From Hospitality to Customer Success with Madelyn DePrey

Full episode transcript

Alper Yurder: All right. So today in the therapy chair, we have Madelyn DePrey, who is the Global VP of Customer Success at Aircall with a background in customer excellence and also hospitality, which is really interesting to me because I also have a background in hospitality. We'll talk about her success, the joy, the pain and the journey. Welcome to Sales Therapy, Madelyn. How are you feeling today?

Madelyn DePrey: Thank you, Alper. Great to be here.

Alper Yurder: Excellent. Thank you so much for being patient with me. I actually have pause doing podcasts for a month. I gave myself a break, which was much needed. And the last time we spoke, I was on a Greek island with choppy Internet, but we had a lot of fun. I'm sure we'll have great fun today, too.

Madelyn DePrey: I can't wait and I felt so bad for you on vacation, but good to be back. Let's do this. Lots to talk about today.

Alper Yurder: Yeah, absolutely. How is your summer going so far, by the way? We're recording this in July.

Madelyn DePrey: Well, it's hot and humid in New York City, so I'm trying to survive the heat wave. But otherwise, it's great. I work for a French company, so I'm gearing up for everyone to be offline for the month of August.

Alper Yurder: Okay, yeah, yeah, I love that. I used to work for an Italian company and Ferragosto is a big thing. And then the whole actually whole of Europe is now flooded by Americans in August. So I feel like there's a good spillover to the states of that culture.

Madelyn DePrey: Yeah, absolutely. And New York City is so quiet in the summer. It's nice. I have Central Park to myself, so I can't complain. Everyone's in the Hamptons or in Europe.

Alper Yurder: Ruff. Yes. Do you have your favorite summer pleasure for New York, like your own little rituals?

Madelyn DePrey: You take a bottle of good rosé, you take a blanket and you lay in Central Park with a good book. That's the New York.

Alper Yurder: There you go. And then you look at the tourists because there's no New Yorkers left as you say. Wonderful. So as you know, Ingo Therp starts with childhood and the growing up experience because I know it shapes the person that we are today at work. Can you tell me a little bit about your growing up? Where, how, what was it? Anything that stands out for you?

Madelyn DePrey: Yeah.

Certainly, and I love this question and I think we're all due for therapy as we plow into age two. So where do I start? I had a wonderful childhood. I grew up in the middle of the country, Minnesota, that's how we say it in the Midwest. So Minneapolis, which is a beautiful part of the country, but the winters are Arctic. And I had wonderful parents. I had a good childhood. I went to an all girls Catholic school. So I had nuns as teachers, but I took...

Alper Yurder: Okay.

Wonderful.

Madelyn DePrey: Latin because it was at the boys school and I would you know put on lipstick and roll up my skirt and walk over to the boys military high school for Latin. So yeah and Alper I have to tell you I also had a flair for the dramatics. So I wanted to be an actor, singer, a dancer and I wasn't great at any of those things but I had very supportive parents and I use acting skills today in sales so I can't complain.

Alper Yurder: I love that. I mean, I love that Latin thing. So learning Latin just so you can see a bit of the other sex, the fair or the unfair sex. OK, good. OK, I think that's called being resourceful. Well done. And did you notice any early connections to your current profession during those formative years?

Madelyn DePrey: Yes. Thank you.

Madelyn DePrey: Well, actually, my dad was in sales. So he had a company called Depre Sales, and he sold manufacturing equipment and saw blades to construction companies. And I just remember seeing him, he was often on the road and he'd be picking up his cell phone, taking calls from customers, and he'd be scribbling down an order and driving with his knee as he was talking to his customers, but he was always connecting with them mentioned us how their kids were, knew the details of their wives. And it was really lovely to see that, was husbands and wives. So it was great. So I think that personality and that connection and kind of being performative in an authentic way always inspired me.

