The Exchanges

Q slipped through the next quarter. It wasn't urgent. And I never really know what to say. I'm like, well, why wasn't it urgent? Like, fuck. Um, my question to you is like, if, if I said to you, well, the deal slipped to next quarter, they said it wasn't urgent. As my boss and my sales leader, What would you say to me and how should we deal with that?

A I would say who with the company is telling you that this is the problem that they need to solve. This is why they need to solve that problem. And this is when they need to solve that problem. And that your, so our solution is what, what they need to solve it. So at Fivetran we say, why do anything? Why do it now? Why do it with Fivetran? Right. And those are the questions that you need to be answering on every deal. And if you don't have an answer to why do it now, slipping isn't even the right term. It was never going to be a deal this month or this quarter. Right. So that's, that's when we really need to battle test what, like, what is the biggest business problem that we're attaching to? What is it that, and this is when I was talking to you about like, Helping, um, taking a customer through a journey that's actually quite painful for them, thinking about their current state without your solution. Um, it's only if we were, are able to really identify and align with the buyer on how painful their problem is that we can then tie a reasonable and predictable timeline to it. Because if it's just kind of an annoyance or a pinch for them, There's no reason there's, there's no reason you're going to get that deal done in the timeframe that you as the seller want to get it done.

AI assessment note: “I would say who with the company is telling you that this is the problem”

Q And so you're seven, you realize the love of sales through selling cookies, which I'm sure you won this competition with other brownie providers. Um, take me forward a little bit. What happened then?

A So then, um, no, I mean, as I, as I moved into my, my career after college, I, I started things at Google. Um, I spent six years in sales at Google, uh, where I learned a ton from the machine that is Google. And really it's, it's a great place to grow up and learn from adults, uh, which is, you know, different from working at a startup. So, uh, learned a lot there and that's, I landed at Google. Um, I'm born and raised in the Bay area in San Francisco. Um, and I landed at Google because I knew it'd be a great place to learn from really smart people. Um, and that to me was what got me excited about sales, uh, learning from the best. After about six years at Google, uh, I decided I had learned enough about sales and I went to business school, uh, where I wanted to learn a little bit more about just how to run a business. And, um, I actually spent a lot of time at Stanford trying to distance myself from being labeled as a salesperson. I think it's, You know, the associations people make with sales professionals are rarely positive. Um, even just the word selling, you know, no, nobody. Right?

AI assessment note: “as I moved into my career after college, I started things at Google”

Q Can I ask, when you think about kind of that wall-to-wall adoption and that expansion internally, um, we often hear about kind of multi-threading and finding, you know, many champions internally. How important is it in the early days to multi-thread, as wonderful a word as that is, and how do you advise your team on ensuring we have enough champions internally?

A Sort of depends on the size of the company or the complexity of the buying process. Um, in enterprise, it's critical. Multi-threading is critical. And every time I'm reviewing deals with my team, we're always asking about the different roles. Who is your champion? Who is the competitor's champion? Who's the champion for doing nothing? Right? That's even before you get to the economic buyer. There are the, the, and then what you do, we talked about this earlier when you're, um, you want to, Pull together current state, future state, negative consequences of current state, positive business outcomes of future state. You don't just get that from one person and then call it done, right? You ask someone those questions and then you ask someone else's questions and say, Hey, I talked to your colleague. This is what I heard from them. Feedback. And then you tweak it and you iterate and you iterate. And finally, you're getting input, enough input such that when you go to the economic buyer, who's the person who has access to discretionary funds and I can actually make a decision. You have said, well, I've met with your entire team, or I've met with this person, this person, this person across all of these. This is what your team is saying about their needs, about what's holding them back from achieving the outcomes that you're trying to drive. And then the economic buyer is like, oh, y…

AI assessment note: “in enterprise, it's critical. Multi-threading is critical.”

Q So help me out here. I'm a sales rep and I've just joined your team. You tell me to go and have this uncomfortable conversation. What's the right way for me to do this? What questions should I ask? How do I make it uncomfortable? When do I make them comfortable again? I'm first day on the job. Can you help me?

