Get Reps Out of the Data Entry Business with InsightSquared CEO Todd Abbott

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This is a podcast episode titled, Get Reps Out of the Data Entry Business with InsightSquared CEO Todd Abbott. The summary for this episode is: <p>It’s rare that a guest prompts us to completely rethink how we approach the work we do and our roles in our companies.</p><p><br></p><p>That’s exactly what happened, though, with this week’s guest, Todd Abbott. Todd is the CEO of InsightSquared, the forecasting and analytics platform.</p><p><br></p><p>Todd has dramatically changed the way he thinks about sales, sales funnels, and what he calls the "science of sales". And on this episode, he shares that evolution with all of us.</p><p><br></p><p>In our conversation, Todd and I talk about what made him change his views, the power of system-captured engagement, and his mission to get reps out of the data entry business.</p><p><br></p><p>Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️&nbsp;review and share the pod with your friends! You can connect with Sean on Twitter @Seany_Biz @DriftPodcasts</p>

Sean Lane: Hi, everyone. Welcome to Operations. The show where we look under the hood of companies in hypergrowth. My name is Sean Lane. In every episode of this show, I try to walk away with a handful of specific, actionable lessons or insights that I can both point out to you, the listeners, and bring back to my own business as well. It's rare though that a guest prompts me to completely rethink how I approach the work that I do and my role in the business. That's exactly what happened though, with this week's guest Todd Abbott. Todd is the CEO of InsightSquared, the forecasting and analytics platform. Prior to joining InsightSquared in late 2019, Todd led sales teams throughout his career at companies like Mitel, Sonus Networks and Cisco. And what's amazing about Todd is this evolution that he has undergone and how he thinks about sales, sales funnels and what he calls the science of sales. And that evolution is what this episode is all about. In our conversation, Todd and I talk about what has made him change his views, the power of system captured engagements and his mission to get reps out of the data entry business. So let's jump right in. What is it exactly that Todd has seen change in the way we look at sales funnels?

Todd Abbott: I think it's what's changed in the way I do it and I think where the market's going, it's going to fundamentally change, right? We've grown up in a world where every sales leader or revenue leader looks at, and goes into a month or quarter, whatever the forecast period is. And you know how many reps you have, you know what to expect from each rep, you know what the typical conversion rates have been. And do I have in a funnel based upon those three data points, there's many other data points that some people have in period out of period, but those are the fundamentals. And we spend the first few weeks doing a lot of interrogation of reps to be able to validate what's real in that funnel and what's not. It's probably the least stimulating aspect of the engagement for both the rep and the manager, but it goes on in every company. And the reality is the big challenge is, you may have enough covers going into this quarter, but how do you assess the quality of that funnel? That's what the interrogation is for. And it's crazy, right? Because that time should be being spent on coaching and helping the rep execute instead, it's an interrogation. And so what's fundamentally changing is that let's get the rep out of the data entry business and let's get the rep out of needing to be interrogated by leveraging data to be able to assess the health of a deal. And health comes from how does a customer, how are they engaging with your team? If your value prop is resonating, they will engage. They will respond to emails. They will schedule the next meeting. They will look at your attachment, but let's stop relying on a rep telling us what it is in the system or verbally, let's get data. Because the digital footprint of the sales process is the data that we've never had, because we've relied on what the rep puts into CRM and reps will give you the least amount possible. There's not a good ROI for that. They want us to be spending time out selling, they don't want to be updating systems. And so the aha moment for me and where technology's going is we can get the rep out of that business, capture all of that digital engagement, even to the point where we're going to how's the customer engaging with the content? So rather than sending them a PowerPoint, send them documents with the capability, with metadata per page. What are they looking at? How much time are they spending? Are they forwarding it? Because a value prop that's resonating is going to get a lot of engagement. And what are they doing on the web? Which is an indication of, did they stop searching competitors or do they start to search competitors based upon how you're progressing? So the digital footprint of how a customer is engaging through the sales process is what's fundamentally changed in this game. And if you can get that data into your system, we can show you what the health of a deal is just by engagement, without having the question or prompt or interrogate the rep at all. That's what's fundamentally changing on a deal by deal basis. And if you have it on a deal by deal basis, then you can combine all that data and tell you, this is the health of this funnel to give you a predictive forecast. What's going to change is two things. You're not going to care about sales stage, when you look at a funnel. You're not going to need to interrogate or inspect, and you're not going to be thinking about funnel coverage anymore, because the system going to tell you what this funnel is going to deliver. It's going to tell you what the quality of that funnel is. Because by golly, if you tell reps you want three times funnel, they're going to give you three times funnel because you've got for the pressures, right? Who cares what the funnel coverage is, I want to know what the funnel is going to deliver. That's the fundamental difference.

