Lori Jiménez: How to Increase Sales; Hiring Tips from Google; Best Way to Grow Sales Teams | E1043

1. 0:00 – 0:21

   Intro

   1. LJLori Jiménez0:00

      One of the most important characteristics, in my opinion, with a great salesperson is being curious. It's someone who can ask a question, who can ask the next question that's connected to that first question, really listen to the first answer, not just for the answer you want to hear, (laughs) but the answer you maybe don't want to hear.

   2. HSHarry Stebbings0:17

      (music) Laurie, I am so excited for this. I- I heard so many

2. 0:21 – 7:57

   Lori's Sales Journey

   1. HSHarry Stebbings0:21

      great things from many past guests, especially the wonderful Rich. So thank you so much for joining me today.

   2. LJLori Jiménez0:26

      Oh, thanks for having me. Appreciate it.

   3. HSHarry Stebbings0:28

      Now, I always love to start with some context. So tell me, how did you make your way into the world of sales and come to lead some of the most incredible sales orgs as you have done?

   4. LJLori Jiménez0:36

      Oh, thank you. Um, great questions. I discovered sales at the ripe age of 15 and a half, um, which was the day I got a worker's permit and could get a job. So I was fired up to get a job and make some money. I, uh, applied for a few retail jobs in my hometown, and the owner of two kind of neighboring boutiques met me and said, "You're hired. Start tomorrow." So, so excited. So I march in on my first day, ready to get working, and he said, "Here are the keys to the other store. Uh, go open it up. Um, there's a shoebox of cash in the back. Use that for the cash register. I'll show up in a few hours and teach you what to do." And I was terrified (laughs) . So he's like, "Open the store and get going." So I'm like, "All right, I'm gonna do this." I go and open the store, and soon after opening the door, customers started coming in. So I had to start selling. (laughs) I did a terrible job. Um, I don't think I charged sales tax to anyone that day. I'm sure there were some very (laughs) good deals made. But what I got from it was the energy of working with customers, like how fun that is, how energizing that is. Um, it's a thrill of partnering with someone, even in- even in the retail capacity in a small boutique. So I got energized by it, and I stayed in retail throughout high school and college. Um, and then fast-forward, I graduated from college during, um, the s- recession in the early '90s. So not a lot of jobs. I was still working in retail, and I was at a barbecue and talking to my oldest sister's friend who had been in the workforce for a number of years ahead of me, and she said, "Hey, Laurie, I work at a software company. Um, we're doing kind of this group call interview for salespeople. Are you interested?" And I was like, "Both hands up." (laughs) "I will... Let me get a, like, a job with a career path sounds good." I knew nothing about the company. I didn't know what they sold. I didn't know how they did it. I didn't know anything about the market. I just really wanted to just get in and get a- get a, you know, kind of a firm job. So I went to the interview, I got the job, and that company was Remedy Corporation, which was later, you know, became part of BMC. I think their software's still on the (laughs) still askew at BMC, which is amazing. And, um, was really, like Harry, so fortunate. It was a formative part of my career, not just 'cause it was my first, but I met mentors and friends that I still talk to just a- as recently as this week from that company and was super fortunate to experience an IPO with them. So just saw, like, what high growth was all about from the start. So that- that was my story. That's how I got here.

   5. HSHarry Stebbings2:54

      So, two things that I just have for you, and one is, like, the takeaways from the organizations you've worked at-

   6. LJLori Jiménez2:58

      Yeah.

   7. HSHarry Stebbings2:58

      ...but just the first thing I'm too fascinated by. You mentioned your instant love of sales. Do you think sales is something that you instantly fall in love with, or do you think it's something that you can learn to love over time? Which one do you think is more common amongst the best you've worked with?

   8. LJLori Jiménez3:13

      Honestly, I think it's the latter. And I say that even though that wasn't my experience, because I think there's a perception sometimes about sales that it is just this, like, kind of robotic, anyone can do it, go and run a script, go, and there's- there's not a lot of humanity to it. And I think when you really learn that there's an art and a science to it, that it's about genuine connection with people, that it's about really, like, listening and actually listening, then I think you can really learn to love it. And I say that because of folks I've seen, that I've been f- super fortunate to partner with and- and, um, coach and mentor, come along the way. So it's folks that really have... I've seen them kind of, you know, them- them just blossom into sales when they maybe didn't think they could, you know. They maybe didn't start as an SDR, they just wanted to get a job just like me, (laughs) you know, and they... but they see it and they see the opportunity. I think it's- I think it's actually more the latter, even though my experience was that instant energy.

   9. HSHarry Stebbings4:01

      I absolutely love the honesty there also, Laurie. (laughs) I was expecting you to be like, "Yeah, the first one," 'cause that's what I just said.

   10. LJLori Jiménez4:06

       I... Yes, of course (laughs) .

   11. HSHarry Stebbings4:07

       (laughs) Um, okay, now, my- my next question was like, we'd normally do a quick fire round at the end, but you've worked at some of the, like, most incredible companies. I was like, "Well, how do I kind of compress this in a way where we get the takeaways-"

   12. LJLori Jiménez4:18

       (laughs) Yeah.

   13. HSHarry Stebbings4:18

       "...um, in an efficient style?" And so we're gonna go through each company-

   14. LJLori Jiménez4:22

       Okay.

   15. HSHarry Stebbings4:22

       ...and you're gonna tell me a takeaway that's really impacted your mindset. And so if we start with Google, what was the takeaway and how did it impact how you think?

   16. LJLori Jiménez4:30

       The real takeaway there is the importance of building, like, genuine connections to do great work. You can't do anything on your own at Google. It is so big, it's so complex, there's so many layers and crossover of teams and initiatives and budgets and structures that you have to learn quickly that the stakeholder partnerships you make are critical to how you get work done. And so from the start, you've got to get out there and- and not just stay in your lane. You've got to go learn about the neighboring businesses. You've got to learn about the partnerships that are gonna help your business grow, and learn about what are their motivations. It's not just about me. I was in Google Cloud. What's happening outside of Google Cloud? What's parallel to us? How can we work together? And if you do that in a genuine way, you can just... eh, there's so much that you can, you know, take that to. That's an applicable, you know, skill and talent that carries over into any role. So that would be my takeaway from Google.

