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  3. #621: How to Find the Buying Signals That Actually Close Deals
30 Minutes to President's Club | No-Nonsense Sales

29 Oct 2026 · 33m · 14 chapters

Episode artwork

#621: How to Find the Buying Signals That Actually Close Deals | Angela Garinger Bennet

In short

How to use “buying signals” to close deals that are already in motion—by mapping signals to each deal stage, using historical data to find your best signals, and shifting management from activity metrics to conversion metrics. Includes deal plays for risk mitigation and acceleration, plus coaching triggers for sellers when signals indicate process or skill gaps.

Guests

Angela Garinger Bennet, VP of AI GTM transformation at Outreach; previously head of global sales development, then VP of commercial sales, then VP of sales.

Key claims

Signals shouldn’t be generic or only top-of-funnel; they must be custom to your motion and context layer (first-party conversations). Managers must inspect conversion/renewal outcomes, not call volume. Signals should trigger both deal actions and coaching actions.

Notable examples

champion changes jobs → “re-anchor” by finding new buying committee members; competitor intent spike → competitive takeout/education; executive buyer “checks out” → “jersey match”/playing Cupid; procurement/legal/security not engaged → multithread and internal deal review; stakeholder goes dark → multi-thread and re-engage using context-layer nuggets.

Written by AI. May contain mistakes.

Chapters

0:00

Data-Driven Insights for Sales Signals

Learn how to leverage past sales data to identify effective buying signals.

“Rather than kind of hypothesizing or sitting down with all of your AEs and going, what do you think we should be looking for?”
1:46

Top Three Actionable Takeaways

Discover three key takeaways for improving sales signals and processes.

“We start every single episode with a top three actionable takeaways.”
3:30

Utilizing Data to Identify Signals

Learn to use historical data to inform your sales signals and strategies.

“But first, my signal has triggered me to ask, what's takeaway number two, Angela?”
5:02

Adjusting Managerial Focus on Sales

Understand the shift from activity-based to signal-based sales metrics.

“Takeaway number three, change what your managers inspect.”
6:24

Custom Signals for Unique Sales Contexts

Explore how to identify custom signals that pertain to your specific sales context.

“I'm really excited for this conversation is I think there is a dominant perspective or paradigm about signals out there in sales right now, which is that they are generic and that they are only meant for top of funnel.”
11:22

Signals During the Deal Cycle

Gain insights into specific signals during the stages of a sales deal.

“Great sellers drive velocity at every stage of their sale.”
14:00

Leveraging AI for Leadership

Learn how AI can help leaders manage data and signals effectively.

“That's the way you get AI working for you as a leader.”
15:00

Identifying Job Changes and Re-anchoring Deals

Understand the impact of job changes in deals and strategies to re-anchor.

“I think everyone knows why that matters.”
17:40

Responding to Competitive Intent

Explore how to react when a competitor's interest spikes in a deal.

“Even in the case of saying, hey, if you are looking at any of our competitors in this evaluation process, here are some things we recommend you asking them.”
19:10

Engaging Executive Buyers

Learn effective strategies for keeping executive buyers engaged in deals.

“Hey, I want to introduce you to, you know, Nick, our CEO, we're so excited to have that connection while you go through this evaluation as a resource.”
Show all 14 chapters
21:30

Addressing Procurement Involvement

Discover the importance of procurement involvement in closing deals.

“And so then the seller didn't have to remind me.”
24:44

Strategies for Handling Ghosting Stakeholders

Identify actions to take when stakeholders become unresponsive.

“Great sellers drive velocity at every stage of their sale.”
28:00

Coaching Signals and Effective Leadership

Learn how to utilize coaching signals to enhance sales leadership effectiveness.

“leaders often are doing kind of a check the box, um, coaching, bring one of your calls and we'll listen to that.”
30:16

60-Second Recap: Key Takeaways

Review the main points discussed, focusing on coaching signals and actionable strategies.

“Everybody stick around for a 60 second recap coming up soon.”
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Transcript

Automatic transcript. May contain errors.

