Philipp Stelzer: Welcome to another edition of the RevOps Lab podcast. Our guest today is Ping Del Giudice. Ping, very warm welcome to our show.

Ping Del Giudice: Thank you so much, Philipp. Thank you so much for having me. Excited to be here.

Philipp Stelzer: Yeah. How about you introduce yourself in maybe two or three sentences for our audience?

Ping Del Giudice: Sure. I live in Brooklyn, New York. I am a mom to two wonderful children. I am passionate about efficiency in general. So for example, when I cook, I will make sure that I have something like bacon cooking while I'm cutting the onions so that I'm not wasting time just waiting around. And also, I'm using the least number of pots and pans to save time cleaning afterwards. Sorry. I guess that was way more than two to three sentences, Philipp.

Philipp Stelzer: That's fine. Yeah. Do you also clean the pots? Do you already start cleaning the pots while other stuff is still on the stove? So you also, like, maximize that time because that's what I do.

Ping Del Giudice: Well, maybe not the pots and pans because that's that one pot cooking on the stove, but the chopping board and the knife, yes. Spot on, Philipp.

Philipp Stelzer: Yeah. Okay. I think we share that then. And, I mean, it already sounds like sort of like a RevOps character you have there going on, but how did you end up in RevOps? Sort of like, what's the background story there?

Ping Del Giudice: I kind of fell into RevOps before it was called RevOps. So when I was working at a company called Macquarie, I had a wonderful manager named Courtney Forbush who was everything I really needed in a manager. She's still my mentor today. We still keep in touch. I really enjoyed working on data, on technology, processes, and then working with sales reps and vendors, and I think that's kind of RevOps in a really generalized way. And I was really good at it, so I continue along the path. I have since built RevOps from the ground up at three different startups, Mecabot, Endela, Channelys. And then I have built upon what others have created at another three subsequent scale ups at Vuex, Lipsum, and I'm at a company now called EV Connect.

Philipp Stelzer: You just dropped a few really interesting names, you know, to the audience. All great SaaS companies. But yeah. I mean, actually, curious, like, what's harder — building from scratch or building on top of what others have already built?

Ping Del Giudice: I mean, they have their own different set of challenges. Right? Building from scratch, you have a blank slate. And in the early days, as when it was in my early days, I was learning as I was going. And then the subsequent startups where I was building from scratch, I could learn from my experience, which is always helpful. And then, you know, in companies that I had joined where the team had already been established, I mean, pulling things apart and rebuilding can often be harder, but then you're not starting from scratch in the sense that there is a system network that already exists, you know, assuming people have done the connections correctly. You can just build on top of it and get running faster, more quickly.

Philipp Stelzer: Yeah. Okay. I think before we deviate too much from today's topic — the number one thing we really wanna talk about with you today is forecasting, which is a topic that's definitely near and dear to our hearts, and I think it's always worth talking about it because it's one of the hardest things to really get right as a revenue organization and master over time. So maybe to start more from a top level approach — how do you think about forecasting in general? What kind of emotions does the word forecasting stir up in you?

Ping Del Giudice: Yeah. You're right, Philipp. Forecasting is not easy. There's no technique that can guarantee a hundred percent accuracy. I mean, at least not that I've discovered yet. But having said that, forecasting, I believe, is critical to running an efficient business because it helps us plan and make decisions. And if we need to pivot, that's how we can find out. So for example, if you're seeing that your forecasting is coming in short, is there anything you can do now to make up for the gap? Right? Do you need to tweak your go to market strategy? Is it potentially advocating for more headcount? If you're not forecasting, you wouldn't know. You're just kind of running blind, and that always makes me nervous.

Philipp Stelzer: Yeah. And I guess that's also, like, you know, you then break it down. Right? Like, new business, existing business, and then it gets you an idea of how it's going with the existing customers and different territories and so on. So yeah, I totally understand that. And going back to RevOps and the connection to forecasting — where do you see the role of RevOps in the forecasting process? Is it purely technical, like just facilitating the process from a tools and process perspective, or is there more to it? Like, how do you think about that?

