20Sales: Why Every Sales Rep Should Do Pipeline Generation & How to Teach Them | Verticalised Sales Playbooks: When and How | How the Best Sales Reps and Leaders Structure Their Time with Carlos Delatorre, CRO @ Harness

Carlos Delatorre is one of the legendary go-to-market leaders of the last 20 years. Today, Carlos is the Chief Revenue Officer (CRO) at Harness, where he oversees global sales and go-to-market (GTM) operations. Before Harness, Carlos was the CRO @ MongoDB and Navan. Carlos is also an investor with a portfolio including the likes of Modern Treasury and Starburst to name a few. In Today’s Sales Masterclass We Discuss: 03:48 The Art and Science of Sales 04:42 How to Hire Sales Talent 06:26 How to Build a Sales Team 15:28 Why Every Sales Rep Should do Pipeline Generation 19:45 How the Best Reps to Pipeline Generation 21:34 Biggest challenges of Pipeline Generation 22:44 Pipeline Generation Success Stories 34:59 Sales Metrics and Conversion Rates 35:32 Customer Acquisition Strategies 37:17 Evaluating Sales Performance 39:14 Effective Sales Training 43:10 Pipeline Generation and Deal Reviews 45:05 Maintaining Sales Team Morale 46:20 Verticalized Sales Playbooks 48:37 Addressing SaaS Churn Rates 49:49 Discounting and Deal Slippage 52:02 Transitioning to CEO Role 54:15 Hiring Mistakes and Sales Rep Evolution 57:03 In-Person vs. Remote Sales Teams 57:55 Account Management Strategies 01:02:47 Creative Sales Tactics 01:04:12 Final Advice for Sales Leaders 01:04:46 Adapting Sales Strategies During Crisis

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  I think for an early stage company, the CEO really has to develop the plays, figure out the message, at least that initial message. 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, is a cherry on top, is extra. I don't believe salespeople sell. Buyers buy. All salespeople can do is create an environment that is conducive to that purchase decision.

• 0:32Harry Stebbings?

  This is 20 Sales with me, Harry Stebbings. Now, 20 Sales is the show that dives into the world of sales, interviewing the best sales leaders to uncover their tips, tactics and strategies to scaling sales teams. Today, I'm so excited to be joined by one of the OGs of the go-to-market world, Carlos Delatorre. Carlos is the CRO at Harness, where he oversees global sales and go-to-market. Before Harness, Carlos was the CRO at MongoDB and Navan, formerly Trip Actions. He's also an investor with a portfolio including the likes of Modern Treasury and Starburst. But before we dive in today, AppSumo started with one simple idea. The tools you need to grow your business shouldn't put you out of business.

• 1:12Harry Stebbings?

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• 1:57Speaker 00

  You have now arrived at your destination.

• 2:00Harry Stebbings?

  Carlos, I've wanted to do this one for a while. I'd heard so many things about you from prior guests. So, thank you so much for joining me today.

• 2:06Speaker 00

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

• 2:10Harry Stebbings?

  It is great to do it in person as well. It makes it so much more special. I love to start with context, though. When did you first realize that you had this love of sales?

• 2:19Speaker 00

  Probably as a teenager. My cousin Tais 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 hundred bucks in the air conditioning in the mall was pretty amazing. And I thought, hmm, there's something to this.

• 3:03Harry Stebbings?

  Do you think people are born salespeople? Or do you think it can be learned?

• 3:07Speaker 00

  I think it absolutely can be learned. I think when people say that someone is born a 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, you know, being genuinely curious, I think those things help, you know, our innate attributes that make people better salespeople. But I think most of it is learned.

• 3:41Harry Stebbings?

  EQ, empathy, that pain tolerance, all feels a little bit like a game of art. And then we see the world today and it feels a lot more scientific. How do you think about sales being art or science?

• 3:55Speaker 00

  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 Picasso's art. And so I think like anything, there are people who are savants, who 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.

• 4:32Harry Stebbings?