Sean Lane: This is this stuff that I was talking about at the top of the show. Todd is basically saying, throw out the way you assess the quality of your pipeline today because this new way is better. And to be honest with you, I buy it. If we stop asking reps for updates on the subjective aspects of their deals and focus on these system captured data points available to us, what could we then unlock in terms of our understanding? My mind was racing thinking about all the different ways to apply his approach, but I wanted to make sure that it's not just helpful for ops folks like me. With Todd's approach, when we throw away things like stage progression or get rid of the" interrogation" that he calls it, what did the new outputs and lenses look like for reps and their managers?

Todd Abbott: It's a now a much more enriching, engaging discussion that's helping a rep execute. Because all the noise is out of the system, right? The stuff that shouldn't be in there, that the rep is trying to rationalize or hope that the customer is going to come back, it's all out. And so now you're spending time on real data that's that's fact- based and all the BS has gone, right? You can't hide deals and upside, you can't hide deals in funnel to give me coverage that are just, they're dead as a doornail, you haven't heard from the customer in a month. All of that becomes exposed and it takes about two forecast cycles for a rep to realize I can't be us. So what fundamentally happens then is it's a much more engaging discussion. So your best reps will say, wow, this is really good because I'm actually getting insights now about benchmarking every one of my deals relative to this activity profile. So I'm actually managing my territory and engagements much more effectively. The system is helping them, prompting them. Hey, you haven't heard from the customer in two weeks. Yeah, you're right, let me go engage. And your lesser performing reps can't hide. They don't want to hide, they want the coaching. They're going to get it earlier. And so you're going to help them get the coaching they need. And so what happens is when you get into these reviews is after the two cycles, the noise is out and now we're focused on the deals that need some help. That's where I, as a first line manager should be coaching. I can validate a high confidence deal in 10 seconds. I don't need the five or 10 minutes to interrogate, do I trust the rep? It's done. Now you can focus on those ones that are maybe 50, 60, 70, 80% confidence, where my insights can help the rep on strategy or tactics or actually getting engaged. Like, I'm going to help you on this deal. And so you remove the noise and now it's a much more engaging coaching discussion, which is what funnel reviews were intended to be in the first place.

Sean Lane: So I'm interested in the how of this, right? Because you mentioned a couple of good examples. So you talked about the content that they're looking at within that digital footprint. You talked about some of the back and forth in terms of activity. Are there other things that we should be thinking about as ops people when we're trying to instrument this system captured version of doing things that's not from rep inputs?

Todd Abbott: So listen, I think the first phase of this is just to get the digital engagement, emails, meetings, file shares. I would tell you that is, in our experience, the best indicator of the health of a deal and feeding a forecasting system. The content and intent I think, is going to become much more applicable to driving cross- functional engagement as to what content works where. And when a customer goes quiet on you, what content actually is effective to get the customer back. And so being able to bring in that additional content, I think is going to be much more strategic. There will be some tactical implementations or value. If you think about I'm at a critical stage, coming out of meeting five customers stopped responding, but if I know that they're engaging in my content and they're passing it on and I can see what the profile is of what they're searching on the web, I can actually be a little bit more patient. Because I know it's germinated. They might not be responding to me right now, but they're talking about me. It's almost like you're on the inside. And so the more experienced rep can be a little bit more patient and figure out when is it time to re- engage to get that customer back? But they're working. Now, conversely, if they're not responding to you and they're not looking at your content, and they're starting to search competition, like you're about to lose that deal, what's the play, right? But at a minimum right now, you've got to be able to get all of that digital engagement and do it without burning your rep. And it's not just the rep, right? You got to get the SEs. How are the SES engaging? If you got an overlay, right? So you need to have all of the engagement to be able to understand what engagement type actually contributes to you winning more effectively. And so there's so much data that now is going to come in. We typically see about it increase about 10 times the amount of data on an opportunity when you do automatic activity capture. Right? So if you're thinking about as a revenue ops or sales ops leader, doing exports of CRM data into a spreadsheet to try to find the insights, forget it. There's too much data. There's no way. You can't connect the dots. So you've got to have'A' number one, get the data in. And then number two is, you're going to need to have a machine learning, architecture or infrastructure that's going to be able to give you the insights, connect the dots. That's the stage we're in. This is the ultimate science of sales stage now because we have the data.