0:00Rather than kind of hypothesizing or sitting down with all of your AEs and going, what do you think we should be looking for? The data already exists. Pull all of your previous fiscal year data. Figure out what your qualified opportunities look like. Figure out what your closed one deals look like, your expansion deals, your renewals, anything that works successfully for you. I want you to pull all that data. Then I want you to layer the signals that you have access to on top of that data. From that exercise, you will be able to find your exact recipe for success, whether it's pipeline generation, successful renewals, or closed one revenue.

0:35they're going to be plays with the perfect recipe.

0:43Good morning, everybody, and welcome to this episode of 30 Minutes to President's Club. I'm your host, Nick Segelsky. And today we have somebody who started as the head of global sales development, got a promotion to the VP of commercial sales, got another promotion to the VP of sales, and now is the VP of AI GTM transformation over at Outreach. Today, We have Angela joining us. And this was a really fun episode because we talked about signals, but not in the context that I think is the dominant theme around signals, which is, okay, I look for new executive started, or I look for company got funding, and that means I prospect them.

1:17We actually spent most of this episode talking about signals in the context of active deals. We talked about the signals that you should look for when you have a deal in motion, and then the specific play that either you or an agent could run to either mitigate risk, accelerate the deal, get a bigger deal, or get access to other stakeholders that you might not otherwise. And so this was a very fun episode. I look forward to welcoming Angela to the show. So let's dive in. A three, a two, a one. Let's roll. All right, Angela, welcome to the show. We start every single episode with a top three actionable takeaways.

1:51So let's get your three. So first takeaway, build a signal to stage map. So most teams stop signal work the moment an opportunity is created. A lot of our leaders are really, really over-indexed on just the top of funnel pipeline generation and how signals are supporting that. But you need to build a map for each deal stage and then list the three or four signals that should change seller behavior or even have agents act on behalf of the seller based off of those signals. So a couple of examples are, you know, a champion changes jobs mid-deal. This happens, right, all the time. Okay, what then triggers from there?

2:30This could then trigger a re-anchor play, right? Within 24 hours, you've now aligned with an additional person on the buying committee so that you've de-risked that deal. Another example is a competitor is brought up in the demo. Okay, what do you do to ensure that you've got in front of that competitive intel, that you've asked the right questions, that you're going head to head based off of the person who all of a sudden seems like they're aligned to your competitor, right? Maybe a third signal, right? A stakeholder goes dark. We see this all the time, especially late stage. All of a sudden, everybody's gotten quiet, okay?

3:05Maybe that triggers a multi-threaded play or a jersey match play so that you can ensure that you can get that person re-engaged again, and then your deal doesn't go off course. So there is a map that exists. You need to figure out what that map is, what those signals are, and what plays are aligned to them. And good news for those of you listening is Angela was so kind as to help us build a full map that we're going to be going over in this episode. But first, my signal has triggered me to ask, what's takeaway number two, Angela? Takeaway number two is that the data will tell you what your signals should be.

3:40So rather than kind of hypothesizing or sitting down with all of your AEs and going, what do you think we should be looking for? The data already exists. Pull all of your previous fiscal year data. Figure out what your qualified opportunities look like. Figure out what your close one deals look like, your expansion deals, your renewals, anything that works successfully for you. I want you to pull all that data. Then I want you to layer the signals that you have access to on top of that data. From that exercise, you will be able to find your exact recipe for success. Whether it's pipeline generation, successful renewals, or closed one revenue, they're going to be plays with the perfect recipe.

4:21So for example, a physical security company watches for a new facility lease announcement. As soon as they see that happening, they know that then they're much more likely to have a short deal cycle. A data integrity company watches for announced ERP migrations. Great. Hop on it. You know that that's going to get you close on revenue. At Outreach, we watch for companies posting three or more AE openings while existing AE headcount stays flat. We know that means they are leaning into increased seller productivity, right? They are trying to grow that company. And so we need to get in there and make sure we're having those conversations.

