Why Every Sales Rep Should Do Pipeline Generation & How to Teach Them

It’s a pleasure, Harry. Thank you for having me. I have arrived.

Probably as a teenager. My cousin Thais was dating a guy who was a manager of a clothing store and I think I was 14 or 15 at the time and I had worked, you know, for several years mowing lawns and raking leaves and doing odd jobs paid by the hour. He decided to give me a shot at the store. He would let me come in on the weekends and sell men’s suits. The commission rate was 10% and the suits were 800 to $1,000, and over the course of a weekend, I could usually sell one suit, maybe two, maybe three.

And so to make a bucks in the air conditioning in the mall was pretty amazing. And I thought, this there’s something to this. Do you think people are born salespeople or do you

I think it absolutely can be learned. I think when people say that someone is born a sales salesperson, usually what they’re referring to is charisma and a big personality, and, I don’t know that those things are necessarily what makes a great salesperson. They don’t hurt, but they’re not the core of it. So sure, having more empathy, being genuinely curious. I think those things help, are innate, attributes that make people better salespeople. But I think most of it is learned. EQ,

Yeah, I think art is what we call something when we don’t understand it yet. People could say, oh, Picasso, that’s art. How does he do it? And then you have, you know, students studying for years and then they break it down. Well, it’s the colors and the shapes or whatever it is that’s the basis of of Picasso’s art. And so I think like anything, there are people who are savants, are gifted, and there are people who can connect dots that others don’t see, but then others can can follow, can learn, and can can replicate those things.

So I think it’s more science than art, candidly.

I think it’s important to think about the job that needs to be done. Arrive at a conclusion, a well formed opinion around whether a candidate is capable of doing that job. A trap and a mistake that people make is over rotating on what they have done in the past and assuming that success in the past predicts success in the future. Certainly, a track record of failures is, is something to to be thoughtful about and to avoid. But success in the past, you have to be able to break down what needs to happen in the future and identify what skills or what attributes are required in order to accomplish this outcome in the future.

And then figure out, almost like take a battery of what this person brings and how much of what they need in the future do they already bring investigate or interrogate what they’ve accomplished in the past, what their life journey is like, and form an opinion around their innate attributes so that you can start to have an opinion around the likelihood of their success in the job that you’re trying to to fill.

a brand new company? We’re

two or three years. Don’t hire a leader yet. Hire individual contributor. First, just hire SDRs and you be the rep so that you get I think for an early stage company, the CEO really has to develop the plays, figure out the message, at least that initial message. And once you have conviction around who do we sell to, what are the personas, what’s the message, then I think you can build an organization around that. Until that exists, I would advise the founder to hire some individual contributors around them, co locate, sit in the same room so you can hear each other, and duke it out and refine the message and refine the plays.

Once you’ve got some conviction that it’s repeatable, go and hire a team around it.

Yeah. And they’re going to be super junior because they’re going to be happy to be at a tech company because it’s probably first tech company they’ve ever worked at, and you’re to have to do a lot of the heavy lifting. You’re to have to train them, you’re to have to remind them that they should wear a shirt to a meeting. opinion But that’s a beautiful part of the journey that I think only a founder can really do well. So we have

I’ll answer the question, but then I’ll answer the question that would have preferred you asked. So I would prefer experience with the type of deal over domain, unless the domain is so specific that it’s going to take a lifetime. if I’m selling some molecular modeling technology and you have to be a biologist to understand it, but outside of that, better to teach the domain and to hire as many of the sales skills as you can. What question would you rather I asked? Yeah, I think when you’re hiring, the thing you can’t change is the innate attributes, the DNA of the person.

That’s where you should spend the most amount of time. Get to understand who that person is in the areas that they can’t change. Then you should have, hopefully, a pretty good idea of what are the skills that they will need to be successful. Once you figure out, okay, this is the type of human being that I need now how many of the skills that they’ll need to be successful do they already possess? And then the skills that they don’t possess, how difficult is it going to be?

How long is it going to be take for them to acquire them? And that is the formula. You can’t change the DNA. If they don’t have any of the skills, it’s going to take a very long time for them to have the ramp. So first the DNA, then the skills, and there’s always going be a gap. So you you need to have negotiables and non negotiables.

I would look for experience at a challenger company. It’s so much harder to operate at a company where you don’t have a big logo that sells for you, that carries for you. Has this person been successful in that kind of environment? Have they had to do their own pipeline generation or have they always relied on SDRs or marketing or partners or what have you? So I would look for a history of self sourcing pipeline generation. Have they sold a product that is of comparable complexity? Have they sold into accounts of comparable size?

Have they sold a solution of comparable price? Which means it would have multiple stakeholders, which means it would require a business case, which means more politics would be involved from the customer’s perspective. Have they sold a solution that involves a comparable number of personas of stakeholders? Have they sold a solution in the same general domain? Meaning, am I selling into IT and they’ve only ever sold business apps or vice versa? Some of those for me are nonnegotiable, some of those are negotiable, but if we have a lot of gaps, then it just means my ramp time is going to be longer.