  It all starts with bluntly bringing reps on. And I spoke to Manny and I spoke to Dav at Mongo before, and they both said that you're amazing when it comes to hiring sales talent. So I wanted to start there. What are the single biggest lessons for you when it comes to effectively recruiting sales reps?

• 4:51Speaker 00

  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 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

• 5:31Speaker 00

  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? And 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 to have an opinion around the likelihood of their success in the job that you're trying to to fill.

• 6:05Harry Stebbings?

  Okay, you're going to advise me today. I'm one of your angel ambassadors and you're the OG. So do I bring on board a sales leader who's got incredible experience, incredible network, and builds out the sales team themselves? Or do I bring on? Young, hungry reps and AEs to go hunt and really go off on their own and be aggressive.

• 6:26Speaker 00

  Are you a brand new company?

• 6:27Harry Stebbings?

  We're a brand new company, first two or three years.

• 6:29Speaker 00

  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

• 7:09Speaker 00

  and refine the plays. Once you've got some conviction that it's repeatable, go and hire a team around it.

• 7:15Harry Stebbings?

  Should I hire those young ones before I actually have messaging and a playbook refined?

• 7:20Speaker 00

  Sure.

• 7:21Harry Stebbings?

  You should.

• 7:21Speaker 00

  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 the first tech company they've ever worked at. And you're going to have to do a lot of the heavy lifting. You're going to have to train them. You're going to have to remind them that they should wear a shirt to a meeting. But that's a beautiful part of the journey that I think only a founder can really do well.

• 7:43Harry Stebbings?

  So we have that. When we're looking for these reps, would we rather they have experience in the domain that we're in or selling the size contracts that we're selling? Which ones are more preferable past history?

• 7:56Speaker 00

  I'll answer the question, but then I'll answer the question that I 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. You know, if I'm selling some like, you know, 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.

• 8:27Harry Stebbings?

  What question would you rather I asked?

• 8:29Speaker 00

  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.

• 9:14Speaker 00

  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 to be a gap. So you should, you need to have negotiables and non-negotiables.

• 9:28Harry Stebbings?

  I love this as granular as possible. You would advise me, make a list of the skills that you need. Test which skills they have. How do you test what skills they have?

• 9:38Speaker 00

  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?

• 10:21Speaker 00

  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 non-negotiable, 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.

• 10:56Harry Stebbings?

  Which would you say are more often non-negotiable for you? I know it's situation dependent, but more often than not, non-negotiable.

• 11:03Speaker 00

  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 non-negotiable. 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, that's a kind of a non-negotiable.

• 11:44Speaker 00

  Maybe they've only sold into mid-market accounts and they've only sold deals in the 50 to 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'd negotiate on.

• 12:08Harry Stebbings?

  When we're testing out these skills and the non-negotiables and negotiables, we're going to get into pipeline generation, I have to later, but are we doing case studies? Are we doing take-home assignments? Are we doing anything physically active to determine these skills?

• 12:23Speaker 00

  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.

• 13:09Harry Stebbings?

  When you think about questions around a hire from that approval board or the people involved in the process. What are the most common reasons why there is conflict in a hiring decision for sales reps?

• 13:21Speaker 00

  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 would be one area where you have disagreements.

• 14:04Harry Stebbings?

  Do you agree with Jason Lampkin, who says that you should always hire two reps at the same time? And subtly enforce this element of competition?

• 14:12Speaker 00

  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. 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 ten seconds to lean over and ask the person next to you.

• 14:57Speaker 00

  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 the minimum profile for a hub.

• 15:24Harry Stebbings?

  Okay. So two people and a sales engineer, that's minimum profile for a hub. I want to get to the pipeline generation. You said it there. Manny was like, pipeline generation Tuesdays are famed with Carlos, and it was so central to how you acted with Mongo and how you execute so well. And so first, I just want to start by asking, we have SDRs, we have demand gen, why do we need to have this extreme focus on pipeline generation for reps?

• 15:51Speaker 00

  Great question. 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 in 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

• 16:36Speaker 00

  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 you, if you 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, 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 are and so now in that kind of a scenario, you need such a huge investment in marketing and such a huge investment

• 17:21Speaker 00

  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.