   17. HSHarry Stebbings5:21

       God, I'd be terrible at that. I'm probably the worst team player in the world. (laughs)

   18. LJLori Jiménez5:24

       (laughs)

   19. HSHarry Stebbings5:25

       You know the job interviewer is like, "Are you a team player?" "No. No." (laughs) "Not at all." Um-

   20. LJLori Jiménez5:30

       You can learn it. You can learn it. (laughs)

   21. HSHarry Stebbings5:32

       You can. Um, okay, next one is Facebook.

   22. LJLori Jiménez5:35

       Yeah.

   23. HSHarry Stebbings5:35

       What was the takeaway from there?

   24. LJLori Jiménez5:37

       Facebook was, I would say, focus on impact. Facebook is- is- while- while a big comp- when I was there, even, you know, bigger company from a numbers perspective, but they do a lot of work in really small teams and focus on just the impact you can make. So narrow your list down to the three things that are gonna make the biggest impact and carry that forward versus getting kind of diluted across a long list of to-do. And you see that the way the company operates.

   25. HSHarry Stebbings6:01

       Next one, navan, or trip actions. What were the takeaways there?

   26. LJLori Jiménez6:05

       Two would be: Be really comfortable with moving fast and being really comfortable with ambiguity. We did not have all the answers, but we were moving fast and we were figuring it out as we went. And not just, like, being comfortable with it, but finding energy in it, like getting excited that you don't know what's next. So what do you craft, you know, to, to build a plan that could go in a few different directions and that can morph and change? So that kind of flexibility, but definitely learned the f- the speed and the ambiguity there.

   27. HSHarry Stebbings6:32

       (laughs) I love that response.

   28. LJLori Jiménez6:33

       (laughs)

   29. HSHarry Stebbings6:34

       Um, we're gonna get into also, like, flexibility and gaining-

   30. LJLori Jiménez6:36

       Sure.
3. 7:57 – 11:22

   Developing Sales Playbooks

   1. LJLori Jiménez7:57

   2. HSHarry Stebbings7:57

      I, I loved having Aaron on the show. Very, very special person. Now I wanna dive into some of the weeds.

   3. LJLori Jiménez8:02

      Sure, sure.

   4. HSHarry Stebbings8:03

      Um, we often hear the term sales playbook.

   5. LJLori Jiménez8:06

      (laughs)

   6. HSHarry Stebbings8:06

      Before we get into, like, whether the founder should be the one to do it or whether someone else should do it, how do you define sales playbook?

   7. LJLori Jiménez8:12

      That's a good question. I think it's... You know, a playbook should be a, think of it as a more of a GPS. So it doesn't have to be a script, like, each step down to the minute detail. Think of it as a guide. So depending on where you are in a sales process, whether it's very early and you're doing discovery and trying to get a, you know, or even earlier trying to get a meeting, and then down to doing discovery and carrying it all the way through, I think a playbook is, like, what's the, what's the successful motion in this stage of the cycle that you should go lean into and flex your strength or get the support around in order to have a successful outcome? So, I think it's all about, like, thinking of it as, like, drawing on the experience and the success you've seen from previous, from previous, um, sales engagements and building that into, like, a guide that can help you navigate through, but enough that still gives that level of creativity and flexibility that accounts for the style of that salesperson, um, depending on d- w- whether they're early, whether they're leader, whether they're directly, direct, you know, individual contributor.

   8. HSHarry Stebbings9:13

      You said that building on the success of prior sales interactions and engagements. Does that mean that the head of sales should be the one to create it, or should founders create it-

   9. LJLori Jiménez9:23

      That's a-

   10. HSHarry Stebbings9:23

       ... and then pass it off?

   11. LJLori Jiménez9:24

       Yeah, good question. I think the founders are the right folks to create it for a few reasons. Um, I mean, th- there's, there's where it started, right? (laughs) They had the passion. They had the idea. No one has more passion than them. No one can better articulate the story. So, they start from that place of like, "This is my belief. This is my idea. This is my baby." So that, that, there's that that you're found- gr- uh, grounding from, and what that creates is the person that knows the why and the what in, in such a deep level that they can anticipate things like, um, what problem, uh, are we trying to solve, and then when they get that customer feedback, pivoting. So, like, is that really as important a problem as I thought it would be for the customer? And if it is or it isn't, how do we change our playbook to amplify how our solution solves that problem? So I think that them being the closest to it allows them to pivot just not only the playbook but also, like, feedback back to product. You know, so for example, at WorkRamp, you know, Ted had, is a go-to-market leader and also has an incredible product background. So what's great about that is his, him setting the playbook, which he did here, is he knows. He knows how customers respond. He knows what really matters to them and how our story fits in. And then if we get some feedback even now where he's less, you know, connected, less, um, as close to the playbook as he was in the early days, he still knows, like, "Hey, Ted, here's what we're hearing. We need to adjust this." He'll take that feedback. So I think it's great formatively in the beginning, but then it can carry through as your company grows as well.

   12. HSHarry Stebbings10:50

       I also think you cannot hire a head of sales unless you know what sort of playbook you're running.

   13. LJLori Jiménez10:55

       Exactly. Like, how do you coach them, and how do you guide them?

   14. HSHarry Stebbings10:57

       Yeah.

   15. LJLori Jiménez10:58

       Exactly.

   16. HSHarry Stebbings10:58

       And also, there are so many different types of heads of sales.

   17. LJLori Jiménez11:00

       Yeah. (laughs)

   18. HSHarry Stebbings11:01

       Some are much more enterprise heavy.

   19. LJLori Jiménez11:03

       Exactly.

   20. HSHarry Stebbings11:03

       Some are much more PLG. Uh, uh, there's just-

   21. LJLori Jiménez11:05

       Exactly.

   22. HSHarry Stebbings11:05

       Yeah.

   23. LJLori Jiménez11:05

       Exactly.