Yeah. I’ve spent almost my entire career at challenger companies. If you’re going to disrupt a marketplace, the risk associated with hiring someone that hasn’t been at a challenger company is really, really, high. So that one is a near nonnegotiable. Pipeline generation. Hiring AEs that have not built their own pipeline, that one is non negotiable because if they say they will, if they say they want to, they just don’t know how hard it is or they don’t remember. Maybe they did it as SDRs a long, long, time ago.

That’s a really big risk. That’s a kind of a non negotiable. Maybe they’ve only sold into mid market accounts and they’ve only sold deals in the 50 to 150k range, 150k range. We’re going to put them in enterprise selling 500k deals with many more stakeholders. But again, we think they’re really smart, we think their drive is really high and so we that’s more negotiable. So those are those are some of the things that I negotiate on.

So we’re reaching a conclusion or we’re developing an opinion on where they are in terms of maturity on the skill through interviews and back channels. But then I’m a big advocate for at the end of the process, we call it a challenge. We have an event where they have a couple of days to go think about some questions, prepare a presentation and come back and present it. But that’s more of a validation around the decision at the end. It wouldn’t be fair to a candidate to do that early on because it does take work.

And so once as a hiring team, we develop conviction around a candidate, we’ll do the challenge just to like, make sure we didn’t miss anything.

I think it’s human nature that we tend to index around our own strengths. When we see pieces of ourselves in someone else, I think it’s very tempting to become enamored with that and then to miss other gaps. And so if you’ve got, in a hiring chain of command, you’ve got people that are quite different. One person that’s super charismatic, has super high EQ, Another person that’s super process oriented. The process oriented person might miss that this person is a little awkward, or the high EQ person might miss that this person is not very tight on process.

And so that that would be one area where you have disagreements.

Yes, but for a different reason. So I do think that having multiple reps co located is far, far, better. You know, at MongoDB, you mentioned that you talked to Dave. At MongoDB, we hired a lot of people and our attrition was higher than we wanted it to be. And so we did a lot of analysis on attrition. And what we found is that lone rangers, and we meant that meaning when we have a single employee in a, you know, if we have a single rep in a city and no one else at MongoDB lives in that city, their attrition rate was like four times higher.

It’s so hard to ramp when you’re all by yourself, when that little tiny, that quick question that would have taken 10 seconds to lean over and ask the person next to you, when that now requires you to schedule time with someone and forget it. So the likelihood of failure is so much higher. So sure, the competitive aspect is part of it, but I think the bigger part of it is just helping each other. So I’m a big advocate of hubs. And so I think at minimum you want two sales.

If it’s a company, if it’s a if it’s a product where you have a sales engineer, two salespeople and a sales engineer, that’s like minimum profile for a hub.

There’s a few reasons. Reason number one, more pipeline, the more the better. Reason number two, think about when a salesperson gets stuck in a deal. Why are they stuck? They’re stuck because maybe they’re too low and they can’t get high, or they’re in one division and they can’t get over to the other division. How do you get unstuck? PG into the person that you need to be to be at. You PG into the more senior person. You PG into the other division. And so the ability to generate pipeline will lead to a higher win rate on existing business.

What else? Well, if you have an organization where pipeline generation is outsourced, let’s say, to another role, it’s a natural tendency for salespeople to get more and more finicky around what inbounds or what leads are worth their time, are worth working. And so the next thing you know, if take that to its logical conclusion, and I’ve seen this, I won’t mention the company, but I’ve seen a company where the AEs said, hey, the definition of a lead worthy of me working is the customer’s ready to see a demo.

They have agreed with the SDR that if the demo goes well, they want a quote and they’re ready to buy after that. So that’s like 80% of the sales cycle is done and the sales so and so now in that kind of a scenario, you need such a huge investment in marketing and such a huge investment in SDRs just to meet that bar of the expectations of the sales reps. Whereas if sales reps are doing the work to generate their own meetings and their own pipeline, man, when they get pipeline from their SDRs or from marketing or from partners, they’ll treat it like gold because they know how much work and how hard it is to get that.

And so your conversion rate on your other, your non AE, sources is a lot higher.

That’s right.

That’s right.

fault. That’s right. So I think the the way to orient it is the AEs are responsible for generating the pipeline that will support them being successful, them hitting quota, then anything they get from the other sources is a gift, a cherry on top, is extra.

That’s the environment under which the AEs operate. Of course, the SDRs have expectations, you know, on them. And so you need to have a system where there’s accountability at every level and there’s expectations and there’s performance management.

Love Chris.

Yeah. First, you have to agree pipeline generation is good. You can also say that roughly excellence in pipeline generation equals excellence in sales. Someone who’s got a massive pipeline that misses some things in the sales cycles, they’re probably still going to do very well. Someone that executes beautifully but doesn’t have enough pipeline, they’re going to miss their number. And so that’s the first thing. Let’s agree pipeline generation by the AE is worthwhile.

