20Sales: Why The Founder Has To Be The One To Create The Sales Playbook, When To Hire Your First Rep, Why Junior is Better Than Senior, How to Manage Sales Rep Compensation, How To Onboard New Sales Reps and more with Lori Jimenez, CRO @ WorkRamp

2 Aug 2023 · 52 min

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In short

Podcast Summary: The Twenty Minute VC (20VC) - Episode with Lori Jimenez

Episode Details

  • Title: 20Sales: Why The Founder Has To Be The One To Create The Sales Playbook, When To Hire Your First Rep, Why Junior is Better Than Senior, How to Manage Sales Rep Compensation, How To Onboard New Sales Reps and more with Lori Jimenez, CRO @ WorkRamp
  • Host: Harry Stebbings
  • Guest: Lori Jimenez, Chief Revenue Officer at WorkRamp
  • Description: Lori discusses her extensive experience in sales and customer success, sharing insights on building effective sales teams, creating playbooks, and managing sales processes.

Key Topics Discussed

  1. Lori's Sales Journey
  2. Early Start: Lori began her sales career at age 15 in retail, where she developed a passion for customer interaction and sales.
  3. Career Path: She has held positions at major companies like Google, Facebook, and Box, learning valuable lessons about teamwork, focus, and ownership.
  1. The Sales Playbook
  2. Definition and Importance: Lori defines the sales playbook as a GPS for sales processes rather than a script, emphasizing its role in guiding sales teams based on past successes.
  3. Founder’s Role: Founders should create the initial playbook due to their deep understanding of the product and customer needs, allowing them to adapt based on feedback.
  1. Hiring the Right Sales Team
  2. First Hires: Lori suggests hiring junior talent over seasoned professionals due to their adaptability and hunger for growth, especially in early-stage startups.
  3. Interview Process: Lori emphasizes the importance of role-related knowledge and the ability to work collaboratively in sales hires.
  4. Compensation Strategies: She highlights the significance of understanding candidates' motivations during compensation discussions and the importance of aligning expectations.
  1. Sales Scaling and Execution
  2. Onboarding Reps: Discusses best practices for onboarding, including structuring training and ensuring new hires understand the company’s sales process.
  3. Sales Goals: Stresses the importance of goal alignment and setting meaningful metrics for sales teams to ensure productivity.
  1. Managing Sales Processes
  2. Deal Reviews: Emphasizes the need for structured deal reviews to identify gaps and support needs, avoiding a mere storytelling exercise.
  3. Customer Engagement: Discusses the importance of maintaining genuine relationships with customers, even as accounts transition from sales to customer success teams.
  1. Sales Strategy and Market Trends
  2. Discounting: Lori explains how to strategically use discounts to enhance customer relationships and drive growth without devaluing the product.
  3. Market Changes: Reflection on the evolution of sales tactics post-COVID, noting how virtual selling has shifted dynamics.

Key Takeaways

  • Human Connection in Sales: The importance of genuine relationships and active listening in the sales process.
  • Flexibility and Adaptability: Sales professionals should embrace ambiguity and be willing to learn and adjust approaches based on customer feedback.
  • Focus on Training and Development: Continuous learning and open communication within teams are vital for success in the rapidly changing sales landscape.
  • Mindset Matters: A growth mindset and resilience are critical attributes for both sales leaders and their teams.

Conclusion Lori Jimenez provides a wealth of knowledge on navigating the complexities of building and managing sales teams, emphasizing the importance of adaptability, genuine connections, and strategic planning in achieving success in sales.

For more insights and resources, visit [20VC](http://www.20vc.com).

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Transcript

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0:00Break down an interview process into chunks. Do they know enough to be dangerous? And then the next day on the process is the how. So how have they been successful? What stories can they lean on to tell you how they've navigated through a win or a loss? How did they bring in different resources? Peel back those layers and ask questions that can help you reveal how they've navigated something really hard. This is 20 sales with me Harry Stabbings. Now 20 sales is the monthly sales focus show where we sit down with the best sales leaders in the world to discuss their tips, tactics and strategies to start scaling sales teams.

0:33Today, I'm so excited to welcome Laurie Jimenez, Chief Revenue Officer at WorkRamp, where she's responsible for sales, customer success, solutions, engineering, sales, development and revenue operations, and over her 25 -year career, Laurie has a track record of scaling high -growth go -to -market teams, a company's like Google, Tripassians, now -Navann, Facebook, and Box to name a few. But before we move into the show's day, you might remember in our amazing episode with Maggie Hott. She mentioned a tool she could not live without called Pocus. What is Pocus? Well, Pocus is a revenue data platform that makes it easy for go -to -market teams to analyze, visualize, and action data about their prospects and customers without needing engineers.

1:13Pocus helps companies like Miro, Webflow, Loom, and Superhuman focus their sales and success teams on the highest priority opportunities by surfacing insights at the right moment and so Raps can take action quickly. Pokers gives you a 360 degree view into product usage, empowering you to act on incison failure funnel efficiently. Sales teams save 10 plus hours per week, digging through data to surface millions of new revenue opportunities, learn more about why top PLG businesses trust Pokers as their revenue data platform by visiting Pokers .com forward slash demo. And sales loft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace.

1:55It's the one place sales teams can go to Prospect, manage active deals and get the insights they need to coach seller performance, forecast with accuracy, and find out what steps to take to close more deals. Some of the world's leading companies like Google, Shopify and Stripe all love a new sales loft and so can you. It's the new way to sell. Find out more at salesloft .com.

