know that they need.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: So you need a culture of conviction around. I can help this customer.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: Be better than they are today. And here's who I'm going to call, here's what I'm going to say and here's the intended outcome. Let's go see if I can pull it off.

Jason Bay: Love that. Love it. Um, channel.

Tara Di-Cristo-Schmitt: Yes.

Jason Bay: This is ah, kind of your thing. Right. So for those organizations that are doing the inbound thing, they're doing the outbound thing. And they want to start to introduce channel. Do you have any guidance on how they might test something like that to see if it's good, how to roll something out like that? How do you guys think about it?

Tara Di-Cristo-Schmitt: Sure, I think start small, um, but find your centers of influence. So if I was in the payroll world, HCM role back then, CPAs, they were the center of influence. Anybody was listening to their cpa. Today if I'm at houzz and I'm talking to contractors and pros, maybe could be their cpa. We're looking, we're looking into that. But I know for sure it's their associations. Yeah, right. The community is a huge center of influence. So how are you sending, how are you creating that channel mechanism? Yeah, to be there. Right. So be where the customers are by being where their centers of influence are. And that takes some whiteboarding, some brainstorming because you know they'll say, oh, if we're housed, let's go into Home Depot and we'll stand at Home Depot and we'll get all of the pros. And we might. But if we look at all the associations across the US who have three groups of 300, we're going to do a lot better from a channel perspective of being part of those communities, being able to show how we can help their job become easier and build their brands in their markets. Um, so I think it's really about understanding the centers of influence for the buyer that you have.

Jason Bay: Yeah, that's a really interesting approach because. And it makes so much sense when you think about it. Because the instinct I think is to look at like if we're houzz, for example, the instinct I think for a lot of sales orgs is to look at other software vendors that they're using already that are complementary and just to go to them. Um, so like I don't even know if this is back when I was doing the contracting thing. I don't know if people are still using things like uh, HomeAdvisor and things like that. But like what are customers, customers using to like buy leads, Contractors using to buy leads. Oh cool. Well, maybe they could use our thing because it doesn't directly compete or whatnot. Um, and it's like really short term thinking, like the going after the associations. This is where like the trust has been built. And from there is it like are you co marketing with them or we'll

Tara Di-Cristo-Schmitt: co market, we'll do events. Um, some of the pros become partners because they're so passionate about how we have helped the software has helped them build their business, that they'll go speak to younger professionals, pros coming in, and they'll show them this is how we do it.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: And this is the software. This is the platform that made it easy.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: That allow us to create this best experience for our clients.

Jason Bay: Yeah. And from there, are you, like, how much time would you expect to give something like this to start working?

Tara Di-Cristo-Schmitt: I think you gotta give it like it can. I don't have a direct answer, but what I would tell you is this. It can happen overnight. So there have been. So we started this. I've been here a year. I've been in halls a year, probably started it six months in, and we're already seeing productivity out of it.

Jason Bay: Wow.

Tara Di-Cristo-Schmitt: So is it at the pinnacle of where I want it to be? Of course not. Uh, but it is catching on like wildflower. And, uh, I believe it's gonna be our highest, uh, we're gonna have the highest close rate through partners.

Jason Bay: Yeah. I mean, the trust and the brand awareness and the marketing, it's. It's interesting because it's like you kind of get the best of both worlds between inbound and outbound. It's like it's more proactive than just sitting around and waiting for organic. But it's got the social proof of organic.

Tara Di-Cristo-Schmitt: And like, the better company gets it outbound, the stronger their inbound becomes.

Jason Bay: Yeah. That's interesting. I've never quite thought of it like that actually. Yeah. Because that's the. Have you heard the term dark social?

Tara Di-Cristo-Schmitt: No.

Jason Bay: Dark social is kind of a funny.

Tara Di-Cristo-Schmitt: Fill me in.

Jason Bay: It's kind of a funny term that marketers have used. And it's nothing crazy. It's basically if you see something that Outbound squad that I post, let's say, on LinkedIn, um, I can see if you've liked, commented, shared like that kind of stuff. Right. But what I can't see is if you just took that link and dropped it into your Slack channel for the rest of your leadership team to look at. That's dark social. So it's all of the conversations that are happening because something started on social media that you cannot track.

Tara Di-Cristo-Schmitt: Wow.

Jason Bay: And that's sort of what you're saying. It's like you can't. Like, totally sure you can see in Salesforce if an email was sent, but you don't know if it, like, what was the click path that someone went through and like, the influence of that. Yeah. Um, I also say the opposite too. I think the ceiling of your outbound engine is Your marketing engine, because, like, you can create demand, but you can only create so much demand if, like, if you're not housed and you don't have the social proof and a great product and the content and the case studies and, like, it kind of puts a ceiling on your outbound efforts too. So it's like, really thinking about all of these things and how they work together is big.