4:58All of those recipes exist. You got to figure out what they are. Awesome. Let's round us out, Angela. What's number three? Takeaway number three, change what your managers inspect. None of this really works if you have both a signal-based sales motion and an activity-based sales motion. We are seeing historically that sales has always been activity-based. Now it is shifting into a signal-based motion. If you are having your sellers really kind of have to appease both of those competing factors, signals and activity, I can tell you activity is always going to win. It's where people feel most comfortable.

5:34So you have to stop measuring volume then. You have to stop measuring activities. as an indicator of success. You know, number of calls, number of customer meetings. Essentially, you're going to have two layers with AI. A productivity measure, you're doing things faster. Great. But you also are going to have a precision layer. You should be able to do things better with more efficiency. And because of that, your indicators of success, you're going to see those in your conversion rates. Everything from calls to booked meetings, booked meetings to qualified opportunities, qualified opportunities to close on revenue, higher renewal rates.

6:17That's where you're going to be able to see the success of all of this signal-based selling. Part of the reason I'm really excited for this conversation is I think there is a dominant perspective or paradigm about signals out there in sales right now, which is that they are generic and that they are only meant for top of funnel. I think pretty much anybody watching or listening to this has heard, oh, look for new funding announcements or look for a new CEO was hired. That's the perfect time to reach out. And yes, you probably do want to reach out if there's a new executive or if a company raises money.

6:52But there's two things that I've gotten from you here. Thing number one is the concept of signals that are custom to your sale. Yes. That honestly, nobody else really gets that much value from. And then also in flight, like when you have a deal in flight signals to help mitigate risk or accelerate the deal or get your deal to be even bigger. So I think we're going to spend more time on the in-flight ones, but I want to just touch on the custom point because gosh, I sold to law firms for a long time And I was able to do this when I sold top of like when I was prospecting, I would look for law firms that had just won a big case.

7:34We sold billing software that would mean they'd be collecting money. And so they might want some billing software or I would look for law firms opening a new office. We had like a full accounting suite and it would help with different like tax things that they would run into. And so those were very, very particular to my like legal financial application sale that I had. But what was nice about that was I wasn't competing with a million other sellers who were reaching out to the same law firms because the signal was specific to the problem that I helped with. And so you mentioned a couple of different signals in the top three takeaways that you had here.

8:09You had the concept of a physical security company looking for new lease announcements. You talked about data integrity companies looking for companies that are saying, hey, we're doing a migration from ERPA to ERPB. You gave the example of outreach looking for, all right, if we see that there are multiple job openings for AEs with AE headcount staying flat, that tells me that there's something going on in this company that creates a condition that outreach can help with. And so my question for you, Angela, on this point, before we talk about the deal cycle stuff, you work with dozens, if not hundreds of companies that are architecting these for themselves.

8:45Are there other examples that you can give to help people get their juices flowing when they create this for their own sale? Yeah. So I think one of the things that I highlighted in the takeaways, those are still third party examples. that kind of gold is really happening in the conversations inside of your organization. And so this context layer. So to get even more specific, if there is a sales motion, maybe it's your new logo sales motion at the enterprise level on stage two of your deal, you notice that when you've got this exact person joining that meeting with you, this exact title, you know that that deal is going to close 30 % quicker, let's say.

9:33That's so specific to you as a company. It's so specific to even that sales motion, potentially, that enterprise motion. Those signals exist inside of those conversations, which is really first party data. I think another example is that if you notice, let's say as a current customer, if you notice that the conversation starts moving in this direction and this particular topic, you know, maybe it's headcount growth or maybe it's, hey, we're starting to go through a transformation of X, Y, and Z, or we're looking at this kind of data migration, whatever it is based off of what you sell, you know, now they are much more primed and ready to buy your other SKU.

10:12If it comes up at this point, those are so specific to you all that data exists inside of your context layer. You got to find it. Great. Today's show is brought to you by ConsenSys, which helps your demo keep selling even when you're not in the room. Before I show a demo, I set it up like it might have to work without me. I include these three slides before I drop in. Number one, the biggest problems I learned in Discovery. Number two, how we solve those problems. And number three, a what does success look like today slide. You can steal that exact 30 MPC demo deck template powered by ConsenSys.

