1. Podcasts
  2. 30 Minutes to President's Club | No-Nonsense Sales
  3. #605 - How to Build a Cleaner Sales Pipeline in the Age of AI
30 Minutes to President's Club | No-Nonsense Sales

3 Sep 2026 · 35m · 9 chapters

Episode artwork

#605 - How to Build a Cleaner Sales Pipeline in the Age of AI | Stevie Case

In short

Building a cleaner, higher-signal sales pipeline in the AI era by reducing “slop” (spray-and-pray outbound that creates noisy, unqualified opportunities) and improving pipeline inspection, data integrity, and outbound quality.

Guest

Stevie Case, GTM/sales leader at Vanta (founded 2018). She helped accelerate revenue from $200M to $300M in nine months and manages a large sales org (~1,600 employees mentioned). She emphasizes data/ops/human factors and uses AI-assisted deal inspection.

Key claims

  1. Don’t just measure conversion; measure conversion timing (e.g., 80% of startup deals convert within 14 days; deals outside that window are excluded from coverage).
  2. Build a “half machine, half human” deal inspection system using discovery frameworks (MedPIC) and AI-scored deal quality; leaders still run live forecasts.
  3. Top outbound reps may be “in the red” on activity metrics because they’ve shifted to higher-human-quality outreach; replace activity benchmarks with quality inspection.

Notable examples

  • Deals slipping because reps lacked economic buyer access; AI transcript extraction (Gong + Dust/Clay) revealed missing economic buyers earlier.
  • Reps entering deal value before meeting (e.g., Comcast $500k) inflated pipeline coverage; added gates for when deal value counts.
  • One rep’s partner-based playbook (in-person networking + account mapping) wasn’t captured by activity metrics; it was scaled to the team.
  • Outbound guidance: cold calling and events (including personalized pre-event outreach like booth headshot intros) outperform generic email slop.

Written by AI. May contain mistakes.

Chapters

0:00

The Problem with Sloppy Sales Pipelines

Learn about the drawbacks of careless outreach and its impact on sales pipelines.

“Slop sometimes does convert and what all of this automation has done is made it very easy to spray and pray.”
1:36

Stevie's Top Three Actionable Takeaways

Explore Stevie Case's insights on pipeline inspection and outbound sales.

“All right, Stevie, welcome back to the show.”
5:38

Building an Intelligent Deal Inspection System

Discover how to balance machine and human insights in sales.

“You said that there's a lot of slop that's leading to a lot of extra pipeline.”
10:48

Data Integrity and Sales Insights

Understand the importance of data integrity in sales processes.

“Can you give me like a couple examples where you were surprised?”
14:00

Building a Clean Sales Pipeline

Learn how to enhance data integrity and utilize AI for an effective sales pipeline.

“We don't have the right governance in place.”
22:05

Adapting Sales Strategies in a Changing Landscape

Explore how to adapt sales strategies by inspecting individual performance metrics.

“that's going to create a certain quality of pipeline.”
28:00

Leveraging Events for Sales Success

Learn how personalizing event outreach can dramatically improve conversion rates.

“at the talk track, getting them better at objection handling, understanding our value prop.”
29:18

Challenging Sales Leadership Beliefs

Discover common misconceptions in sales leadership and how to overcome them.

“Go to these places where people are excited to get together.”
31:39

Embracing Multi-Dimensional Skills

Understand the importance of diversifying your skill set beyond sales.

“If you've come up in sales, you need to understand customer success.”
A man walking through an airport, asking his phone a question

Ask about this episode

Get the gist, explore an idea or ask about something said.

Claude

On 30 Minutes to President's Club | No-Nonsense Sales, what are the key points of this episode?

Searching your listening

Transcript

Automatic transcript. May contain errors.

0:00Slop sometimes does convert and what all of this automation has done is made it very easy to spray and pray. You got folks out there just blanketing the world with outreach. But when you're just doing spray and pray slop, you're not really qualifying those deals. You're setting up meetings that may not be the right fit, may not be ICP. You end up with this very messy pipeline. Conversion rates sometimes go down. So it just creates a tremendous amount of noise. And those noise might look like real opportunities. The key is you have to inspect more deeply because the noise isn't just the outbound noise.