A Well, I think it starts with an outside in perspective. You ask about the current state. You get the potential customer to really define what it is they're, how, What their current world looks like, feels like, and what, frankly, the negative consequences of their current situation are. And so the, the types of questions are always open-ended, tell me about, describe for me, that kind of thing. You don't want to lead with yes, no questions, because you'll miss the opportunity to really uncover some good, some good understanding of what they're truly experiencing. Um, so What we do is we try and pair a current state with the negative consequences of doing nothing or taking a different approach. And then you start to ask about future state. What imagine what a future state could look like for your business. If you could X, Y, Z, what would that unlock for you? Tell me about your ideal, whatever data infrastructure, the implications on the business. And then you take them from future state to what are the positive business outcomes associated with that future state? And really help them articulate, not just like, oh, a technical solution would enable this technical thing to happen. It's like, okay, so what, and then what, what are the implications on the business? Is it revenue driving? Is it cost saving? Is it risk mitigation? Is it accelerating time to market? Those are the type…

AI assessment note: “the types of questions are always open-ended, tell me about, describe for me”

Q easy to just like Pop on Slack or pop on email just quickly. It was just half an hour a day, but then you're kind of in and you're kind of out and it's kind of tough for your team then. And is that right or is that wrong? How do you think about that? Like fully in, fully out, checking in, not checking in. What's the right answer there?

A Yeah. I think it's a choose your own adventure for everyone. What makes them most comfortable? Uh, so I'd say for me, I really tried to honor the fact that it was, uh, A once in a lifetime experience to, or multiple times depending on, on your family structure, but, um, to experience that time with my newborn and really just expand the scope of what life means. And every time I thought about it with that level of gravity, it was, um, really easy for me to say the slack and wait or, uh, you know, empower someone else on the team to make a decision. Ideally what I've done is Create a team that can function in my absence. And so, um, yes, of course, always tempted to engage and, you know, folks reach out sometimes, uh, and that's really, really hard to, to, to create that boundary. But, um, for me, it was, you know, setting out times where I was like, okay, I'm going to devote this hour to thinking about what's going on in the business. And then after that, I'm going to sign off. No guilt. I assigned myself a schedule. I'm following the schedule and I'm going to refocus on This, again, really magical, once in a lifetime exhausting experience.

AI assessment note: “I think it's a choose your own adventure for everyone. What makes them most comfortable?”

Q useless decision-making structures. Companies are very inefficient in many different ways. Is there anything that you see and like to do to create urgency in the process, be it discounting, be it really playing on personal relationships? It would really help me, Lauren, if you could close it this quarter. Um, how do you think about creating urgency yourself as a sales leader, and how do you advise your team?

A I don't really buy into discounting or relationship selling personally to me. That's a sort of cheapening the value that this company is going to get from their investment in your product. For me, it's, it's, it's less about, um, Artificially accelerating the timeline. And it's more about helping a customer realize how long it's going to take them to realize value from their investment. So we do a lot of like backward timelines, like, Hey, what we talked about the positive business outcome you're trying to achieve. When do you need to achieve that by? Oh, well, it needs to happen by the end of Q four. Okay, great. So in order for you to get that, this is, let's walk backwards, right? It's a mutual action plan, but you do it in reverse. And so you're saying, great, in order to achieve that value, you're going to need to be live in production in this timeline. You're going to need to be doing it in, uh, you're going to You may not even leverage like your production environment until this time, right? We're going to roll out professional services. We're going to need to get buy-in from your leadership, blah, blah, blah. All of a sudden, like three or four months earlier, um, is when the deal needs to be signed. And so that's how you help accelerate urgency in terms of the timeline, but what you're, you're not. Cheapening the outcome or the impact that your product is having. You'r…

AI assessment note: “how you help accelerate urgency in terms of the timeline”

Q You know, having done 20 sales now for 10 episodes, I, um, I, I definitely see that. Yeah, it's, it's a real problem. Um, uh, tell me, what is the hardest element of your role with Five Tram today?