10:46Go check it out in the show notes. Today's show is brought to you by Pipedrive's easy to use and customizable CRM with built-in meeting intelligence. My favorite discovery question is the multiple choice question, which sounds like typically when I'm talking with folks like you, they're focused on A, B, or C. Which is it for you? Now, A, B, and C have to be problems that you can solve because that's how you steer the conversation in the direction of places you can help them. Now, Pipedrive's built-in meeting intelligence helps you focus on your follow-up question, not on scrambling to take live notes.

11:13And we built a full discovery toolkit with them free in the 30MPC closers hub. There's a link in the show notes. Today's show was brought to you by Outreach, the agentic AI platform for driving execution across every stage of your deal. Great sellers drive velocity at every stage of their sale. And one thing that's worked well for me is assigning redline deadlines to my prospects when we kick off vendor review. Even artificial micro deadlines for things like first cut of redlines and security review helps my prospects get their internal team moving. We built a guide on how to help you drive six and seven figure deals with our friends at Outreach.

11:48Get it free in the show notes. So let's talk about now, signals in deals and then the plays that you run in companion to those signals. So when we were prepping for this, you were so kind as to help me generate a list of signals for early stage deals, mid stage deals, and late stage deals. Let's talk about the signal and then let's talk about the play that you run. So the first signal, this one's a depressing one, is hesitancy from the customer to share metrics tied to a business outcome. What I want to hear from you is why does this matter? And then what is the play that you recommend gets run in companion to that?

12:26This is a tale as old as time. In a discovery meeting, right? The first thing you need to do is try to align the business outcomes, right? Align your product to the business outcomes. If you can't metric that, if you can't make sure it's like this quantitative thing that you can identify and talk through and speak to throughout the sales cycle, you're putting yourself in a bad way as a seller. You're making this way harder on yourself. We have found, right, and every seller feels this, that sometimes in those first initial conversations, the buyer is hesitant to actually give you those metrics.

12:58So there's really two plays here. One, we found that often that means that you're not talking to the right person. Maybe they're not high enough. And so then it can trigger an external play of multi-threading, of getting higher up, ACL at this particular title, making sure that they're looped in. There's also an internal trigger that happens because at the front line, if you have noticed that this keeps happening for one of your reps, they're having a hard time building rapport. They're not doing a good job of building trust where that person feels safe enough to share these metrics. That's an internal coaching opportunity.

13:32That's an internal signal for skill development, which I think is equally as important. That's really good. So if I see that one of my reps is running into this hesitancy again and again and again, one, we're going to trigger a let's get access to other people play. But two, that's a signal for me to say this rep might need a little bit of extra coaching. They're not building a relationship. They're not making this person feel safe. Or they're talking to people so far below the line that, of course, they can't share any data. But either way, I can fix the problem with the rep if I see this happening.

14:02Absolutely. And that's another way, too. That's the way you get AI working for you as a leader. and we're going to talk a little bit about that, but we're overrun as leaders, right? With data. And so having those signals to trigger things that you need to be paying attention to is so, so important. Yeah, that's really good. I mean, that's making me think of an example at our company where we had one rep who was booking a lot of meetings, but they were with companies that were like, we do tiering of our customers that we try to reach out to, tier one, tier two, two, three. And there were a lot of tier threes that they were booking and they were doing a great job with the tier threes, but they closed at a lower rate than our tier ones.

14:34And so what should have happened was we probably could have set up some sort of agent to look at the percentage of their open opportunities that were not tier one or tier two. And that would have triggered a coaching opportunity and helped us get ahead of an issue a month earlier than it happened. Wow. I'm learning a lot today. Let's move to the next one here. So the next one is job change. So you've got a champion in a deal and they leave. That always broke my heart as a rep. Why? I think everyone knows why that matters. What is the play to run when this happens? Yeah. So the idea, of course, is that even if you have a job change for someone that is inside of that buying cycle, you have multi-threaded it.