Alper Yurder: I love that. I love how you talk about the performance side of things, which I think as an extrovert, it drives me and attracts me. But I think as a founder, I have to do the performance quite a lot all day every day. And I think now in the summer, I'm like, I'm a bit using a bit of a downtime. Like, you know, do you ever feel that performance sometimes is a little bit challenging as well? Or, you know, you're fine with that all day every day.

Madelyn DePrey: It's funny you asked that. I too am an extrovert. I scored the highest possible on the extrovert test on the Myers-Briggs. So we have that in common, Elper. But it is exhausting. And especially, I do run a big global team today, which is a blessing. But it's a lot of performing and putting on a show and being the one in control to your team and then your customers as well. And it's quite exhausting. So it's very important to have downtime to resettle and get back to your authentic self.

Alper Yurder: I'm sorry.

Yeah.

And that not letting the hair down kind of thing, if that's the right expression. To be honest, I sometimes miss not being a manager. And it's been a while that I have not not been a manager because, you know, but now we have quite a small team. We're like a team of 11. But obviously I manage big teams like 50 and whatever, not 100 like you. But and it's always that, you know, you have to put the show on, try to be as authentic as yourself. But some things you need to keep to yourself because.

Madelyn DePrey: Yeah.

Alper Yurder: People are looking to you and sometimes your hand gesture might signal something to them. And I think that's sometimes a little difficult, I find.

Madelyn DePrey: Absolutely.

Alper Yurder: I started this new section or I decided to start this new section with a little icebreakers because in the last few podcasts that I had was a guest, they asked me one question that I think was really cool was what are you snobbish about? I'm not going to ask you that, but I'll ask you two things. One is what are you most proud about? And it doesn't have to be work in general.

Madelyn DePrey: Well, you know, top of mind right now is I've been in New York City for 10 years and it was always my dream to live in New York. And I worked really hard to build a life for myself here and I've met an incredibly supportive husband and I'm proud of living my dream in New York City right now.

Alper Yurder: I love that. Don't you? Whenever I feel, I can't even express those words. Like I feel like a good place in my life and I had some struggles and blah, but I struggle to say that it's good because I feel like I'm going to jinx it. I don't know. Don't you have that?

Madelyn DePrey: I have that, absolutely. It's like, keep your, you know, look behind your shoulder to see, make sure that you're still in control and things are still good. But it's also important to remember that life is long. I always say, it's not short, it's long. And so let's enjoy the good and celebrate our accomplishments and revel in the goodness around us.

Alper Yurder: Good webs and what drives you mad?

Madelyn DePrey: I think, overanalyzing and not executing. So especially in, in work, and I'm in a fast-paced hyper-growth company, when we, when we sit and stew and we think too much about what went wrong in the past or what could go wrong. And we don't just do, we don't have a bias towards action that really drives me mad. And so like, let's, let's fail quickly. Let's make mistakes. Let's take risks and let's learn from them and evolve and move forward.

Alper Yurder: Yeah, I love that. Have you always been like that or has life and experience brought you to that place where, you know, let's move.

Madelyn DePrey: You know, that's a, it's an interesting question. And again, thanks for the therapy today. I think, I think I needed it.

Alper Yurder: I mean, that's the whole point. We're going to we're going to talk boring stuff to don't worry, but I make the boring stuff fun too, so we'll be fine.

Madelyn DePrey: You know, I'm not a perfectionist. And so I've always had a little bit of an air of, you know, let's just try something and not worry so much about making mistakes. And so that used to bother me where I'd be surrounded by very type A individuals who were so perfect and did everything to a T and I'd be self-conscious of that. But now I think it's worked well for me particularly as a leader where it's important to sometimes improvise and like I said, you know, take risks, but also fail quickly and level set and not focus so much on the what if and over analyzing all the possibilities. So I've settled into that, but I haven't always been comfortable with that side of myself.

Alper Yurder: Yeah, well, we grow and I agree. I feel the same. Now about your career, what really, for me, what's most interesting is that, yes, you're now supporting and leading a huge customer success team in a very successful software company, et cetera. And you've done software for a while, but also you have a bit of a hospitality background and travel and hotel management. And I've done my share of those things back in the day. And I think that...