Sean Lane: The ultimate science of sales stage. What Todd is getting at here is that we've entered a new era in how we approach sales process, sales predictability, and sales management. My main takeaway there is that when you cut out all of the unnecessary noise out of the system, the key question that you have left to answer is, what engagement types contribute to you winning more effectively? And to Todd's point, yes, it'd be helpful to have a tool like InsightSquared help you to identify those engagement types more easily for you. But to start, I challenge you to do something even more simple. Answer the question, how many calls or meetings does it take for you to win a deal? Then take Todd's advice. And instead of mapping your deals by stage, map them by which call number your deal is at. This alone will shine a light on what's real and what's not in your pipeline. More on that in a little bit. All right, so these have been some pretty sales specific tactical outcomes of this new system captured approach, right? Todd's description also made me think that there might be some more cross- functional impacts and learnings that you can take advantage of with his approach as well. Learnings that could impact not just sales, but your entire go to market organization. Todd said that he's seen that exact thing firsthand.

Todd Abbott: As an ex hero myself for many years, the thing I always struggled with is, we come into these management or executive business reviews monthly, quarterly, every function comes with their data and their interpretation of the data, right? And the biggest friction points tend to be between marketing and sales. Right? I've got all these website hits, all these downloads, all these leads I've created, and sales is sitting there going, yeah, but you know, they're not converting. And X percent of them are crap and sales says, yeah, but yeah, your guys aren't responding to them quickly and you've got to respond on leads. You're not meeting your SLM. I mean, this friction goes on in every company to some degree or another. And so what you're really looking for is get out of the siloed, bring your own data and your own interpretation and get one data set to say like, here's the sales process. Here's where the content works or doesn't work, right? Another good example is I've had this happen to me many times in my career. Product says I've got the best product, you should never be losing. Why are you losing? Well, if this competitor gets engaged and I can show that my win rate drops by 20% with this competitor, I can go, Hey mate, Hey, product manager, stop telling me how great your product is and help me compete against this competitor, because when they're engaged by this stage, my win rate actually drops. Here's the data. So as a vehicle to bring cross- functional teams together to one view, grounded in facts and data, it really drives the cross- functional execution. And I've seen this, this is a real struggle for CEOs, right? Because CEOs are sitting here with all these functions, giving their views and it's not aligned. And they know in their heart of hearts that they're sub- optimized, cross- functionally, because we've never had the data. Everybody's got their own tech stack with their own analytics and their own interpretation of the analytics. And so this whole revenue analytics breaks down those silos and brings everybody to the table. I used to always think sales has more dependencies cross- functionally than any other function, but I've always liked the data to bring everybody to the table and say, no, call BS. Stop telling me your products are great, you should never be losing. I lose here. I'm not winning in these industries or that content is not really helping me. So help me, help us execute as a sales team, by understanding the friction points in your sales process to drive alignment to remove those friction points. So it's pretty cool stuff.

Sean Lane: Yeah, it is. And I want to come back to the CEO thing in a minute, because you have a really unique perspective there. But I'm thinking in real time about this competitive example. Right? And so if I were to take this competitive example and think about the way things typically work inside of a sales organization versus the way you're prescribing, right? Typically we would say, all right, Mr. And Mrs. Rep tell us which competitor is in your deal, you've got to fill in the field, pick it from the dropdown, tell us where they're at. And if I think about the new version, I'm going to be looking at a call recording for key words of competitors that are coming up and not just who's coming up. But forget about the sales stage, they come up on call number four and that's where we usually find out the competitor. And then that's where we get the winner loss movement on the size of our deal. Am I piecing those dots together the right way?