15:14And so then you're able to re-anchor that deal to another person in that buying committee. And so that's the trigger there. I think another one internally, though, is that if there is no one there for that trigger to execute on, now you've got another a coaching opportunity. And so there's another internal signal to the leader. Both of those, I think, are really important. And your recommendation is that you are recommending companies set up agents to action on these plays. Can you give me a little bit of detail around what actually happens in this re-anchor play? Is the agent just like mass emailing a bunch of executives who weren't involved in the deal or might've been on a meeting three weeks ago being like, hey, Shelby left, but we talked to you in a meeting three weeks ago.

15:54I want to talk now. It might not be perfect, but could you give me a sense of the shape of what that play looks like? Sure. So if if we see that somebody on the buying committee responds to an email and says, hey, actually, Joe isn't here with the company anymore. You can have a research agent. One of our agents internally will go and listen to the previous calls, identify who else is on the buying committee. We can tell it, go find other people on the buying committee, make, and then reach out to them. Also bring up, personalize the things that we talked about, or this particular person said in the last meeting and why that's so important in that you want to make sure you get on a call with them immediately.

16:34We can, that will just execute on behalf of the seller. Sometimes before the seller has even had a chance to read that response email that says, Hey, Joe's no longer here. that agents already including the new buyer or the new person before the rep has an opportunity to kind of fumble it, honestly. Amazing. I mean that in the most respectful way, but I just mean like you don't insert human error. Trust me, I've fumbled many a deal over the years. Or you just don't act fast enough. Even if you do it with a tremendous amount of precision, you're not doing it quickly enough. And so, yeah, we can eliminate all of those things.

17:08Let's move to the next one here. So competitor intent. So competitor intent keyword spike on a deal that I am working. Now, that means that the prospect might not have explicitly told me, oh, we're looking at Betacorp, but you're seeing via your intent tool, they're looking at Betacorp. Let's talk about the play that you get, that you recommend folks run in response to that. Yeah. So you would have a competitive takeout play, of course, execute on that if you start to see that. But I think - For folks who don't, what should that look like? Because we actually, we don't have one at my company. A competitive takeout play.

17:43A lot of times what we do internally and what I recommend our customers do is that if you've got a ton, and most companies do a ton of information on how you're differentiated from this particular competitor, a lot of times what is necessary is just education of that. Even in the case of saying, hey, if you are looking at any of our competitors in this evaluation process, here are some things we recommend you asking them. Yeah, that's good. And so that way you're not actually saying anything. You know, it's a really, it's an education play to the buying committee. I think one of the things about this competitive intent though is that even if you have the spike in competitive intent, right, it means that you haven't actually had a conversation with them.

18:22You can get really specific with a different agent though is that if it's mentioned inside of a conversation during one of those meetings across the sales stage, depending on where it is, depending on who it is, you can really get that message exact. So if it's that the contract is up in this amount of time, that message is going to be different than just the competitive intent play at the very beginning. Just something to think about. You get really, really super specific. Really good. So let's talk about what I never do when I'm on Zoom meetings, which is checking out. So the executive buyer checks out.

18:56The executive buyer goes to see in the deal. They're not there. What is the play that we should be running to get them back in our deal? this one feels easy, right? This is something that I feel like a lot of sellers don't use often enough, but we always just jersey match. And I think that you can do this reactively when an EB checks out, but I think even proactively ensuring that before the executive buyer checks out that once or the economic buyer is in the deal, as soon as that happens, then there's a proactive jersey match email. Hey, I want to introduce you to, you know, Nick, our CEO, we're so excited to have that connection while you go through this evaluation as a resource.

19:38That kind of proactive signal almost ensures that you don't put the deal at risk. And in fact, I would bet that doing that proactively would help the deal in some way, whether it's increase the size of it or shorten the deal cycle. Yes. The reality is, is if your title is account executive, or nowadays GTM, or sales manager, sales director, a lot of prospects don't want to talk to you, especially technical prospects. And that's just the reality of being in sales. That doesn't mean that you won't be able to get access to these people. But this is where you can, we recently had the number one global AE at a company called ThoughtSpot on the podcast.