0:41It truly is noise that's ending up in your pipeline.

0:48Good morning, everybody, and welcome to this leadership episode of 30 Minutes to Presidents Club. I'm your host, Nick Segelski, with my co-host, the wonderful Mark Kosaglow. And today we have a$300 million sales leader, the phenomenal Stevie Case. Mark, this was a mind-blowing one. Why should people listen?

1:08Stevie Case: Stevie Case is one of the best go-to-market operators on the planet. She understands the data side. She understands the operational side. She understands the human side. She understands the sales side. And I think what you'll find in this episode is when you combine those three or four things together, you really start to accelerate. And the fact that she went from$200 to$300 million in nine months says that this stuff works. All right, Stevie, welcome back to the show. You might remember that we start every single episode with your top three actionable takeaways. So let's get your three. Okay, let's go.

1:45We're going to start with takeaway number one, and that is everyone knows slop is everywhere. When you're looking at pipeline inspection, You need to be thinking a lot more deeply about what real coverage looks like. So the key here is don't just measure pipeline conversion. You need to be looking at the window within which things convert. Now, what that looked like in our business is we've got lots of segments. One of those is our early stage segment. It's our startup segment. The deals are the shortest in length there. What we found is that 80 % of deals converted within a 14-day window. So what we started doing is if deals fell outside of that 14-day window, we excluded them from the coverage ratio because we knew that they were probably not good deals that were going to close anymore.

2:31The downside, if you don't do this, is you start diluting yourself into thinking you've got real pipeline and real coverage when you actually don't. And this is particularly dangerous when it is so easy to inflate this with slop that's hard to inspect. What's number two? You need to build a deal inspection system that's half machine and half woman. And you got to know which is which. I'm a huge, I'm very clawed pilled. I love AI. It's great. It is also dangerous. You can fall into the trap of just trusting the agent. You know, we have trained our team deeply on a discovery framework. We use MedPic here.

3:07We're a MedPic shop. We've built a system that takes all that great data from transcripts, puts it into CRM without AEs getting involved. So we're trying to discover, have they actually discovered every bit of MedPic? And what's the quality of that discovery? We're then rolling that up into deal insights. And then we're rolling that up into a score. And that score is telling us, have we actually effectively done discovery? Are there digital engagement signals here? What's the quality of this opportunity in a way that is not subjective, but is based on real world conversation? Now, I do still have my leaders run real live forecasts, human led.

3:47I want their voice. I want the narrative and the point of view. I take all those recordings and those decks. I roll them up and I run analysis with my own custom built agent. That agent highlights those weak spots. And then when I have a conversation with my leaders, I'm asking specifically about areas the agent has identified that we need to talk about in more depth. Let's round us out. What's number three, Stevie? Okay. Number three. Now, this was a painful one. This is all about outbound, which is a critical part of our business. So number three is your best outbound reps might be violating your activity metrics and your benchmarks.

4:26They might be right. We all know everything has changed. The landscape has changed. The way you outbound effectively has changed. We, like many others who have a big SDR team and do a lot of outbound, had these very clear classic activity benchmarks. Number of emails sent, number of prospects reached, number of connects and calls. And we were measuring every week if every individual hit those benchmarks. We had a real awakening when we realized that some of our folks on the leaderboard, in fact, some even in our top three outbound producers, were actually in the red on the activity benchmarks.

5:04And what we discovered when we pulled back the covers there was that they had created a new playbook that was completely unique to the moment. They recognized there's a ton of written slops. So they started leaning into humanity and the kind of connections that are actually harder to measure in some cases, events, social connections, and really personalized outbound. And they were having a lot more success. So we ended up learning from them and rebuilding the playbook. and threw those benchmarks out the window. And now we're looking at something completely different when it comes to quality outbound.