Todd Abbott: 100%. 100%. So whether it's in a call recording transcription, whether it's in an email exchange, this is why you got to have the activity capture from the whole team, because everybody's going to be engaging with different people in the sales process. And so where is the competition? By whom from a decision process standpoint and where in the process and what happens when that's identified, right? Without that pull down menu, right? Because the pull down menu from reps and everybody like 20 competitors in there, it's like make it easy. Get them out of the data entry business. So now if I know when they're engaging or when they're coming up and how often they're coming up, trip that indicator. Okay, now let's watch what happens with that competitor and be able to see win rate before and after. Now you've got the data.

Sean Lane: Take that competitor playbook, write it down, listen to it again, whatever you need to do and then go and copy it for your company. You will be bringing so much value to your entire organization, not just sales. I do have one hesitation though, around Todd's approach. And this is something that I've experienced firsthand in my career. When it comes to AI models or machine learning, sales and marketing leaders are a bit skeptical when a model just spits out a forecast number or says, this is a good lead, this is a bad lead. This is a good deal. This deal is going nowhere. Anything that resembles a black box can be off- putting. So I was curious how Todd has handled that both internally at InsightSquared and how he helps his customers to bridge that same gap. It turns out he was a converted cynic himself.

Todd Abbott: It takes about two quarters. And I was no different. When I joined and saw this, the vast majority of my customers, I said, yes, that's not true. And the hard part is that a benchmark in confidence to close score, it's not black and white. It's directional. You have to be able to interpret it. In order to interpret it, you have to know what are the variables that actually impact the win rate in my business. I'll give you a couple of examples. And in some of my customers, numbers of pushes is a very strong indicator. I had a customer the day after three pushes in the last 15 months, they never won. Zero win rate. I have other customers that push rate has zero bearing. They're very undisciplined and it's the same win rate if I push it two times or nine times. And I don't think that's necessarily good-

Sean Lane: But they know that.

Todd Abbott: ...but now I can show them, yeah, you have an undisciplined model, now I can't give you any indicators that you should be looking at deals that push five times versus the first guy. You want to be able to identify every deal that went to the third push because this is the last time, because you don't win after this. And so that's where you start to now give you the rep that heads up too. Hey mate, third push, like last time, we don't win after three. And so now everybody gets focused. So the variables that contribute to win, think of them as their characteristics, that when they're present, they add to the confidence to close probability to win. And some of those characteristics have bigger impacts than others. Like that three times push has a bigger impact than the other. So numbers of pushes, it would do nothing to confidence to close in that second example. So, we can tell you, when do you really win? In my business, when I get to eight meetings, my win rate is 70%. And so I know I want to get to eight meetings because anybody would take a 70% win rate. I know I don't win before four meetings. And I know the fourth meeting is like really important because that sets the trajectory to get to eight. If I don't get past four, I don't get there. And so it's forced me to really think so differently about sales stages because the problem with sales stages in forecasting is you're depending upon the rep putting it into the proper stage, which they don't do. There's nothing in it for them. I spent a career hitting them over the head, come on crosstalk Yeah, okay, sure. I'll go fix it. So I don't think about sales stage, now I think about meetings.

Sean Lane: That's super interesting.

Todd Abbott: I know where my key inflection points are. I know when I win, so I can immediately translate, oh, you're in the second meeting, I know where you are. You're in qual discovery. Got it. Oh, you're in meeting six? Oh, okay. We are clearly in eval and we're getting close to the decision. And so I can typically, I translate it in my head because I now know tha.t I didn't know that before this tool, but now I do.

Sean Lane: That's so interesting. And like being able to kind of gauge your customer journey on that call spectrum is so interesting. I love that you are candid about the fact like, Hey, look, this took me two quarters to really buy into and feel good about and you're the CEO, so people are going to buy in around you after you do. For folks like me who are in these operating roles and maybe presenting to CEOs or presenting to CROs who either have not gone through the progression that you have or have and we're trying to simplify and cut out all that other noise that you're talking about, what are your recommendations? What are your advice for people like us who have to package all of this noise together and try and put forth kind of a simplified insight or version of this for their company?