20:17And one of the things she talks about is a strategy she calls playing Cupid. And what she'll try to do is jersey match across the entire org so she'll get her executives reaching out to their executives her technical people reaching out to their technical people her cs people reaching out to the champion and so what happens is is like all of a sudden it's not just you as an ae trying to multi-thread with a bunch of different people she's essentially matchmaking from her org to their org and attaching people who have similar personalities things that they can talk about etc and it's really really powerful and then she does one other thing to the point of what you talked about which is it's one thing if your executive reaches out one time it's another and this is she's brilliant she literally puts a reminder on their calendar every couple weeks to be like hey check in with that executive you met with check in with that executive that you met with so that it's not just like a one-time thing but it actually feels like and they are like the orgs are building a relationship and so if someone's listening to this being like i'm struggling multi-threading or I'm getting ghosted.

21:20That playing Cupid strategy, that play can be really, really powerful. I love that. That's exactly it. And I bet if you pulled the data, you said she's the most successful seller. Beautiful. If they could automate that through agents across the entire sales organization to replicate that same process that she does, not only so that all of the reps are doing that proactively, but then even on behalf of the leader, I know as an executive, if I had an agent, then all of those times I had been matched with someone, the agent was then going just reaching out every two weeks. And so then the seller didn't have to remind me.

21:59Beautiful. It's the machine is working. Yes. Great. Now, Laura is going to hit 700 percent of quota. Lovely. Call me, Laura. I'll help you do it. Yeah. All right. So let's talk about the next one. This is procurement's involvement or lack thereof at a certain stage. What's the play we should be running here? And I guess, why does this matter? Because for most sellers, you're like, great, procurement's not involved. They're not going to negotiate whatsoever. Yeah. So I think if I had a nickel, right, and every sales leader listening to this is like, no, no, no, no, Angel, I promise this gigantic deal is going to close in a week.

22:36And no, I haven't talked to procurement. And no, I haven't talked to legal. And no, we haven't gotten through security. You know, depending on the size of the deal. And there is no way that deal is going to close. This is a process, a buying process inside of a large organization. And so if there is a risk, a flag there based off of even the deal stage, the forecast category, the close date, this is really, I think, better for sometimes an internal trigger, right? All of a sudden now the VP knows, hey, this is at risk of closing based off of the close date here. And then now we need to do a deeper deal review.

23:15If you've already got a lot of deal health scores, you can bake that in there as it exists, which is great. But you can also, of course, make sure that they've started those conversations. So the external play here is that then it multithreats, legal, security, procurement, Whatever is necessary to get that deal closed based off of the decision process that you know is needed for that particular organization, those things can trigger, but it also should have an internal trigger too. Today's show is brought to you by ConsenSys, which helps your demo keep selling even when you're not in the room.

23:47Before I show a demo, I set it up like it might have to work without me. I include these three slides before I drop in. Number one, the biggest problems I learned in discovery. Number two, how we solve those problems. and number three, a what-does-success-look-like-today slide. You can steal that exact 30 MPC demo deck template powered by ConsenSys. Go check it out in the show notes. Today's show is brought to you by Pipedrive's easy-to-use and customizable CRM with built-in meeting intelligence. My favorite discovery question is the multiple-choice question, which sounds like typically when I'm talking with folks like you, they're focused on A, B, or C.

24:22Which is it for you? Now, A, B, and C have to be problems that you can solve because that's how you steer the conversation in the direction of places you can help them. Now, Pipedrive's built-in meeting intelligence helps you focus on your follow-up question, not on scrambling to take live notes. And we built a full discovery toolkit with them free in the 30MPC closers hub. There's a link in the show notes. Today's show is brought to you by Outreach, the agentic AI platform for driving execution across every stage of your deal. Great sellers drive velocity at every stage of their sale. And one thing that's worked well for me is assigning redline deadlines to my prospects when we kick off vendor review.