   24. HSHarry Stebbings11:05

       Totally. Okay, so when we think about that first kind of hire, so to speak, most often go for the logoed rep or the logoed person, but you feel differently. Why do you believe this approach of, like, the hailed logo person isn't maybe the right one?

4. 11:22 – 21:21

   Building Sales Teams

   1. HSHarry Stebbings11:22

   2. LJLori Jiménez11:22

      A couple reasons. I believe, especially in the early stages, that, um, there's a huge opportunity to not only, like, identify and sprout new talent in a startup because you're looking for someone who's demonstrated drive and ambition and all that good stuff, but that doesn't just translate into a huge logo person. It's like, what gets them energized? How do they, uh, navigate through ambiguity? They don't come in with a like, "This is the only way to do things." There's an openness to like, "I am in it 'cause I'm passionate, and I believe in this, and I have all the talent to go navigate challenges and to go build something, but I'm not so set in a way that there's only one way to do it." So, I think there's a, there's a, a great benefit you get from not just, like, creating that environment where you're gonna create some great leaders that are gonna go grow into other, you know, amazing things and help that company or future companies grow. But there's a mindset that, um, there's a grit and a scrappiness that can help you really accelerate through that energy of that team. So I'm a big believer in you can really do great things with maybe a more junior, per- perceived junior talent, um, because of the creativity they can bring and they don't have kind of a bias from a previous experience.

   3. HSHarry Stebbings12:30

      Can I ask you, does this change if we're doing an enterprise motion versus a PLG motion?

   4. LJLori Jiménez12:36

      Certainly, I think a PLG motion, you know, lends itself to that scale up, right? So you can have volume, you can have velocity, you can have a lot of tries, right, which is good be- for just testing messaging. It's good for just trying different sales plays. So I think there's... It's easier, to your point, to do that with a, you know, PLG stepping into SMB mid-market and beyond versus top down. So, I would just say on the enterprise side, um, it, you know, it's more, there's probably a lot of nuance to what market you're entering. You know, if you're going into security, you probably want some folks with, with that, you know, gravitas that can go speak to a CISO and go s- you know, have those conversations. But I think there's still an element to it, is you can still find some up-and-comers that could play there as long as they've got a good surrounding support, you know, team around them to, to help them be successful.

   5. HSHarry Stebbings13:23

      So Laurie, I'm with you in terms of the scrappiness, the hunger of those early reps.

   6. LJLori Jiménez13:27

      (laughs)

   7. HSHarry Stebbings13:27

      The hard question is when.

   8. LJLori Jiménez13:29

      Yeah.

   9. HSHarry Stebbings13:30

      Some founders just hate it-

   10. LJLori Jiménez13:31

       (laughs)

   11. HSHarry Stebbings13:31

       ... se- selling and so they want it as soon as possible. Some wait far too long.

   12. LJLori Jiménez13:36

       Yeah.

   13. HSHarry Stebbings13:36

       How do you advise founders on when's the right time to add that scrappy, hungry profile?

   14. LJLori Jiménez13:41

       I think it's all about thinking about scale. So if the founder's doing it, and let's say you've got 10 to 20 customers, like how much more can they do? Like just in their, in their straight daily capacity, you know, how much can they get done in re- in addition to growing and scaling the company through all the other disciplines, through engineering, through product, through all the other things they're kind of overseeing, just the operations of the business? So I think it's that moment where you find a repeatable... You've got enough customers and you find enough of a repeatable process that can take your good work and grow it, you know, and, and take and get and have feedback. I think also just a... Someone that you can work with. Like, "Hey, we've been trying this for the first X number of customers. Let's try something. Let's tune that a little bit. I'll go try that and come back to you with feedback, you try it." You know, there's a, there's someone you can play with, which I think there's huge value in having partnership, you know, that kind of how many people do you hire at a certain time. There's huge value being able to learn from someone that's, that's next to you. So I think it's a combination of customers, how many you have, and just thinking about the CEO or founder needs to now scale beyond and focus on other things and this person can help them do that, but they can still stay close.

   15. HSHarry Stebbings14:45

       I was gonna ask exactly that, which is like Jason Lampkin says about hiring the two by two.

   16. LJLori Jiménez14:49

       Two. (laughs)

   17. HSHarry Stebbings14:50

       You know, hung- hunger games, you know-

   18. LJLori Jiménez14:51

       Yeah, yeah.

   19. HSHarry Stebbings14:52

       ... fight till death and, you know, kill the other one-

   20. LJLori Jiménez14:54

       (laughs)

   21. HSHarry Stebbings14:54

       ... who doesn't, you know, get a million in ARR. Um, uh, my point... But he doesn't actually say that. That's really unfair of me. (laughs)

   22. LJLori Jiménez15:00

       (laughs) Oh, no, it's all good.

   23. HSHarry Stebbings15:02

       But my point is, should we hire more than one at a time, or does that actually impact quality of onboarding and the challenge of re- ramping them?

   24. LJLori Jiménez15:10

       Yeah, no, good question. I do. I think you should hire more than, than one at a time for a few reasons. Less about the competition. I think they're, you know, that's kind of gonna happen maybe naturally, but it's more about you can work es- work for scale. I think o- if you're onboarding one person, it's onboard, onboard as many as you can 'cause just that time and investment in onboarding, you know, is a big commitment. So if you're onboarding one, there's huge value in onboarding more. I think there's goodness in creating a team and having, um, a place for those first sellers to collaborate and say, "Hey, I'm gonna try this message, this motion, this sales play. Maybe let's tune it a bit. You try this. We can test and see what's working." And then you just, you know, you created, uh, that first like kind of group founding team. There's nothing like it. You know, there's, there's learnings, there's energy, there's culture that comes from that. So there's just so much positive, like, byproduct from building a team through having, you know, a small group that starts. Just back to my own experience, you know, I'm still connected to that first team that founded back at Remedy. You know, those first sellers are still people I talk to and they have such a bond. So I think there's this common like, "We're gonna go do this together," that you get that carries through and just reverberates through the company culture and is very foundational.

   25. HSHarry Stebbings16:16

       I, I'm totally with you, especially on the efficiency of batching onboarding. I find it a nightmare.