5:38Stevie Case: You said that there's a lot of slop that's leading to a lot of extra pipeline. When I hear that in my mind, I'm like, we're sending a lot of slop. I thought slop didn't convert. Are you seeing slop actually convert into, I'm gonna put in quotes, pipeline? Yes, I am. What I am seeing here is that slop sometimes does convert. And what all of this automation has done is made it very easy to spray and pray. You got folks out there just blanketing the world with outreach. And some of that stuff does convert. You occasionally get a bite on that stuff. But when you're just doing spray and pray slop, you're not really qualifying those deals.

6:23You're setting up meetings that may not be the right fit, may not be ICP. you end up with this very messy pipeline. Conversion rates sometimes go down. So it just creates a tremendous amount of noise. And those noise might look like real opportunities. The key is you have to inspect more deeply because the noise isn't just the outbound noise. It truly is noise that's ending up in your pipeline.

6:50Stevie Case: Stevie, I think I saw recently, maybe in the the last six months. Vanta just crossed a hundred million bucks. So you guys are at scale. Wait, 300 million. 300 million. Correct. Yes. Yes. Thank you. We did that about nine months after we crossed 200 million. So we are actually accelerating right now at this scale, which is wild. So she's getting a ton of deals that are closing fast, which means she's seeing a ton of information. So when you're moving at that speed, how are you taking a huge pipeline, three,$400 million pipeline, and looking and finding the deals that are slop generated? Yeah, we have built a tremendous amount of intelligence and inspection into the machine.

7:35And then we're leveraging our humans intelligently on top of that. So, you know, we had to really do a fundamental re-architecture of our stack. You know, Vanta founded in 2018, we started with what looked like a very classic stack, your Salesforce, your outreach. We were doing all the things that were normal at that point. That doesn't work anymore, especially at this volume. The danger you run into when you can spray and pray and hit the world, and this is true whether you're a 10-person company or a Vanta where it's 1 ,600 folks, you can burn through your TAM really quickly. You can also, with those kind of reply rates and open rates you were talking about a minute ago really damaged your email deliverability, your credibility in the market.

8:20So what we have done is get really thoughtful about the system we've built to inspect before it even gets to a human. So what that looks like is we no longer use Salesforce as our database. All of our data today pushes into Snowflake. We've built a semantic layer on top of that. All data in the business is agent accessible. We've hooked up basically every MCP you can possibly reach. And in the micro sense, what this looks like is every call is recorded. We're taking all of that intelligence, pulling it into a system that analyzes strengths and weaknesses of opportunities. And then instead of asking for the first point of view from the rep or their manager, we're asking them to respond to the machine's analysis.

9:08We do give humans the right to correct. Machine's not always right. But we are bringing a lot of intelligence before we get there, both at the individual deal level and at the aggregate level across segments and across the whole business. Today's show is brought to you by Proposify, the proposal management software designed to make every deal a closed deal. When you send a proposal to a prospect, include a video of yourself walking through the proposal because it's going to be shared with stakeholders beyond just your champion. You want to make it easy for those other people to digest, and you want to be able to control the narrative with your presentation.

9:41And bonus, Proposify data shows that when buyers watch the video, it increases your chances of winning by over 3x. So do not let your proposals become a disappointing plot twist. Get our proposal success guide free in the show notes. Today's show is brought to you by Ambition, the coaching and performance platform helping sales leaders turn metrics into action. Did you know that sales orgs where the majority of reps are coached weekly are twice as likely to see high quota attainment than those who don't? and that is from Ambition's new state-of-sales coaching report that also found teams using a system like Ambition coach almost 60 % more frequently than those who don't have one.

10:11Now, we built a toolkit with our friends in Ambition on how to actually use data to coach your team. Get it for free 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.

10:43And we built a full discovery toolkit with them free in the 30MPC closers hub. There's a link in the show notes.