If they agree with that, and I feel very strongly that that’s the case, then roughly a third of your time, 20% of your time, one day a week is dedicated to just outbound cold calling. then there’s another probably 10 to 15% of your time that is devoted to prep for the cold calling and follow-up from the cold calling. So that’s kind of how you get to the 30 how I get to the 35%.

Yeah. so remember, I’m not hiring folks that haven’t had that haven’t had to do it and been successful doing it.

It is. Yeah, it is because the likelihood, if they’ve been successful not having done pipeline generation, when they get in that dark, lonely room, and what I mean by the dark lonely room is making the phone calls and saying, wow, that is the 19th phone call where no one has picked up. And I’ve left the same fucking voicemail 19 times now. If they haven’t done that and they haven’t been in that lonely place, the likelihood that they are willing to make that 20th call is low.

Even if they were willing upfront, when they actually get into it, you have to have been through that journey and seen the other side. The other side meaning the joy of landing that big meeting, the joy, the fulfillment of creating an opportunity and closing a deal and knowing that deal exists because I PG’d it. That company solved this problem, generated this value because I invested in them. There’s a pride that comes with that, that if you haven’t had it, you’re probably gonna you’re probably not you’re probably gonna give up on the journey towards PG excellence.

That’s crazy talk. You strongly disagree. Yeah, Yeah, Yeah, I strongly disagree. cold cooling still works? Absolutely. Absolutely. But I’m really glad that other companies don’t, and I hope a lot of those companies are our competitors.

Yeah. I don’t know that you can yet, but you will. But really the most effective means of pipeline generation is outbound cold calling, the human voice based interaction over the phone. The emailing is you do it, that softens the field, that creates some familiarity so that when they pick up the phone, they’re like, oh, Harry, why does that sound familiar? And maybe they don’t even know why it sounds familiar, but it sounds familiar because they’ve received a bunch of emails and those emails had your name on it.

They landed with some sort of a positive aura around them. I’ll give you an anecdote. There was a sales rep who I love named David Boyle, and he was calling on Dun and Bradstreet, and Dave is an epic PGer. And so we were at a company, Oblix, and the pinnacle person to talk to at Oblix is the chief security officer, chief information security. We’ve got a meeting with the CISO at Dun and Bradstreet, and we’re in the lobby. The CISO had like a little a little, a lobby just for the CISO’s office.

This is, you know, a few years ago. As we’re waiting for the CISO, Dave is in the hall doing PG, leaving voicemails, pacing up and down the hall. He’s looking every every once in a while to see if, if his assistant has called us in. We go in, we meet the guy, and before we even start the meeting, he says, it must be nice to be able to just call a CISO like that and have him bring you in. You’re welcome. So tell me about your product.

So we go through the meeting, we tell him about the product, and on the way out, I was like, Dave, really? Just one call? It’s like, that guy’s got no idea. And he opens up his book and he shows me. He had sent him 11 emails, eight phone calls. He had become friendly with his executive admin. He convinced the admin to write a post it note and put it on his screen. Says, Dave from Oblix wants to meet with you because of xyz. The guy was on another call, read that, nodded and that’s how we got the meeting.

He had no idea about the 18 other touches that had preceded that. And so that’s what happens. We have to break through the noise. People are getting lots and lots and so that’s where email’s good and social media and all the other things. But most meetings are set, like two thirds are set as a cold call.

Half? Of the world of sales reps? Yeah. Oh, no. less than 10%. It’s elite. It is highly, highly, correlated with elite salespeople that have the ability and the tenacity, the willingness. It’s hard work. Is it Do you people then

Sure. Better to start on Thursday. There’s kind of a wheel. Sure. You guide the way. Alright. right. So before I get into the weekly cadence, let’s say for the quarter, I’m an enterprise salesperson. I might select from my territory 20 top targets for the quarter. And I’ll sit down with my manager the first or second day of the quarter and I’ll validate. Hey. are these good? Yeah. No. you missed this one’s not very good. Great. Okay, Now I’ve got 20 accounts that I’m gonna go after over the next three months.

On a given week, I’m gonna focus on one or two accounts, maybe three if they’re on the smaller side. So let’s say an average of two. I declare those on Thursday. Those are my focus accounts for next week. Thursday night, I declare them, which is just I click a couple of things in Salesforce. Now, over the course of Friday and over the weekend, as a salesperson, I do some research. What’s the research? I look at what the execs are saying on social media. I read the 10K.

Now you can use AI to make a lot of this stuff so much better. I research the company. I look at their job postings. I look at what you might even go in looking blind and see what engineers are saying, see what people are griping about. I try to get a sense for what’s really going on inside the company. And then I develop a hypothesis about something that I think they care about that we can impact. Maybe I develop two or three hypotheses. This is for the account.

Then I go in and I say, okay, let me come up with let’s say it’s two account. Let me identify 25 human beings in that account that based on their title, based on their LinkedIn profile, I think are relevant to what I sell. And let me capture those 25 names, their email address, their LinkedIn. I’m going to check to see if I can find them on social media. And then I’m going to go into some database and find their phone numbers. So I’ve got their mobile numbers, and I do that for two accounts.