   26. LJLori Jiménez16:22

       (laughs)

   27. HSHarry Stebbings16:22

       And so when we can do more than-

   28. LJLori Jiménez16:23

       It's a lot of work.

   29. HSHarry Stebbings16:24

       ... one-on-one-

   30. LJLori Jiménez16:24

       Yeah.
5. 21:21 – 31:36

   Sales Techniques and Success

   1. HSHarry Stebbings21:21

      it to them. What are some of your biggest lessons on compensation and title when it comes to sales ..........................?

   2. LJLori Jiménez21:29

      So on compensation, I think you learn a lot in that moment with the candidate. So you learn a lot about them. And especially if it's competitive and they might come to you and say, "Hey, I'm getting, you know, 50K more OTE over here," and then you ask, "Okay, well what does that mean for you? What does that represent? What i- is it an equity? Is it an OTE? What is it, and what's driving that ask?" So I think with compensation, it's a opportunity to really understand what motivates that person, and also if they have real... Like, it's a startup. Like, do they really believe they're taking a risk? Are they excited about that future opportunity that shows up in equity? You know, what are their questions around equity? Do the, you see an excitement in those questions? And if it comes down to just, uh, dollars on OTE I'm always a little bit like, that's a little... It's not a full red flag depending on, you know, where the conversation goes, but it's something that I, concerns me because that will come back, you know, in the future where someone's gonna be, maybe, you know, you have a hard quarter. How do they navigate that, you know, if, if things don't come together? Do they have the staying power to work through, you know, eh, uh, the ups and downs that can happen in a startup? So, I think it's a moment to really understand what someone's motivations are, and also just like, see kind of where their, um, research went. You know, wha- how, how deeply do they, are they, do they care about the opportunity in front of them? Is it just a OTE, or is it they really care about the mission of the company and they wanna be a part of building?

   3. HSHarry Stebbings22:49

      How do you think about whether to pay up for someone versus say, "You know what? You go for the other role." You, if that's-

   4. LJLori Jiménez22:55

      I've done that. I've done that. I've said, you know, when someone's really like, "This OTE is so... I can't step away from this." And e- that, we, maybe, maybe you could get closer and bridge it enough, but if that is all they're talking about, sometimes you have t- you have to walk away and say, "You know what? That sounds like it's a better fit for you, and if that changes let's..." You know. I always leave a door open. I think it's important. Uh, the valley's small, right? (laughs) You just cannot, you know, shut a door. And so, I think it's okay to leave it open, but I think it's okay to sometimes walk away. I'm trying to think if there's anyone that we walk away from there was like, "Oh, that got away," and I, no one's coming to mind, so, you know, that tells me that those weren't the wrong decisions.

   5. HSHarry Stebbings23:30

      Do you have any lessons on title, and what people want in title that's important?

   6. LJLori Jiménez23:34

      It's honestly like a discovery call (laughs) in sales. It's like, what's the why behind the title? What are they... Are they looking because they wanna demonstrate a certain level of progression on their LinkedIn profile? Is it that they wanna demonstrate scope? Is it someone who's maybe... And I've seen this, like, gotten stuck with title at a big company where it, you know, titles get a little murkier and are a little more flat, and they come out and they're like, "I need to break out of this, you know, kind of big company title level conundrum that I'm st- (laughs) that I'm trapped in, and I want something to demonstrate my scope." So, I think it's be- it's a very individual conversation, but I also think it's important to keep in mind, and this is hard to do, what you're setting up for will impact the future. So if you get too aggressive on title, then you're a couple years down the road and your next person comes in and they're like, "Well wait, I'm... Why am I not a senior director?" You know, maybe that first person wasn't, you know? And so you're like, "Okay, now we gotta unwind this a little bit." So I think it's... And it's okay to be comfortable with some of that in the beginning, but I think you just have to be aware of like, all right, this might be something that we have to navigate or walk back a bit as we grow.

   7. HSHarry Stebbings24:35

      The one that I've learnt is the external accreditation that can be needed, and when they say, "Hey.... as you said, to the why. "Hey, my chances of selling more are increased with a inflated title because I have so much more." I'm like, "I get that." Completely, exactly. You're using it to go accelerate growth. That's a good answer, right? (laughs) So- Yeah. (laughs)

   8. LJLori Jiménez24:54

      (laughs)

   9. HSHarry Stebbings24:54

      Yeah, 100%. Yeah. No.

   10. LJLori Jiménez24:58

       (laughs)

   11. HSHarry Stebbings24:59

       (laughs)

   12. LJLori Jiménez24:59

       (laughs)

   13. HSHarry Stebbings24:59

       Not doing that. Uh, fi- is there any other red flags in the interview process where you were like, "Oof-"

   14. LJLori Jiménez25:04

       Um...

   15. HSHarry Stebbings25:04

       ... "you should get the heebie-jeebies if you hit, you know, this?"

   16. LJLori Jiménez25:08

       Yeah. (laughs) You know, I think, again, it's like if, if, uh, you know, there's, to your point, people can interview well. If the answers just are shallow, if they're just very canned and shallow, and you feel like, "Okay, any, I could play back, you know, a bunch of different LinkedIn posts and collect a bunch of these (laughs) and this would be an answer," you know, if they can't connect to an actual, uh, customer engagement. Like, I, I like it when someone's, like, to your point, the stats that are really showing you, like, passion behind the work they did, and then a real, like, customer story and team story. If there aren't enough of those, like, there's not enough depth. And that, you know, that means you might get some performance for a while, but that's gonna fizzle out.

   17. HSHarry Stebbings25:42

       We are gonna move to your biggest strength for which apparently is the kind of onboarding and trust-building process. But I do just have to ask, before that, when we reflect on the hiring process and your hires that you've made, what are the biggest hiring mistakes that you've made? And how has that shaped your mindset?

   18. LJLori Jiménez25:59

       I think, you know, transparently, if I didn't vet some of those things as deeply as I just walked through. So, I've had, um, folks that it came off in an interview were super ambitious, right? They're like, "I'm gonna do this. I'm gonna build this. I, I, I." And they had this energy about them. But when you really peeled back how they're gonna do it, you know, not vetting the how enough, I've had that happen in the past where it's like it looked really good, but we didn't go deep enough on that how. I'm not, you know, I don't think you need to do-

   19. HSHarry Stebbings26:27

       What do you mean the how? Like, the ways in which they achieved were murky? Like, it was non-ethical?