Customer-centric mindset, guest-centric excellence. You know, I used to work at Ritz. So there's this excellence culture and, you know, the client before you, which to me, to be honest, it all comes very naturally. Does that come to you naturally as well since you've been doing all these things? And the next question will be maybe a 30-second to one-minute summary of your career, because we're going to talk about that. So don't give me every little detail, maybe like a high level for people to gather like who is Madelyn?

Madelyn DePrey: You know, it's funny you mentioned the Ritz, the book of the Ritz -Carlton Gold Standards. It's all about ladies and gentlemen serving ladies and gentlemen. And maybe we need to make it more gender-neutral now. But that concept of, you know, we are all in the art and the act of hospitality. I've had my teams read that book over the years. And I think it's so important to come back to that. Right now, I'm in very much an SMB business.

Alper Yurder: Yeah.

Madelyn DePrey: And so it's a lot of transactional sales and conversations at scale. And I really feel we've gotten too far away from getting back to understanding the customer and creating wow moments and kind of those hospitality pillars that I think are so important in customer experience and in sales. And so it's something that maybe I've gotten a little bit away from that I want to return to my hospitality roots around.

Alper Yurder: I love that creating wow moments. Was that from the Ritz as well? It is from or whatever everybody talks about.

Madelyn DePrey: I think so. Danny Meyer is setting the table. That's another great read about the art of hospitality. Right. And so. yeah, that's great.

Alper Yurder: Yes. My co-founder loves that book. I mean, yeah, I know it's the restaurant chef, right? Creating Guamons. Absolutely. And that's what sticks with anybody, customer, user, whatever, people in general. If you do me a favor, it might not even be a favor, but something nice, gesture, kind, something heartfelt, like go the extra mile. I think IKEA does that. I had read that about IKEA.

They basically make you go and fetch your own furniture, which is horrible. Like if you think about it, you know, 20 years ago, nobody would be like people were like, are you mad? Just bring my furniture home. But then they give you the experience inside the store and they give you the meatballs and this and that. So they create different moments of connection. Let's let's go back to your career. I side way there. So how did your career start?

Madelyn DePrey: Thank you.

Alper Yurder: And can you share a bit of like pivotal moments, highlights and lowlights from the journey so far?

Madelyn DePrey: Sure, so as mentioned, I thought I was gonna be in the arts and I pursued performance and that didn't work out as it often doesn't. And so I got a degree in education because it was gonna be a fallback. Wasn't for me, learned that very quickly. So I ended up in waitressing and figuring out what I wanted to do with my life.

I was also working for a nonprofit for a bit, so worked for the YMCA of America and did fundraising and marketing. And nonprofits are much like startups, so learned a ton there. But I really love the hospitality world. And I met someone in the Midwest who was opening a hotel in New York. And I put myself out there. And he ended up offering me a job. And I moved to New York with two suitcases and took a job to open a new luxury hotel in New York City.

And that's where I learned all of these things. So we were building a brand, we were building an experience, we were greeting our guests and I was kind of front office manager. And so I had a team of bellmen and doorman and front desk agents and had to work at the desk myself. I met my husband who's on the restaurant side of the business and learned a ton there about that world and creating memorable experiences. And the ugly side of it too, like when you get a negative TripAdvisor review and what do you do with that?

How do you pivot? And then I met someone who was building software for hotels, and that's what moved me into tech. So I joined a very early-stage startup. I was one of the first 20 employees to build technology for hotels. And I was at that company for six years, traveled the world training some of the best hotels from the Maldives to MGM in Las Vegas on how to use software to better operate their hotel. And over that time, I had the privilege of building customer success function from scratch. And from there, I've continued my career in customer success. 

And now I'm at Aircall where I'm in a global position. I have a global team of customer success managers that carry a sales quota. They own customer retention, but also upsell and expansion. And so I very much am part of the go-to-market function. So that's kind of what got me to where I am today in a nutshell.