24:56Even artificial micro deadlines for things like first cut of red lines and security review helps my prospects get their internal team moving. We built a guide on how to help you drive six and seven figure deals with our friends at Outreach. Get it free in the show notes. The last one, this is really similar to like siloed in a function, but this is like the stakeholder that I'm talking to ghosts me. What do I do? What's the play that I should be running here? Yeah, I think that this is where the multi-threading is so important. And so that is an easy trigger to add there. One of the things I would recommend, though, especially if it's a late stage deal and the stakeholder starts to get quiet, certainly you want to do the jersey matching if necessary, you know, going above that particular economic buyer and aligning C-suite to C-suite.

25:45But I think that this is another coaching signal. If you see this over and over again, that a rep is getting to this stage and then it's starting to kind of falter. what happened in their discovery calls potentially that got them to this stall deal. So yes, multi-threading, jersey matching, but I would even take it a step further. Go and look in the context layer. What's happening during those meetings that they could, when they multi-thread, they could go back and pull in either with that economic buyer that's gone quiet or with the C-suite that they try to get included. there are some nuggets in those conversations that they need to highlight and get them reengaged.

26:30One thing that's really standing out to me is this concept of you've got these signals when a deal happens. And my previous perspective was great, was, okay, signal happens. What action do I take in the deal? What I'm hearing from you is there's actually two actions that happen. There's a deal-related action, and then there is oftentimes a coaching-related action, especially when one of these signals is related to risk that we could have addressed had we run proper process. And so that brings me to sort of the last topic I want to hit on with you, which is really just around like coaching. If I'm a leader listening to this, I might be getting overwhelmed because I'm like, great, now I've got to figure out signals and agents and infrastructure and pipeline reviews.

27:08And I've got a lot on my plate. I don't have time for coaching. How are you seeing sales leaders operationalize coaching, especially now that they have AI able to help them? I'm going to say this from the executive level. The best executives who are inserting agents into their organization, their sales organization, they are being very thoughtful and discerning about what the leadership framework now looks like, right? What are people inspecting? Um, what are they, what metrics, if it's conversion metrics, what are they moving towards in regards to that? That then helps to identify these agents to signal even for the manager, what they should be paying attention to.

27:55I think often frontline leaders, there's two things I want to say here, Nick, frontline leaders often are doing kind of a check the box, um, coaching, bring one of your calls and we'll listen to that. If you guides and you should have AI telling you based off of this particular coaching card, this is the call that you need to be leaning into for that. And then for this particular seller, if it's Nick, Nick is struggling with this particular skill in this particular stage in this particular kind of meeting. Great. Every time now I've coached Nick on exactly what he needs to do. Nick leaves my one on one.

28:34He leaves my one on one. And then because I've set up the agent to listen for the progress there, now I, as a manager, don't have to wait till our next one-on-one to know if Nick needs more support, if he needs real-time coaching. Like, immediately it's happening. So there's a couple of things that I want to land the plane on. Oftentimes, you could ask a manager, what does good discovery look like and how do you know if it's happening? They can't answer either of those questions. Your data will tell you, one, what does good discovery look like because it's leading to the next stage. And then two, you can set up coaching cards with your CI to ensure that it's happening immediately.

29:12All right. So there's that point. But here's where I get really excited, Nick. That requires you to stop doing certain things as a leader. And that's the thing I think that they're not paying attention to. If you have put all of these pieces in place, you're leaning on signals, you've got agents helping you ensure that you're coaching to the right things, overseeing it, defining what good looks like, you can't then go back to your, hey, slack me the call you want me to look at when you get into your one-on-one. Hey, let's look at this sales spreadsheet that I've built of the deals and we'll talk through it.

29:48You have to stop. You decide what you're going to kill, when you're going to kill it, right? What replaces it? When does it end? And how do you make sure it doesn't come back? Those are the things you have to identify. Otherwise, you'll have these shadow spreadsheets and these shadow deal reviews and these shadow coaching sessions that are ineffective and not serving you. Amazing. Well, that's a mic drop moment. Angela, thank you for joining us. Everybody stick around for a 60 second recap coming up soon. All right, it is time for your 60-second recap, and it's just Nick today. So my top four takeaways here.