   20. LJLori Jiménez26:32

       Yeah.

   21. HSHarry Stebbings26:32

       Like-

   22. LJLori Jiménez26:32

       Yeah.

   23. HSHarry Stebbings26:33

       Yeah.

   24. LJLori Jiménez26:33

       Exactly. And then I think another piece is, um, you know, I don't think you need to do a million references. 'Cause people are gonna send you the references, of course, that are gonna say all the good things. But I do think if you can get some connection to people that have worked alongside with some sort of, you know, reference backdoor that shares a little bit more insight is helpful. And I think in places we're maybe moving too fast 'cause we really had to get it done and, and couldn't get some of that, those, those additional touch points that, that we could have maybe seen around a corner, um, in advance. And I think, you know, again, it's, it's, a lot of it is folks want to say they're ready for startup (laughs) , you know, and like, "I'm all about it. It's gonna be great. I'm in for the, I'm in for the journey." And then they get there, and they're like, "Wait, what?" You know? (laughs) So, it's, so, I think that's, I mean, I've made some mistakes there. It's, uh, it's hard to vet, honestly, 'cause it's hard to say, like, you can anticipate everything and prepare someone for that. But there's been some places where it's like, this is just too fast and too ambiguous and too crazy, and I, I can't, you know? So, um, but that, that's, that's, I think you should expect one of those every once in a while, right? 'Cause it's just-

   25. HSHarry Stebbings27:38

       I think the most com- the most common I see with young founders is actually an insecurity in themselves of their lack of experience, which leads to what you said earlier, which was the logo hire. They look for the Salesforce logo because they're aware that they don't have that experience.

   26. LJLori Jiménez27:52

       Right. Right.

   27. HSHarry Stebbings27:52

       Mm-hmm.

   28. LJLori Jiménez27:52

       100%. I 100% agree with you, and it's, it's not about that.

   29. HSHarry Stebbings27:56

       Okay, so now we've got this brilliant talent. We've got this team on board.

   30. LJLori Jiménez27:59

       Great.
6. 31:36 – 35:42

   Aligning Goals and Sales Rep Performance

   1. LJLori Jiménez31:36

      Yeah.

   2. HSHarry Stebbings31:36

      ... um, uh, discovery can be leaning towards approving it more so than not.

   3. LJLori Jiménez31:41

      Yeah.

   4. HSHarry Stebbings31:41

      How do you create goals that actually align to outcomes versus ticking the box?

   5. LJLori Jiménez31:46

      Yeah, no, and I've seen that definitely, have had that happen. So that, that is a (laughs) , you know, I think anyone who's led any sort of sales development team or the team right after the sales development team has experienced that. And I think the way to mitigate that is... a few ways, is having, you know, a qualification criteria that has to be met. So if it's a BANT, if it's a... you know, whatever the structure is that identifies kind of the core drivers of that call. But also, I think what can make... like can validate if that's quality is to have some, um, sort of checkpoint, if you will, of sale stage progression. So let's say you set a meeting, an opportunity, it's early in stage. But we're gonna incentivize when that opportunity goes to the next stage. So when the seller takes over, but they move it forward, 'cause that, that is a vote of quality, right? That demonstrates that that opportunity that you created for that salesperson moved forward in their funnel. And that... and I think that's a moment of, like, yes, we had stage progression off this. This wasn't just like, to your point, like a fluffy meeting that didn't went anywhere, that checked a box, that got the list on the dashboard, all that good stuff. It actually is turning into something. So, I think that's another way to just counterbalance and mitigate that. But I think having... you have to have some sort of structure. So, you know, I've used BANT in the past, we've used there's all sorts of different ones you can use. But something that says, "This person is giving a signal that they want to continue the conversation with us, and there's a timeframe and there's a budget and there's... and they have some understanding of the buying process."

   6. HSHarry Stebbings33:07

      So I've got so many questions.

   7. LJLori Jiménez33:08

      (laughs)

   8. HSHarry Stebbings33:08

      One, what are the biggest signs that a sales rep is not working? When are me and you gonna sit down and go, "Oh, no"?

   9. LJLori Jiménez33:16

      (laughs) I think it's, um, it's activity. I mean, you, you have to put in the activity. If you're not having enough conversations and you're not working to accelerate the pipeline you have or create the pipeline that you need to have, then what are you doing? So I think you have to go back to pipeline acquisition and pipeline acceleration. What are you doing on both? Most of the time's gonna be on acceleration, right? Because the intention is they're not creating all of their own pipeline. But I do think it's very important for sellers to create s- some of their own pipeline. They're not fully responsible for it, but they have to have skin in the game on creating pipeline. So I look at those, those two metrics, it's acceleration and acquisition, and how... and then also, how are they, you know, taking feedback? So let's say they have an opportunity that doesn't progress. Let's dissect that. Like, let's do some, you know, postmortem and then learn in the next one. If you're not seeing that learning pick up, you know, after giving the right coaching and resourcing, then that's a sign to have a conversation.

   10. HSHarry Stebbings34:14

       I, I... Uh, the reason the show is successful is 'cause I ruthlessly use guests just for their advice on my own life.

   11. LJLori Jiménez34:19

       (laughs)

   12. HSHarry Stebbings34:19

       Uh, I sit on quite a few boards, and they, uh, often say, "Ah, the deal was about to convert, but then they pushed it to next quarter." And I'm always like, "How do I respond to that?"

   13. LJLori Jiménez34:30

       Yeah.

   14. HSHarry Stebbings34:30

       Like, legitimately there could be reasons-

   15. LJLori Jiménez34:31

       Yeah.

   16. HSHarry Stebbings34:31

       ... and then otherwise it could just not be legitimate reasons.

   17. LJLori Jiménez34:34

       Yeah.

   18. HSHarry Stebbings34:34

       How do you respond to the statement, "Ah, it got pushed to next quarter?"