A You know, it's, it's, Ironic a little bit because one of the things that Fivedran does so well is our product is really simple. Uh, it solves a really hard problem and, and I'm behind the curtains. It's very, it's complicated, but it's a simple user experience. And, um, as a sales leader scaling a sales org, uh, I find that we try to solve too many problems sometimes internally. And so keeping it simple for my team to be really focused Is, is the biggest challenge I have because you're looking at, you know, we want sellers to land new logos. We want sellers to expand those logos. We want sellers to make sure that they're retaining their customers. We want them to drive consumption. And all of a sudden the laundry list of things that, you know, you, you try to solve with a comp plan, it becomes very complex and you lose focus. So, uh, what's really, really important to me is to drive simplicity and focus for the team.

AI assessment note: “keeping it simple for my team to be really focused Is, is the biggest challenge”

Q I agree. I think it's fantastic, especially when you have the partners that you do. The challenge is as an early stage startup, you don't have the ability to have high quality partnerships with such incredible companies. And so I guess my question to you is at what point do partnerships become a viable option? And does one do traditional outbound before then?

A Again, it's like follow the path of least resistance and turn like the, the term Cold calling to me is like, I would so much rather a warm call, right? You're an early stage founder. You have been selling your product from the beginning. You've earned some funding round and you have investors who can create introductions for you, right? You have Your YC cohort or whatever community you've built, um, of founders to, to introduce you, right? Take the A-sixteen Z model, for example, um, you're getting introduced to partners where you can go to market together. So I don't actually think there is ever a time that's too early, um, in a founders in, in a startup's life cycle to lean on the connections you have in your community to start developing those partnerships.

AI assessment note: “I don't actually think there is ever a time that's too early”

Q slipped through the next quarter. It wasn't urgent. And I never really know what to say. I'm like, well, why wasn't it urgent? Like, fuck. Um, my question to you is like, if, if I said to you, well, the deal slipped to next quarter, they said it wasn't urgent. As my boss and my sales leader, What would you say to me and how should we deal with that?

A I would say who with the company is telling you that this is the problem that they need to solve. This is why they need to solve that problem. And this is when they need to solve that problem. And that your, so our solution is what, what they need to solve it. So at Fivetran we say, why do anything? Why do it now? Why do it with Fivetran? Right. And those are the questions that you need to be answering on every deal. And if you don't have an answer to why do it now, slipping isn't even the right term. It was never going to be a deal this month or this quarter. Right. So that's, that's when we really need to battle test what, like, what is the biggest business problem that we're attaching to? What is it that, and this is when I was talking to you about like, Helping, um, taking a customer through a journey that's actually quite painful for them, thinking about their current state without your solution. Um, it's only if we were, are able to really identify and align with the buyer on how painful their problem is that we can then tie a reasonable and predictable timeline to it. Because if it's just kind of an annoyance or a pinch for them, There's no reason there's, there's no reason you're going to get that deal done in the timeframe that you as the seller want to get it done.

AI assessment note: “I would say who with the company is telling you that this is the problem”

Q The cat is here. I do have to ask that, you know, I think the big thing that I think about, I'm a founder in this hypothetical situation, very early stage company. Do I hire sales reps first? Do they do that, you know, data exploration discovery process? Or do I hire a head of sales and let them build out their team beneath them? Which is the right profile?

A Just depends. We talked a little bit about, um, the role of a seller in collecting information about the market, right? That's when you're really early stage. You don't need someone who has spent their career scaling sales organizations and building out a ton of process. You need someone who is willing to get out there And kick down doors and ask the hard questions that will allow you to have to, to take that feedback and use it to improve your product or your messaging. Um, and so those people can be, um, yeah, like I said, you don't need it to be someone who is like, uh, Tenured head of sales. What you do need though, when you're thinking about hiring the first sales rep is someone who can run process. So a lot of times we say, oh yeah, you can hire like a Renaissance AE or someone who's just like a more of an artist than a scientist. And they're going to go out. But the reality is how are you going to learn from that person? If they're just doing something different in every sales cycle, there's no pattern recognition there. So you need someone who has this like great intersection of fearlessness and ability to operate within ambiguity, but someone who can show you, Hey, when we ran it this way, we got these results. We tweaked it and did it this way. We got these results. This is what we need to do from here.