30:26Number one was the concept of the internal coaching signal. So Angela talked about there are often signals you're going to get that would prompt an action that you take in the deal. For example, if a champion leaves and there's nobody else to talk to, the play you're going to run in the deal is let's go get access to other people. But that should also trigger a coaching moment of, seller, you only have one person. You were single-threaded. Let's talk about and let's coach around how to get multi-threaded. So number one was the concept of the internal coaching signal. Number two, the concept of the jersey match.

30:59I also talked about playing Cupid, meaning if you're trying to get access to people that especially more technical folks that don't want to talk to a salesperson, pull in an executive or pull in a technical resource on your side as an incentive for them to actually get on the call. So the jersey match can be a way for you to expand your access to the entire buying committee. Number three, custom signals. So lots of folks are looking at the same signals, job changes, funding round, new product announcement, etc. The recommendation is to reverse engineer for your specific business what signals create conditions that your product can help with.

31:34Examples that we talked about, I'll give the law firm one was, okay, when I sold billing software, if somebody won a big case, well, that meant that they were going to be collecting money. They might need some billing software. Or if they had just opened a new office that would create tax complications, they might need our accounting and tax software. And so think about what observable triggers or signals create conditions that would mean somebody needs my product. And then the last one was at the very end, the concept of the stop doing list. If you are adding all of these signals and these plays on and these deal review approaches on, it's really, really tough to keep running all the old stuff.

32:12So you have to be really intentional about your stop doing or not to do list. Otherwise, you were going to bloat everybody's schedule and they won't have any time to sell. That's it. Thanks for watching. If you enjoyed this episode, we'd appreciate a subscription so you get every episode of 30 MPC beamed directly to your device. Thanks for watching. Thanks for listening. We'll see you next week on the show. Today's show is brought to you by ConsenSys, which helps your demo keep selling even when you're not in the room. Before I show a demo, I set it up like it might have to work without me. I include these three slides before I drop in.

32:44Number one, the biggest problems I learned in discovery. Number two, how we solve those problems. And number three, a what does success look like today slide. You can steal that exact 30 MPC demo deck template powered by ConsenSys. Go check it out in the show notes. today show is brought to you by pipe drives easy to use and customizable crm with built-in meeting intelligence my favorite discovery question is the multiple choice question which sounds like typically when i'm talking with folks like you they're focused on a b or c which is it for you now a b and c have to be problems that you can solve because that's how you steer the conversation in the direction of places you can help them now pipe drives built-in meeting intelligence helps you focus on your follow-up question not on scrambling to take live notes and we built a full discovery toolkit with them free in the 30MPC closers hub.

33:30There's a link in the show notes. Today's show is brought to you by Outreach, the agentic AI platform for driving execution across every stage of your deal. Great sellers drive velocity at every stage of their sale. And one thing that's worked well for me is assigning redline deadlines to my prospects when we kick off vendor review. Even artificial micro deadlines for things like first cut of redlines and security review helps my prospects get their internal team moving. We built a guide on how to help you drive six and seven figure deals with our friends at Outreach. Get it free in the show notes.

From the publisher

Angela Garinger Bennett, VP of AI GTM Transformation at Outreach, breaks down how sales leaders can use buying signals and AI agents to accelerate deals, identify risks, and coach their teams more effectively.

🚨 Build a signal-to-stage map that triggers the right sales play when deals are at risk

📊 Reverse-engineer your closed-won deals to uncover the buying signals that actually drive revenue

🎯 Use AI to identify coaching opportunities and shift your team's focus from activity volume to conversion rates

You’re one step closer to President’s Club!:

🏋 30MPC Training: https://www.30mpc.com/course/team-training

🛠 Weekly Newsletter: https://hubs.li/Q02NJQ8p0 

📚 Things you can steal and use today: https://linktr.ee/30mpc_youtube

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