   19. LJLori Jiménez34:39

       So, the first question would be, did you have mutual agreement with the prospect on when we would execute? So, did you work on a mutual evaluation plan or some sort of joint evaluation plan that had milestones that said, "This is the timeframe that we both agree to?" If the answer is yes, and the circumstance that pushed it is something like, you know, and we've seen this in 2023 and the end of 2022, if there's some internal event, let's say there's a RIF. You know, like, "Hey, we were going down this process, we were all in with you, but we just had a reduction in force. We have to pause, we have to reassess, but this is still a priority," then that's, you know... It's hard to anticipate that, right? (laughs) Like, an external person can't anticipate that. But if it's like, "I... You know, I was told this was the timing, my person agreed," okay, maybe you never had access to the economic buyer. You really were just working with a champion that didn't have the power to really understand the buying process. So, a lot of the core of that, like if it's, if it's, um, a result of the salesperson's engagement, it's because we... there wasn't access to the economic buyer. That's usually, like, the number one part of MEDDIC that makes it fail, is you're just not, you're not

7. 35:42 – 39:31

   Relationship Building and Sales Growth

   1. LJLori Jiménez35:42

      there.

   2. HSHarry Stebbings35:42

      How do you know whether you're actually speaking to the economic buyer? A lot of people internally like to pump their chest and, "I can do this, I can do this."

   3. LJLori Jiménez35:49

      (laughs) Yeah.

   4. HSHarry Stebbings35:49

      Can, can-

   5. LJLori Jiménez35:49

      Well, I think you start from, from doing the discovery with your champion and coach to understand, like, who are the stakeholders? Like, who ultimately signs? Like, who actually (laughs) docusigns this? Whose budget does it come from? And how does this fit into their priorities? That's super important. Because especially right now, you know, when a lot of companies are looking at saving, you know, and cost cutting and where can they s- where can they consolidate? If you haven't sold to the economic buyer that really understands the true value of what you're, you're bringing-... it's very likely that you can be consolidated, you know, from, w- a- away from. But if you have built value and connection with that economic buyer and they understand what, how that's solving a problem for them, you're mitigating that chance of being, of being consolidated against. So, um, I think it's really understanding, like, who's the ultimate person where this impacts, and if they are looking at their P&L and this is part of it, are they, you know, thumbs up, "I'm not changing."

   6. HSHarry Stebbings36:43

      Having a single champion is dangerous. They can leave. You need to multi-thread. How do you multi-thread without making someone feel quite commoditized-

   7. LJLori Jiménez36:51

      (laughs)

   8. HSHarry Stebbings36:51

      ... of like, "Oh, I get it, they want to speak to multiple people-"

   9. LJLori Jiménez36:53

      (laughs) Yeah, you're trying to build your stakeholder map, right? Right.

   10. HSHarry Stebbings36:55

       Yeah, yeah, exactly. How do you do that?

   11. LJLori Jiménez36:57

       Totally. 'Cause we can... No, in fact I... It's so funny, I was just having this conversation this week. You know, if you've got a great champion, it's like there's such opportunity with that. And letting them know that, like, if we partner to share this story on what we're doing together inside your organization, that can... Like, how can that make their experience and life and goals and career path and exposure, whatever it might be that they're looking for, get amplified, right? So first you gotta get the buy-in with the champion instead of, like, going around them and trying to meet a bunch of people. You know, going on LinkedIn to figure out, "Who else (laughs) in this company do I know?" It's like, first get the buy-in from the champion of why. Like, it's so important in every sales engagement, explain the why. Explain why you're doing it, and then get some of their buy-in. "Can you refer me to..." Like, for example, our... Is there another department that we might partner, that might be using our solution? How would they interact with it? Could I get a conversation with them just to better understand their goals? And also, always say, "I'm not gonna take an hour of their time." You know, make sure (laughs) you're, you're also setting the stage that you're gonna be respectful, that they have a job to do and other priorities that don't include you. So, making sure you bring that humanity to the conversation, um, is super important. But I think it's, like, not doing it just... It's back to that checklist question, is, like, not doing it just to check a... The thing to really understand curiously, like, how will my solution stretch across an organization and how to meet the people that are gonna be part of that.

   12. HSHarry Stebbings38:13

       Lori, is old-school enterprise selling dead in the way that you take them to the Super Bowl-

   13. LJLori Jiménez38:19

       (laughs)

   14. HSHarry Stebbings38:19

       ... you take them to Beyonce, Taylor Swift. You know, the old-school, like, you know-

   15. LJLori Jiménez38:23

       All that stuff.

   16. HSHarry Stebbings38:24

       ... courting. Is that dead or is that alive, actually?

   17. LJLori Jiménez38:27

       I don't think it's fully dead. Um, I mean it was, it was the play when I started. (laughs) Like, that was it. You know, you flew out to Texas, you took them to the steakhouse, you did all that stuff, right? I think with COVID and realizing what we can do remote, that has absolutely changed the game with how much selling you can do virtually. And I think if you do that right and it doesn't feel transactional, you can still have a very genuine connection with a buyer. I think it hasn't died, but I think it's just been kind of, uh, relegated to, like, a very specific motion that's happening. And it's almost additive, if that makes sense. It's like you've gotta still do all the work to have that moment be... Really have strong ROI. Um, but, but still, you know, inherently, people like getting together and connecting and building that. So I think there's a lot of goodness to that. It's just like, how do you use that moment and what's the, what's the return for the customer and for the company?

   18. HSHarry Stebbings39:16

       I think it's also, like, know your buyer.

   19. LJLori Jiménez39:18

       Exactly. Exactly.

   20. HSHarry Stebbings39:18

       And this sounds awful, but, like, the oldest school company...

   21. LJLori Jiménez39:20

       Do they care about that?

   22. HSHarry Stebbings39:20

       Yeah, exactly.

   23. LJLori Jiménez39:21

       Yeah, yeah. They might be like, "You know what? I don't wanna hang out with you (laughs) after work."

   24. HSHarry Stebbings39:25

       Yeah.