2:21You are now arrived at your destination. Laurie, I am so excited for this. I had so many great things from many past guests, especially the wonderful rich. So thank you so much for joining me today. Oh, thanks for having me. Appreciate it. Now, I always love to start with some contact. So tell me, how did you make your way into the world of sales and come to lead some of the most incredible sales awks as you have done? My path into sales, I discovered sales at the right page of 15 and a half, which was the day I got a workers permit and could get a job. So I was fired up to get a job and make some money.

2:52So I 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 marched in on my first day ready to get working. And he said, here are the keys to the other store. Go open it up. There's a shoe box 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. So he's like, open the store and get going. So I'm like, all right, I'm going to do this. I go and open the store and soon after opening the door, customers started coming in.

3:24So I had to start selling. I did a terrible job. I don't think I charge sales taxed anyone that day. I'm sure there were some very good deals made. But what I got from it was the energy of working with customers. And I stayed in retail throughout high school and college. And then fast forward, I graduated from college during their 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, Lori, I work in a software company. We're doing kind of this group call interview for salespeople, are you interested?

3:59And I was like, both hands up. I will let me get a job with it. 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 firm job. So I went to the interview, I got the job, and that company was Remedy Corporation, which was later, you know, being part of BMC. I think their software still on the still -escue BMC, which is amazing. It was a formative part of my career. Super fortunate to experience an IPO with them. So I just saw like what Hygroth was all about from the start.

4:31So that was my story. That's how I got here. Two things that I just have to do. And one is the takeaways from the organizations you've worked at, 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? 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 in, run a script, go, there's not a a lot of humanity to it.

5:04And 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, then I think you can really learn to love it. So I think it's actually more the latter, even though my experience was that instant energy. I absolutely love the honesty there also, Laurie. How is he sped you to be like, yeah, the first one, that's what I was like, I was like, what's that? I was like, okay. Now my nice question was like, we'd normally do a quick far round at the end, but you've worked at some of the most incredible companies.

5:29I was like, well, how do I kind of compress this in a way where we get the takeaways in an efficient style. And so we're going to go through each company, and you're going to 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? 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, 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.

6:06And so from the start, you've got to get out there 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 going to 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, there's so much that you can take that to. That's an applicable skill and talent that carries over into any role. So that would be my takeaway from Google. God, I'd be terrible.

6:32I'm probably worth who I am wearing. Well, you know, the Jolene viewers, like, are you a team player? No, no, not a jolt. They're not, you can learn it. You can. OK, next one is Facebook. What was the take from that? Facebook was, I would say, focus on impact. 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 going to make the biggest impact and carry that forward versus getting kind of diluted across a long list of two do. So definitely, and you see that the way the company operates. Nice one. Navine or Tripassians?

7:06Sure. Two would 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 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 to build a plan that could go in a few different directions and that could morph and change? So that kind of flexibility, but definitely learned the speed and the ambiguity there. Final idea after I asked his box. What was the take away for books? That was probably a favorite place of mine.

7:35One big learning that has been kind of core to the way they've run the company from the start is to be an owner. Really believe that we collectively are the company. It isn't someone else. It isn't above you, below you, from the sides. It's from the way you put your attention into an email you're sending a prospect to the way you're navigating big operational organizational change management. You're part of it. You're doing it with a team. It's not happening to you. You're help getting it done. And that's really something, Aaron, just has built and made core to the culture. And I've carried it forward in every place.

8:07I've been since. Is that why it was your favorite? It's one of the reasons definitely. You really felt that you were part of something at box. You were part of the build. And that meant for the goods and the bads, right? it's not just the highs that everyone was in for all of it. And you really felt it. You felt it, and you could get that energy inspired across a team of SDRs or sales rep coming in, like the energy that creates is just it's palpable. Now I want to dive into some of the weeds. We often hear the term sales playbook. Before we get into whether the founder should be the one stood or whether someone else stood, how do you define sales playbook?

8:39Think 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. I'll think of it as a guide. So depending on where you are in a sales process where they're very early and you're doing discovery 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 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 sales engagements and building that into like a guide that can help you navigate through.

9:19But enough that still gives that level of creativity and flexibility that accounts for the style of that salesperson. You said that building on the success of prior sales interactions and engagements. Does that mean that the head of sales should be the ones created or should founders create it and then park at all? Yeah, good question. The founders are the right folks to create it for a few reasons. things where it started, right? 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.

9:54So there's that that you're for grounding from and what that creates is the person that knows the why and the what in such a deep level that they can anticipate things like what problem 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 there and 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 work RAM, you know, Ted is a go -to -market leader and also has an incredible product background.

10:31So what's great about that is his 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 And if we get some feedback even now, or he's less connected, less 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. I also think you cannot hire a head of sales unless you know what sort of playbook you're running.

11:00Exactly. Like, how do you coach them? And how do you guide them? I know there's so many different types of heads of sales. Some are much more enterprise -heavy, some are much more than the LG. Yeah, there's just okay. So when we think about that first higher, so to speak, most often go for the logo'd rap or the logo'd person But you feel differently. Why do you believe this approach of like the hailed logo person isn't maybe the right one a couple reasons I believe especially in the early stages There's a huge opportunity to not only like identify and sprout new talent in a startup But also you're looking for someone who's demonstrating driving ambition and all that good stuff But that doesn't just translate into a huge logo person.