10:49Stevie Case: Can you give me like a couple examples where you were surprised? Like, oh, this looks good, but the data is telling me it's not good. What are a couple examples people could look out for in their own pipelines? Yeah, one big one is on close date. So this is one it can be so hard to inspect for. You got reps with happy ears. We have a very high velocity business. We close every month. So we had a couple of months where what we saw was we had a lot of pipeline coming into the final week of the month. We were looking good. Coverage ratios were great. And then a ton of deals slipped. And what we ultimately ended up realizing is that we actually didn't have access to the economic buyer in a bunch of the deals where we, you know, they were telling us, the rep was telling us they did.

11:33But what we did is when we built this mechanism to pull, we record our calls with Gong. We pull data out of that in a couple of different ways. We pull it out using Dust, which agent builder platform we love. We also pull stuff out using Clay. And so we were pulling all of those MedPIC fields into CRM using Clay. And what we found was that like the percentage of deals without an economic buyer identified was lower than we thought it was. So we recalibrated and we started inspecting for that much sooner and we dialed up the focus on that specific field and the completion rate. And then we also built a mechanism to inspect how we actually made contact with that economic buyer or do we have an indirect connection?

12:19So like that deeper level of intelligence, we can do that deal by deal in our enterprise segment. We do sell into the Fortune 500. But to your point, we're doing hundreds of deals a month with startups. you can't do that deal by deal. We needed the machine to be able to inspect that and tell us if we had access. That has really helped us get much more realistic about if a deal is going to close in period or not. I had reps that were creating opportunities and they were putting in deal values on opportunities the day that the opportunity was created before they even met with somebody. And so I'll never forget, I was looking at our pipeline coverage and it went up dramatically.

12:55And I was like, what happened? And I saw one of my reps had booked a meeting with Comcast and they put in$500 ,000 on the deal value. And I'm like, dude, you haven't even met with this person yet. And so he put in place, okay, you have to have gotten to a certain stage before we put the deal value in and start counting that. But that was a mistake that I made. I was reporting on data that was really different than what matched reality. That's a very micro, small example. I'm curious about other places where you see this happen, either in your business or in other businesses where leaders can and need to put some control around the data integrity of what they are reporting on or basing decisions on?

13:35Yeah, this is a deep, deep problem. And I will tell you, this is one of the biggest things that we struggled with on this journey to create a machine that actually works for us in this way. We had data integrity problems at every level. We had all of our account data. It was slop. We realized as we got into this and started doing analysis, that was our first thing that we recognized was, oh, my gosh, like our account data is slop. Our contact contact data is slop. We don't have the right governance in place. We just and then it was like, oh, my gosh, humans have entered all of this deal data. We don't trust it.

14:13So mission one before we could make the machine work was to ensure that we had a system to protect data integrity. So I had to make a key hire on my team. And this is to lead my GTM systems team. You know, that team used to be a team of system administrators. That no longer works. You need like an actual engineering and product organization now. I've got a systems architect who leads my systems team. He's the one that took this project on and really reinforced both data governance and data integrity. He rebuilt our entire account data layer. He's currently rebuilding the contact data layer. He worked with our data engineering org, and that's when we started pushing everything to snowflake with real governance.

14:57And then you sort of get to the deal by deal. And this is where you do always have humans in the mix. The data is never going to be perfect. And this is what we use forecast for. So in our forecast cadence, every month, every week, we're looking for the patterns you talked about. So did we miss something? Is there a layer where we didn't have a control or we didn't catch something? And when we catch something, we try to build automation to catch it going forward. So that will forever be iterative. And the economic buyer thing was one example. But to your point, sometimes it's like, oh, people are putting in deal values too early or deal values that are speculative.

15:38Or, you know, it's we in some cases, one thing we realized is we were very single threaded on deals. So then we started inspecting for how many contacts do we actually have associated with this account. Every week and every month, we are looking for new ways to institute additional checks that will either feed into a gate that will force the rep to do something differently, or it will feed into a score so we know something is off and it'll throw a flag that the manager can then inspect. And that is a very dynamic system. We also built an ICP score and we use that ICP score to when we built territories to tier those territories.