Alper Yurder: Yeah. You're very much sales as well. I mean, I think those two things are kind of converging now more than ever due to both macro trends and economic concerns and blah, blah, but also like the way people buy. Like they don't want to, you know, somebody once explained this to me. I mean, one of my guests, I forgot, but it was like, we create the silos, we create customer success sales and, you know, inbound, outbound and pre -post. Like they don't care. They just want one point of… and they want a stellar experience throughout, which resonates a lot with me as somebody building a digital sales room which people use as a client's success portal, like that continuity. The whole team is looking into one single source of truth. They know exactly where the buyer is, where the client is in their journey, and they're having an easy breezy experience. And I think now because of that, customer success has become not just that customer success or support or whatever, it is… like one joint commercial function more than ever it feels like. I don't know. Does that make sense to you any of what I just said?

Madelyn DePrey: Absolutely. I love that you said that. I think a lot of my time goes to breaking down silos and making sure you act as one team. Because like you said, the customer doesn't care. They just want to get value out of the product. And what I find is it's funny you say that that's becoming more common. I will say something a bit controversial. I feel a lot of customer success leaders really shy away from having a seat at the revenue table. They're afraid of that. They're against it. They don't want their customers to think of them as sellers.

Well, guess what? It's job security to own a quota. So I've embraced that, but it's also better for the customer, especially in SMB. They don't want to have an introduction to another salesperson at renewal. They like having that continuity of someone that knows the value they've experienced in the product and is selling value and longevity and knows them and their DNA instead of, hey, now I bring in someone that's just going to try to upsell you.

Right, so it's hard, it's not for every organization, but it works well in SMB, that it's a one -stop shop. The CSM does that component of the customer journey.

Alper Yurder: I like that we start the conversation there. A lot of our listeners are people who are kind of earlier in their careers and they look up to you and they see a person like, okay, well, we've got some success at Aircall. I want to be that. So when we go into this level of detail of what your day-to-day is like and how you perceive things and what's your vision, I think it's really, really appealing to people. So I'm going to dig on to those a little bit, but just to give us a sense of what is your day-to-day or week-to-week look like these days.

Can you tell us a little bit about that?

Madelyn DePrey: Well, first of all, I'm quite humbled by that because I'm still figuring it out. So to those listening, you get to a stage in your career and you're still figuring it out and I've got a long way to go and so it's quite humbling. But a lot of my day-to-day today is, as mentioned, it's a global function. So I do tend to work crazy hours, which I quite enjoy. I like the global aspect. So I often wake up.

Alper Yurder: Okay.

Madelyn DePrey: And I'm online by 6:37 and I'm greeted by a dozen Slack messages by them because we a lot of our team is in Europe. And so I try to catch up and get through the day-to-day of making sure I'm supporting the teams in each kind of satellite office across Europe. and then I I'm on calls pretty solid throughout the morning and the calls are often working closely with product. we have a fairly new chief product officer chief to

Technology Officer here at Aircall that have really been a game changer in terms of our handshake across the customer team and the product team and making sure we're aligned in product strategy. We're bringing the customer voice to the table. We're talking about roadmap. We're talking about go to market with product marketing. And so meetings along those lines is one aspect. Meetings along the lines of supporting my team, I try to speak of course with my direct leaders, but also with skip levels on a regular basis and understanding their day-to-day, being there to support them, getting a sense of what's happening on the ground and giving feedback around strategies, but also hearing them out so I can then take their feedback to my leaders at the executive level. And I try to jump on customer calls. So as much as possible, I try to stay close to customers, whether it's a renewal conversation. Yeah.

Alper Yurder: I was going to say it all sounds very leaderly, but then finally you came to the point where you're still in the trenches, which is like keeping the pulse of the customer. And in terms of like, if we departmentalize those things to like challenges that you're facing in terms of your role. by the way, I was just going blah, blah BS here. So this is for our editor, cut this whole thing. I'm trying to make a point. So what I'm trying to get to is this.