Ping Del Giudice: I wanna say there's more to it. I think forecasting is very much a key part of RevOps, and maybe I can start very briefly by saying how I think of RevOps. Right? I see RevOps as kind of four buckets, if you will, and I will break down the four buckets as I go through how RevOps plays a key role in the forecasting process. So starting from the data side — we wanna find out what the historical data is showing us and then use this trend to somewhat predict the future. So I think it also helps to make sure that we have the right resources in place, and we are creating, for example, realistic budgets to hit those targets. So that's from the data side. Then from the process side, I think oftentimes people could throw out terms like commit and best case and not really defining what they mean. So everyone has different definitions, which could easily create problems very quickly. Right? So on the process side, make sure that we're defining the terms that we're using so everybody's on the same page. And then tying in things like pipeline management into forecasting. Right? I think forecasting is not a standalone thing, if you will. So what's the process of tying in that pipeline management? And then what should the cadence be? How often should people be doing pipeline management with their manager, forecasting with the greater company as a whole, you know, including the CFO, CEO even at times? To the third bucket from the technology side — things like what fields are we using, what's important to capture, and what tools are we using. I think it's important to stay as tool agnostic as possible. You know, Excel could be a tool. Then if there are technologies out there, like what you guys do, it can also be utilized for sure. And then the fourth factor from the enablement side — if the forecast isn't met, how can we train the team to make sure that we're addressing the gap? And then, I guess, kind of the fifth part — I know I said four, but I'm doing the fifth thing there — all of that stuff, how does that help support and define the company's strategy? A key part of RevOps is also kind of shaping the strategy of the go to market team. And I talked a lot right there.

Philipp Stelzer: Awesome. I mean, I love it. I think it's very much how we think about forecasting. It's not a number. It's not about the final number, but it's really about the process. And it has so many components as you just outlined. Right? Like, I mean, I think we've all been there — the data quality side and the snapshotting and the field history tracking, basically the foundational elements are quite broken in many places. And then essentially that rigor around trusting what you actually submit as a forecast call is really challenging because you're actually missing the visibility into the reality of what's going on. And I think, you know, in the end, that's all connected. I mean, one thing you mentioned in our prep session is that forecasting is like training a muscle. Can you explain a bit more what you mean with that?

Ping Del Giudice: Yeah. Training muscles take discipline. It doesn't happen overnight. You said again, it's like forecasting is art and science. Getting good at forecasting also takes discipline — that's kind of how muscle building is why I say what I did, and I go on forecasting. Like, data hygiene is like making sure you eat well. I know I started with a cooking analogy at the beginning. Making sure that you do the pipeline review regularly is like making sure that you're doing the regular exercise so that you're training your muscles gradually. Right? And then when you come within five percent accuracy on your forecasting, it's like your muscles being ready and finally completing that marathon and, like, all the biking trip or getting to the top of Mount Kilimanjaro, you know, whatever you might be training for.

Philipp Stelzer: Yeah. I love that analogy. I mean, you're basically referring to what we call the revenue cadence. Right? Kind of a quarterly cadence — or most companies run it as a quarterly cadence. Can you explain a bit more how you typically have seen that set up? How you run such a cadence?

Ping Del Giudice: I would say, quarterly — if you do forecasting quarterly, it's not nearly as often as you should be. It's like if you're only training once a quarter, uh-uh. You're not gonna get there. My recommendation is, you know, broken down by a few parts. Right? The sales managers will do some one on ones with the team members, and I get it — one on ones shouldn't be all about the work. It should be focusing on the employee as well. So part of that, a smaller part of the one on one time, should be on some kind of pipeline review. And then my recommendation is also, often within your team, you as a sales manager will do a weekly forecasting call with your team. And then on top of that — I know it sounds like potentially a lot of meetings — another weekly cadence. I usually like to do it first thing Monday morning. I know time zones can make it a little tricky, but almost first thing Monday morning, depending on where you are in the world. This is where the different sales leadership teams — if you have different sales teams, all of them get together with, assuming you have a head of sales, a CRO, let's say — that's where I would also join the call as RevOps. Sometimes a CFO wants to join those calls. And then legal, as necessary, CEO sometimes wants to join. Sometimes I do find it helpful to have marketing join as well, because if we are seeing that, hey, there's a pattern that pipeline creation is an issue, it's good for the head of marketing to hear that as well and, you know, to ask questions as needed.

Philipp Stelzer: Yeah. So you basically run your cadence weekly across the hierarchy. And then do you have bigger check-ins once a month or every other month? Or is it really centered around a weekly cadence you would recommend?

Ping Del Giudice: I wanna say it probably depends on the type of business that you are. Right? If it's going after the SMBs or maybe even mid market, more often than not, the data can pull a relatively good amount of forecasting, if you will. And then if a sales rep has been forecasting for long enough, you kind of know — hey, you sandbag a lot, or hey, you are really optimistic about your deals, which we love. You kind of somehow build that into your calculations. But if a lot of your deals are more the enterprise deals or, you know, the million dollar deals, and a deal could make or break your number, I tend to want to find out about those deals a lot more frequently. I'm somewhat an impatient person, and I also like to get things right. I would look at the activities in your CRM or whatever tools you might be using to track deals and opportunities, look at the close date — if the activities, if the close date is still not in the past, if it's getting close to the close date, I would want to do follow-up with the reps or get updates more frequently.