16:17So when a rep gets their territory, they've got tier one through tier three accounts and then they've got un-tiered accounts. The whole hypothesis here is focus them on the accounts that are most likely to convert. Well, what we learned this year is we saw our reps, particularly in our mid-market segment, were actually getting tier threes to convert at a pretty high rate. And so it was clear we had gotten something wrong here. And in a way, we had artificially limited our addressable market in a way that actually wasn't serving us. So we ended up rebuilding the ICP score and we built a different playbook because what we learned is that our traditional deals that are large and like we want to pursue, they do end up in tier one or two.

17:04The deals in tier three, though, are great like beachhead land deals at great enterprise and mid-market logos. We want those, but it's a different playbook. So then we use that ICP score to recategorize accounts and help reps understand from day one of a deal, am I pursuing a large platform deal or am I pursuing a quick land beachhead? And then they can run a different playbook. And we've actually seen not just like the top line results improve, but deal cycles shorten in a very positive way because of those insights. So, Stevie, I want to ask you, I want you to pretend that I'm a sales leader listening to this and I'm like, this sounds fucking awesome.

17:41I haven't instituted any of this. Could you give me the use cases that you would recommend that person prioritize rolling out? And maybe like the one, two, three steps of how they can at least start taking action on these things. Yes, I absolutely will. And what I will tell you, the encouragement I would give to anybody who hasn't started is this stuff sounds complicated. It's actually really not. and it is best to start from day one. You don't have to be a huge team and company with a lot of revenue. It's actually more effective to start when you're small with this stuff. And these small things can be super effective.

18:21So what I would start with is, one, do make sure you've got great data governance in place from day one. You will save yourselves a lot of trouble. And that is basic controls over how accounts and opportunities are created, how contacts are created. Like start there and don't treat what you've got in CRM as static. The world is super dynamic. So get yourself multiple data sources, you know, go out there and use something like a crust data in addition to like a clay, in addition to a zoom info and build yourself a system for dynamic data. That's kind of day one. And you can do a very simple version of that.

18:58Then you want to start to get to how can I really identify that, that addressable market quickly. Now there are systems out there that will make this very easy for you. Clay is a great system for this. You don't need an engineer to go build a simple clay table that will give you not just sort of a targeted list of what accounts to go after based on your ICP. You can build a basic ICP score with clay. You can go identify accounts that fit into that ICP score. And then you can do outreach. Then you can also build a clay table to get yourself basic signaling. So when somebody does something that is relevant to your business, it will flag for you and you can reach out.

19:39That can be basic intent signals. It could be they visited your website. It could be they hired somebody with a relevant title that's relevant to your business. This is something like I spent a day about a month ago and built a very sophisticated clay table to do this in about six hours. This is not something you need to take months to do. You don't need an engineer. Like you can sit down as a sales leader and build this today. And that signaling system, again, don't need to stand up a backend. The way I've done this is I've set up the clay table. It fires off alerts that go into Slack and get those real time alerts in Slack.

20:17I've also built a canvas in Slack that gives me a little bit more of an ongoing sort of briefing. And that gives me my focus areas. So you can use the tools you've already got to build these very simple signaling systems that will make you way more effective, especially when things are changing in real time. So I would start there. That alone is going to give you a huge head start over lots of others. Today's show is brought to you by Proposify, the proposal management software designed to make every deal a closed deal. When you send a proposal to a prospect, include a video of yourself walking through the proposal because it's going to be shared with stakeholders beyond just your champion.

20:50You want to make it easy for those other people to digest, and you want to be able to control the narrative with your presentation. And bonus, Proposify data shows that when buyers watch the video, it increases your chances of winning by over 3x. So do not let your proposals become a disappointing plot twist. Get our proposal success guide free in the show notes. Today's show is brought to you by Ambition, the coaching and performance platform helping sales leaders turn metrics into action. Did you know that sales orgs where the majority of reps are coached weekly are twice as likely to see high quota attainment than those who don't?

21:19and that is from Ambition's new state-of-sales coaching report that also found teams using a system like Ambition coach almost 60 % more frequently than those who don't have one. Now, we built a toolkit with our friends in Ambition on how to actually use data to coach your team. Get it for free 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?