Madelyn DePrey: I'm sorry.

Alper Yurder: I'm just very curious about some of the biggest challenges that you feel like you face currently. And actually, even better, when you came into your role, what did you feel like? What felt like, ugh, this isn't great, we need to change this? And how you're making progress on those things. What are those things?

Madelyn DePrey: I think two things. The first thing is context switching. So as mentioned, I'll be on a call with somebody who's an onboarding specialist and really in the weeds. And then I'll be on a call with the CEO and then I'll be in a customer call. That's an escalation. And so context switching for 30 minute intermix is quite hard as a leader at scale. The second thing is there's a constant battle in customer success between what is in our control and what is, I'm not going to say not in our control, but less in our control.

Alper Yurder: Mm-hmm. Yes.

Yeah. Yes. Yes. I love that.

Madelyn DePrey: That we're thinking about, okay, where are we driving value? Where are we making sure that we're identifying opportunities to gap sell and upsell and expansion or retain our customers? But also sometimes the customer is going to get acquired and they're gonna go to a competitor and that's what it is. How do you handle that situation? And how do you find ways to bridge that gap? So balancing the controllables and the non -controllables is what I say to my team.

Alper Yurder: No, no, no.

I love that. I think that's one of the highlights of this conversation, which is going to definitely become a teaser. Can you can you go into the detail of that a little bit? Like, I'm going to simplify and say, like, when do you when do you say it's OK, we let go. And how does it feel to say that really?

Madelyn DePrey: It's really difficult. And it's important not to do it all the time. It's important to say, did you go to every level, to every extreme in order to keep this customer, in order to close this expansion? And even if you did, let's still walk backwards. What could we have done 12 months ago to identify risk and get ahead of it, to multi -threat, to make sure we were talking to the right decision maker, et cetera?

Alper Yurder: Yeah.

Hmm. Yes.

Madelyn DePrey: But it's very difficult. And then sometimes, the customer has made the decision. They're moving away from you. There might be a churn. Is it worth spending hours to speak to that customer, to get more information? Or you say, let's focus on our customers that have potential. Do we kind of say, let's do a postmortem, but let's move on, and let's make sure we're addressing customers with potential? It's a constant balance.

Alper Yurder: And those things are very real. How have you multi -threaded? Have you done everything that's in your control to do? Have you kind of given a stellar onboarding experience? Have we solved the right thing to begin with? Those are actually really, really cool and interesting topics I speak day and day out about because those are the main reasons why people, especially in customer success functions, use Flola. So I'm going to dive into one or two of those, for example, which are very interesting.

Multithreading, like how do you make sure that happens? How do you train your team to multithread? What tips do you give them? What tools do you use for it? How do you track it? Anything there?

Madelyn DePrey: Yeah, absolutely. So it's an ongoing effort. So we do do sales training. We use some different sales methodologies. We use our CRM to make sure that they have a touch point with each point of contact by type. And we require a...

what we call an annual business review with a more senior decision-maker. Because CSMs often tend to talk to more of the tactical day-to-day sponsors. And so we hold them accountable to one decision maker call within the course of a customer term, but also that they have a touch point that they've tried to meet with them. And the other thing that we've done is we've done an executive sponsorship program where we've taken some of our key customers and we've paired them with our executives to make sure that they have an opportunity to stay speak peer to peer with our executives as well. So those are some of the things that we've leveraged from multithreading.

Alper Yurder: In my experience, it's not enough just to say there's an executive sponsorship program, but also to train the executives on what is expected of them to do because they will tend to run away or shy away and find an excuse unless there's like big money. So I think it's really cool that you start that program, but I think it's also important that they understand their role in it. Like what can you really contribute to? And in terms of onboarding,

Madelyn DePrey: Absolutely.