Todd Abbott: Well, listen for the exec levels, for board levels, I call them the big animal pictures, right? We're all very visually wired. You have to be able to tell the story. And so you, we fortunately have had a history from the very beginning. That's the business we've been in is dashboards. And so dashboards are really helpful. And so you have to be able to translate this analytics into the big animal pictures that people don't want to get into the interworkings can translate to how's the business going and where do we need to focus? And so we spend a lot of time helping them to understand what's the analytics. What really is what I call their advanced sales map? Meeting four or meeting eight. How many contexts... I've just had another customer where their key win rate is when they have four contacts. When they have one or two, like their win rate was horrible. Well, if you know these things, you start to look at the funnels differently and you start to drive strategies and field enablement, and then marketing support. Right? To go back to your question, you have to be able to translate all this into the big animal pictures. And I have some CEOs that are very data analytic oriented, and you have to give them the ability to drill down, right? So a dashboard, that's a picture with no ability to drill down is very ineffective. And there's a whole industry out there on these dashboards that are static reports that you can't drill down. They're not execution- oriented dashboards. And so we can give you big animal picture for a customer that doesn't want to drill down, but for that CEO that does, where he or she is frustrated with the different analytics from between functions and they want to be able to drill down and have the cross- functional dialogue, we help them set up, how do you look at your business? We'll help them understand what your process actually is. What do you want to focus on? And then we put those dashboards in place to say, what do you want to look at weekly? What do you want to look at monthly? What do you want to look at quarterly? Because some things change weekly. Some things are much better looked at monthly. The dashboards become the agenda for how they want to run their meetings. These are the important things we're going to look at. Why, because we now understand the sales process. We understand what the interdependencies are. And so let's set up the dashboards for your weekly, monthly board reviews, with the ability to drill down. So it will vary depending upon the characteristics of that senior team and that CEO. Some guys love it, some guys just want the high level picture.

Sean Lane: I would also imagine too, that once you pick, let's say one of those key win rates and you put it on that dashboard, you run your senior leadership meetings off of that, that helps reduce a little bit what you were talking about before, where everybody brings their own version of the truth to the meeting, right? Because you can say, look, everyone's job is to get at least four contacts on every opportunity. Marketing, get these people engaged in the customer journey. Sales, get them engaged in the meetings that you're having. Right? Everyone now can galvanize around that metric.

Todd Abbott: Yep. I'll give you the best example, right? That the big friction point marketing, right? Volume, quantity versus quality. And are your BDRs, STRs engaging, right? So I start my staff meeting every Monday, first dashboard is top of funnel. How many MQLs did we create last week? Where are we month to date, quarter to date. And I've got a dashboard. I can see visually that the STRs BDRs engaged within the week. And it's within the day, right? The RSLA you got to hop on it. So there's no longer any debate relative to meeting SLAs because it's right there and we look at it together as a team. How many did you bring in? What's the conversion rates? Are the conversion rates holding or not? Quality versus quantity. And we were able to look at which deals came in, which deals closed. From a lead standpoint, which ones are progressing, which ones converted to an SQL. And now moves into, okay, now it's in the funnel. So it drives an agenda, right? And the marketing person's not presenting their slides and sales is presenting, no it's one set.

Sean Lane: Before we go at the end of each show, we're going to ask each guest the same lightning round of questions. Ready? Here we go. Best book you've read in the last six months?

Todd Abbott: Oh wow, the best book I've read actually is nothing to do with business. It's Factfulness. I think I got the heading right. It's really about social economics and classes of poverty and how actually the advancement of the world as a society, actually has progressed so much more than what the cable news networks will make you feel, right? It's a great perspective of just the world and how far we've come on healthcare and death rates and poverty. It really opened my eyes to thinking about the world in a way that I found to be really enlightening and inspiring.

Sean Lane: That's all amazing. I'll have to check that out. All right. Next one, I usually ask ops people what their favorite part about working in ops is? I'll ask you, what's your favorite part about working with ops, whether it's internally or with your customers?