Tara Di-Cristo-Schmitt: Yeah. So it's funny you say that, because one of the things that I learned stepping into the CRO role from just leading a sales team is I went from leading pipeline and results to now really moving a. Like a system. It was, Wait a minute. The sales team is doing what? And the customer success team is doing what? And marketing is saying what?

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: And we're not all together saying the exact same thing. Well, how are we gonna. How are we gonna build our brand in software? Right. We had an excellent brand in advertising, but we did not build our brand in software. And our brand. We were all saying different things. And so that was a big focus of this past year is realigning. What is that messaging? What is marketing building? How are we going to market? And then how is. How are we giving that content? You were there for part of it, right? We were building it from scratch. How are we building that for the sales team? And then how does that convert from the sales conversation to customer success? And how are we threading that all the way through?

Jason Bay: Yeah. God, when I think about it, that's happened really quickly.

Tara Di-Cristo-Schmitt: It did have a pretty quick.

Jason Bay: That's pretty cool. Yeah.

Tara Di-Cristo-Schmitt: Well, I had great help.

Jason Bay: I mean, yeah, I'll take a little tiny bit of credit. Um, okay. There's a couple other things that I want to make sure to get into before we take off. Um, okay. I'm really curious because I don't see a lot of content on this. What does your weekly rhythm look like? How do you set up your week? Um, how do you plan your week? What do kind of the days or themes of the week look like? How do you think about where to spend your time and how to spend your time?

Tara Di-Cristo-Schmitt: Yeah. Um, so I have this concept that was taught years ago of, like, get on autopilot. Which, as a sales leader is like, doesn't even compute. It's like, what do you mean? Get on sale, get on autopilot. We can't get on autopilot. We have to keep doing more. You have to keep doing better. But the, uh, idea is have systems in place that you can be on autopilot to a sense of the Plane's gonna fly.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: And you're going to be, you're going to be, you're going be able to get there. Mhm. Quickly. Because you know what's happening, you know what's coming up. And so I've always built my schedule to be on autopilot in the sense of I don't have to guess what's happening.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: So Mondays, um, is going to be before I'm doing any. And people will say, well, her mornings are sacred. And they are. But I'll tell you something that not enough people admit. My Mondays, my mornings, they don't start with let me look at data, they start with let me get to the gym. And if I don't get to the gym, it is not going to be a good day for anybody. And so we know that, I know that and they know that. So it's critical that that's where my day starts. And then after that I go into devotion every morning because I need to be clear, uh, in my mind. And then I think before my first call, I will sit and say, okay, what, what are we doing? Well, where are we missing? And what do I have to do this week? What does that look like for the week? Um, and then I open my calendar. I'm giving you Monday right now. And I open my calendar and I look at everything that's on there. Because no matter what state of autopilot I'm on, people are piling things onto my calendar.

Jason Bay: Interview. Of course.

Tara Di-Cristo-Schmitt: Yeah, right. I gotta get the podcast, all that stuff. And I will remove things that aren't aligned to the work I just did, saying what's important right now. Um, and then, and so my Mondays are really, believe it or not, around, uh, me and understanding what I need to do for the rest of the week. Tuesdays are my one on ones with my teams, um, and my boss, my CEO, um, and then I spend Wednesdays and Thursdays in being, I call it being in the business. So I'm either in listening tours, I'm talking to customers, um, or I'm moving projects forward. So that's one of the other things that has been really cool stepping into a CRO role is I'm moving things along more so than actually doing them. Um, and then Friday is about connection. That is where I'm really focused on reflecting back. Did we do what we said we were gonna do? What else needs to be done and who needs to feel good? I actually call it Feel Good Friday. And if I need to feel good, I'll go to my CEO and be like, yes, I'm good that I'm doing here. Just remind me of what's working. Um, and then it's also Friday is I connect with everybody. Um, um, I'm going to say pillar, but that's the wrong thing. But every partner in the business. So I will make a point to connect with product. I'll make a point to connect with marketing. If I hadn't already done so. Um, and then I've got customer success and sales.

Jason Bay: Got it. So the anchor it sounds like for your week is like the Monday morning workout.

Tara Di-Cristo-Schmitt: Yes.