   25. LJLori Jiménez39:25

       "I'd rather (laughs) hang out with my family and friends, so no thank you, but I appreciate the offer," right? (laughs)

   26. HSHarry Stebbings39:29

       No, I, I, I totally get...

8. 39:31 – 53:23

   Strategies for Sales Growth

   1. HSHarry Stebbings39:31

      Can I ask, do you ever do discounting? It's often the lever to get deals over the line. How do you think about discounting and how do you advise founders on whether to or not to do it?

   2. LJLori Jiménez39:40

      I mean, there's some dependence on, you know, what market you're in, how many competitors, all that good stuff. Like, if you're just, if you're, if it's a really competitive market and, and there's not as much differentiation as you'd like, you might need to do it to just get a foothold and to make sure you're grabbing market share where you can. I, you know, definitely understand when that has to happen. I think it's all about a trade-off. It's like, what are you, what are you demonstrating from a value trade for that? Is there something that, "Hey, I'm gonna give you this discount, but in exchange for that," um, especially in the early stages, "I need references." You know, "I need f- folks that will speak on our behalf beyond just me," said founder or, or sales leader, whomever the person is that's in the engagement. So I think you should just make sure you're preserving value through what that trade-off is with the discount. And I think in the early days, it's, like, customer stories, it's references, it's introductions to, you know, "Hey, could you... Are there referrals you can help me with that can help me broaden my reach that I maybe couldn't get myself?" And then also just, of course, you just... You wanna not... Make sure you're demonstrating what that discount represents. So I think it's also... I'm a big fan of, like, when you're even going to proposal stage, showing it. Like, "This is exactly what's coming off of this original list price. This is what that means," so you really see it visually. And that sits with, um, the buyers. They, they recognize that, "The collection of your good work to get to th- this stage has produced this discount. We're gonna support it, provide good work, and execute on the timeframe that we agreed to mutually."

   3. HSHarry Stebbings41:01

      How do you think about multi-year deals and paid upfront? What's your advice on that?

   4. LJLori Jiménez41:05

      Yeah.

   5. HSHarry Stebbings41:06

      Um...

   6. LJLori Jiménez41:06

      I mean, multi-year deals es- right now especially are a good thing, right? Because you're, you know, (laughs) like, gross retention, gross retention, right? (laughs) And so they're a good thing. I think, again, you can put some financial incentive behind it and make them very compelling for the customer and for, um, you know, the vendor. So I think it's a good thing to do. I think, um, you... And there's ways to also incent a sales team to do it well, so you're not... You know, you're thinking about, like, "Hey, if you get a multi-year deal, this is some things we can do from a future pricing perspective," or things like that.

   7. HSHarry Stebbings41:31

      I thought it was interesting, I had Mark Goldberger on, who I think you maybe worked with at Navan-

   8. LJLori Jiménez41:34

      Yeah, I worked with him.

   9. HSHarry Stebbings41:35

      ... yeah.

   10. LJLori Jiménez41:35

       I worked with him at, at Navan, yeah.

   11. HSHarry Stebbings41:37

       Yeah, so when I spoke to him about testimonials, he said, "With all our customers, we basically have it baked in that they will give us customer testimonials," which is a bold statement.

   12. LJLori Jiménez41:46

       That is bold.

   13. HSHarry Stebbings41:47

       Um...

   14. LJLori Jiménez41:47

       Yeah.

   15. HSHarry Stebbings41:47

       Yeah.

   16. LJLori Jiménez41:48

       (laughs)

   17. HSHarry Stebbings41:48

       Um, how do you feel about customer testimonials and what works in terms of getting them?

   18. LJLori Jiménez41:52

       I think you have to... That's bold, but (laughs) I think you have to, um... And I'm a big fan of Mark. But, um, you have to say... There's a caveat around that. Like, we've gotta prove value, so we've gotta prove what we've been telling you for whatever this selling motion period is. We're confident we're gonna do that, and w- in exchange for that, we'd like a testimonial. But I think it's, it's important to ask, but I think it's important to set the framework, is like, "We're gonna meet the goal, the mutual goals that we agreed on. We're gonna get you to what you're trying to reach from a, you know, organization perspective." And then ask, and then, and say... And at that moment, I'm gonna come back and ask for it. And I think it's like it's a seeding opportunity. It also demonstrates that you're staying connected to them for the long term. I think when a customer really is in partnership with you and believes that you genuinely are looking for a long-term fruitful partnership...... they're gonna be apt to do that 'cause they believe that, that, you know, genuine human connection that you've demonstrated and that great discovery and that great listening is gonna prove to be a really good investment long term. So, I think if you set that stage, then you can get that t- testimonial. But you should, I think, make sure you're going back to you're gonna prove the value that you said you would bring.

   19. HSHarry Stebbings43:01

       I love people. Okay? I'm all in for this-

   20. LJLori Jiménez43:03

       (laughs)

   21. HSHarry Stebbings43:03

       ... genuine human connection shit that you've got going. I love it.

   22. LJLori Jiménez43:06

       (laughs)

   23. HSHarry Stebbings43:06

       I'm there, okay? Uh, I know, uh, someone described me the other day as the Ricky Gervais of venture and startups. I was like, "I don't know if that's a-"

   24. LJLori Jiménez43:13

       (laughs) That's pretty good.

   25. HSHarry Stebbings43:14

       "... don't know if that's a positive or not." (laughs)

   26. LJLori Jiménez43:16

       You're like, do I like that? Do I not like that?

   27. HSHarry Stebbings43:17

       Uh, but I'm all in for this. But then my problem is, okay, we've got this beautiful genuine, you know, connection-

   28. LJLori Jiménez43:22

       Yeah.

   29. HSHarry Stebbings43:22

       ... human relationship. Speak to my CS team now 'cause you were handed off. That handoff feels quite dehumanized. How do you think about retaining genuine human connection, care, relationship, with a very efficient but qu- dehumanized handoff?