So I’ve got 50 names. For my 10 most important people on those 50 names, I’m going to also now investigate the person. Have they been on a podcast? Have they written a book? Have they written a blog? What do they care about? And I’m gonna develop a hypothesis to a conversation starter for the top 10 of those people. Okay, that constitutes PG prep. So I’ve got two accounts. I’ve got, let’s say, two or three hypotheses per account. I’ve got 50 names with all the requisite information, email, phone number, and I’ve got hypotheses per contact for my top 10 contacts.

I can get some help in my prep. Where do I get help? Marketing on Fridays at noon is going to send out a PG passport, news of the week. Everything that happened this week curated for use or reuse in the PG setting. So we had this new release. let me boil that release down into two or three sentences that can be read or can be included in a in a PG email. There was a new case study. Here’s the case study, but here’s like a, again, two or three sentences.

So marketing sends out this PG passport on Fridays at noon. Then the manager knows what the focus accounts were because they were declared on Thursday, takes that PG passport, takes their experience and forwards the PG passport back to their team with some advice. Hey, Harry, I see you’re going after this account. This would really resonate with them. Hey, Jill, my neighbor works at HR in this account. I I asked her, she said she’d be willing to take a call from you to validate your contacts and make sure those are the right people.

Okay, so now the manager’s involved in PG prep.

Yeah, it takes takes an hour or two. You know, remember, the manager is in the role because they know they know what they’re doing, they’ve got some experience. And so it’s not to say that the manager going to have a really great insight for every single focus account, but they’ll as they scan the 10 accounts, there’ll be two, three, four accounts where they have an idea. Oh, Barclays. I read an article two years ago. Let me find it. Or I heard something on Bloomberg Radio. Let me go find it for you.

So that’s the PG prep. So the reps got the reps got help from marketing, help from their manager. You know, You might even have a team of data analysts that help with the PG prep. I’ll talk about that in a moment. Then Monday morning, there’s a conversation, a one on one conversation between the manager and the AE to review their PG prep. And this is where the manager really digs in to make it better. Obviously, it’s an accountability event to make sure that the prep was done, but more importantly, it’s about making the prep even better.

Hey, I don’t think you’re aiming sufficiently high. You don’t have the CIO in here, you don’t have any senior people. or they’re too high. Jamie Dimon is not going to respond to an email about, you know, cloud cost management. Adjust the PG prep. Monday afternoons is a great time to do training, especially training that’s related to PG skills. Hey, let’s role play how to talk to this persona, or let’s role play how to describe this product’s value prop or let’s role play whatever. And so we’ll meet up together on a Monday afternoon, do some role plays with feedback and the opportunity to do role play again, etcetera.

And so then Tuesday morning, when the butts hit the chairs, ready. We do have a quick round robin just to get everyone excited and ready for the day. But remember, they’ve prepped, they’ve trained yesterday. And so Tuesday is like a really important day. We’ll bring, you know, cater meals meals into the office. There’s a real camaraderie. We laugh when somebody gets hung up on, we applaud when somebody, you know, scores a meeting. We hear each other. This is where the lone Ranger becomes terrible. They’re all by themselves.

All they hear is themselves. You’ve got a room full of people. Hey, Don, that was really great. Can you say that again? Let me write it down because I’m going to use that. Hey, Jimmy, I would have said this a little bit differently. So they help each other and then at the end of the day, hey, let’s all go get a beer at the pub next door. Let’s celebrate the day, let’s laugh together. Let’s really develop pride because we know that most salespeople on the planet are not doing what we do.

couple other things. So, yeah, Thursday we declare. Friday and over the weekend, we prepare. Monday morning, we review the preparation. Monday afternoon, we train. Tuesday, we do PG all day. And then obviously throughout the week, there’s follow-up, there’s harvesting. And then I love to do a a wrap up on Friday. So I typically run that myself and it’s the whole sales team. And we celebrate the PG success of the week. stories of success. We tell stories about successful meetings. We also tell stories about opportunities that have been created from previous week’s PG, and it really builds, I think, an enthusiasm, a belief, and it really. and it reinforces this thing we do that’s so important, so powerful, but also so hard.

And so that’s kind of the circle of life, if you will.

In the early days, you know, the first time I was ever exposed to it was at Parametric Technology early in my career, and we called them power hours. Whatever, Thursday at 9:00am, everybody be in the office. And so Thursday at 9:00am, you’d pull up act, this is before Salesforce, and you just start making cold calls and it wasn’t very structured. And the problem with doing just an hour is you can easily go for an hour and never talk to anyone. And so you need that positive reinforcement of a conversation, even if it’s a conversation that doesn’t land a meeting, because you learn from that.

You think, oh, if I had handled it differently, I could have gotten the meeting. But if you do, if you do a bunch of cold calling and not zero comes from it, it’s really hard to bring your A game for the next power hour.