Alper Yurder: Like what do you feel like is the general experience of people who are on boarded to an air cold product? Like what are some of the areas where you felt like there was friction and challenges and how did you overcome those or how are you still working on overcoming those? Can you tell us a little bit about that?

Madelyn DePrey: Certainly. So onboarding is part of my scope and we're actually, we've made a lot of improvements to how we measure the success of onboarding. I have a great leader on the onboarding team and he and I have worked together to say, let's make sure we're driving long -term adoption and we're looking at adoption indicators within onboarding.

Alper Yurder: Perfect.

Madelyn DePrey: Early, so we've rolled out a health score to indicate long -term success before we can mark them onboarded. So it's not that the customer has checked boxes and attended a couple calls, it's that they've actually wore phone systems, so they've made X amount of calls, or they've looked at the analytics dashboard, or they have ported numbers.

There's specific indicators that we have in a health score to generate a metric of success that we can then leverage to move them out of onboarding. So that's one of the things that we've done. 

The other thing I alluded to earlier is we are looking at the handover process and we have account executives who tend to do a lot of the upfront kind of setup and even assisting the customer with getting them configured because we have a trial period, then they go to an onboarding specialist and then they go to a CSM. So historically, our customers have had three handovers within a 30, 45 day period. And we're reimagining that where we're getting the CSM involved much earlier. We're introducing them at point of sale. 

So it goes from an introduction to the account executives. Sometimes the CSM helps close the the deal is on the call, then the onboarding happens, but the CSM is really still involved as that long -term project manager. So we're reimagining that handover to make it much more streamlined for the customer experience.

Alper Yurder: Handover is usually where a lot of friction happens, both internally and externally. I mean, I know for God's sake, like in my first sales jobs, how much I was grilled by the head of customer success. Like, you know, you're just going on selling your thing. You're not like keeping us up to date. You're just doing your own Alper show in your own silo and like we need to be more included and involved and all that. And of course I've been told off and learned it the hard way in six months and..

Ever since, you know, it's different and I started managing CS teams. So I know better now, I hope, but a lot of salespeople will be in my position. That sales person who has the quota in mind, except what are some of those frictions that people generally cause or come across? And how do you tackle those frictions? Like what do you do to make sure that there's less friction between CS and sales in your teams?

Madelyn DePrey: Kind of the age old question, right? I have gone out of my way to try to be extremely empathetic to my counterparts in sales and really learn that side of the business. And so I think the hardest part about being a seller is the fact that you are expected to have integrity in the types of deals that you bring in and think about the ICP and think about long -term growth.

Alper Yurder: Yeah, of course. 

Madelyn DePrey: Out you have a monthly quota. And so you have to be transactional. You've got to get things done. You're under a tremendous amount of pressure. The CRO might not care. You've got to close your deal, right? 

And so balancing that juxtapose of integrity and making sure the customer is going to be successful, the CSMs are going to be successful with the monthly quota is the hardest part of selling. And so one of the things we do at Aircall is we've actually put forward a ramp up period. So the AE, the account executive, within the first three months, they are responsible for what happens to the customer. 

If the customer grows and expands, they get that towards that commission. But if they contract or churn, they're going to take that hit as well. And we are largely SMB. There's a good portion of our business that is on month-to-month contracts. And so it puts a lot more on the account executive to make sure that they are setting their customer up for success within that period and creating a streamlined handover.

Now this is still a work in progress because it's a bit of a weird limbo for the customer. Are they going to the AE or are they going to the CSM? So we're figuring that out, but it's been good in terms of building that accountability in terms of the quality of deals we bring in that they're going to be successful for the AE within that ramp-up period.

Alper Yurder: Is there like a typical deal where you can say, you know, at least we have five people in a deal that we need to take care of different types of people that you need to, you know, their needs that you can get your to like, do you have like an overall like 60, 70 % of deals? We have those things. Can you maybe name a few of them? If you have.

Madelyn DePrey: Sorry, the question is, 67% of deals that have...