AI assessment note: “you don't need it to be someone who is like a Tenured head of sales”

Q then I want to unpack, like, how we actually discover these talents with someone, because everyone can present a good show in an interview process. So, um, how do you structure? Say we're going to hire these two reps for our startup. We're co-founders. Well done. We have new jobs. Um, uh, how do we actually structure the process for hiring these two sales reps? What does that look like?

A You know, what, what's really important when you're interviewing salespeople is that you don't leave it open-ended for storytelling because any good seller can sell you a dream, right? And so unless you are testing for the specifics and the metrics and the repeatable performance, you really don't know what you're getting. So in, in the process, in terms of structuring the process, it's really important not to just Um, you know, ask theoretical, like, oh, how would you ramp in your first 90 days? Like, that's not, there's no, they could have read an article 10 minutes before the interview and they say, oh, this is what you do. You build a 30, 60, 90, like, no. You want to be asking people like, Hey, tell me about your attainment the last year. Tell me about your attainment the year before. Oh, interesting. Okay. So how did you get there? Who else was involved in those deals? What did you, what could you have done differently? One of my favorite questions to ask is, um, tell me about the deal. Tell me the name of the logo of the deal that you're most proud of. And someone's like, oh, you know, bank of America. And I'm like, cool. I don't want to talk about bank of America. Tell me about your second The deal that you're, that comes behind that. Tell me about the, the, I don't know what the word is, the deal you're second most proud of. And all of a sudden it's like, oh shit, I did…

AI assessment note: “You want to be asking people like, Hey, tell me about your attainment”

Q Oh yeah, that is a good one. I like that a lot. Um, can I ask you, do we do a case study at all? We've got a seemingly very good candidate. They're progressing through our process. Well, do we do a case study with them where they do a pitch, a demo for us at all, or do we not like that?

A I've done it in both ways. Uh, I've spent a lot of time hiring people with, when they had to come pitch their product, That's not usually that valuable because often the people in the room, uh, like on the panel don't, they haven't been in the seat of the buyer. And so no one really knows what to ask and it becomes a monologue and not super engaging. And again, then that's not a good indication of what real life is like. Um, I've done it where they need to pitch your product, um, which also has its own implications like, Everyone in the room is like ready to ask them the tough questions that they just face on their last call. And the candidate is like, I don't know. I, you know, and you sort of lose, uh, the ability to tell if they're actually good because you're like, ah, stumped them. They're not good. Right. So the pitch is, is a tough one. Um, I actually like, you know, so, so we talked about, it's really important to identify the actual material impact in previous performance. But when we're talking about, um, Real trying to recreate real life scenarios. I often will just do a role play with them that they're not prepared for. So something like, all right, real life situation that I'm facing. We're deep in procurement with this customer. Here's a situation. Okay. You're the sales rep on procurement. Let's go. And then I, I just walk, do it live off the cuff. Again, this is…

AI assessment note: “That's not usually that valuable because often the people in the room”

Q The cat is here. I do have to ask that, you know, I think the big thing that I think about, I'm a founder in this hypothetical situation, very early stage company. Do I hire sales reps first? Do they do that, you know, data exploration discovery process? Or do I hire a head of sales and let them build out their team beneath them? Which is the right profile?

A Just depends. We talked a little bit about, um, the role of a seller in collecting information about the market, right? That's when you're really early stage. You don't need someone who has spent their career scaling sales organizations and building out a ton of process. You need someone who is willing to get out there And kick down doors and ask the hard questions that will allow you to have to, to take that feedback and use it to improve your product or your messaging. Um, and so those people can be, um, yeah, like I said, you don't need it to be someone who is like, uh, Tenured head of sales. What you do need though, when you're thinking about hiring the first sales rep is someone who can run process. So a lot of times we say, oh yeah, you can hire like a Renaissance AE or someone who's just like a more of an artist than a scientist. And they're going to go out. But the reality is how are you going to learn from that person? If they're just doing something different in every sales cycle, there's no pattern recognition there. So you need someone who has this like great intersection of fearlessness and ability to operate within ambiguity, but someone who can show you, Hey, when we ran it this way, we got these results. We tweaked it and did it this way. We got these results. This is what we need to do from here.