• 17:49Harry Stebbings?

  I do have to ask also, what I do have to say also, I think it means you don't have the loss of accountability, which is like, it's so easy to be like, if I didn't hit my number, yeah, but demand gen gave me shit leads.

• 18:00Speaker 00

  That's right.

• 18:01Harry Stebbings?

  It's like, well, that's your lead.

• 18:02Speaker 00

  That's right.

• 18:03Harry Stebbings?

  It's your fault.

• 18:04Speaker 00

  That's right. So I think 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, is a cherry on top, is extra.

• 18:19Harry Stebbings?

  Does that not take all weight off SDRs and demand gen? How do you prevent them from going, poof, we're just the cherry on top, so it doesn't really matter?

• 18:27Speaker 00

  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.

• 18:41Harry Stebbings?

  My question to you is, you know, we had Chris Dagnan on the show from Snowflake.

• 18:44Speaker 00

  Love Chris.

• 18:45Harry Stebbings?

  Yeah, love Chris. Great dude. And he's like, you can really only take, I think it was like six to eight meetings a week as a rep. If you really want to come prepared and really smash it. Your time is going to be so conflicted or changed differently by suddenly having pipeline generation as a core part of it and an expectation. How do you advise reps on time allocation now pipeline generation is a core part of their expectations?

• 19:10Speaker 00

  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, 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. And then there's

• 19:52Speaker 00

  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%. [00:01:03]

• 20:03Harry Stebbings?

  When you're hiring these reps and they haven't had pipeline generation as such a big part of their role before, how do you teach them to be good at pipeline generation?

• 20:13Speaker 00

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

• 20:20Harry Stebbings?

  Is that a complete non-negotiable for you?

• 20:22Speaker 00

  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

• 21:06Speaker 00

  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, you're probably gonna give up on the journey towards PG excellence.

• 21:33Harry Stebbings?

  Everyone says to me on the show, the change in sales is that outbound in 2025 is dead.

• 21:39Speaker 00

  That's crazy talk.

• 21:42Harry Stebbings?

  You strongly disagree.

• 21:43Speaker 00

  Yeah, yeah, yeah, I strongly disagree.

• 21:45Harry Stebbings?

  Do you think cold calling still works?

• 21:46Speaker 00

  Absolutely, absolutely. But I'm really glad that other companies don't. And I hope a lot of those companies are our competitors.

• 21:54Harry Stebbings?

  Does AI change the effectiveness of outbound? When you think about supply, I can now send infinite emails beautifully personalized with effective AI agents, tooling data. Does that change outbound?

• 22:07Speaker 00

  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, 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 & Bradstreet.

• 22:52Speaker 00

  And Dave is an epic P G-er. 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 & Bradstreet. And we're in the lobby, the CISO had like a little, a little 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 at everyone 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."

• 23:36Speaker 00

  So we go through the meeting, we tell him about the product. And I, 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 X, Y, Z. 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. You have to break through the noise. People are getting lots and lots of, and so that's where email's good and social media and all the other things.

• 24:21Speaker 00

  But most meetings are set, like two thirds are set as a cold call.

• 24:26Harry Stebbings?

  I think you're always underestimating the familiarity of naming. And what I mean by that is you post 10 times a month on LinkedIn. Me responding to five of them, go Carlos, so awesome to see. After five, you're like, oh, the name rings a bell. The name rings a bell. We have it with fans of the show where I'm like, I don't know what they do or who they are, but the name rings a bell.

• 24:48Speaker 00

  So true.

• 24:48Harry Stebbings?

  And that really works. How many, are we talking about unicorn reps though here? Cause like, he sounds fantastic, love him, but how many are actually good at PG? Half?

• 24:59Speaker 00

  Of the world of sales reps?

• 25:00Harry Stebbings?

  Yeah.

• 25:01Speaker 00

  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.

• 25:12Harry Stebbings?

  Is it, do you have people then in your teams who are not good at PG?

• 25:15Speaker 00

  No.

• 25:18Harry Stebbings?

  Okay, so then we don't. How do we form structure around it? Can you take me to pipeline generation Tuesdays? What is that? How do you structure it?