Well, I think there’s a risk of over obsessing on the number of meetings booked. Obviously, that’s the easiest thing to track. And so typically if someone if someone is doing good PG, they should be able to, on average, get two meetings in a given week. Sometimes people will get more, sometimes people will get less, and they might get one or they might get zero, and still they did a good job. It was just an unlucky week or a particularly tough account, and sometimes, you know, people hit a hot streak and they’ll get four or five, but two to two to 2.5, that’s kind of the sweet spot of like really good PG with the process that I just told you about.

But the thing to really obsess about is a little bit further down the, you know, down the line, is there qualified pipeline coming out of it?

what?

The numbers that you just you just shared doesn’t take into account you had a paying customer and you did some expansions in your paying customer. You had a partner bring you a lead that was like 70% sold. So that is purely just the rep going cold into a, you know, into a completely green territory. There’s to be some good stuff, some some low hanging fruit.

Yeah. Or maybe it’s four to one on yours and you can be at six to one.

Depends where you are in the journey. Early on when product market fit isn’t isn’t really good, yeah, it might be three to one. You know, the rule of thumb, once you’re scaling, you know, you want be at five to one or better.

Oh, that’s a good question. Certainly down to 50k, maybe below 50k probably, you know, starts to break down because down to 50k, k, you know, your reps are to be earlier in career and so their their OTE is not as high. And then, you know, when you’re up into the enterprise level, then you know, your your your average deal is probably more in the 2 to 400k range. It certainly works there.

We are not lacking for pipeline. The thing we’re lacking for is ramped salespeople that can go that can go pursue it. I think How long do you give someone to ramp? I think what you’re asking is when do you sort of declare you know, failure and part ways? I think ideally what you have is a series of milestones over the course of someone’s journey that start in the first few weeks. They go to training. They prepare for training, they go to training. How did they do on the entrance exam?

How did they do in their role play? How did they do in the final exam? Were they able to get meetings coming out of their first, you know, boot camp? Were some of those early meetings converting? Are they able to get to an economic buyer in their third month? So there’s all sorts of milestones along the way. And so if you sort of decompose a salesperson’s ramp to productivity, then what you can do is you can identify at any moment, hopefully very, very, early if they’re going off course and you can figure out why.

A lot of companies, they’ll start to worry about someone that hasn’t sold at, you know, nine, ten, eleven, twelve months. And so then they’ll make a decision to part ways at 18 months. That’s so expensive, not just in terms of

Yeah, you’ve got milestones along the way. And so if they’re achieving the leading indicators to success, then we figure out why and we try to fix it. and if it’s fixable, great, they’re back on track. And if it’s not fixable, then, you know, that means they’re in the wrong role or at the wrong company. and so, yeah, we can we’ve parted ways with people at boot camp. It was It was clear in their first month that, we’d made a mistake and, we apologize for that because we hired them.

But why wait nine months and waste their time and waste our time and opportunity costs?

Yeah, the mental model that we used is we started with this hypothetical fully ramped salesperson, this individual who has every single skill, every single knowledge needed to be successful, you know, in the full gamut of selling our solution. Then we said, okay, let’s break down all those skills and knowledges into competencies that we think can be learned in three hours or less. Then let’s group them by what is the ideal modality to learn it. Is it something that they can learn on their own? Is it something that they can learn on a Zoom call?

Is it something that they really need to be in a classroom to learn? Great. Now let’s look at the ideal sequence. What’s the right sequence so that we can get them to land a good healthy new logo as early as possible. And then what we did is we’ve created a learning journey that really spans about almost nine months. And it has three week long trainings, a boot camp, an intermediate, and an advanced. And then coming out of boot camp, there’s a roughly half a day, there’s a three hour remote session that they attend with the same cohort that they went to boot camp with that goes deep on one competency.

And so what we end up with is people coming out of bootcamp able to do pipeline generation. They’re able to have a conversation, start meetings, they’re able to do discovery, do a good first meeting. By the time they get through intermediate, they can land a new logo with our core product. And that’s really the key. Once somebody can land a new logo with the core product, the likelihood that they’re going to be successful is very high. even though they don’t have some of the advanced knowledge or the advanced skill.

So that’s kind of what we’re doing.

You mean just the sales cycle? Yeah. The sales cycles are not that long. It’s about four months. Four months. About 120 days.

Soon, early. We have a messaging framework that we’ve built and a lot of times salespeople get it even before they start. So they’re able to read, understand our value prop. It’s got sample questions in there, proof points, cetera. And so they can be on the phone in the first couple of days on board, even before they go to boot camp. They typically go to boot camp maybe week three, four, but they’re on the phone even before. And then certainly at boot camp, they’re doing pipeline generation and they will typically have set their first meeting for sure before the end of boot camp.