11:39What gets them energized? How do they navigate through ambiguity? They don't come in with it like this is the only way to do things. There's an openness to like, I am in it because 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. There's a mindset that 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 talent because of the creativity They can bring and they don't have kind of a bias from a previous experience.

12:14Laurie, I'm with you in terms of the scrappiness the hunger of those early reps. Sure, the other question is when some founders just hate it, selling them so they want it as soon as possible. Some wait for too long. How do you advise founders on when's the right time to add that scrappy hungry profile? I think it's all about thinking about scale. So if the founder is doing it and let's say you've got 10 to 20 customers, like how much more can they do? Like just in their street, daily capacity. You know, how much can they get done in addition to growing and scaling the company through all the other disciplines?

12:47So I think it's that moment where you've got enough customers and you find enough of a repeatable process that can take your good work and grow it and have feedback. I think also just someone that you can work with, like, hey, we've been trying this for the for ex number of customers, let's tune that a little bit. I'll go try that and come back to you with feedback. There's huge value in having partnership, the kind of how many people do you hire at a certain time. There's huge value in being the learn from someone 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.

13:21Jason and I'm just about hiring the two by two. Two? Yeah, hiring the games, you know. Yeah, yeah. I till death and you know kill the other one who doesn't get a million in air off. At the end my point of view doesn't actually say that. That's really unfair of me. 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 ramping them? I do. I think you should hire more than one at a time for a few reasons. Less about the competition. I think that's kind of going to happen maybe naturally. But it's more about you or it's work for scale.

13:51I think if you're onboarding one person, on board as many as you can, because 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 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 in a bit. You try this, we can test and see what's working. That first slide kind of group founding team, there's nothing like it. You know, there's learning, there's energy, there's culture that comes from that.

14:20So there's just so much positive byproduct from building a team through having a small group that starts, that you get that carries through and just reverberates through the company culture and is very foundational. I will run a hypothetical process with you. You're an advisor or angel in my company and I am a founder scaling sales team. We've now identified that I need this scrappy hustlementality and profile. How do I literally stretch the process for hiring a new sales team member? From a process perspective, is you break down an interview process into kind of chunks, if you will. So the first part would be just vetting for, and this is a term I learned at Google, which the way just they framed it is really helpful, is vetting for just role -related knowledge.

15:04So it's like, do they have knowledge that relates to the role that you feel would say, yes, I want them to kind of go through to the next phase in the process. So do they demonstrate the characteristics? Do they know enough to be dangerous? Right? who didn't some experience that they can lean on to go forward from and roll it with the company. And then the next day on the process is the how. So how have they been successful? What stories can they lean on to tell you how they've navigated through a win or a loss, most importantly a loss, who like how did they bring in different resources? How did they navigate change?

15:36Because you know, a lot of folks will say, oh yes, I want to be part of a startup. I'm ready for it. I'm ready for all the crazy and the chaos, but like, are they really? They really want that. So really kind of peel back those layers and ask questions that can help you reveal how they've navigated something really hard and does that energize them or does that make them go ah run away so. Well questions do you ask? Because sales people sell a good game. Oh they do, they do, you're absolutely right because there's some great people can interview really well and tricky right so the things to dig in on is I like to ask about like a loss and less about like tell me why you lost but what did they do?

16:09So they're not pointing to someone else they're saying, oh, is this person's fault? It was my territory. There's something else other than me, but it was like, what resources did you bring in to help you? Like, give me an example of what you learned from that loss and how you brought it to your next win. And what that demonstrates is not only like an ability to kind of reflect and, you know, take an experience learned from it and turn it action, but also how do they work on a team? Because I think especially in a startup, like the team is so critical to the success. So how do they partner with other resources in the company to go get something done.

16:42So I think vetting for that is really important. And then I think, you know, if you hear too many mentions of III, I mean, of course it's sales and you want folks to be proud of their performance. But if it's too much on just what they did independently, for me, that's a red flag. Because I think no one wins, you know, independently. It's a team sport. I was thinking data is just so important. Like the most love by yeah, I love it when you see it. I increase net revenue retention by 12 % through these three channels and that. Exactly. And it also demonstrates that they're proud of that. Right?

17:12So it's like they're sharing that data with you because they're proud of what they did to get there. So there's two really interesting parts of that answer. Okay. So we have phase one which is like role knowledge fit. Phase two which is kind of like data and supporting evidence to death quality. What next? So I think you know if you're going to go through the steps of having them maybe present to your team or give do some sort of mock discovery, mock sales call whenever case study work that you do. I think that's an important step in the exercise. I don't think it is like an income that it has to be on their current solution or it has to be on yours.

17:47I've seen it done both ways. I like putting in front of the candidate about the company they're gonna come join, not because I'm looking for like the perfect answer, but more I like that they just do go and do homework. Like are they curious? To me it's like a critical characteristic of a great salesperson is curiosity. What they gonna learn about us, they might find something in our story that we aren't leaning into as much that we should amplify more. So I like to have some sort of case study discovery call whatever it might be that has that's on the company that they're going to interview that you're representing and so that they can come and kind of tell how they interpret that.

18:19You know, that's not an easy situation to be in also so it's kind of high stakes. So how do they operate in that? Like are they comfortable being uncomfortable because that's what the lab sales is? I'm with you totally on the doing it on your company. It's not that popular or an answer, but I like it way more. My favorite is I want to say, dude, on a company that we know nothing about it. Right. They could say anything, right? We wouldn't know. We had to hear something like, why don't you even vetting for it that way? Exactly. Thank you, your suggestion. I would. I would. In terms of the next step, they've blown us away.

