YouSaid · the spoken record

Lori Jimenez

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61
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2023-08-02
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2023-08-02
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  1. “Yeah, actually, it's recency, but we recently bought Vitally for a customer success team, so a customer success platform. What 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 up front, but they're continuing it through all the way as we've become a customer. So I've been very impressed by that.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “To your point, it's changed a ton, which is great, but we just can't. Like, we got to take our eye off the ball. That has to be still priority.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “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.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “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 got to go deep in understanding and get in as many customer calls as you can and really work to understand the mechanics and the operating rhythm of the business. But then you will take that basis of foundation and you're going to learn it again because you're going to have all that context and you're going to pivot your mindset and build off of that first 90 days. So I think it's like the expectation to just be ready to keep learning. That's not going to stop. You're not done after quarter one.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “Setting expectations. I think it's really important to both have a common like here's where we think we can go here's where I, you know, like really having a mutual understanding and joint belief in those expectations, but you got to set them because if the founder believes here and the for sales leader thinks we can only get to here because those expectations weren't set, then you're just going to have a mismatch.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “We talked about it a bit, but I think on sites are dying of death. They're not gone, but I think we learned how much we can do virtually. And so that old, like everything must be on site in person handshaking has really changed. And 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 that's definitely, I don't know if it's died of death, but it's dying.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “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 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.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “Have the benefit of a buffer. We don't have a growing macroeconomic environment that's different. So I think that's really important. It's just acknowledge that and go in with some skepticism.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “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 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. Forecast 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. And you've got 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 they couldn't look beautiful, but like, let's just go in with a skeptical mindset and shoot holes in this because we don't.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “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.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  11. “I think a good reason is if there really is just a mismatch in what the customer needs from like a feature perspective. 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. You know, so you got to anticipate like, is this customer going to stay with us for the long term? Are 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 that's a really good fit. Like our real ICP. So I think that's an okay reason to lose. And it's okay to like you're going to lose some. So you also have to be comfortable with that. Like you're going to lose some. You're going to lose some competitively sometimes. I think first getting comfortable with that and realizing like, how do you find those ones that are going to be really solid wins?”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  12. “Person, I talked to this person. 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. Who's making a decision? Where are we in that process? What roadblocks? And what resources do you need? The whole point of a deal review 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.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  13. “I think what's important is a good deal review is based on a common framework. So whatever your framework might be, let's say it's MATIC just for the structure's 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, you know, writing a PhD dissertation to do a deal review. But, you know, 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 in decision-making, you know, structure. So we're going to talk about those. So 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 met with this person who's connected.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  14. “Step in and say, hey, I understand these were reoriginal 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 bump it up on their priority list. So 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.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  15. “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 of, you know, let's say a quarterly fiscal, whatever the timeframe is. And that could 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 missed the calls. Let's say they continue to put like back to your question. it keeps getting pushed why is getting pushed we're not in the priority take that information bury 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 could 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 and 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”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  16. “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 got to slow down to speed up and you're doing back to the checkbox exercise of like, here's what we did. We're going to kind of just read back versus actually like articulate and connect. I think when it just lacks depth, and it usually is because you're just going too fast.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  17. “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, LaunchGo. What else is happening? How do you activate the roadmap? How do you activate what's coming in the future? Here's some insight into what we're building. We think this could help you reach your goal. So that's what that moment's all about. 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.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  18. “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. So let's say that is you're going to launch in our environment and WordCramp, you'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 court, whatever certifications, whatever it might be. We're going to walk through how did you do, like, how 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, really use data back to your day. Like show them with data what is happening with their investment and then show them opportunities. Like 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 originally set, but also”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  19. “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. 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 going to be apt to do that because they believe that that, you know, 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.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  20. “Yeah, I mean, multi year deals right now, especially, are a good thing, right? Because you're like gross retention, gross retention, right? 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, you know, the vendor. So I think it's a good thing to do. And there's ways to also incent a sales team to do it well. So 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.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  21. “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 the buyers. They recognize that the collection of your good work to get that this stage has produced this discount. We're going to support it, provided we're going to execute on the timeframe that we agreed to eventually.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  22. “Yeah, I mean, there's some dependence on what market you're in, how many competitors, all that good stuff, if it's really competitive market 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 are grabbing market share where you can. So 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 in exchange 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 or 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, its references, its 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. I'm a big fan of like when you're even going to proposal stage show”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  23. “They might be like, you know what? I don't want to hang out with you after work. I'd rather hang out with my family and friends. So no, thank you.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  24. “I don't think it's fully dead. It was the play when I started. 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 is 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?”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  25. “It's back to that checklist question is like not doing it just to check the thing to really understand curiously how will my solution stretch across an organization and how to meet the people that are going to be part of that.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  26. “You know, if you've got a great champion, it's like there's such opportunity with that letting them know that if we partner to share this story on what we're doing together inside your organization, how can that make their experience in life and goals and career path and exposure or whatever it might be that they're looking for get amplified, right? So first you got to 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 in this company do I know. It'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 you know make sure you're 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 so making sure you bring that humanity to the conversation but”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  27. “Yeah, well, I think you start from doing the discovery with your champion and coach to understand 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 cost cutting, where can 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. But if you have built value and connection with that economic buyer and they understand how that's 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 where this impacts 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.