Yeah, you wouldn’t be able to afford from financial perspective, but also just in terms of bandwidth, you wouldn’t be able to afford to build that. And frankly, you wouldn’t know what to build with an early stage. That’s why I go back to what I said before is for a founder, let’s say a series a company, I would get some really smart, hardworking, enthusiastic individual contributors and go build it, And you’ll be able to build your enablement after you’ve closed, you know, 10 or 20 customers and you’re like, okay, now I’ve closed, let’s say 20 customers, which means I’ve probably failed to close another 60 customers.

So I’ve got 80 sales cycles of experience. Now I can identify the things to do, the things not to do, and I can build V1 of my training based on that. And maybe that’s just two or three days.

I’m a big fan of the Medpick methodology. I know you had Mark Goldberger on here. I think he talked about it. That’s the soundest framework that I’m familiar with for deal qualification. I think Dan might have talked about it as well. When to do it. You do it when you need it. What do I mean by that? When it’s great to do it early in a sales cycle when it’s messy and there’s, you know, so many different strings to pull on and trying to come up with a strategy.

It’s also great to do it late in the sales cycle where, man, we’re forecasting this deal we better not miss something. Let’s make sure we didn’t miss something. So I wouldn’t say there’s a key moment to do it, but the real, the beauty of operationalizing a qualification framework like like Medpick the real beauty of it is that any given sales rep who, let’s say, is going through a deal review, they are learning the concepts in the context of this one deal, but then now they know that concept and they will apply it to other deals.

So you know that MedPick is working when you see salespeople talking to each other without a manager involved and they’re using medpick terminology or you see a sales rep grab an SC, hey, can I run this deal by you and just like try to poke holes in it. And the conversation is in that Medpick framework. When qualification just becomes part of the culture and it happens all by itself all the time, that’s kind of where you want to be. And then the manager is just spot checking or When you have pipeline

Yeah, I’ve definitely seen that happen. It definitely, a team can get in a funk. I think the best thing to do is just to stop. Let’s all get in a room and let’s talk about it. Let’s talk about how we’re feeling. Typically what’ll happen, as a manager, one of your responsibilities, I think, of a great manager is maintain intimacy with the team, intimacy with how they’re feeling, intimacy with where their skills are at. And so hopefully the manager can get ahead of that and see it before it happens and interact and course, interrupt and course correct, But let’s say, you know, it gets to a point where the team is in a funk and you can just kind of smell it.

You can smell it in the air. Hey, let’s stop. Let’s let’s get in a room and let’s all talk about it and let’s talk about how we’re feeling and let’s reach a conclusion. Maybe the conclusion is they’re not bought in. They don’t believe that this even works. Let’s talk about that. Let’s talk about why PG is important. Or maybe they believe it’s important, but they just don’t believe that they can do it. Okay, maybe it’s a training issue. So getting to the bottom of what is the driver for for their feeling the way they’re feeling and fixing that.

How do you

Yeah, so I have a different opinion about the playbook versus verticalized teams. Now, let me caveat this. If you have a solution where it’s just radically different in one, like ERP, how you implement ERP at a company that, at a paint company versus a software company is completely different, so much so that it would be unreasonable to ask a sales rep to be able to do both. So centralizing knowledge around what’s going on in an industry so that salespeople can be more relevant more quickly with accounts in that industry, I think is absolutely a thing to do.

Even if you have a horizontal solution, like a technology solution, IT infrastructure, the challenges, the things that customers in a particular vertical cares about are very, very, different. So empowering salespeople with that is really valuable. Verticalizing the sales force when you have a horizontal solution, cuts against meritocracy because there’s typically going to be some verticals that are better than others, like maybe, oh, financial services is just like the cat’s meow. What a great, you know, it’s such a great fit. And so, hey, the team in New York, are they amazing or do they have all the banks?

Mixing up the territories, I think, is really good for, meritocracy and for having a fair distribution of opportunity. And so, like I said, the exception would be if the solution is just so different that you have to do it, then do it. But if you can avoid it, I’d rather have salespeople that have a mix of the really great ICP and then the ICP that or the customers that are a little bit harder to sell to.

You mean that we’ve oversold customers? Yeah. I do think that a lot of that has worked through the system already. Companies that I’m a little closer to, I think most of that seems to be the trough, let’s say, is behind us. I do think that the future, whether it’s a consumption business or even if it’s traditional SaaS, having sales reps truly involved in driving customer outcomes and creating customer value, I think is really healthy for the long term viability of a company.

The days of, you know, the big sales rep with the fancy suit that comes in and does the big deal and then walks off to another to another, you know, to another account, I don’t think that’s healthy and I think those days are long gone.

I think that using discount to close a deal that was not otherwise works. If it’s a considered purchase, there is either a champion that is willing to advocate for this purchase and advocate with the economic buyer for this purchase versus all the other things on the economic buyer’s plate. Like either that champion exists or doesn’t. And whether that cost 250k or 200k is not going make the difference. It’s binary. Now, once you get a decision to buy, there could be budget constraints and maybe, well, because it’s $2.50, we can’t do it until next fiscal year and we make it 180k and they can do it now or we let them ramp in.