• 25:27Speaker 00

  Sure. Better to start on Thursday. There's kind of a wheel.

• 25:30Harry Stebbings?

  Sure, you guide the way.

• 25:31Speaker 00

  All right, all 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. It's not very good. Great. Okay, now I've got 20 accounts that I'm going to go after over the next three months. On a given week, I'm going to 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.

• 26:12Speaker 00

  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 their 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 accounts.

• 26:56Speaker 00

  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 going to develop a hypothesis to a conversation starter for the top 10 of those people.

• 27:40Speaker 00

  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

• 28:21Speaker 00

  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. She, 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.

• 29:03Harry Stebbings?

  Is that, sorry, is that scalable? The manager is having to look through, what, 10 different target people's accounts? There's too many people for them to be going, oh, Jill's my neighbor. Oh, I know that this piece of the report is perfect for them. Is that possible to ask them to do that across the mall?

• 29:18Speaker 00

  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's 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.

• 30:00Speaker 00

  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.

• 30:41Speaker 00

  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, et cetera. And so then Tuesday morning, when the butts hit the chairs, people are ready. People are 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 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.

• 31:24Speaker 00

  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.

• 31:54Harry Stebbings?

  So just so I know how we structure the week, it kind of starts on the Thursday with the planning. That progresses through to Action Day on Tuesday. Tuesday is when we do action. We are actually hitting the accounts, hitting the targets. And then for the rest of the week, we're harvesting?

• 32:09Speaker 00

  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 wrap up on Fridays. So I typically run that myself and it's the whole sales team and we celebrate the PG success of the week. We tell stories of success. We tell stories about successful meetings. We also tell some stories about opportunities that have been created from previous week's PG and it really builds, I think, an enthusiasm,

• 32:49Speaker 00

  a belief and it reinforces this thing we do that's so important, so powerful, but also so hard. And so that's kind of the the circle of life, if you will.

• 33:00Harry Stebbings?

  How has the way that you do pipeline generation, week structuring changed over time?

• 33:07Speaker 00

  In the early days, you know, the first time I was ever exposed to it was at at Parametric Technology early in my career and we called them power hours, whatever, Thursday at nine AM, everybody be in the office. And so Thursday at nine AM, you 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

• 33:48Speaker 00

  and not zero comes from it, it's really hard to bring your A game for the next power hour.

• 33:54Harry Stebbings?

  How do you think about effective goal setting around pipeline generation? Because every number can be gamified. How do you think about effective goal setting around PG?

• 34:02Speaker 00

  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.

• 34:45Speaker 00

  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?

• 34:54Harry Stebbings?

  I don't understand how this is a good business. Let me pause. What? Okay, so you have eight meetings a month. If you think two meetings a week is good. Let's say 25% of those convert into paying customers and the customers are a hundred grand a year. Let's just say that's 1.2 million a year, correct? And the rep is on fully baked everything in 200, 250? Well, then they're at like four, five to one. That's pretty good. But that's if everyone is fully ramped, everyone is effective like that. And that's a good, good one.

• 35:28Speaker 00

  The numbers that you just, um, that 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 going to be some good stuff, some, some low hanging fruit.

• 35:52Harry Stebbings?

  And so you're like, right, I get it. It's like three to one on your economics, Harry. But when you add in partner demand gen, SDR, luck, you can be at five to one.

• 36:02Speaker 00

  Yeah, or maybe it's four to one on yours and you can be at six to one.

• 36:05Harry Stebbings?

  What is okay in terms of those numbers? A lot of founders are like, is it okay to be at three to one?

• 36:11Speaker 00

  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 to be at five to one or better.

• 36:23Harry Stebbings?

  What level of contract size warrants outbound in this way?

• 36:28Speaker 00

  Oh, that's a good question. Certainly down to 50K. Maybe below 50K, it probably, you know, starts to break down. Cause down to 50K, you know, your reps are going 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 two to. Three, four hundred K range. It certainly works there.

• 36:53Harry Stebbings?