AI assessment note: “You don't need someone who has spent their career scaling sales organizations”

Q You know, having done 20 sales now for 10 episodes, I, um, I, I definitely see that. Yeah, it's, it's a real problem. Um, uh, tell me, what is the hardest element of your role with Five Tram today?

A You know, it's, it's, Ironic a little bit because one of the things that Fivedran does so well is our product is really simple. Uh, it solves a really hard problem and, and I'm behind the curtains. It's very, it's complicated, but it's a simple user experience. And, um, as a sales leader scaling a sales org, uh, I find that we try to solve too many problems sometimes internally. And so keeping it simple for my team to be really focused Is, is the biggest challenge I have because you're looking at, you know, we want sellers to land new logos. We want sellers to expand those logos. We want sellers to make sure that they're retaining their customers. We want them to drive consumption. And all of a sudden the laundry list of things that, you know, you, you try to solve with a comp plan, it becomes very complex and you lose focus. So, uh, what's really, really important to me is to drive simplicity and focus for the team.

AI assessment note: “keeping it simple for my team to be really focused Is, is the biggest challenge”

Q Enterprise. Obviously, Enterprise at Google, SMB at Segment, now Enterprise at, um, Fivetran. When we think about, like, startups, and again, you are advising me in early stage company, um, there's this kind of decision, like, are you going to be PLG, or are you going to be Enterprise? Do you need to make that decision? Can you be both, or do you have to be one or the other?

A There are companies who can succeed with just an enter, like a sales led growth, sales led motion. I think, um, often companies wait too long, you know, founders and product are like, yeah, this product sells itself. Like, I don't think there's always an appreciation early on for the skillset that actually is selling. Um, and so often I see, uh, startups going too long, just relying on product led growth, but the reality is in an enterprise, Product. It's not just, you know, a couple of users and then, um, then you're done. Like you do your first deal with some big enterprise logo and it's just like really a narrow land. Um, the, the reality is there's the only enterprise sales teams can actually expose and create recognition and a market for a product across the whole enterprise. So. That like top-down sales combined with, uh, product-led growth is how you truly drive momentum.

AI assessment note: “top-down sales combined with, uh, product-led growth is how you truly drive momentum.”

Q useless decision-making structures. Companies are very inefficient in many different ways. Is there anything that you see and like to do to create urgency in the process, be it discounting, be it really playing on personal relationships? It would really help me, Lauren, if you could close it this quarter. Um, how do you think about creating urgency yourself as a sales leader, and how do you advise your team?

A I don't really buy into discounting or relationship selling personally to me. That's a sort of cheapening the value that this company is going to get from their investment in your product. For me, it's, it's, it's less about, um, Artificially accelerating the timeline. And it's more about helping a customer realize how long it's going to take them to realize value from their investment. So we do a lot of like backward timelines, like, Hey, what we talked about the positive business outcome you're trying to achieve. When do you need to achieve that by? Oh, well, it needs to happen by the end of Q four. Okay, great. So in order for you to get that, this is, let's walk backwards, right? It's a mutual action plan, but you do it in reverse. And so you're saying, great, in order to achieve that value, you're going to need to be live in production in this timeline. You're going to need to be doing it in, uh, you're going to You may not even leverage like your production environment until this time, right? We're going to roll out professional services. We're going to need to get buy-in from your leadership, blah, blah, blah. All of a sudden, like three or four months earlier, um, is when the deal needs to be signed. And so that's how you help accelerate urgency in terms of the timeline, but what you're, you're not. Cheapening the outcome or the impact that your product is having. You'r…

AI assessment note: “we do a lot of like backward timelines”

Q then I want to unpack, like, how we actually discover these talents with someone, because everyone can present a good show in an interview process. So, um, how do you structure? Say we're going to hire these two reps for our startup. We're co-founders. Well done. We have new jobs. Um, uh, how do we actually structure the process for hiring these two sales reps? What does that look like?

