The Pipeline You're Overlooking: Revenue Hiding in Your CRM

Full transcript

Angus Robertson 00:00
Welcome to Outcome Marketing Live. I'm Angus Robertson, fractional CMO at Outcome Marketing. When a company needs more pipeline, the usual answer is more leads, more spend, another channel. My guest makes a different argument: the fastest revenue is usually already in your CRM — opportunities you've already paid for. Nate Rupple is the founder and CEO of Upside Sales. They build and run outbound engines for B2B companies. Nate, welcome. Let's get right into it. When a company tells you "we need more pipeline," why is the answer often not more leads?

Nate Rupple 00:43
Well, I think that's probably the natural reaction for anybody — I need more pipeline today. So we assume that we just got to stuff the top of the funnel with more leads, which means spend more on ads, buy another list, call more people. And those things are great. But sometimes, stop and pivot and look inward before we just start spending, because we already have some acquisition costs. We have a CRM. We have a bunch of opportunities, and not every one of those opportunities has said no. So our philosophy is really: keep creating new opportunities, don't stop there. But before you start spending more to create more, make sure you're really developing the opportunities that already exist within your CRM. So before asking "should we put more into the funnel?" — ask what we can recover from what's already in the funnel.

Angus Robertson 01:38
It sounds very logical when you paint it out that way, Nate. It's funny — when we're all under pressure and we have to get those new business, those new leads, we don't always think as logically as perhaps we could. So what's hiding in the CRM? I remember in our prep session, you talked about this boomerang buyer. What is a boomerang buyer, and what else is hiding in the CRM that we can look to leverage or take advantage of?

Nate Rupple 02:12
Yeah, well, the boomerang buyers are frustrating because they're the people you can't really control, and they take away predictability in your pipeline. They essentially come in with real intent. Maybe they have a demo, maybe they've got pricing that showed interest. They're moving down the sales pipeline. You think, oh, hey, I got a close here. This is good, generating more revenue. And then they disappear. Time goes by. They kind of ninja vanish and then come back later. Maybe timing's changed, maybe budgets opened up, but they come back and then they purchase from you. But there's this big gap, and it's opportunities like that — lying dormant and often stalled in your pipeline — that are just these hidden gems. They're basically just overlooked and can create new sales volume very quickly. Things like stalled opportunities, people saying "not interested right now," timing's bad, maybe it's just not a fit at the moment, maybe they have a competitor they're still looking at — but they kind of fall off the face of the earth and don't close.

Nate Rupple 03:29
We saw this really clearly with one of our software clients. They had a really good sales process where people were coming in, they were getting the demos, they were getting pricing, they were getting proposals sent out — and then they'd disappear. Mainly their clients were within the automotive space. Think of dealerships: they're busy, they've got a lot of things going on, a lot of activity, a lot of pressure. So as they were going through the process, they would take that proposal, go back to the dealership, socialize it within the group, priorities shift, new fire drills happen, and they just never come back. So sales would naturally move on to the new and next. But what happened is we saw this pattern emerge where these dealerships would come back 90 to 120 days later and just kind of show up on your doorstep and say, "ready."

Nate Rupple 04:26
So we thought to ourselves: what happens if we stop waiting for them to come back? What if we took an outbound engine we built for our client and we pointed it at them and said, let's try to re-engage, let's readjust timing, and let's see if we can reactivate them. And what immediately happened was we saw a 34% lift in reactivated opportunities and a 21% lift in closed deals. So the idea of "not now" and "not interested" are really two different things. And if you treat them as such, and you try to bring them back into the sales process, you have a lot of overlooked gems that can lead to revenue very quickly.

Angus Robertson 05:10
Well, 34% and 21% — with opportunities or deals or contacts or accounts that are already in your CRM, in terms of more pipeline and more won deals — you can't really argue with those numbers. So that's a great proof point. It's probably frustrating, though, when you look back in the mirror and go, oh, that was sitting there.

Nate Rupple 05:36
The fun part is when you reactivate it, you realize that those opportunities do exist. It's just: how do you get to them? How do you find them?

Angus Robertson 05:47
And it does require a level of discipline and analysis. I'm just going to speak in broad terms here, but for a B2B SMB, if you're doing great, perhaps your new logo win rate is 20, 25%. And maybe you're losing another 20, 25% to competition. But I would argue more than half of the deals go away because there are things happening outside of our control. We're so in our own bubble, doing our own activities, we can't anticipate all the things that that customer or that prospect or that dealer is thinking about. They obviously have other things going on in their life besides our solution and our company. So it seems what you've done is mined into that to figure out how that works.

Nate Rupple 06:42
Yeah. Well, you know, the idea is "I need more today." And so before you start digging up all the earth, let's figure out what's sitting on top of it. And when you look back, you realize, okay, we have a lot of opportunities here, but not all of them should be treated the same. And as you start cultivating that — the speed of the close — these people know you. They've been there.