Alper Yurder: Yeah. I guess what I'm trying to get to is like, like trying to understand the level of complexity in a deal because you keep mentioning the SMB, but it's still very complex. Like how do you define complexity in your team? Like what are your deals generally like? I wanted to learn a little bit about that.

Madelyn DePrey: Boom.

Yeah, it's a great question. So we play both down market, which was much more velocity, and that's actually an area where we're building more of a digital motion. And so in partnership with what's happening at top of funnel and kind of in onboarding and in customer success, we're trying to be much more automated and need less human intervention, but we still need human intervention. Then we have a little bit more of the velocity that it takes a human to close, but we're.

Alper Yurder: Yes.

Madelyn DePrey: We're pretty transactional. There may only be two point of contacts. The decisions are quick. We close most of that business within one month period of it coming into pipeline.

And then we of course have more strategic deals. So we do play in kind of each of these levels and the strategic deals is where we certainly have multi -threading. We certainly have to leverage some of the spice methodology to understand the pain point and bring that back at the renewal stage, et cetera. So it depends on the type of deal. And that's something that I'm working closely with both product and the sales team on is how do we build a customer journey for each of those three buckets that have that continuity?

Alper Yurder: Yeah.

Madelyn DePrey: What's transactional? What's automated at top of funnel? How do we continue that experience and set that expectation for the customer throughout their journey? Where is human intervention needed? At what level? At what deal size? So it's really thinking about the customer journey starts at point of trial instead of at point of handover and signature is one of the areas we're working on in terms of building out the stakeholders, the touch points, et cetera. So it's a top of mind kind of thing for me.

Alper Yurder: Generally, when I talk to a CRO, they'll tell me like there is one thing that I couldn't do without. And obviously, you know, they do the my people, my et cetera, which is fine, which I'll skip. But then they get to things like, you know, rev ops. If there was rev ops, I couldn't do without or XYZ tool. I couldn't do without. Do you have your, I couldn't do without tools, frameworks, functions that you think make your life better every day?

Madelyn DePrey: Absolutely. So a couple come to mind. So one, I'll shamelessly plug our own product. So AirCall is, we are a contact center. So we are the phone system that plugs into your CRM or your help desk. And we, I use AirCall every day to listen to call recordings, to track connections. My team is in Salesforce and has AirCall as the phone that can pop up so they can look at kind of a card summarizing the customer while they're talking to them.

And so we use that as a coaching tool. So whether it's in air call or it's in Gong, if we're, if we're leveraging, zoom to listen to call recordings, to leverage some of the AI functionality, to look at how much are we listening versus talking to coach and to also to, to do a session where we sit and we listen to a call together and we, we talk about, you know, what worked and what didn't work. So, so that's one area. the other is we have a customer data person. 

So, we, we have a pretty robust kind of data function, not a big team, but an important team that has helped build out dashboards and metrics that have been critical to my ability to forecast, but also drill into insights such as turn, such as risks that I can, adoption that I can then work backwards from to be preventative and to be prescriptive and redesign and reimagine the customer journey. So that we use Looker, but we have a team that's built Looker to be a tool for me. That's been a critical aspect of my ability to be successful in my work.

Alper Yurder: I love that. And in terms of, since we're going to the specifics of what helps you in your job, I think it was the VP of customer success at Loom, if I'm not wrong, who told like, if we are six months into the contract and we had a certain level of, you know, 70%, 80 % utilization or whatever, that's good. If we're under that, that's not great because that means like we won't be able to oversell, et cetera.

In terms of some leading indicators of what you look at day in, day out, do you have any of those that you can share as well?

Madelyn DePrey: Certainly, and it's a work in progress, but what I try to do is I try to very specifically identify not just the fact that the customer is using the product, but is the usage meaningful? So an example of that is to say, it's hard, it's so hard, and it depends on the use case, it's so hard.

Alper Yurder: Mm -hmm.

Yeah. hard. The hardest thing. But it's the best thing.