18:47The fantastic. And we want to offer it to them. What are some of your biggest lessons on compensation and title when it comes to sales in addition? That's a good one. 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 50K more OTE over here. And then you ask, Okay, well, what does that mean for you? What does that represent? What is it inequity? Is it an OTE? What is it? And what's driving that ask? So I think with compensation, it's an opportunity to really understand what motivates that person.

19:22And also like as a startup, like, do they really believe they're taking a risk? Are they excited about that future opportunity that shows up in equity. What are the questions around equity? Do you see an excitement in those questions? If it comes down to just a dollars on OT, I'm always a little bit like, it's not a full red flag depending on where the conversation goes, but it's something that concerns me because that will come back in the future where someone's going to be. Maybe you have a hard quarter? How do they navigate that? If things don't come together, do they have the staying power to work through the ups and downs that can happen in a startup?

19:56So I think it's a moment to really understand what someone's motivations are and also just like see kind of where their Research went, you know, how deeply 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 want to be a part of building? How do you think about whether to pay up for someone versus say, you know what you go for the other role? 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 maybe you could get closer and bridge it enough. But if that is all they're talking about, sometimes you have to walk away and say, you know what, that sounds like it's a better fit for you.

20:30And if that changes, let's, you know, I always leave a door open. I think it's important. The valley is small, right? You just cannot shut a door. And so I think it's okay to leave it open, but it's okay to sometimes walk away. And I'm trying to think if there's anyone that we walk away from there, I was like, that got away. And I know one's coming to mind. So, you know, that tells me that those were the wrong decisions. Do you have any lessons on Tysel? And what people want in Tysel? that's important. Yeah, so I think that it's honestly like a discovery call in sales. It's like, what's the why behind the title?

21:00Are they looking because they want to demonstrate a certain level of progression on their LinkedIn profile? Is it that they want to demonstrate scope? Is it someone who's maybe, and I've seen this like gotten stuck with title at a big company where titles get a little murkier and are a little more flat and they come out, they're like, I need to break out of this kind of big company title level conundrum that I'm that I'm trapped in and I want something to demonstrate my scope. 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.

21:33So if you get too aggressive on title, and then you're a couple years down the road, and your next person comes in and they're like, well, why am I not a senior director? Maybe that first person wasn't. You know, and so you're like, okay, now we got to unwind this a little bit. So I think 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. The one that I've learned 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.

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22:04I get that. Exactly. You're using it to go accelerate growth. That's a good answer, right? Yeah. So yeah, 100%. Yeah. No. No doing that. And it's really other red flags in the interview process where you're like, oh, you should get the heebie's if they could love this. People can interview wealth. The answers just are shallow. If they're just very canned in 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. And this would be an answer. You know, if they can't connect to an actual customer engagement, I like it when someone's like, to your point, the stats that are really showing you like passion behind the work they did.

22:41And then a real like customer story and team story. If there weren't enough of those, like there's not enough depth, you know, that means you might get some performance for a while, but that's gonna fizzle out. When we reflect on the hiring process, and your highs that you've made, what are the biggest hiring mistakes that you've made? And how's that shaped your mindset? Yeah, that's a good question. I've had folks that it came off in an interview or super ambitious, right? They're like, I'm gonna do this, I'm gonna build this II and they had this energy about them, but when you really peel back how they're going to do it, you know, not vetting the how enough.

23:14I'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. And then I think another piece is, I don't think you need to do a million references because people are going to send you the references, of course, that are going to 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 inside is helpful. And I think in places where we may be moving too fast because we really had to get it done and couldn't get some of those additional touch points that we could have maybe seen around a corner in advance.

23:46And I think, you know, again, a lot of it is folks want to say they're ready for a start -up. You know, I'm like, I'm all about it. It's going to be great. I'm in for the journey. And then they get there and they're like, wait, what? You know, so I've met some mistakes there. It's hard to bet, honestly, because 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 can't I think you should expect one of those Every once in a while right 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 higher they look for the Salesforce logo because they're aware that they don't have that Experience right 100 % I 100 % agree with you and it's it's not about that.

24:28So now we've got this brilliant talent we've got this team on board, we're going to hear the process of onboarding and working with them. And you said to me that selling requires active listening and genuine human connection. I read it, felt warm and fuzzy, and respectfully didn't have a clue what it meant. What specifically and handgrably can be done to create this active listening and genuine human connection? Yeah. One of the most important characteristics in my opinion with a great salesperson is being curious. So what active listening means is it's discovery. 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 to inform the next question.

25:09And listen, not just for the answer you want to hear, but the answer you maybe don't want to hear, which is, you know, some red flag roadblock that's going to slow down or make the selling engagement difficult. So it's listening for the places where there's alignment and it's listening for the places where there isn't alignment that we need to go build that alignment through a really tight sales engagement. The way you teach that, I think you have to shadow a lot and listen a lot and it's a practice. So you have to prioritize that as the sales team and make sure that those questions are happening so you have to enable around it and then you have to listen for it.

25:44So for example, with my current team, we do a lot of re -listening of calls and we publicly in a Slack channel, mark them when they're perfect. And we say this is a perfect call, and we want to highlight why this is perfect. Now, perfect doesn't mean you get every single piece right, but it means that you were really demonstrating that it was linked. So we demonstrate with our leadership that this is important and matters, and we're going to teach you how to do it by giving you an example of one of your peers who does it great. That's how that turns into action beyond the warm and fuzzy. What tool do you use for your listening?