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  28. “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, 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. Then that's, you know, it's hard.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  29. “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? So 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 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 the sum 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. Like let's do some post mortem and then learn in the next one. If you're not saying that learning pickup, you know, after giving the right coaching and resourcing, then that's a sign to have a conversation.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  30. “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. So, you know, I've used Bant in the past, I've used Annum Infestors, 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 they have some understanding of the buying process.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  31. “Yeah, no, and I've seen that definitely have had that happen. So that is, 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 bant, if it's, 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 set a meeting and the opportunity is early in stage, but we're going to incentivize when that opportunity goes to the next stage. So 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 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 go anywhere, checked a box, they got the list on the dashboard.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  32. “Is bad. I think when a salesperson is just going through a script and maybe we inform them through enablement, 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 checkbox. You know, it goes back to that perception sometimes with sales of being just a, you know, kind of robotic method. It'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's then you're wasting the customer's time and you're wasting your own time because you didn't get anything from that experience.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  33. “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 the activist link. 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.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  34. “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 and 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 a 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. So for example, with my current team, we do a lot of research.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  35. “For the journey, and then they get there and they're like, wait, what? You know, so I made some mistakes there. It's hard to vet, 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?”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  36. “That's a good question. I've had folks that it came off in an interview were super ambitious, right? They're like, I'm going to do this. I'm going to build this I. And they had this energy about them. But when you really peeled back how they're going to do it, you know, not bidding 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. 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 reference backdoor that shares a little bit more insight is helpful. And I think in places where maybe 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. And I think, you know, again, a lot of it is folks want to say they're ready for startup. And like I'm all about it, it's going to be great.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  37. “People can interview well if the answers just are shallow if they're just very canned and shallow and you feel like, okay, Annie, 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 and then a real like customer story and team story. If there aren'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 going to fizzle out.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  38. “Yeah, so I think that it's honestly like a discovery call in sales. It's like, what's the why behind the title? Are 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 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 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. So 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, wait, 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, and it's okay to be comfortable with some of that at the beginning, but I think you just have to be aware of like.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  39. “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. And if that changes, let's leave a door open. I think it's important the valley's small, right? You just cannot, you know, 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 no one's coming to mind. So, you know, that tells me that those were the wrong decisions.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  40. “Don't come together? Do they have the staying power to work through 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 research went, you know, how deeply do they care about the opportunity in front of them? Is it just an OTE? Or is it they really care about the mission of the company and they want to be a part of building?”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  41. “A good one. So, on compensation, I think you learn a lot in that moment with the candidates. 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 OT over here. And then you ask, okay, well, what does that mean for you? What does that represent? Is it in equity? 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. And also 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 the questions around equity? Do you see an excitement in those questions? And if it comes down to just a dollars on OTE, 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 I concerns me because that will come back in the future where someone's going to be maybe, you know, you have a hard quarter. How do they navigate that? You know, if things.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  42. “So I think if you're going to go through the steps of having them maybe present to your team or give you some sort of mock discovery mock sales call whatever case study work that you do, I think that's an important step in the exercise. I don't think it is like incumbent that it has to be on their current solution or it has to be on yours. I've seen it done both ways. I like putting in front of the candidate about the company they're going to 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 is 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. You 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?”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  43. “Exactly. And it also demonstrates that they're proud of that, right? So 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.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  44. “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.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  45. “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 telling me why you lost, but what did they do? So they're not pointing to someone else. They're not saying, oh, it's 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 take an experience, learn from it, and turn into 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? So 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.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  46. “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 like vetting for just role related knowledge. So 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? And some experience that they can lean on to go forward from enrolling with the company. And then the next stale in the process is the how. So how have they been successful? What stories can they lean on and tell you how they've navigated through a”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  47. “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 work for scale. If you're onboarding one person, onboard as many as you can because just that time and investment in onboarding 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 going to try this message, this motion, this sales play. Maybe let's tune in a bit and you try this. We can test and see what's working. That first kind of group founding team, there's nothing like it. You know, there's learnings, there's energy, there's culture that comes from that. So there's just so much positive byproduct from building a team through having, you know, a small group that starts that you get that carries through and just reverberates through the company culture and is very foundational.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  48. “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 street daily capacity, you know, how much can they get done in addition to growing and scaling the company through all the other disciplines? So 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 first X 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, you know, the kind of how many people do you hire at a certain time? There's huge value in being to 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.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  49. “Couple reasons. I believe, especially in the early stages, there's a huge opportunity to not only identify and sprout new talent in a startup, but also 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. What gets them energized? How do they navigate through ambiguity? They don't come in with 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. 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.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  50. “So, what's great about that is him setting the playbook, which he did here is 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 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.”

    2023-08-02 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source