Jason Bay: Which I'm very similar. It's like I'm up at 4:40 in the morning. I do an early morning workout. Like, ah, okay, cool. I started the week off doing something that, honestly, I really like the workout group that I'm in, but it's not like fun to wake up at that time. Never again, you know, but you feel really good. The reflection questions that you have, um, is this just you sitting and kind of thinking about it? Are there other prompts that you're using? Are you looking back at the previous week or is this just all like, hey, what's top of mind for me right now?

Tara Di-Cristo-Schmitt: It's usually what's top of mind M for me. And I'm in a very specific space every time. Not all over the house. I go to a very specific space and it's what's going on because a lot goes on. Yeah, right. Uh, there's a hamster definitely going around in my head pretty quickly. And so I gotta slow that down so that I can focus on what's the task at hand for the work we gotta do.

Jason Bay: What's something that you are typically canceling in your week? Like, what's a common time waster? Maybe even something that other people might overlook or feel guilty about canceling or whatever it might be.

Tara Di-Cristo-Schmitt: Yeah. The most common ones are like, meetings that don't need to be optional. I'm, um, put on as optional.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: Or it's those meetings and the truth is, like, I don't need to be there because you're there to do the work that needs to be done and there's recorded. Or give me a, uh, you know, tldr on what happened. Or put time on my calendar when you get stuck and you need to talk through where we need to go. Now, I won't always cancel them. I'll recognize I have been removed from this. I should step in. I should go to that optional meeting. But it's mostly those optionals and there's a lot of those optionals that get thrown out.

Jason Bay: So the rest of Monday, you're game planning for the week and you will look at data. I'm assuming at some point, I mean,

Tara Di-Cristo-Schmitt: finance and my LT team, which is my peers, those meetings are on Mondays.

Jason Bay: Got it.

Tara Di-Cristo-Schmitt: Right. So I've spent probably the majority of the morning doing my work and then it's getting with the team and just validating that everything is. What I'm seeing is right. The state is correct. This is where we are. This is what we need to do.

Jason Bay: Yeah, Yeah. I love the way that throughout the week you are, um, one of our old clients rippling. They have a company value called Go and see. And I thought this was really cool. Jonas, he's their VP of sales and he shared it with me and he's like everyone from our CEO on down, Parker on down, it's like, go and see. Get in the field. Like, no one is above. Like, what is the customer actually saying? What is the rep actually experiencing? And that's like a big part of your week at sea. Sounds like where you're very strategic on Monday and Tuesdays and then Wednesday, Thursday, like you want to be in the field, like experiencing what the reps are experiencing.

Tara Di-Cristo-Schmitt: Yes. You know, GONG is not going to like me for this and I probably should cover this when I say this.

Jason Bay: This is not sponsored by gong.

Tara Di-Cristo-Schmitt: I love gong. I love Gong. But I do think we have over rotated on, um, listening to recordings.

Jason Bay: Oh, like Async. Yeah.

Tara Di-Cristo-Schmitt: And I think we miss something. Right? We miss that follow up question that we can ask if we're live in that conversation either with the rep immediately after the meeting ends or with the customer, because you're in it with them and you can say, hey, let me just clarify something you just said and tell me more about. We really miss that if we're not going and seeing.

Jason Bay: Uh, that's such a big point. Um, I mean there's a. Here in the city, there's a conference coming up and like you're gonna be at the conference, right.

Tara Di-Cristo-Schmitt: Tomorrow. Yeah.

Jason Bay: So like that stuff's big. Um, I'm curious with your team and how you manage them.

Tara Di-Cristo-Schmitt: The

Jason Bay: learning curve of rep to manager is one thing. Right. Where you're one step removed, you're a second line leader and you're trying to get a team of people to do something very similar to what you did. Now for you, you're at fourth or fifth line leader. I'm curious because again, I don't see a lot of content or Direction on this. How do you look at the relationship with your and VPs? What are those one on ones? Like, is there a lot of coaching? Is it strategy? Is there some accountability in there? Like, how do you kind of think about the one on um, ones that you're doing with your direct reports and just that relationship and that rhythm on a weekly basis? How do you think about that part?

Tara Di-Cristo-Schmitt: Yeah, there's not a lot of coaching on that for senior leaders. Kind of you come into it and you're like, how do I, what do I do now? Um, and so I'd say it's all the above. So, um, I spend time and I focus on bringing outside leadership in. I think that's important. I think sometimes we could be too focused on, I'm your leader and so I'm supposed to know all and we are running this big business together. So what is the outside influence I can get? So TLC is a program that I work very closely with. Um, for the leaders one on ones. Um, you know, I always, when I started at Houzz, what I learned is they would come in with lists of things. So I got a lot of things on my list. And can we just run through the list?