26:13Gone. So we have that and we mark it as a perfect call. What makes an imperfect call on the flip side? If that's what we should look for, where is it like, this is not a good call. This is bad. I think when a salesperson is just going through a script, and maybe we inform them to enable it, like here's some great questions that can help guide a call, and instead of asking them and pausing and listening about where that question takes that, they just go to the next question. So it's like, and it's more of just like a check box, you know, it goes back to that perception sometimes with sales being just a, you know, kind of robotic method.

26:45It's like, no, no, there's a list and we might give you that to help guide you, But that is not meant to be just something you kind of check check check check check Because what then what then you're wasting the customer's time and you're wasting your own time because you didn't get anything from that experience How do you think about effective goal setting for STRs because I find discovery can be Minipulated to align to the output desired for the goal and so what I mean by that is like, you know Leads generated discovery can be leaning towards approving it more so than not Yeah, how do you create goals that actually align to outcomes versus ticking the balls?

27:19Yeah, no, then I've seen that definitely have had that happen. So that that is it. 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 a qualification criteria that has to be met. So if it's a band, 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 validate if that's quality is to have some sort of checkpoint if you will of sales stage progression. So let's say you said a meeting and the opportunity is early in stage, but we're gonna incentivize when that opportunity goes to the next stage.

27:55So when the seller takes over, but they move it forward because that is a vote of quality. That demonstrates that that opportunity that you created for that salesperson moved forward in their funnel. And that 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 win anywhere, that we checked a box that got the list on the dashboard, all that good stuff. It actually is turning into something. So that's another way to just counterbalance and mitigate that. But I think you have to have some sort of structure.

28:21So, you know, I've used band, the passers, and the professors, 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 time frame and there's a budget and there's and they have some understanding of the buying process. I've got so many questions. What are the biggest signs that a sales rep is not working? When am I going to sit down and go, oh no. I think it's activity. 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?

28:54So I think you have to go back to pipeline acquisition and pipeline acceleration. What are you doing on both? Most of the time it's going to be on a 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 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 two metrics. It's acceleration and acquisition. And how are they taking feedback? So let's say they have an opportunity that doesn't progress. Let's dissect that.

29:23Like let's do some post -mortem and then learn in the next one. If you're not saying that learning pickup, after giving the right coaching and resourcing, then that's assigned to have a conversation. The reason they showed success was because I ruthlessly used gas just for their advice on my own life. I sit on quite a few boards and they 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? Like, legitimately, there could be reasons and then otherwise it just not be legitimate reason. How do you respond to the statement, ah, I got pushed to next quarter?

29:55So 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 time frame that we both agree to? If the answer is yes, and the circumstance that pushed it is something like, you know, we've seen this in 2023 and the end of 2022, if there's some internal event, let's say there's a riff, 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.

30:28Then that's, you know, it's hard to anticipate that, right? Like an external person can't anticipate that. But if it's like, 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 a result of the sales person's engagement, it's because there wasn't access to the economic buyer. That's usually like the number one part of medic that makes it fail is you're just not, you're not there.

30:55How 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. Yeah, well I think you start from doing the discovery with your champion in coach to understand like who are the stakeholders? Like who ultimately signs 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, cost -cutting the work and they consolidate. If you haven't sold to the economic buyer that really understands the true value of what you're bringing, it's very likely that you can be consolidated away from.

31:31But if you have built value and connection with that economic buyer and they understand how that solving a problem for them, you're mitigating that chance of being of being consolidated against. So I think it's really understanding like who's the ultimate person with this impact? And if they are looking at their P &L and this is part of it or they, you know, thumbs up. I'm not changing. 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. They're like, oh, I get it. They want to see people. You're trying to build your statement.

32:00Yeah. Yeah. How do you know? Because I can know, in fact, I had so far, 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. letting them know that like if we partner to share this story on what we're doing together inside your organization How can that make their experience and life and goals and career path and exposure or whatever it might be that they're looking for get amplified right? So first you have to get the buy -in with the champion instead of like going around and training meet a bunch of people You know going on LinkedIn and figure out who else in this company do I know?

32:31It's like first get the buy -in for 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. Could you refer me to, like, for example, 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 going to take an hour of their time. Make sure you're also setting the stage that you're going to be respectful, that they have a job to do and other priorities that don't include you.

32:58So making sure you bring that humanity to the conversation. But it's back to that checklist question. It's like not doing it just to check 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? Lori, is old school and price selling dead in the way that you take them to the Super Bowl and take them to Beyoncé, Taylor Swift? You know the old school, you know? All that stuff. All -thing. Is that dead or is that alive actually? I don't think it's fully dead. It was the play when I started. Like that was it.

33:30You flew out to Texas, you took them to the stake house, you'd 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 relegated to like a very specific Motion that's happening and it's almost additive if that makes sense It's like you've got to still do all the work to have that moment really have strong ROI It's just like how do you use that moment and what's the return for the customer and for the company?

34:05I think it's also like know your buyer. Yeah, they might be like you know what? I don't want to hang out with you after work. I prefer to hang out with my family and friends so no thank you Do you ever do discounting? It's often the lever to get deals over the line How do you think about this county and how do you advise founders on whether to or not to do it? Yeah, I mean there's some dependence on you know what market you're in and how many competitors all that good stuff If it's a really competitive market and there's not as much differentiations you'd like, you might need to do it to just get a foothold into make sure you're grabbing market share where you can.