Madelyn DePrey: Often sometimes a customer will be using the product at high volume and they still turn because you don't know what's going on behind the scenes. And so an example is we have a robust analytics aspect of our platform and a decision maker, a leader is going to be looking at analytics to identify, you know, call quality, to identify the outbound call rate, the missed call rate, those insights to then coach their team and build that accountability. 

And so I make sure that we have customers leveraging our analytics platform or leveraging maybe call recordings, listening to call recordings, because that's the decision maker that is getting value from the product, not just using the phone. Right. And so that's one example of what is the meaningful usage that leads to retention? How are we tracking that and how are we building triggers for a CSM to maybe intervene and try to upsell or to try to prevent risk along the journey?

Alper Yurder: I love that I'm completely agreeing. It's really hard to gather and I'm glad you have, you know, somehow you're able to track that because not just the usage, but like the meaningful usage is so important. And hopefully they will be coming back to you with some, you know, negative things like, we need this or positive things like, can you build this? And that's going to be even better. Like that's the type of user that you want in Xplend. And maybe the last question, of course, I'll be asking you this about, you know, our space.

Like how familiar are you with digital sales rooms or client success portals? Do you use one? What do you think about Flowla and the space that we're in in terms of buyer enablements? Like, do you have any commentary on that area?

Madelyn DePrey: Yes. So thank you for asking. So I think it's really critical what you're doing. I think in particular, because you're trying to ease that handover and create that one stop experience for internal teams. Because like we've been saying all along, the customer doesn't care. Right. And so I think what you're doing is so critical. 

And a lot of companies or a lot of products out there haven't thought about kind of that end-to-end journey. And I think Flola is indeed thinking about that. So thank you for the work you're doing. I'm excited to dig in and learn more, but it's so important to think about not just the one tiny fraction of the top of funnel or of the onboarding, but thinking about it much more holistically.

Alper Yurder: Thank you.

Yeah, end to end, definitely. As we're coming to the end of our conversation, I'm curious, like, is there any question that I should have asked you that I haven't, Madeline?

Madelyn DePrey: Well, my favorite question when I'm interviewing somebody or when I'm talking to a leader myself is what keeps you up at night? Because I think it's interesting to learn about the aspects of where are the challenges.

Alper Yurder: Okay. I think I've handed over my sales heads to my co -founder and the team that I stopped doing that. Yeah. Also because that's a great question I used to ask. What keeps you awake at night? I don't know why I don't ask that anymore. Thanks for reminding me. What keeps you awake at night? Tell us.

Madelyn DePrey: I think it comes back to talking about the controllable and the non -controllable aspects of customer success. And so there's times, I own net retention and there's aspects when I can say, okay, what can we diagnose and hold the CSM accountable to better serving the customer and creating better predictability.

Alper Yurder: Okay.

Madelyn DePrey: But then what are the aspects that are more macro or what are the aspects that maybe we get surprised by and how do we make sure that we're getting ahead of that and we're mitigating for that? So can we find upsell revenue if we have risks that might not be in our control? That I think is something that keeps me up at night is back to the controllables and the non -controllables.

Alper Yurder: Yeah, yeah. And I think that tells something about your personality as well. But the therapy is over. We're on clock and I need to stop the clock like any good therapist. Madelyn, it's been a great conversation. Thank you very much. Do you have any closing remarks before I say my final words?

Madelyn DePrey: Okay. You're doing great work and I love all the diversity and voices you have in your podcast. So thank you, Alper. Great to be here today.

Alper Yurder: Thank you very much. And it was a great conversation. We'll keep in touch, I hope. But that's going to be a wrap on this episode of Sales Therapy. If you enjoyed the show, subscribe to us on YouTube and in your favorite podcast platform. Otherwise, I thank my dear guest, Madelyn DePrey. I hope I said that right. I can't believe I at first I thought you were in French or Dutch, then then you were from Minneapolis. And thank you for being with us on the show, Madelyn. And until the next episode. Bye, everyone.

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