Angus Robertson 07:07
Right. You've already done the hard work. That's great. So how do you tell the difference between an opportunity worth reactivating and one that's truly dead and you don't want to focus on anymore?

Nate Rupple 07:25
Well, this is really where the CRM discipline becomes really important. Closed-lost isn't always just closed-lost, and they shouldn't all be treated the same. There could be a variety of different reasons. It could be — we talked about before — timing, it could be budget, it could be no decision. Now, looking at your CRM and being able to identify and segment off of those opportunities is really where the gold's at. Even taking a moment at that closed-lost moment and being able to say, is this closed-lost because of this reason or this intent, will help you later to find what's real and what's really actually dead. One thing we like to tell our clients: closed-lost isn't really the end of the opportunity. It's really a data-collection moment. So if you view it as such and say, okay, what can we mine from this closed-lost opportunity? What could this tell us potentially later? That's where you can start to figure out the difference between something worth reactivation and something that maybe never was a qualified opportunity to begin with. And that then is the catalyst to where you can start to segment and message and really engage those people to bring them back on track and accelerate the timeline — to close more business faster without having to dump a lot more money into all the different channels you're doing currently.

Angus Robertson 08:57
Got it. And what are the typical closed-lost scenarios that you find? I mean, there's obviously competition, there's price.

Nate Rupple 09:07
I think those are two that come up a lot. I think behind the scenes, there's also priority. If that prospect or that customer doesn't feel like this is the biggest priority right now, or can't convince the team internally that this is a big priority — that it's a burning platform that has to be solved right now, that there's urgency associated with it — these prospects aren't really necessarily wanting to deliver the bad news.

Angus Robertson 09:36
So there's also ghosting. I feel like the majority of the time it's ghosting. So if someone's not engaging with the salesperson anymore, what do you do? Do you let it rest for a while? Do you have any tactics or strategies for how you get that re-engagement to happen?

Nate Rupple 10:03
Yeah. Outbound is not just a way to generate leads — even though net new leads is a great use of outbound. Think of it more as a revenue engine that you can leverage in different ways. A salesperson has spent a lot of time with a specific prospect. Like you said, they've now been ghosted, and maybe they try to call, but they just haven't been able to get any traction. One way we work with our clients is we take our outbound engine and point it at that specific segment or that specific group. It's a great way to release the salesperson to go back into the wild, hunt the new and next, while re-engaging the prospect who ghosted and went away. I think the concept of relationship before revenue is really important. The salespeople own that relationship at first, trying to bring that person back. When they truly get to a place where they're ghosted — okay, I think this person's gone away — that's where outbound can kick in, take the baton, and start following up for them, with marketing nurture on top of that. Layering those things together is a great way to stay in front of them, pursue a new timeline, and bring them back.

Angus Robertson 11:23
I think you said two things that are very important there. One is a revenue engine. You can't think of your revenue engine as just "I make a phone call, I get a deal." It's going to be a lot of contacts over time and a lot of channels. And then the other point you made about relationship — how do you establish that relationship? Is it some kind of referral introduction, or is there some way you can provide value to help them out? So all those pieces come into it, right?

Nate Rupple 12:06
Absolutely.

Angus Robertson 12:08
So we've got these opportunities, we've got these lost deals and other contacts and accounts in the database. So what do we do? Do we just send an email blast to everybody? Is that how it works? Do we send everybody the same campaign?

Nate Rupple 12:23
Technically speaking, you can. I just highly—

Angus Robertson 12:26
No one ever does that, though, right?

Nate Rupple 12:28
I would highly not recommend it. It's mainly because the people in your CRM don't all have the same relationship with you. There are going to be people in there who had a demo, had pricing, had conversations with sales — and they're not the same as somebody who came in through inbound, maybe had a quick phone call with sales, priorities changed, and then they haven't talked again. Those are two different segments of people, and they should be treated differently, and the message you create for them should be unique to their intent. We use a six-step framework: identify, segment, message, engage, prioritize, and pursue. So you're looking at your CRM, this ecosystem, and saying, all right, let's identify where opportunities may still live, may still be active. Then let's segment them into different groups, and then we'll build out messaging specific to each one of those. Then we can engage those people — for us, that's leveraging outbound, that revenue engine of pointing outreach toward those people. But then, as you engage them, where the fun starts to happen is you can start prioritizing the people who are engaging at the highest levels — the people who maybe visited the pricing pages a couple of times, they've gone to multiple things, they've clicked multiple times. You can use all these different lead-scoring points and then push that off to sales pursuance. Hey, give this guy a call — because now you're creating that reactivation. With people who are not unknown — they have a sense of who you are, what the product is, what you do — those sales cycles move very quickly. So even to the premise of our conversation: you really can unlock this overlooked revenue that's just sitting dormant. The framework helps the segmentation build the relevance, and then your outbound creates the consistency, so you build this momentum that generates faster without having to actually have more leads.