34:35So definitely understand when that has to happen. I think it's all about a trade off. It's like, what are you demonstrating from a value trade for that? Is there something that, hey, I'm going to give you this discount, but it's changed for that, especially in the early stages, I need references. You know, I need folks that will speak on our behalf beyond just me, said founder or sales leader, whomever the person is, is in the engagement. So I think you should just make sure you're preserving value through what that trade -off is with the discount. I think in the early days, it's like customer stories, it's references, it's introductions to other 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 Want to not make sure you're demonstrating what that discount represents.

35:14I'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. You really see it visually. And that sits with the buyers. They recognize that the collection of your good work to get the ZIS stage has produced this discount. We're gonna support it, provided work and execute on the timeframe that we agreed to mutually. How do you think about multi -adoles and paid upfront? What's your advice on that? Yeah, I mean, multi -adoles is right now, especially your good thing, right? Because you're, you know, like gross retention, gross retention, right?

35:46And 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 the vendor. So I think it's a good thing to do. And there's ways to also incentivize sales team to do it well. So you're thinking about, hey, if you get a multi -year deal, this is some things we can do from a future pricing perspective or things like that. I thought it was interesting. I have Mark Goldberger on who, I think you may be words with it. Yeah, I worked with him. I worked with him at Nivania. Yeah, so when I spoke to him about testimonials, he said, with all our customers, we basically have it baited in that they will give us customer testimonials, which is a bold statement.

36:18That's not. How do you feel about customer testimonials and what were in terms of getting them? That's bold. But I think you have to say there's a caveat around that. Like we've got to prove value. So we've got to prove what we've been telling you for whatever this selling motion period is. We're confident. We're going to do that. And in exchange for that, we like a testimonial. But I think it's important to ask, but I think it's important to set the framework. Is like we're going to meet the mutual goals that we agreed on. We're going to get you to what you're trying to reach from a, you know, organization perspective and say, and at that moment, I'm going to come back and ask for it.

36:50And 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 going to be apt to do that because they believe that that genuine human connection that you've demonstrated in that great discovery and that great listening is going to prove to be a really good investment long term. So I think if you set that stage, then you can get that testimonial, but you should make sure you're going back to you're gonna prove the value that you've said you would bring.

37:21I love people, okay? I'm all in for this genuine human connection shit that you've got going. I love it. I'm that, okay? I know someone described me the other day as the Ricky Javace eventually and start up. So I was like, don't know if that's a positive or not. I like that, I do. I'm all in for this, but then my problem is, okay, because beautiful genuine, in connection, human relationship. Speak to my CS team now, because you're handed off. That hand off feels quite dehumanized. Yeah. How do you think about retaining genuine human connection care relationship with a very efficient but dehumanized hand off?

37:55Yeah, no, I think you can't make it dehumanized. I'm in my role today. I'm responsible 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 an 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 closing out our quarter and we're about to plan an implementation in the next phase of that customer's journey, that implementation managers on that last call.

38:29And they meet them and they say, this is my colleague. These are some of the customers that they worked with. They're a rock star. they're going to carry you through. And I'm going to join when you go to launch that last call. So it's like, you've got a hand of a ton off but say, I'm coming back and I'm going to 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 got to show it. Like you actually have to show up to the call and stay engaged. And then let's say you're now as a customer, so you've launched your with a customer success manager.

38:57I 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 managers leading, but they need to show up. And what that shows is like, I care about you as a customer. I'm not just closing the deal, moving on, closing the deal, moving on. I'm staying with you through the lifecycle of and seeing your success through. For those that don't know, what's the QBR and how are the best structured? So quarterly business review, and there's argument to do quarterly or monthly, but essentially a regularly scheduled business review with your customer that demonstrates how they are progressing against the goals we originally set.

39:32So let's say that is you're going to launch in our environment. We're going to launch a certain number of classes. You're going to build a certain number of guides. You're going to hold this many whatever you know, certifications, whatever it might be. We're going to walk through how do you do? And how did we agree on those? And how did we set you up to have that engagement? And how did the engagement go? What was the activity from it? How are your users engaged? So really use data back to your day. Like show them with this. What is happening with their investment? And then show them opportunities.

40:01Like here's some things that you aren't doing yet. And we have five customers that look just like you that are doing this really well. We want to share that. We think we should try it. Let's get a call on the calendar to talk through how we can do that. So it should be a moment where you're validating the goals of what we're originally set, but also really bringing the value of what else can you do. Because it shouldn't just be a checkbox, right? Like, great. You purchased it. You got it. Launch go. What else is happening? How do you activate the roadmap? How do you activate what's coming in the future?

40:26Here's some insight in what we're building. We think this could help you reach your goals. So that's what that moment's all about it. I think there's arguments for doing it more frequently, less frequently, but the importance is to have it, you know, it's like at a regular schedule. Have you ever had a KBOR where you went, I wasn't proud handing off to that CS person, like they didn't deem me justice? Sure. I think that when that happens, it's probably because you're just going too fast. You know, it's like it's one of those moments where you gotta slow down to speed up and you're doing back to the checkbox exercise.

40:54Like here's what we did, we're gonna kind of just read back versus actually articulate. and connect. I think when it just lacks depth and it usually is because you're just going too fast. Do you think you can anticipate, Sean, ahead of time? Yeah, you've got to look for signals and then some of it is subjective, of course, because anticipation is going to come from a customer success manager connecting with a customer and like reading that experience and figuring out what does that mean. But I think you can measure a customer's health throughout, you know, let's say a quarterly fiscal, whatever the timeframe is.