Todd Abbott: Well, I get to ask the question two ways, right? Because I get a really interesting data point of there's really two different types of ops people. And I try to help the latter category here a lot. There are some ops that are absolutely at the table and they're business partners to the CRL. They're helping to interpret the data. They're helping to improve the business process. I can typically tell them in about three minutes. They're a treat. The ones that are just reactionary. They're trying to figure out the next report. They're actually a struggle for me because they want to create a dashboard with 20 carts, 20 graphs. The CRO doesn't want 20. They want five, but they're trying to anticipate every question. My challenge to them is help them to grow and develop, to get a seat at the table, to be more of an analytical interpreter of the data versus just reporting it. And I try really hard to engage them. So I love that aspect of it in helping younger people grow and develop and really be a true ops leader. And then the other category, boy, it's just a lot of fun, right? Because they love this new capability to even add more value. So I put them in those two categories and they're both intellectually challenged, but from different ways.

Sean Lane: Yeah. So you might've already answered this then with that answer but least favorite part about working with ops?

Todd Abbott: The least favorite part is the second category. They don't want me to get in front of the CEO, CRO, because they want to be, it's the information is power, right? Don't add another project to minority stressful day. And so that's probably the hardest. It's an intellectually challenging aspect to my job, right? I mean, it's one that I cherish, I enjoy because I think people in general wants to get better, want to grow, want to develop. And I just have to connect with them to help them understand, I can help you grow. I can help you bring a whole different value problem. I'm not creating another project that you don't have time to do.

Sean Lane: Yeah. I wouldn't have thought of that, but I would imagine that that is a challenge for anybody in a customer facing role at InsightSquared companies like InsightSquared for sure.

Todd Abbott: Yeah. Yeah. But I view it as a challenge that's fun though.

Sean Lane: The next one, someone who impacted you getting to the job you have today.

Todd Abbott: Oh, there's so many people. I would say that I've had a bunch of really good mentors in my day. And my time at Cisco developed quite a few mentors. And the guy that hired me at Cisco, Carlos Dominguez, who was just a really good down to earth, genuine guy, but a great business guy and a great coach. And I could go to him with any issues, any challenges over the years, he was more of a mentor to me than he probably realizes. Very wise beyond his years and very balanced and just always gave it to you straight.

Sean Lane: Love it. All right. Last one for you, one piece of advice for people who want to have your job someday.

Todd Abbott: Yeah. I think the biggest advice I'd give you is that, when you move into a new role, new job, don't feel like you have to answer all the questions. Learn the job. Don't speak to speak. You're faking it till you make it a little bit. I had an experience when I got my first head of sales, the founder came to me about six months later. He said," Listen, man, I was really concerned about you for the first 60 days, because you didn't say anything." I had gotten this advice." You didn't say anything for like the first 60 days." I'm like," Well, I didn't know your business. I was really asking all the questions." And so my advice to everybody is ask all the stupid questions in the first 60 days. We were all products of our background, our experience, you're not expected to know. As long as you're not asking the same question, three or four times, people will ask we'll answer those questions and help you. Don't feel like you have to have the answers, ask all the dumb questions, and then when you start to connect the dots, that's when it's time to speak and time to contribute.

Sean Lane: Thanks so much to Todd Abbott for joining us on this week's episode of Operations. If you liked what you heard, make sure you are subscribed to our show. A new episode comes out every other Friday. Also this marks our 60th episodes. So if you're new to our show, go back and check out some of our earlier episodes. And if you really liked what you heard, make sure you leave us a six star review on Apple podcasts or wherever you get your podcasts, six star reviews only. All right, that's going to do it for me. Thanks so much for listening. We'll see you next time.


It’s rare that a guest prompts us to completely rethink how we approach the work we do and our roles in our companies.

That’s exactly what happened, though, with this week’s guest, Todd Abbott. Todd is the CEO of InsightSquared, the forecasting and analytics platform.

Todd has dramatically changed the way he thinks about sales, sales funnels, and what he calls the "science of sales". And on this episode, he shares that evolution with all of us.

In our conversation, Todd and I talk about what made him change his views, the power of system-captured engagement, and his mission to get reps out of the data entry business.

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️ review and share the pod with your friends! You can connect with Sean on Twitter @Seany_Biz @DriftPodcasts