21:47Now, 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.

22:04Stevie Case: When we're talking about pipeline, that your third takeaway becomes more interesting now because, okay, I'm going to have my reps hit their activity metrics. that's going to create a certain quality of pipeline. Then I have these other people that aren't hitting their number. And I think our normal way of dealing with that is correction, not inspection. It's like, you need to make more phone calls, Bobby. What's going on, Bobby? Make more phone calls, not Bobby. What have you tripped into that's causing you to make less phone calls, right? So talk to me about like, that's a pretty big mindset shift for a revenue leader.

22:38Stevie Case: Correction is easy. Inspection requires work and changing a bunch of stuff. So what happened? What's the story? Why would you all of a sudden start doing that? You know, I think that the key here is really understanding for each individual. And this is possible now with AI. You can really get deep on individual plans. What is working for that individual and why are other things not working for them? And I'll give you an example of this. So we had a guy on our team totally missing his activity benchmarks and was crushing his pipeline targets. We went super deep into what he was doing. Turned out what he was doing was deeply leaning into a partnership with one of our partners.

23:22And so we inspected how he was doing that. And it turned out like he had networked with that partner in person. He had gotten a bunch of their reps on the phone and done count mapping with them. And none of that was showing up in his activity metrics. But he had almost created like a monopoly on opportunities from that partner for himself through his own relationships. That playbook was so good that we ended up taking that and teaching others to run it and to do it at scale. And then we created better ways to track the deals and ways to actually track the activity. Same time, we've had folks who are missing the activity benchmarks and missing the pipeline targets.

24:00What we'd like to do there is go deep into, there's always something working for these folks. And sometimes they'll have a story for you about, oh, well, I'm not hitting the activity benchmarks because I'm really busy writing super personalized emails. That's my style or my style as I go to events. in those cases, you've got to look really deeply at like when they did produce successful opportunities, where did they come from? What worked about it? And how can you help them amplify that rather than trying to like course correct them onto like suddenly you're going to put somebody on the phone who's not great on the phones.

24:35Look at what they're good at. If it is events, great. How can you do more of that? How can we help you go bigger on that? Because you still have to hit your pipeline targets. And if you're pursuing something that cannot generate that level of volume, then you got to challenge them and give them, okay, maybe there's, you can do that, but maybe there's a second path you need to add that'll help you create more.

24:54Stevie Case: So you're, you're saying to them, Hey, I'm going to look first. And if the results are down, do you immediately dismiss what they're doing? Or are you taking an extra layer of inspection? We are absolutely taking an extra layer of inspection. It is like everything has changed in the world. So we are seeing the things that work to create pipeline change. You know, we email barely works anymore, even though we track email sent. You know, what we see is events are working. Real world events are working. We're seeing, you know, personal introductions and working of your network working. Partner source is working.

25:34Social engagement and not just like I'm going to fire off like a cold, you know, in mail on LinkedIn. This is like, you know, if you're working to build a relationship with somebody over social, that's working. It's the humanity. It's the stuff that sets you apart from the robots. And that stuff can be harder to track. And the reality is like, even of that human stuff, what works is changing month to month right now because the landscape is so dynamic. So you got to pause first and really deeply inspect. is it a lack of effort or is it that they are pursuing a different strategy that's worth consideration?

26:09Stevie Case: Are you taking what you're learning from an individual and let's say it's really working like this partnership thing? Did you stretch that to the whole team or did you just say, hey, Bobby, you can keep doing the partner thing because it's working for you? Like, how do you know when to do a up level of the process or just like let somebody have individual freedom? Yeah, we stretched that to the whole team because two reasons. One is a playbook that works. Two, we know it will scale. We know that, for example, Atlanta, this partner ecosystem is a huge part of our future. There are dozens of massive partners out there that we work well with that have their own sales forces.