Angus Robertson 14:41
Yeah, another two good points there. The sales velocity — because you already have some intent and some relationship — can obviously be a lot faster than some cold prospect that's just getting to know you. And I like what you said about intent: you're going behind the lead, behind the engagement, to understand all the different things that that person or that company has been doing. You have to make sure that you have the ability to capture that data and that you have that data organized. How much of your engagement is just making sure that those touch points are being captured and the data is organized so you can do that analysis and segmentation?

Nate Rupple 15:36
Well, it's a little bit like the conversations we have where someone says, you know, I've never done any outbound, I don't know if we have the infrastructure for it or the resources. And that's really where our team can jump in. The thing I would always say is: just one foot in front of the other. Just start. If you're not organized and you haven't done anything yet, begin by picking one segmentation — one group that you feel is a "not now," not a completely closed-lost. Pick that one group and start looking for those patterns within your CRM. It'll help you expedite the process of identifying who that is. And then it's all about: how do we accelerate, add that velocity, and ensure the people who are pursuing can come back and get reactivated faster?

Angus Robertson 16:24
Got it. Well, a lot of people watching may say, we've got nurture going on already with our marketing department. Marketing has this covered. So where does marketing nurture fit in versus what you're talking about with outbound reactivation?

Nate Rupple 16:56
I feel like this is the push-pull that we get in these conversations all the time with our clients. Even when we start the conversation about looking inward at their CRM, that's one of the first things they say: oh, we've got that handled. And my first answer would always be: absolutely keep doing the nurture. That's wonderful. This isn't actually a conversation about sales versus marketing — and it very quickly turns into that, where they're like, well, we have marketing for this. It's actually way more powerful, and it really gets exciting, when the combination of the two come together. Because as these leads go through the sales cycle, they get to a point and become stalled, they become dormant, and they just sit. Marketing is staying present. It's staying top of mind. It's educating people. It's letting them know they're there, so when they're ready, they'll come back. And that's incredibly powerful. When you leverage outbound and outreach on top of that, now what you're doing is testing time. Nurture is keeping that relationship alive, but outbound is testing whether the timing has changed for that prospect. As you're staying in their orbit with nurture and marketing playing up top, outreach gives you a much more deliberate way of re-entering the conversation and finding out if we should talk now and if there's an opportunity to pursue. So having both going at the same time — that duality is actually much more powerful than having one on its own.

Angus Robertson 18:40
And they do complement each other, and I think the combination does help the outcome you want. Got it. One other area I find is really important is working with your existing customers who are getting value from you and are happy with the service or the product — because obviously they can be an amazing source of references or advocacy, case studies, online reviews, but also referrals: introducing you to their network, to other companies like them who are dealing with the same problems and need help as well. I find that a lot of companies — perhaps even most companies — don't really have good formalized programs for managing references and referrals. Sometimes it's in sales, sometimes it's in marketing, sometimes it's in customer success or support, and everybody seems to have a bit of responsibility, but it's not very organized. What's your experience here, and is that something worth focusing on?

Nate Rupple 19:50
Well, I think the answer, of course, is yes. Leveraging your existing client base to generate referrals, and putting together a structured way of — one, what triggers that event? We have a new client: do we wait until a certain point in our onboarding? When does that event happen where their happiness with what we deliver equals a willingness to refer you to other people? But it's also looking at existing accounts and saying, do we have a structured way of seeing what other programs or divisions or other places we can expand our current business with them? Sometimes it's upselling or cross-selling opportunities. What outreach really does — even in the pursuit part of our six-step framework — is this: everyone's time is already 100% accounted for. They're busy from the time they get there to the time they go, and they need to be followed up with. In fact, something that hit me really hard is when I heard somebody say: they're actually counting on you to follow up with them. When you don't, you're actually disappointing them — because they need what you have that could make their life better. They can maybe get out of work to see little Timmy's T-ball game, go to Sally's soccer game, whatever that may be. As soon as we get to that closed-lost point, if we jump right back to the front of the line — which we still need to do to generate new leads — but if we just let that piece go, a lot of times the "not right now" is simply because their time is already occupied. They have a million other things going on, and they do need that follow-up. Whether it's following up for referrals, following up to introduce new divisions and programs to expand client relationships, or just following up on net new leads — having a structured process to do all that helps you scale those efforts, add momentum, and cultivate more wins for your business faster, especially with those you've already paid for. Those costs are sunk, just sitting in your CRM. Creating a process — a framework to identify, segment, and then go after and pursue — can create a lot of new wins without necessarily having to increase expense.