41:25And that can be with data and usage, but it also can be like, hey, we set up these milestone calls. We're going to have these calls to make sure we're progressing. Let's say they miss the calls. Let's say they continue to put back to your question, it keeps getting pushed. Why is getting pushed? We're not in the priority. Take that information, marry it with the customer data. If both are down, that's a signal that you could be stepping into an area of risk. So I definitely think you can, you know, basically measure the health score of a customer and using both data and anecdotal experience and seeing like, what does that tell us?

41:54And then how do we get ahead of it? Okay, so let's say they're not attending calls. Does a leader in the customer success or revenue organization need to step in and say, hey, I understand, you know, these were original goals. We're excited to really continue to work with you. We'd really like to get a call. We've understood there's been some challenges. Could we get that? So, you know, go title match, go to their leader and try to get a call and kind of shake something loose. That oftentimes can do it because sometimes it's just the person below who doesn't have the time. So they just need someone to kind of lump it up on their priority list.

42:21So a lot of times just intervening works. or going back to what was their original goal and bringing that up. Like, we were set to achieve this. We see this as risk. We want to help you achieve it. So I think it's driving that activity and trying to get that connection back. You said there were measuring health score, a final one I could do it all day. The final one is actually deal reviews. I'm crucial part of what we do. How do you stretch them? How often do you do them? Who sets the agenda? I've never done them before. I'm this Angel Investor yours. What would you advise me? I think what's important is a good deal review is based on a common framework.

42:56So whatever your framework might be, let's say it's Maddick, just for the structure sake, the team participating in the deal review knows what you're going to be asking and can prepare. Not that it should be a big exercise and huge prep. You're not writing a PhD dissertation to do a deal review. But know what we're going to talk about. We're going to talk about the metrics that are important to that customer. We're going to talk about who the economic buyer is. We're going to talk about their process from a decision -making process and a decision -making you know, structures. So we're going to talk about those.

43:22So common language, really important. Second is you use the deal review to learn and diagnose. You're looking to see, are we on the right track? You're not looking to just tell someone they're doing a bad job. Like they're going to come in with a defense and tell you what you want to hear and make the deal review not as productive. Also, deal review should not be story time. I always say this. It's not your time to tell me a story. Like don't say, oh, I'm not with this person who's connected to this person. I talk to this person. And this is what we said and they said this last like, no, I don't that's fine that there's a story, but let's get back to that framework.

43:53Who's making a decision? Where are we in that process? What roadblocks and what resources do you need? The whole point of a deal or you should be what resources and support is needed to go make this accelerate and where are the gaps right now? So I think that makes a really good deal review. What's a good reason to lose a deal versus a bad reason? I think a good reason is like if there really is just a mismatch in what the customer needs from like a feature perspective and they're saying they want this and you realize like we're just not going to fit that for them and we might in the beginning but then it's going to create churn.

44:24So you got to anticipate like is this customer going to stay with us for long term or we really a match? So I think it's okay to sometimes say we're just not going to meet their needs. They want this very specific use case. Yeah, we could put some resources behind it and make this happen but are we going to do that on repeat? Probably not. So let's move on to a customer where this is a really good fit like our real ICP. So I think that's an okay reason to lose and it's okay to be like you're gonna lose some So you also have to be comfortable with that like you're gonna lose some you're gonna lose some competitively Sometimes I think first getting comfortable with that and realizing like how do you find those ones that are gonna be really You know solid wins totally get you.

44:56What's a bad reason bad reason loses you didn't anticipate the competition and How they were engaged or how much the competition was positioning like what really the customer cared about how the competition could answer that question and how we could answer that question. So it's back to discovery, like really not understanding what the core goals were for the customer and that a competitor could outsell you in that moment and you didn't ask the deeper questions on what their top priorities were. Final, final one I promise, but like this is like all predicting pipeline and predicting how much we're going to mate bluntly.

45:26One of your friends said you're one of the best in the world to quote at predictable sales execution. How do you think about forecasting with accuracy? when times are as challenging as they are in terms of volatility. Back to that balance of, you know, you have to set the foundation that there's going to be a level of accountability to the forecast. And you have to dig in with the forecast when you are in a high and when you are in a low. So oftentimes you'll see like the forecast inspection happens when you're having a down quarter. For guests, inspection needs to happen in the best of quarters because if you just only pivot to when you're down, then it's in a fear -based moment and you're making decisions that are informed by that stress of missing, you've got to have that same level of rigor all the time.

46:10And you're going to teach your leaders that. You've got to demonstrate that that's really important. You're going to have rigor when you're having the best quarter and you're going to have rigor when you're having the worst quarter. And so you learn that and you teach that and that becomes kind of your basis for accountability. And I think right now, especially in 2023, it's hard to anticipate. So it's back to like having really healthy skepticism about every deal. Like I couldn't look beautiful, but like let's just go in with a skeptical mindset and shoot holes in this because we don't have the benefit of a buffer We don't have a growing, you know, macro economic environment that's different.

46:41So I think that's really important It's just acknowledge that and go in with some skepticism. Now I love this segment. It's a quick fire. I say a short statement You give me your immediate thoughts. Does that sound okay? Let's do it. So what sales tactics have not changed over the last five years. I would say selling is an art and a science but at its core it's about really good listening and bringing value so it's back to people buy from people and so it's really good listening connecting with that buyer and bringing value in response to their answer so I don't think that's changed. What sales tactics have died of death?