  Everyone today feels like they're suffering with just not enough pipe. People aren't buying the way they used to. Everything's gone back to the CIO in terms of buying powers. What do you say to sales leaders today who go, Carlos, there just isn't the pipe?

• 37:09Speaker 00

  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.

• 37:17Harry Stebbings?

  How long do you give someone to ramp?

• 37:19Speaker 00

  I think what you're asking is, when do you sort of declare, uh, 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, um, 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, uh, you know, bootcamp? 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,

• 38:04Speaker 00

  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, 10, 11, 12 months. And so then they'll make a decision to part ways at 18 months. That's so expensive, not just in terms of.

• 38:28Harry Stebbings?

  Well, how would you do it differently? Are you able to let go of someone after six months? If enterprise sales cycles generally a year?

• 38:35Speaker 00

  Yeah, you've got milestones along the way. And so if they're not, if they're not 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 bootcamp. It was, it was clear in their first month that, you know, we'd made a mistake. You know, we we apologize for that because we hired them. But why wait nine months and waste their time and and waste our time and opportunity cost?

• 39:08Harry Stebbings?

  I totally get you. Ramp time is determined often by quality of training.

• 39:14Speaker 00

  Yeah.

• 39:14Harry Stebbings?

  And when we think about skill development, what have been your biggest lessons on how to train reps effectively? Especially in this ramp time.

• 39:22Speaker 00

  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.

• 40:06Speaker 00

  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 bootcamp, an intermediate and an advanced. And then coming out of bootcamp, 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 bootcamp 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 start meetings. They're able to do discovery, do a good first meeting.

• 40:51Speaker 00

  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 what we're doing.

• 41:11Harry Stebbings?

  What is the average time it takes for someone to land a core logo?

• 41:15Speaker 00

  You mean just the sales cycle? The sales cycles are not that long. It's about four months.

• 41:19Harry Stebbings?

  Four months.

• 41:20Speaker 00

  About one hundred and twenty days.

• 41:21Harry Stebbings?

  How fast do we let someone get on a customer call? Because obviously customers and pipeline is very precious. First week, young rap, you don't want to just throw on there who doesn't know that shit.

• 41:31Speaker 00

  Yeah.

• 41:32Harry Stebbings?

  When do you let them?

• 41:33Speaker 00

  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, et cetera. And so they can be on their on the phone in the first couple of days on board, even before they go to bootcamp. They typically go to bootcamp, maybe week three, four, but they're on the phone even before. And then certainly at bootcamp, they're doing pipeline generation and they will typically have set their first meeting for sure before the end of bootcamp.

• 42:03Harry Stebbings?

  With respect, bootcamp sounds quite a resource-heavy institutional-grade training program. As you say, enablement three point O.

• 42:11Speaker 00

  Yeah.

• 42:11Harry Stebbings?

  Great. If you're an early-stage founder, how do you think about the rep training and being as effective as possible?

• 42:18Speaker 00

  Yeah, you wouldn't you wouldn't be able to afford, from a 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.

• 42:29Harry Stebbings?

  Yeah.

• 42:29Speaker 00

  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, hard-working, enthusiastic individual contributors and go build it. And you'll be able to build your enablement after you've closed, you know, ten or twenty customers. And you're like, okay, now I've closed, let's say, twenty customers, which means I've probably failed to close another sixty customers. So I've got eighty sales cycles of experience. Now I can identify the things to do, the things not to do, and I can build V one of my training based on that. And maybe that's just two or three days.

• 43:09Harry Stebbings?

  I do actually just want to go back to kind of the pipe generation because all the skills really come back to that in a lot of ways. When we then review the output of that, we have deal reviews. How do you approach deal reviews? And what makes a good versus a bad one? When do you do them in the week as well?

• 43:25Speaker 00

  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 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 and 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

• 44:08Speaker 00

  framework 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. And 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

• 44:50Speaker 00

  you want to be. And then the manager is just spot checking or...

• 44:54Harry Stebbings?

  When you have pipeline generation day and it's just spit off, whatever it is, the team morale is low, pipeline is not hitting, conversions are not coming.

• 45:05Speaker 00

  Yeah.