I’m not like against discounting, but to use it as a lever to manufacture a deal, I don’t think really works, not in, you know, considered purchases. Maybe with a commodity where I’m gonna need it anyway, I could buy it now, I could buy it later. Sure, you could discount your way into that, but So

What do you say to me? Well, having a deal slip is painful, and to have pain and not extract the learning is really is to squander an opportunity. Pain is a great teacher. If we revel in that pain and really analyze, we have to figure out, okay, why why did the deal slip? And the answer has to be something we failed to do or something we did that we shouldn’t have done. What must we learn or what should we learn, and what’s what must we do differently in the future?

That’s the key thing. Of course, deals are gonna slip. We’re gonna lose deals. you know, shit happens. Let’s figure out why it happened, what we learn, and and and let’s get better as a result.

good question. I would say make sure you know what you’re walking into. What I mean by that is if a company is looking for a new CEO, that means that there’s a problem or a set of problems that need to be solved. Do whatever diligence you need to do to gain a high conviction that you understand what those problems are and then honestly map your abilities and your experience against those problems. So if you’re a go to market leader and you assess and you reach the conclusion that the problems are largely in go to market, could be a great fit.

If the problems are outside of go to market, then look in the mirror and really ask yourself, am I the best person or am I able to solve these problems? That was the that was the challenge, frankly, that, that I encountered in my CEO journey. I thought I was walking into a to a situation where the primary, you know, the problems were mostly go to market, And sure, there were opportunities for improvement in the go to market realm, but the company needed to mature and to refine its product to really land on on the proper product market fit. the reality is that, you know, I didn’t have I didn’t have a toolkit, I didn’t have skills to guide the company.

So I wasn’t particularly effective at guiding the company through that period of refining product market fit. And you know, it took me a while to figure that out. Unfortunately, it was a painful experience. I brought people I care about. Keith Butler came over to be the head of sales. And through that journey, we did make go to market better, but we found that there was a more fundamental, you know, problem around the product and I wasn’t the right I wasn’t the right person to solve that problem.

Can I ask you,

It is a podcast after

One that I have made that was particularly painful was to hire someone based on relationships. It was early in my career and I was at a startup and this person was very successful at EMC. The numbers that they had posted and the relationships that they had were so senior, I thought this guy is just to light it up.

I brought him on and I spent the first three months going on these fancy lunches at steak houses in New Jersey with these very senior folks who had, who were completely irrelevant to the product that we sold and fancy lunch, And the conclusion of the fancy lunch is, oh yeah, I’ll ask so and so who’s the person you need to get to and see if they’re interested. And the vast majority were not. and so nothing came of it. And what I realized is that this individual lacked the skills to go build pipeline.

He just didn’t know how to do it. He was a relationship seller, a competent guy, a hardworking guy, but the skills to actually go and call a stranger and deliver a value prop and have that resonate and secure a meeting and then come in and do a great meeting. All of those skills, he didn’t have them and so that was painful because he was expensive and I had advocated for him and we had to go like outside of the standard hiring, you know, parameters to get him.

That was one that was that was painful. How will the role of a sales rep

I think AI will automate a lot of the research, a lot of the prep work.

Yeah, I think they’re more productive. Yeah, I think we’ll see salespeople I think we’ll we’ll see sales productivity trend upwards. I think we’ll also see attrition rates come down because we’ll be able to use AI to supplement onboarding. I think we’ll probably see better and better AI tools to help companies and candidates match so that the fit is better. So yeah, I think we’ll see higher productivity across the

Probably they over index on the value of relationship building and charisma and being the big personality you know, that that doesn’t hurt, but it’s not it’s not really that impactful.

trend is is moving back in the other direction, and I’m I’m glad to see that. Our sales teams in person much more productive? 100%. No question about it. Absolutely. They learn faster, their morale is higher. If I’m having a bad day, but the person next to me is having a great day, that gives me hope, that gets me through the trough. And so yeah, they’re absolutely more productive. Also, managers are there to solve problems, managers are there to course correct. You know, maybe somebody’s doing it wrong and they don’t know they’re doing it wrong, but the manager can see it and help them.

So yeah, it’s much more productive in person.

It’s a great question. So I think when you say farmer, what you’re referring to is when you have an account manager that is owning one or multiple paying customers whose job it is to maintain and maybe grow those customers, but is not out there hunting for new business. And by the way, what’s baked into your question is acknowledgement of the power of PG. That hunter is able to PG and that’s why that hunter is the more effective sales rep. So first of all, farmers, I don’t like the term, I prefer account manager.

Your account managers should also be excellent at pipeline generation because they’re trying to get into other divisions, cetera. But I think if your if your account manager is driving real value with the account, then that account becomes, you know, very difficult for a hunter to crack. So I’d say you want your farmer hunting inside of the account, but you also want your account manager to care deeply about customer value. And with that customer value comes trust. And if there’s a question about a new technology, they’ll probably bring it to the account manager and give the account manager the opportunity to either fix something in our current, you know, in our current offering or or or change

No. Say it again.