Angus Robertson 22:23
Got it. Playing devil's advocate here: does this mining of the existing CRM mean companies can ease off net-new pipeline?

Nate Rupple 22:37
Oh, no. Absolutely not. You absolutely need a motion of building and having new opportunities enter your business at all times. We've had this conversation with some of our clients who said, hey, if we can move faster on what we have — we have a robust database, a lot of contacts in there — if we just pursue those, and you've segmented these people and identified new opportunities, we think we can generate new business from these faster because they're known. If we just did that, your CRM at some point will be exhausted. And once you exhaust that, if you don't have anything else coming in, that creates a monster revenue momentum problem for you down the road. Now, if you don't have any leads coming in at all through new channels, that's a very different conversation — something worth diagnosing: who's your ICP, what channels would be the best fit. But you absolutely should have a focus on different channels, on building out new accounts, getting that new business, driving new sales conversations — while uncovering those overlooked leads and past opportunities that are sitting dormant in your CRM, ready to be reactivated and sold again. And then also looking at existing accounts and asking, where else can I mine new opportunities? Outbound can become that opportunity-development engine for you. When all these sources are working together, that's really where you see growth, as well as these spikes from leveraging those overlooked opportunities in your CRM.

Angus Robertson 24:30
All right, so when all these pieces come together — you were talking about a revenue engine — how does this look? How do all those pieces look as you plug them together and get the momentum going? And what kind of numbers can you achieve from that?

Nate Rupple 24:53
One of my favorite examples: one of our clients is a precision metal fabrication company serving aerospace, defense, industrial components. They didn't have an outbound motion in place; we built an outbound engine for them. So that was one component — check: new RFQs, new opportunities, new sales conversations coming in through that channel. And then they made a significant investment in new machines. That investment meant they needed to fill that capacity — because when machines are running, you're making money. So it was, okay, we're going to need more now to meet that investment and that open capacity. Where can we spend? Where can we put more money? And our first step was: hey, we have outbound working, you have some inbound coming in, we're pointing our outbound as a follow-up engine for your inbound — before we spend more, let's look at what you have in the CRM. Because in manufacturing, if you're not a fit right now, the next part or the next program that comes up may be a fit. It's really just about staying in front. So we ran our six-step process. We looked through their existing CRM, we segmented out different categories, different groups, started that messaging. And in three months, we developed 14 new RFQs and sales opportunities. That's a big deal for them, because their average deal size is somewhere between $50,000 and $250,000. So you can see very quickly that solved that capacity issue and brought in new programs. Then we can take a step back: now let's look at some of the other channels, and do it in a way where — because of the additional sales volume — you can be a little more picky. You can choose the work that you want. We can be more targeted, because we're not fighting for velocity anymore. Now it's more about optimizing the different channels, because production is running at the clip it is. So sometimes the fastest way to accelerate a pipeline isn't necessarily adding another channel and spending more money.

Angus Robertson 27:13
Well, I'm sure as soon as they saw that progress in that pipeline building, they're like, well, maybe we should add some more capacity.

Nate Rupple 27:23
Yeah, maybe so. We'll see down the line. I'll have to keep you updated.

Angus Robertson 27:27
All right. Well, as we wrap up here — appreciate folks joining or watching this. If somebody in our audience wants to start doing this tomorrow — looking into their CRM, identifying some of these boomerang buyers and opportunities they could take advantage of to build their pipeline and increase won deals, without necessarily adding a lot of new leads or cold calling — where should they begin?

Nate Rupple 27:56
Well, the CRM would obviously be the place you want to start. But what I would do is start small. You don't have to boil the whole ocean. Start small, jump in, look at maybe 12 to 18 months back, and go through and start segmenting by intent — why these were closed-lost, what happened. And as you start to do that, if you've never done it before, start adopting a process now, because good in is better out later. Start thinking about the different intent categories you may have based on your closed-lost. That'll really help you segment as you go, and it'll strengthen the messaging you have for each of those segments. The result will be, as you pursue those, you'll notice that you're going to bring people back faster — because you're speaking to the reasons why they didn't move forward with you in the first place, and you're reactivating their timing to bring them back into sales conversations. And you'll be able to do that without pushing budget toward other channels just to cultivate more. Now, later, should you do that? Sometimes that is the right thing to do. But there is this overlooked group of opportunities that, with the right mining and the right pursuit, can really generate more revenue faster.

Angus Robertson 29:19
Great. Well, Nate, I really appreciate you taking the time to share your insights on boomerang buyers and how our audience can take advantage of what they already have inside their existing CRM. And thanks, everybody, for watching, and we'll see you on the next Outcome Marketing Live. Thanks again, Nate.

Nate Rupple 29:38
Thank you very much for having me. Appreciate it.