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: And so I said, okay, we can run through. Yes, we'll run through the list. But we also need to talk about what are you doing to help drive culture? What are you doing to help increase skill? What are you doing? I would ask different things and then I would save, uh, a part for the end and it's what do you want to work on for you? And not every one on one goes as smooth as that. But those are the pillars of the one on one. Because as senior leaders you could get too far away from focusing on that individual. You also think they should know how to do it. And you have to pull yourself back from that and say they don't know because they've stepped into this role for the first time. Um, and you have to keep redirecting them because they get pulled in a lot of directions once they hit that director level. And um, that redirection every week I think is critical to their success.

Jason Bay: Yeah. What are some of the skills? Do you have any examples of skills with people that are more senior leaders, like directors, VPs? What are some of the skills that you've worked on with folks?

Tara Di-Cristo-Schmitt: Okay, so I don't know what skill we'll call this, but maybe we'll call it. We're just for fun's sake, we're going to call it the Go and See skill. Or I'll call it the skill of connection. Meaningful connection, that's what we'll call it. And accountability. Mhm. So we'll tie those two together. And what I was finding is that once they got promoted, they were just now doing, meaning they would take calls, uh, they would react to anything that the team that was supporting them needed. And so I asked them, I said, do you do director days? And they're like, what's a director day? And I said, a director day is where you go to see if what you're asking is being done and what you're coaching them on is actually happening. It's an inspection. Right. And I said, so I want you to do it for, for, for three days. So how many teams do you have? I have four teams. Okay. So over the course of a quarter, you should be doing this three times with each team.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: And you pick your days. And then in your days, you want to see team meetings, you want to see one on ones, you want to do seat rides. If you're in the field, you want to do field rides, you want to observe a, what you might call a roll call or a pump up meeting, a huddle. And, uh, it was mind blowing. Use your career conversations with people. Um, what they learned was the ability to connect and hold people accountable. And what they learned is there were gaps in the skills that their people had. And so they were able to then bring that back and assess what they saw and then put that training in place so people become better. This is.

Jason Bay: Was it Ronald Reagan that said trust but verify? One of the presidents, I feel like

Tara Di-Cristo-Schmitt: it was my CEO at adp, but yeah.

Jason Bay: Oh, I just, I'm such a big component on that. It's like, yes. It's not to micromanage. It's like, I have to go see. And how hard is that to do in a virtual environment? Especially because back in the office it was great because you could just go to the sales floor.

Tara Di-Cristo-Schmitt: You could just go to the sales floor. Now you have to open their calendars. You have to get permission to say, show me your calendar so I could see what you're doing so I can help you build a calendar so you could be successful.

Jason Bay: Yeah. That's crazy.

Tara Di-Cristo-Schmitt: I know.

Jason Bay: So I love that idea of director days. You're encouraging that. It's like, hey, you need to have space in your calendar where you're inspecting. Right. Um, one more question I want to ask you. Sort of related to this is the amount of internal meetings. Sometimes that I see a sales org forced to participate in like reps especially. It's like two or three hours a day sometimes. How do you think about at Houzz, like just protecting the reps time, the manager's time to like make sure that they do have the ability to execute, that the managers do have the space to really coach and rub shoulders with the team. How do you think about that?

Tara Di-Cristo-Schmitt: Well, I mean, I've come a long way with how I think about it. Going inside after Covid and being remote was really changed everything. Right. It was like all of a sudden you have more meetings than you've ever had. I grew up in the. You wake up, you are in the field by 7:30. If we see you in the office, it means you're not working. And uh, you're back in the office at 4:30 and you have one meeting on Monday to kick off everything. And you've got one meeting on Friday, which is rah rah, how do we do a new forecast? Um, and I've been trying really hard to recreate that environment, uh, in the uh, remote world, which has not been easy because you need that point of connection. But it goes back to the same thing I said about getting on autopilot. It's defining when the meetings are and making sure you're not in selling hours and not having people have to guess when things will show up. So if you have something that you feel is a fire drill and you need that to get on the sales calendar. And it can get on, but it can only get on on this time and date because it's already pre scheduled.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: And that has helped sales teams to stay in the motion.

Jason Bay: Yeah. So you institute like a weekly rhythm essentially. Like here's like a guiding principles on how like you should run your team and that sort of thing. Yeah, yeah, love that. Um, let's get to the rapid fire questions.

Tara Di-Cristo-Schmitt: Okay.

Jason Bay: You ready? By the way, this, the wall on this side is a little trippy looking.

Tara Di-Cristo-Schmitt: I told you. Now imagine if I was over there. I would have been like the whole time. Fine.

Jason Bay: First question is, what's your hot take on AI? Where do you see all of this heading for sales?