It’s hard. It’s hard, but I think you I think you can. I think you can. I think a salesperson is probably in a mature territory, is probably going to spend a third of their time a third of their time generating pipeline generation, maybe 20 to 30% of their time taking care of their customers. And then what’s in the middle is is prosecuting deals. And of course, you know, maybe you’ve got a sales rep with 25 greenfield accounts and two paying customers. They’re going to be, you know, more on the PG and hunting side, or you have an account manager with just two paying customers.

And for them, pipeline generation is going to be easier because they’re they’re doing PG into an account that they know super well and they’ve got plenty of contacts. And so for maybe for that person, PG is only 20% of the time. So there’s you you want to move the dials across, but I think to be really effective, you want a salesperson generating pipeline, prosecuting that pipeline, and taking care of customers. And how the weighting of each of those things is to, you know, be determined by the type of territory they have.

I’m a closer. I know how to just convince this idea that you can coerce a customer or do some psychological gymnastics to get someone to sign a piece of paper when they weren’t actually intending to. First of all, if you do that’s a that deal is probably going churn later or they’re to find a way to rescind the order, but, I don’t believe salespeople sell, Buyers buy. All salespeople can do is create an environment that is conducive to that purchase decision. How do you create that environment?

Well, by doing good discovery, by finding challenges, by educating on how your solution meets those challenges. And once you do that, they want to buy. But the art of closing, that’s baloney.

Brand. Sure. I think it’s probably always been important. Yeah, I think brand is brand is is highly important. That’s why when you are a challenger, you need a higher caliber of salesperson because you don’t have the brand. As your brand gets bigger and bigger either great salespeople become more productive or, you know, you’re able to get more junior or less talented salespeople. What’s the most creative thing you’ve done to get a deal over the line? The story I have to tell you goes way back to the beginning of my to the beginning of my career when I was selling medical equipment before I got even into software.

I was selling this blood analyzer called a Coulter counter. I PG’d into an account, into a doctor’s office, and the office manager told me they had just bought my competitor’s product, Becton Dickinson. And I said, but you got talk to me. Mine is better. All the reasons, I’m rattling off all the reasons. She’s like, no, the deal is done. And I’m like, is it installed yet? No, it, you know, it arrives next Tuesday. You got to talk to me. No, I can’t. And then I thought, shit, I just upgraded an account that had one of those Becton Dickinson’s, I still, haven’t sent it back to corporate.

It’s still in my closet. I’ll tell you what, office manager, you tell the doctor, she’s got to see me, and if she sees me and she still thinks the Becton Dickinson is the better machine, I’ll bring one with me and she can have it for free and she can cancel the order for the other machine. Well, yeah, but you got to be here before the in service on Monday. Great, I’ll drive. I had to drive all night, snowstorm into Jackson, California, and I demoed this doctor on Friday, and I brought the competitor’s machine with me, and I was able to close the deal.

Yeah.

Yeah.

You’re to have pressure to build the team quickly. Better to be late than to hire mediocre people. What would you most like to change about the world of sales? Maybe the reputation salespeople are slimy or greedy or anything like that, because I think it prevents some capable people from pursuing a job that could be the best job that they’ve ever had.

I I was at Navan. We were a travel solution and COVID hit and nobody was buying travel. The company made Were there when that happened? Absolutely. I joined in January of and the world locked down in March. What do you do I mean, your numbers

Yeah, close to it, close to it. We had about a 90% drop in revenues. I’m almost amazed that

Yeah, there were just some large enterprise accounts that were still traveling a little bit. You know, we had companies that were in the, what did they call it, category necessary, essential workers. We had companies that had essential workers, government, some manufacturing. Anyway, we made two key pivots during that period that saved the company. Ariel, the founder, came back from a vacation and he said, by God, we’ve got to build an expense management solution and we’ve got to do it fast and burn the ships. And what he meant by that was he pivoted the whole engineering organization from one day to the next.

And you know, candidly, the executive team thought, man, this is a this is a bit dramatic. You’re betting the whole company. Because remember at the beginning of of COVID, we thought it was to be two weeks and maybe it’s to be four weeks and maybe it’s be six weeks. So nobody thought it was going to take as long as it you know, as long as it did. So the idea of putting 90% of the engineers to go build a brand new product when we had this like pretty hot company was really scary.

And And he was single-minded about doing it and that was the right decision. And then the other thing we did was go up market because the large enterprises believed that there was going to be a day after. They might not know when the day after was was going be. And so we were able to basically pivot the company way up market and go to people and say, listen, you know, were you happy with your travel program before COVID? No. What better time to overhaul it than now when no one’s traveling and you can have a great program when the world resumes.

And so by going upmarket and by building a second product, that company didn’t die and it would have. I’d say that that that was a pretty good strategy.

for having me, Harry. I love what you’re doing. bring a curiosity and a passion to highlight the journey that that founders and executives are on. So thank you for having me. I’m honored.