• 45:05Harry Stebbings?

  What are your biggest lessons as a sales leader on how to really maintain morale when it's just harder?

• 45:10Speaker 00

  Yeah, I've definitely seen that happen. It definitely, you know, 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, you know, as a manager, you know, one of your responsibilities, I think, of a great manager is to maintain intimacy with the team, intimacy with how they're feeling, intimacy with...

• 45:35Speaker 00

  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.

• 46:20Harry Stebbings?

  How do you feel about verticalized sales playbooks?

• 46:23Speaker 00

  About what? Sorry?

• 46:23Harry Stebbings?

  Verticalized sales playbook. So if we take Nirvana as an example, somewhere where you're at, you could have a playbook for financial services companies, for media companies, for healthcare companies, and then reps who are specifically allocated to those verticals. And then can have incredibly granular detailed use cases, insights about those industries. How do you feel about very verticalized playbooks?

• 46:46Speaker 00

  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.

• 47:30Speaker 00

  Even if you have a horizontal solution, you know, like a technology solution, IT infrastructure. The challenge is 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, it 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

• 48:13Speaker 00

  for, you know, for meritocracy and for having a fair distribution of opportunity. And so, like I said, the 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 are the customers that are a little bit harder, a little bit harder to sell to.

• 48:36Harry Stebbings?

  The big problem I think I'm seeing with average SaaS companies today is just churn rates. Everyone realizes that they bought too many seats and they're not actually using them. The 50 seats they bought, they're only using 12 of them and the churn rates are just incredibly high. Do you share the concern of many that actually the SaaS business that we've had was so overpaid on a seat basis that we're really moving into a tough period?

• 48:59Speaker 00

  You mean that we've oversold customers?

• 49:01Harry Stebbings?

  Yeah.

• 49:02Speaker 00

  I do think that a lot of that has worked through the system already. Companies that I'm, you know, a little closer to, I think most of that seems to be the trough, let's say, is, you know, 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,

• 49:45Speaker 00

  you know, to another account, I don't think that's healthy and I think those days are long gone.

• 49:49Harry Stebbings?

  What do you feel about discounting? You know, often we want to get deals done in a quarter. Discounting is often used as this. Panacea of, oh, we'll give you an extra 15% off Carlos.

• 49:58Speaker 00

  Yeah.

• 49:58Harry Stebbings?

  How do you feel?

• 50:00Speaker 00

  I think that using discount to close a deal that was not otherwise going to close rarely 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 costs 250K or 200K is not going to 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 250, we can't do it until next fiscal year.

• 50:43Speaker 00

  And we, you know, 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.

• 50:59Harry Stebbings?

  Okay.

• 50:59Speaker 00

  Maybe with a commodity where I'm going to need it anyway. I could buy it now, I could buy it later. Sure, you could discount your way into that, but.

• 51:07Harry Stebbings?

  So we don't use discounting then and the deal slips. Okay, deal slips into next quarter and you're my boss and you're the sales leader. And I say, Carlos, I'm sorry, the deal just slipped, it slipped. What do you say to me?

• 51:19Speaker 00

  Well, having a deal slip is a 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 must we do differently in the future? That's the key thing. Of course, deals are going to slip, we're going to 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.

• 52:02Harry Stebbings?

  When we think about a lot of sales leader ambitions, a lot. A lot of sales leaders want to move into the role of CEO. You did move into the role of CEO. I'm really interested in Manny asks this one. With the perspective you have of moving into the role of CEO, what do you know now that you would advise other go to market leaders about becoming a CEO?

• 52:22Speaker 00

  It's a 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 is your, 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?

• 53:07Speaker 00

  That was the, that was the challenge frankly, that, um, that I encountered in my CEO journey. I thought I was walking into a, to a situation where the primary, uh, 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. And 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.

• 53:52Speaker 00

  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. So.

• 54:06Harry Stebbings?

  Can I ask you, when you think about, and sorry, I'm peppering you with questions here that I've been thinking about.

• 54:11Speaker 00

  It is a podcast after all.

• 54:12Harry Stebbings?