   30. LJLori Jiménez43:38

       Yeah, no, I think you can't make it dehumanized. And I'm m- for, in my role today, I'm responsible for all of, you know, from sales through to customer success through to support, and we operate as a revenue organization. So we don't operate as a sales organization, and a implementation organization, and a success organization, and a support organization, it's one. And what we prioritize to make that not feel like a handoff is the conversation that happens. We are engaged in each part, so for example, if we're gonna, uh, if we're, you know, closing out our quarter and we're about to plan an implementation in the next phase of that customer's journey, that implementation manager's on that last call. And they meet them, and they say, "This is my colleague. These are some of the customers that they've worked with. They're a rockstar. They're gonna carry you through, and I'm gonna join when you go to launch that last call." So it's like you've gotta not hand the baton off and then let go. You've gotta hand the baton off but say, "I'm coming back and I'm gonna stay connected." And you can also do that with just, like, structure of how you compensate people with upsell and things like that, so to make sure there's an incentive. But I think you've gotta show it. Like, you actually have to show up (laughs) to the call and, and stay engaged. And then additionally, let's say you're now with a customer s- you've launched, you're with a customer success manager, uh, I think the account executive needs to join those QBRs. They need to listen. They need to participate. They need to not be maybe the one driving the QBR that the customer success manager's leading, but they need to show up. And what that shows is, like, I care about you as a customer. I'm not just, you know, closing the deal, moving on, closing the deal, moving on. I'm staying with you through the lifecycle of... and seeing your success through.
9. 53:23 – 57:06

   Quick-Fire Round

   1. LJLori Jiménez53:23

   2. HSHarry Stebbings53:23

      Now, I love this segment. It's a quick fire.

   3. LJLori Jiménez53:25

      Okay.

   4. HSHarry Stebbings53:25

      I say a short statement, you give me your immediate thoughts. Does that sound okay?

   5. LJLori Jiménez53:29

      Let's do it. Let's do it.

   6. HSHarry Stebbings53:30

      So what sales tactics have not changed over the last five years?

   7. LJLori Jiménez53:34

      I would say, you know, selling is an art and a science, and I think, um, but at its core, it's about really good listening and bringing value. So it, it's back to, like, people buy from people. And so it's really, like, good listening, connecting with that buyer, and bringing value in response to their answer, so I don't think that's changed.

   8. HSHarry Stebbings53:50

      What sales tactics have died a death?

   9. LJLori Jiménez53:53

      We talked about it a bit, but I think onsites are dying a death. Not f- they're not gone, but I think we've learned how much we can do virtually. And so that old, like, everything must be onsite, in-person handshaking has really changed, and it's a g- it's crazy to see that we're not all on airplanes like we were just, you know, a few years ago, but it's changed. So I think it's, that's, that's definitely, I don't know if it's died a death, but it's, it's dying.

   10. HSHarry Stebbings54:16

       What is the biggest mistake founders make when hiring sales teams?

   11. LJLori Jiménez54:21

       Setting expectations (laughs) . I think it's really important to both have a common, like, "Here's where we think we need to, we can go. Here's where I..." You know, like, really having a mutual understanding and joint belief in those expectations, but you gotta set 'em. Because if the founder believes here and the, the first sales leader thinks we can only get to here because those expectations were set, then you're just gonna have a mismatch.

   12. HSHarry Stebbings54:42

       You call up a new sales leader the night before they start their role. What would, advice would you give them?

   13. LJLori Jiménez54:49

       I would give them the advice of...... like, really dig in and learn in those first, you know, 90 days deeply, but be prepared to relearn everything in 90 days. So it's, like, you gotta go deep, and understand, and get in as many customer calls as you can, and really under- work to understand the mechanics and the operating rhythm of the business. But then you will take that basis of foundation, and you're gonna learn it again because you're gonna have all that context and you're gonna pivot your mindset and build off of that first 90 days. So I think it's, like, the expectation is just be ready to keep learning. That's not gonna stop. You're not done after quarter one.

   14. HSHarry Stebbings55:21

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

   15. LJLori Jiménez55:24

       This has changed tremendously in my career, but I would like to see more female leadership at the top. I think, um, it... And it... Again, it's changed so much in my, my time in sales, but just more female leadership, um, would be something I would change.

   16. HSHarry Stebbings55:38

       I mean, we have 20 Sales Fun, which is, like, eight of the most incredible sales leaders, and it was funny how it came together. Like, it was not meant to be, like, an all-female group. And then, you're like, "Oh, wow." P- (laughs) I learned that actually women are just better than men at sales.

   17. LJLori Jiménez55:53

       (laughs)

   18. HSHarry Stebbings55:53

       (laughs)

   19. LJLori Jiménez55:53

       And I... To your point, it's changed a ton, but it... Which is great, but we just can't. Like, we can't take our eye off the ball. That has to be still a priority. So I would change that.

   20. HSHarry Stebbings56:00

       No, I totally agree. Final one for you. Which company sales strategy have you most been impressed by recently, where you look at it and you're like, "Smart"?

   21. LJLori Jiménez56:07

       Yeah. Actually, we recently, um... It's recency, but we recently bought Vitally for our customer success team, so a customer success platform. And what I was really impressed with is, um, really clear communication the whole way and very direct and engaging. But what I really have noticed is post-sale is how they continue to stay connected and care about the success of our launch. And especially in this time where gross retention, you know, is so important and thinking about retaining every customer that you spent so much time earning, they've stayed connected through that whole process. So really clear communication, great sales process upfront, but they're continuing it through all the way as we've become a customer. So I've been very impressed by that.

   22. HSHarry Stebbings56:46

       That was a great answer.

   23. LJLori Jiménez56:47

       (laughs)

   24. HSHarry Stebbings56:47

       Some people, some people give their own company and I'm like, "Oh, for fuck's sake." (laughs)

   25. LJLori Jiménez56:51

       (laughs) Don't do that.

   26. HSHarry Stebbings56:52

       But that was amazing. Uh, listen, I love this. Thank you so much for putting up with my very wayward, but I think brilliant questions.

   27. LJLori Jiménez57:00

       They were great. Yeah. Love them.

   28. HSHarry Stebbings57:01

       (laughs) Uh, no, seriously, I love this. You're a star.

   29. LJLori Jiménez57:04

       Thank you. Thank you. It was a great conversation. I appreciate the time.

Episode duration: 57:06