Philipp Stelzer: I think that's such an important point because, I mean, forecasting is not just like you have these ceremonies, like weekly forecast call and so on. Right? Like, it starts basically at the beginning — you need to have a clear sales process. Then as part of that sales process, you need to collect correct data points to evaluate whether the sales process is going as it should be going. So activity data, of course, is probably one of the most important things. Like, how often does the prospect respond? Do they respond at all? How long does it take them? Are you multithreading? It's very, very common — I think one of the biggest signals to see actually whether you are close to or even have a chance at winning that deal. So yeah, I mean, it all really starts with the solid foundation of capturing the data, processing the data, and then also surfacing the data. I think you have to do that last part too. Right? Just capturing it is not enough. And then also, ideally, have some automations around that. Like, okay — if close date is overdue or no activity has been tracked since a week or two weeks or whatever makes sense for your business, send a warning to the reps, send a warning to the manager, get them back on the right path to not lose that deal. I think that's super super super critical. So it's not just the forecasting meeting — it starts way before that.

Ping Del Giudice: Yeah. That's what I'm trying to say. Totally. I feel like also with the automation — thank you so much for bringing that up. I feel like sometimes people forget automation, or they just expect reps to update things as they go. And I like to not just have the reminder emails because I feel like we potentially get too many emails this day and age, and it's too easy to ignore. I like having kind of a report or dashboard that you can just go there and click on it. Like, the reps can go there, the managers can go there, I can go there.

Philipp Stelzer: I think it's so interesting. I really like this weekly habit where you basically go through similar ceremonies across different hierarchies, and I think surfacing — one is capturing the data, but then surfacing the data in the core workflows, and really making sure that you can, from a roll up, easily drill down into the specific opportunities that are driving pipeline, and then also identifying where's risk. Right? Like, what is basically at risk and then essentially taking action. And I think that's something that is just so crucial because one thing is to have the data, but then the question is, do people actually adopt that process? Right? And so you need to get into the rhythm so that behavior is essentially a self-fulfilling prophecy, and you actually look at it with closed eyes. And I think that's where the middle management plays a huge role, right, in terms of enabling them to actually identify risk and then take action. So yeah, curious if you have any thoughts on that.

Ping Del Giudice: A hundred percent, the middle management does play a big role. I think it's key that — not just middle management — the reps themselves, I like to teach them how to fish, right, so that they don't have to come to me for everything. Right? Do they have what they need from the data side? Do they have the information that they need? And the fields that they think are important — is it truly important? The ones we think they should capture, do they know about it? And it's also important for RevOps to be very close with the head of sales. Right? Because I like to call us partners in crime. Like, you gotta be on the same page and running in the same direction.

Philipp Stelzer: Now you mentioned in the beginning that you also built RevOps from the ground up at a couple of startups. Right? So I'm curious — in your mind, when is a good time to actually start with the whole forecasting process? Is it day one in a startup? When would you actually begin? When would you say, hey, now is a good time to get it rolling?

Ping Del Giudice: I would say from day one. Easier said than done. Did I do it? Not really. I mean, if you have an idea already on starting a company before you launch the company, ideally, you already have some prospects who you're probably already speaking with. If not, you're planning to have them be your pilot customers. Right? You won't have the historical data per se, but you're setting some kind of benchmark and starting to build those muscles that we talked about earlier, day one.

Philipp Stelzer: Yeah. And is that then more like a top down approach, or would you already sort of go bottom up there?

Ping Del Giudice: Great question. I think maybe we should define what top down and bottom up means so that we're all on the same page. So to me, top down is looking at the outside factors. Right? Like the market, who the competitors are out there, potential market share — the big stuff, the macro stuff. At an early stage when you don't have the historical data of your own information, definitely top down. Right? Because bottom up is looking at the individual performance drivers and using historical data to build some kind of a model. So things like what lead source and how much are you spending to generate those leads and the conversion rates of these varied lead sources from MQL to SQL, sales process, closed won opportunities, and then the upsell and the churn on existing customers. Right? So going back to that brand new startup where you don't have that historical data — doing the top down gives you that high level sense of what is possible. And once you have the sufficient data, you should always do the bottom up. Like, I always advocate for bottom up because it is data driven. I can't make decisions without data. It helps us understand why we may have been successful or not successful. It's also important to learn from the failure. And it feels like it's also much more collaborative, as you're ideally working with marketing, sales, customer success, finance because of payment stuff, product because of features and what customers or prospects are saying about the product. HR — I think people forget about HR. Things like, you know, can we hire x number of people by this specific time frame? Like, does the TA team have the resources to do the hiring that we are saying we may need to hit these numbers? And then, something to note for sure — you are very likely making assumptions when you're building the bottom up model. So it's important to always regularly go back and check, compare your actuals to the assumptions that you're putting into your model.