  Yeah, yeah, yeah. But it's throughout the show. I've been thinking this, it's just like. When you reflect on your biggest hiring mistakes, what are the ones where you look back now and go, ah, that's one I've made time and time again?

• 54:23Speaker 00

  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 gonna 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.

• 55:04Speaker 00

  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, 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, just 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, uh, you know,

• 55:49Speaker 00

  uh, parameters to get him. That was one that was, that was painful.

• 55:53Harry Stebbings?

  How will the role of a sales rep change in the next five years?

• 55:57Speaker 00

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

• 56:04Harry Stebbings?

  What does that mean then? We do double the accounts because we have so much more time available?

• 56:09Speaker 00

  Yeah, I think they, 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.

• 56:25Speaker 00

  Onboarding, I think we'll probably see better and better AI tools to to help companies and candidates match so that the fit is better. So yeah, I think we'll see we'll see higher productivity across the board.

• 56:39Harry Stebbings?

  What does everyone think they know about sales that they most often get wrong?

• 56:44Speaker 00

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

• 56:59Harry Stebbings?

  You've mentioned before the lone wolf and the dangers of it. How do you feel about in person versus remote working, especially given the rise that we've seen in the last few years of remote companies?

• 57:11Speaker 00

  I think the trend is is moving back in the other direction and I'm glad to see that.

• 57:15Harry Stebbings?

  Are sales teams in person much more productive?

• 57:18Speaker 00

  Hundred percent. No question about it. Absolutely. They learn faster. They 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 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 can see it and help them. So yeah, it's much more productive in person.

• 57:49Harry Stebbings?

  I will never forget Dave Kellogg telling me, you never want your farmer against someone else's hunter. How do you structure account management between CS and reps to ensure that your farmer is never being fought by someone else's hunter?

• 58:04Speaker 00

  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, your 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, et cetera.

• 58:48Speaker 00

  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, 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 change.

• 59:29Harry Stebbings?

  It's interesting because you're basically saying that reps need to shift earlier to embrace PG and actually CS need to shift earlier and embrace PG also. Because if you think about like the spectrum, you can't have a rep who's now embracing PG and then him equally embracing CS. You can't have both embracements. Do you see what I mean?

• 59:47Speaker 00

  No, say it again.

• 59:49Harry Stebbings?

  Well, so if you have a rep in the middle whose core goal is hunting and you're like, great, you need to embrace PG now much more actively. On this side of it, which is the kind of post hunt, you can't say to them, as well as PG, you also need to really embrace CS.

• 1:00:03Speaker 00

  Well.

• 1:00:04Harry Stebbings?

  Because a lot of sales leaders today are like, no, no, we really like reps to be engaged post-sale, to hand off effectively and really keep that relationship going. You can't do that if you're embracing PG.

• 1:00:15Speaker 00

  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 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

• 1:00:59Speaker 00

  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 going to, you know, be determined by the type of territory they have.

• 1:01:23Harry Stebbings?

  I'm going to do a quick fire round with you. Are you ready?

• 1:01:26Speaker 00

  All right.

• 1:01:27Harry Stebbings?

  What sales tactic has died a death? We've à la pubelled outbound that is still alive and well. What has died a death?

• 1:01:34Speaker 00

  Closing. 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 to churn later, or they're going 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

• 1:02:16Speaker 00

  once you do that, they want to buy. But the art of closing, that's baloney.

• 1:02:21Harry Stebbings?

  If sellers don't sell, buyers buy. I love that. Is brand not more important than ever?

• 1:02:26Speaker 00

  Brand. Sure. I think it's probably always been important. Yeah, I think brand is, 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.

• 1:02:47Harry Stebbings?

  What's the most creative thing you've done to get a deal over the line?

• 1:02:51Speaker 00

  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 Colter 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, a Beckton Dickinson. And I said, but you gotta 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, you know, it arrives next Tuesday. You gotta talk to me. No, I can't. And then I thought, shit, I just upgraded an account that had one of those Beckton Dickinsons. I still, I haven't sent it back to corporate.