26:47They've got hundreds of sellers. and this pocket of proof that this playbook worked was the proof that we wanted to build on. So what we did is we took that person and we put them in front of the team at the next all hands and had them share that case study of here is what I did. I got on the phone with their reps. I met this sales rep through this person and then I did account mapping with them and here's what it looked like and here's how I convinced them to spend the time with me. And then we taught the whole team that playbook. And now we've got dozens of reps doing that and it's working for all of them.

27:20So that's how we kind of turned it from one person's success into a strategy that's scaled. I'm curious the guidance that you have given to your leaders and your reps around where they should be allocating their outbound time. It sounds like email is having a diminishing return. What sort of guidance are you giving folks? What are you seeing work? Yeah, what we're seeing work, number one, is cold calling. I know everybody hates to hear that answer, but man, is it effective. I've got a whole floor here in San Francisco of SDRs, and they are picking up the phone, and they're smiling and dialing.

27:52And it works. It works. And we are spending a lot of time evolving their skills in this area, getting them stronger at the talk track, getting them better at objection handling, understanding our value prop. Like, that cold calling does work. The math is unbelievably favorable, and that has not changed at all in the last year. That remains true. Beyond that, events. Events is a huge winner for us right now, whether that is everything from huge conferences and really getting tight on working the booth and the way we tee up people to meet people. One of my SDRs told me the other day we ran a kind of medium-sized event, and the thing he did was he sent out emails in advance of the event and he sent a, here is a headshot of my rep who's going to be at the booth.

28:42His name is Sean. He's going to be looking for you. Like say hi to him. Here's his story. So he made it feel much more personal and he introduced the human who was going to be at the event. And we had off the charts conversion for that event. And like that rep was ecstatic. Like it was a huge success. And then we're seeing it with small dinners too, But it's that in-person connections. And this is going to pain some people, but you really got to get outside of New York and San Francisco and London with your events. Like everybody in the coastal cities, they're sick of it. It's so hard to get people to events.

29:15Go to Kansas City, man. Go to Dallas. Go to these places where people are excited to get together. The payoff in these large cities that aren't tech hubs is actually greater than it is in tech hubs. You have the opportunity here to like talk to thousands of sales leaders listening to 30MPC. I'm wondering if you can give me the top three things that you think many sales leaders believe to be true, whether that's about sales or sales leadership that you think are wrong and are hurting them more than they help. I'm looking for your top three. So the number one thing I would put on this list that's a self-limiting belief is that building with AI or building these kind of machines is beyond the organization or requires like heavy duty engineering.

30:03Absolutely not true. Like I expect every leader on my team, regardless if they are technical or not technical, if they've never written code, you can build things with Claude Code and with Clay. Sit down and build. if you don't do it, your organization will never change and your team won't buy in. You have to do it. I would say the second is that there's so much noise in the market that it's just impossible to break through because, you know, so many new companies, there's all this slop outbound. Absolutely not true. You have to get creative. You have to think differently. And you just have to like accept that the world is changing.

30:42What you thought, what did work yesterday probably doesn't work today. That doesn't mean nothing is working. So if you can't figure it out yourself, get out and talk to other people. Like that is the way I learn stuff these days. I go talk to my peers. I talk to other companies and leaders and, you know, ask other people. You'll find things that are working. The third self-limiting belief is that this is not going to be popular, but that you have to have a ton of sales experience to be a sales leader. I think that is less true than ever before. I think that this is a moment for people who are unicorns and get product, get technology, can build with AI.

31:22You can lead a killer revenue function with pretty limited sales experience these days. So this is both good news and bad news, depending on who you are. But I would challenge everybody who is trying to grow their career at this point. You have to become multi-dimensional. If you've come up in sales, you need to understand customer success. You need to understand product and you need to understand AI. This is the moment to develop new skills, not to try to just stay on the sales path. Stevie, thank you for joining us. My pleasure. Everybody stick around for a 60 second recap coming up soon. All right, Mark, it's time for our two by two recap.