47:12We talked about it a bit but I think on sites are dying of death. They're not gone but I think we've learned how much we can do virtually and so that that all like everything must be on site in person, handshaking has really changed. And it's crazy to see that we're not on airplanes like we were just you know a few years ago, but it's changed. So I think that's definitely, I don't know if it's died of death, but it's dying. What is the biggest mistake found as make when hiring sales teams? Setting expectations. I think it's really important to both have a common like here's where we think we can go.

47:44Here's where I, you know, like really having a mutual understanding and joint belief in those expectations, but you gotta set them. Because if the founder believes here, and the first sales leader thinks we can only get to here because those expectations weren't set, then you're just gonna have them this match. You cool up a new sales leader the night before they start their role. What would advice would you give them? I would give them the advice, 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've gotta go deep and understand and get in as many customer calls as you can and really work to understand the mechanics and the operating rhythm of the business.

48:19But 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 experience just be ready to keep learning that's not gonna stop. You're not done after quarter one. What would you most like to change about the world of sales? This has changed tremendously in my career, but I would like to see more female leadership at the top. And again, it's changed so much in my time in sales, but just more female leadership would be something I would change.

48:46I mean we have 20 sales from which is like eight of the most incredible sales leaders And it was funny how it came together like there was not meant to be like an all female group And then you're like oh wow, I learned that actually women are just better than men it says And at your point it's changed a ton which is great But we just can't like we got take our eye off the ball. That has to be still priority final one for you Which company sales strategy have you most been impressed by recently? Were you living in your life small? Yeah, actually it's recently but we recently bought vitally for a customer success team, so customer success platform.

49:18What I was really impressed with is 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 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.

49:48That was a great answer. Listen, I love this. Thank you so much for putting out with my very wayward but I think brilliant questions. They were great. I see that. No, seriously, I love this. You are still. Thank you. It was a great conversation. I appreciate the time. I mean, what a fantastic guest. If you want to see more from us behind the scenes, of course, you can by watching the full video interview on 20VC. That's 2ZeroVC on YouTube. You can check us out there, but before we leave it today, you might remember in our amazing episode with Maggie Hott, she mentioned a tool she could not live without called Pocus.

50:20What is Pocus? Or Pocus is a revenue data platform that makes it easy for go -to -market teams to analyse, visualise and action data about their prospects and customers without needing engineers. Pocus helps companies like Miro, Webflow, Lumin, Superhuman focus their sales and success teams on the highest priority opportunities. By surfacing insights at the right moment, so reps can take action quickly. Pokers gives you a 360 degree view into product usage, empowering you to act on insights and fill your funnel efficiently. Sales teams save 10 plus hours per week, digging through data to surface millions of new revenue opportunities, learn more about wide top PLG businesses, trust Pokers as their revenue data platform by visiting Pokers .com forward slash Demo and sales loft is the leading sales engagement platform helping sales teams drive more revenue with the modern revenue workspace.

51:13It's the one place sales teams can go to prospect, manage active deals and get the insights they need to coach seller performance, forecast with accuracy and find out what steps to take to close more deals. Some of the world's leading companies like Google, Shopify and Stripe all love a new sales loft and And so can you. It's the new way to sell. Find out more at salesloft .com. As always I so appreciate your amazing sport for the show and stay tuned for an incredible episode on Friday with Elias Slice with just the most incredible story and journey.

From the publisher

Lori Jimenez is the Chief Revenue Officer at WorkRamp where she is responsible for sales, customer success, solutions engineering, sales development, and revenue operations. Over her 25-year career, Lori has a track record of scaling high-growth GTM teams at companies including Google, TripActions/Navan, Facebook, and Box.

In Today's Episode with Lori Jimenez We Discuss:

1. From a First Sales Job at 15 Years Old to Leading Sales Teams at Google and Facebook:

  • How Lori made her foray into the world of sales at the age of 15?
  • What are 1-2 of Lori's biggest takeaways from her time at Google, Facebook and Box?
  • What does Lori know now that she wishes she had known at the start of her career in sales?

2. The Sales Playbook: What, When and How:

  • How does Lori define the "sales playbook"? What is it not?
  • Should the founder be the one to create the sales playbook?
  • When is the right time for founders to make their first sales hires?
  • What is the right profile for the first sales hires?
  • Should founders hire 2 sales reps at a time? What are the pros and cons?

3. The Hiring Process: Building the Sales Team:

  • How does Lori structure the hiring process for all new sales hires?
  • What are the must-ask questions to ask in every sales hiring meeting?
  • What are the biggest red flags founders should look for when hiring for sales?
  • What are Lori's biggest lessons on how to navigate compensation discussions with potential sales hires?
  • What are Lori's biggest lessons on what title negotiation says about a candidate?
  • What are the single biggest mistakes founders make when hiring for sales teams?

4. Scaling the Machine: Bringing the Dollars In:

  • How does Lori approach discounting? When is the right time to do it?
  • Is old-school enterprise sales and entertaining dead? How has it changed?
  • How does Lori structure deal reviews? What is a good vs a bad reason to lose a deal?
  • How does Lori approach multi-year deals? What is good? What is bad?

More from The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

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20Sales: Why The Founder Has To Be The One To Create The Sales Playbook, When To Hire Your First Rep, Why Junior is Better Than Senior, How to Manage Sales Rep Compensation, How To Onboard New Sales Reps and more with Lori Jimenez, CRO @ WorkRampThe Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · 52 min
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