Philipp Stelzer: Yeah. I love it. I mean, now we're actually kind of deviating from the bottom up forecasting to — well, there's actually an annual plan. Right? And typically, companies start in Q3 or Q4 to develop that financial model, essentially. That is essentially a top down model of planning out the budget for the next year. And I think that in the best case scenario, that is very much informed by the bottom up reality of the business. The reality also is I think that often that's not the case, and it is more driven from a board direction. Okay, this is what we need to hit to be ready for our next funding round. Right? And then there's a big gap between the financial forecast and the actual bottom up sales forecast. But what I really like what you just said is, obviously, the forecasting doesn't start with pipeline. Right? It starts with pipeline generation. So looking at what drives pipeline for the quarters to come and then going into the pipeline conversion and then also post sale — your renewals, upsell, cross sell, expansion. Right? I think that essentially is holistic revenue forecasting and is something that is still really hard to achieve, especially in the last couple of years where there were so many macro changes. And then I think another challenge is, obviously, kind of the dark funnel where it's gotten pretty clear to many people that it's very, very unclear what is actually driving success on the pipeline generation side. But that's maybe a different topic we can talk about at a different time. Do you have any other recommendations with regards to forecasting, training that muscle?

Ping Del Giudice: Yeah. Make it a habit. Make sure that the team actually — I mentioned you do the forecasting weekly. Like, as your deals are progressing or things change to your deal, make the changes immediately. Right? There's absolutely no reason to wait for that Monday morning or whenever you do your forecast call to make your updates, because you may not remember. I probably won't. And that's probably where tools also come in — what automation can we use to make sure that it's easy enough for the reps to do, so it takes like two seconds or less than thirty seconds.

Philipp Stelzer: I'm curious — to use just the last couple of minutes we have for the recording because I know we have a hard stop — I just wanna get a couple of nuggets out of you until then. So forecast categories. Do you use them? Which ones do you use?

Ping Del Giudice: Yeah. I definitely use forecast categories. I like to use commit, best case, pipeline — just what's in the pipeline. I typically don't include best case in commit. Right? Commit is commit. Right? A forecast call — commit is a number that you know you can bring in. Plus or minus, let's say, five percent. Like, how I would define a commit — at the opportunity level, you're confident that you can close the opportunity in that time period. And the only reason why something like that won't close is something totally unpredictable or unexpected happening. Right? Like, the whole COVID thing that happened, or your economic buyer suddenly falling ill. There's also a compelling reason to add to it — there's a compelling reason on the prospect side to act now. Right? And you really do understand that whole purchasing process and who the decision makers are, and they have actually confirmed the timeline for getting started. I know I threw a lot of things out there. I think it's really important to define commit well. Like, it's not just a willy nilly thing where you're like, oh yeah, I'm committing to this, I feel good about it. No. It's a commitment.

Philipp Stelzer: It's a commitment. Exactly. Yeah. And overrides — for how many days should owners of opportunities be able to override, or should they be able to at all?

Ping Del Giudice: Up to the week. You can change it during the week because life happens. Things change.

Philipp Stelzer: Okay. And last one — should commit include best case?

Ping Del Giudice: I don't think so. No.

Philipp Stelzer: Yeah. Okay. Great. So in the interest of time, our last and closing question. Just looking back at your career, what advice would you give your younger self or someone just starting in their career now in RevOps?

Ping Del Giudice: Speak up. You have good ideas and good feedback and good opinions. Make sure you speak up. Ask questions. You know, even when you're early in your career, there are a lot of things you don't know. Heck, there's still a lot of things I don't know. Ask for help. Like, you are doing it with a group of people for the most part. You're not alone. Like, you're not on an island. Make sure you ask for help. And most importantly, enjoy the journey for sure.

Philipp Stelzer: Love it. Great. Wise words. Thank you so much, Ping. It was a pleasure, and talk to you soon. Bye.

Ping Del Giudice: Thank you so much. Enjoyed it too. Thank you. Bye.