32:01Stevie Case: What do you got for your two? Two by two, one. You better start with that data layer first. If you don't have somebody that can get your data right. There's no chance that your agents or the AI that you're going to build are going to be worth a darn. Get that data layer straight. That's the first investment you make when you go into AI. And then second is don't just correct. Take a second to inspect. And I think that, you know, looking at somebody who's off their numbers and your first reaction is go make more calls and get on your number. Your first reaction is, is wait a second. Maybe they're doing something different.

32:35Stevie Case: That's cool. And then inspecting that. and then being unable to understand, is that scalable? So you can roll it out to your team or just encourage them to stay in their own level of personal genius. I just love that idea. Yeah, my two were one was a use case. One was a thing that listeners could actually do. The use case that I thought was really interesting was Stevie's team uses medic for forecasting. And when they get on their pipe review forecast calls, what Stevie has done is she set up some sort of automation to be able to go into the call transcripts and pull all of the medic fields and fill those out.

33:06So it is not based off the reps reporting of the news. It is based on what the prospect actually says. And then my last one was a thing you can do. And Stevie gave this story about how she spent six hours building this really sophisticated like clay table that was pulling all sorts of different signals. And the reality is, it's like nobody sat down and said, Stevie, here is your tutorial on this. And I think one of the things that she was even telling us in the pre-show is like, this takes work to learn, but you can start. And I think a limiting belief that she shared a lot of folks have is that this requires you as a sales leader or seller to be uber, uber technical.

33:45When in reality, one of my favorite quotes, this actually comes from Alex Hormozzi, Mark, he says, fear, it's a mile wide and an inch deep. And I would say the same thing applies here, where it is really easy to get overwhelmed. I have felt this, and I still feel this to a degree, by all of the things that you could be doing with AI as a sales leader. That is the mile wide. You look at this pond of all of the things you have to do, and you're like, holy shit, that's way too much. But the first step is just an inch deep. The first step is blocking off those six hours and at least trying. And you will oftentimes find that you get way further.

34:20And the biggest barrier to getting honestly very, very competent at this stuff is just taking the first step into the inch. That's what we got. Thanks for listening, folks. Instead of you helping us out, help yourself out and go take a step into the inch. We'll see you next week on 30 MPC.

34:58Do not let your proposals become a disappointing plot twist. Get our proposal success guide free in the show notes. Today's show is brought to you by Ambition, the coaching and performance platform helping sales leaders turn metrics into action. Did you know that sales orgs where the majority of reps are coached weekly are twice as likely to see high quota attainment than those who don't? And that is from Ambition's new state of sales coaching report that also found teams using a system like Ambition coach almost 60 % more frequently than those who don't have one. Now, we built a toolkit with our friends in Ambition on how to actually use data to coach your team.

35:27Get it for free 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.

35:55and we built a full discovery toolkit with them free in the 30MPC closers hub. There's a link in the show notes.

From the publisher

Our new Social Selling course with Sam McKenna is live! Save $50 during launch week, through October 25. Order here →

Stevie Case breaks down how modern sales leaders can use AI, clean CRM data, and human judgment to inspect pipeline, improve sales forecasting, and rethink outbound strategy.

Learn how to separate real pipeline from automated outreach “slop,” uncover what your best reps are doing differently, and build practical AI sales workflows without waiting on engineering.

🧱 Clean your data before layering on AI. Put governance around accounts, contacts, and opportunities so your AI systems are analyzing reality instead of CRM slop.

🔍 Inspect before you correct. When a rep misses activity benchmarks, figure out what they’re actually doing and whether they’ve discovered a better play before simply demanding more calls or emails.

🤖 Use AI to inspect deals, not replace sales leaders. Pull qualification evidence directly from call transcripts, surface gaps automatically, then use human-led forecasts to investigate the areas that need judgment.

🛠️ Start building instead of waiting for engineering. Block a few hours to create a simple Clay signaling or pipeline workflow yourself. The fastest way for sales leaders to become competent with AI is to actually use it.

You're one step closer to President's Club!

🏋 30MPC Training

🛠 Weekly Tactical Breakdowns

📚 Things you can steal and use today

More from 30 Minutes to President's Club | No-Nonsense Sales

All episodes