Tara Di-Cristo-Schmitt: Listen, I think AI is an important part of our future and I believe that we have to embrace it. I think it's a little bit scary. I do, I think it's a scary thing. Um, but I think it will put us in a position to be more efficient, more effective. But I believe it will never replace a true salesperson because I think that trust is so critical. And so I believe it's gonna play a role in making you more effective. I think it's gonna allow salespeople to not have to do the things that they don't do that we as leaders are constantly ask them to do. Um, and it's, it's gonna allow salespeople to be who they wanna be, really. Right. And that's out talking to people and helping businesses grow better businesses.

Jason Bay: How are you guys leveraging AI right now?

Tara Di-Cristo-Schmitt: So from a product standpoint, we are building it into our product. Everything that we do from a sales perspective, we are, um, building it into our SDR motion. So we're working with salesape. That pilot starts next week and I'm m excited to see how that, uh, goes. And then, of course, we have AI in, um, the customer success side of the business. Because there's a lot of work that's done there that can certainly be automated.

Jason Bay: Yeah, there's God. I mean, we could do a whole episode just on AI, you know, in sales. But it doesn't sound like you're. You're of the belief that it's replacing salespeople anytime soon.

Tara Di-Cristo-Schmitt: I don't, I am a believer of that because the person on the other end is still a human.

Jason Bay: Yep.

Tara Di-Cristo-Schmitt: And it's like we talked about outbound creating, inbound creating. I think it would create a more streamlined way to get to the conversation. But I think there's still going to be a large population that wants that conversation.

Jason Bay: I think especially your market too, as contractors.

Tara Di-Cristo-Schmitt: Yes.

Jason Bay: They barely trust other people outside of contracting.

Tara Di-Cristo-Schmitt: That's exactly right.

Jason Bay: You, um, sort of answered this question already. But I'm curious if there's anything else. Uh, how do you prevent and deal with stress?

Tara Di-Cristo-Schmitt: Um, working out is my number one is how I deal with stress.

Jason Bay: Do you have any tips on how you fit that in? Like, you have a family and stuff and you have all of the excuses that you could make to not do something like that. How do you fit in? I don't have kids.

Tara Di-Cristo-Schmitt: Oh, yeah.

Jason Bay: To have a wife, it's like my life is way easier in this department to fit stuff in. Like, how do you fit that in as a way?

Tara Di-Cristo-Schmitt: Well, remember I said earlier that if I don't work out, everybody knows it. Right. So the kids, my husband, they're like, let's make sure she has her workout. But I do early. I get up early. So I will always do it early. And by the way, there were years where that was hard to do. But that morning where nobody's up, you're back from your Workout and people still are not up and you have that time to yourself that's irreplaceable. And, um, I would coach anybody to find that time now as the world has grown, um, there's more time in a day. You have a half hour free. Get outside and walk.

Jason Bay: Yeah.

Tara Di-Cristo-Schmitt: Have the walking desk. Like, keep yourself moving. Um, especially if you're in sales, because sales is an energy driven career.

Jason Bay: 100%. Ah, last question. If you were a first time, we could say VP of sales manager, rep, whatever it might be. Knowing what you know now, like, what advice would you give yourself?

Tara Di-Cristo-Schmitt: Oh, that's a good question. Knowing what I know now, I would say have patience, um, with yourself, have patience with your team. Often when you're new to a new role, you think you have to go in and prove something. But just being hired into the role is proof enough that you've done something in your past to be there. So spend time getting to know your people. Go on listening tours. Um, and when I say patience, your leaders. So whether it be a senior SVP or a CRO or a CEO will be pushing you to do something now. M. Just hold true to. I have to really understand what's happening before I make decisions because these decisions will impact the trajectory of the business. And that would be my best advice. And then my asterisk. Best advice is if you're reporting to a CEO or CRO or an SVP of sales, quickly get aligned to what their vision is and how they like to communicate. And I think that'll set anyone up for a future of success in senior leadership.

Jason Bay: Love it. Where can people go to connect with you? Um, is Houzz, like, are you guys hiring? Like, where can people learn more about that?

Tara Di-Cristo-Schmitt: Yeah, House. We are hiring. We're actually going to hire in Nashville. So if anyone's living in Nashville, we're going to build a little hub there, which is really exciting. Um, we're also remote, so we're on LinkedIn and, um, houzz.com so come see us there. And me, you can find me, you know, taraouse.com and, and I'm on LinkedIn too.

Jason Bay: Cool. Great to have you on the chef.

Tara Di-Cristo-Schmitt: Thanks for having me.

Jason Bay: Let's go.