• 1:03:33Speaker 00

  It's still in my closet. I'll tell you what, office manager, you tell the doctor, she's gotta see me. And if she sees me and she still thinks the Beckton 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 gotta be here before the, before the in-service on, on Monday. Great. I'll drive. I had to drive all night, snowstorm into Jackson, California. And I demoed this doctor on, on Friday and I, I brought the, I brought the competitor's machine with me and I was able to close the deal.

• 1:04:04Harry Stebbings?

  And so you did it live and she saw the difference between the two machines?

• 1:04:08Speaker 00

  Yeah, yeah.

• 1:04:09Harry Stebbings?

  Loved that.

• 1:04:10Speaker 00

  Yeah.

• 1:04:11Harry Stebbings?

  Yeah, that's a, that's a creative one. What one piece of advice would you give to a sales leader starting a new role today?

• 1:04:15Speaker 00

  You're gonna have pressure to build the team quickly. Better to be late than to hire mediocre people.

• 1:04:22Harry Stebbings?

  What would you most like to change about the world of sales?

• 1:04:25Speaker 00

  Maybe the reputation. Salespeople are, are slimy or greedy or anything like that. Because I think it, it prevents some capable people from pursuing a job that could be the best job that they've ever had.

• 1:04:38Harry Stebbings?

  Final one for you. When you look at sales strategies over the last few years, what company sales strategy have you been most impressed by?

• 1:04:46Speaker 00

  I was at I was at uh Nivan. We were a travel solution and COVID hit and nobody was buying travel. The company made-

• 1:04:53Harry Stebbings?

  Were you there when that happened?

• 1:04:54Speaker 00

  Absolutely. I joined in uh January of twenty and the world locked down in March.

• 1:05:00Harry Stebbings?

  What did you do? I mean, your numbers must have just gone to zero.

• 1:05:03Speaker 00

  Yeah, uh, close to it, close to it. We had about a ninety percent uh drop in revenues.

• 1:05:08Harry Stebbings?

  I'm almost amazed that ten percent remained in a travel ban.

• 1:05:12Speaker 00

  Yeah, there were just some large enterprise accounts that were still traveling a little bit. You know, we had companies that that were in the uh, what did they call it? The that category-

• 1:05:22Harry Stebbings?

  Government.

• 1:05:23Speaker 00

  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, you know, 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 and, you know, burn the ships." And what he meant by that was he pivoted like 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 going to be two weeks and maybe it's going to be four weeks and maybe it's going to be six weeks. So nobody thought it was going to take as long as it, you know, as long as it did.

• 1:06:06Speaker 00

  So the idea of putting ninety percent 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 to 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 a great program when the world resumes."

• 1:06:46Speaker 00

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

• 1:06:54Harry Stebbings?

  Carlos, I've loved doing this. I wanted to do it for a long time. As I said, I heard so many good things for a long time. So thank you so much for joining me today.

• 1:07:01Speaker 00

  Thank you for having me, Harry. I love what you're doing. You're you 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.

• 1:07:14Harry Stebbings?

  That was so special, Stu, in person. I want to thank Carlos for giving up the time. And if you want to watch the episode in full from the studio, you can find it on YouTube by searching for 20VC. That's 2-0-V-C. But before we leave you today, AppSumo started with one simple idea. The tools you need to grow your business shouldn't put you out of business. That's why they work directly with developers to get exclusive discounts of 80 to 90%, 80 to 90% off software, saving entrepreneurs over half a billion dollars since 2010. Some of the biggest names in tech like Mailchimp, Zapier and Dropbox got their start on AppSumo. And with a rotating selection of hundreds of tools, you'll find all the software you need to make your life easier in 2025. Plus, with a 60-day money-back guarantee, you can try any tool

• 1:07:59Harry Stebbings?

  risk-free. Start the year off with savings. Get 10% off your first order with the code 20, lowercase v-c, and a free tool exclusively for 20VC listeners. That's code 20, lowercase v-c for 10% off, plus a free tool at appsumo.com. As always, I so appreciate all your support. And stay tuned for an incredible episode with Lime CEO Wayne coming out on Monday.