A You know, what, what's really important when you're interviewing salespeople is that you don't leave it open-ended for storytelling because any good seller can sell you a dream, right? And so unless you are testing for the specifics and the metrics and the repeatable performance, you really don't know what you're getting. So in, in the process, in terms of structuring the process, it's really important not to just Um, you know, ask theoretical, like, oh, how would you ramp in your first 90 days? Like, that's not, there's no, they could have read an article 10 minutes before the interview and they say, oh, this is what you do. You build a 30, 60, 90, like, no. You want to be asking people like, Hey, tell me about your attainment the last year. Tell me about your attainment the year before. Oh, interesting. Okay. So how did you get there? Who else was involved in those deals? What did you, what could you have done differently? One of my favorite questions to ask is, um, tell me about the deal. Tell me the name of the logo of the deal that you're most proud of. And someone's like, oh, you know, bank of America. And I'm like, cool. I don't want to talk about bank of America. Tell me about your second The deal that you're, that comes behind that. Tell me about the, the, I don't know what the word is, the deal you're second most proud of. And all of a sudden it's like, oh shit, I did…

AI assessment note: “unless you are testing for the specifics and the metrics and the repeatable performance”

Q So we have, um, tell me about your deal you're most proud of. Tell me about a deal you lost. Are there any other questions that I should ask? Again, I'm literally Googling what do I ask in a sales interview? Are there any others where you're like, oh, that's a revealing one of character?

A Oh man. Well, just to, just to clarify, it's not tell me about your deal you're most proud of. It's tell me that deal, and then tell me about the next deal. Um, because I don't want, I don't want the, the rehearsed answer. Um, other questions. I, I really want to understand the customer experience with them. So often I'll say, what would your customer say about working with you? Who would say that at the customer? Would you put me in touch with that customer? Right. And just like ultimately trying to get. Some validation outside of just, you know, we talk about references and how important references are rather than saying, oh, send over some references. And it's like their best friend and someone they wrote the reference for. It's like, well, tell me about a customer that you sold to, right? Well, what would they say about you? Okay, great. Can I reach out to them? And if you're a candidate, you're not going to say no, you know, you want, but then that's when you really get, um, clarity into what they experience is to buy from them.

AI assessment note: “So often I'll say, what would your customer say about working with you?”

Q Oh yeah, that is a good one. I like that a lot. Um, can I ask you, do we do a case study at all? We've got a seemingly very good candidate. They're progressing through our process. Well, do we do a case study with them where they do a pitch, a demo for us at all, or do we not like that?

A I've done it in both ways. Uh, I've spent a lot of time hiring people with, when they had to come pitch their product, That's not usually that valuable because often the people in the room, uh, like on the panel don't, they haven't been in the seat of the buyer. And so no one really knows what to ask and it becomes a monologue and not super engaging. And again, then that's not a good indication of what real life is like. Um, I've done it where they need to pitch your product, um, which also has its own implications like, Everyone in the room is like ready to ask them the tough questions that they just face on their last call. And the candidate is like, I don't know. I, you know, and you sort of lose, uh, the ability to tell if they're actually good because you're like, ah, stumped them. They're not good. Right. So the pitch is, is a tough one. Um, I actually like, you know, so, so we talked about, it's really important to identify the actual material impact in previous performance. But when we're talking about, um, Real trying to recreate real life scenarios. I often will just do a role play with them that they're not prepared for. So something like, all right, real life situation that I'm facing. We're deep in procurement with this customer. Here's a situation. Okay. You're the sales rep on procurement. Let's go. And then I, I just walk, do it live off the cuff. Again, this is…

AI assessment note: “I've done it in both ways... So the pitch is, is a tough one.”

Q Can I ask you a question that's quite direct? What's the single biggest mistakes you've made in hiring when you reflect on them?

A Oh, I would say making assumptions about their experience. I hired someone once. Who did this was back when I was doing, we were doing pitches and his pitch was so smooth. And I was like, oh, great. You know, he's very comfortable, um, off the cuff, blah, blah. And I had asked, but I hadn't done the work of digging deep into what are the types of deals that you've done before? What, how, how did you drive the outcomes that you drove, right? The specifics that I was talking about earlier, I ended up hiring this person and, uh, it turned out. What I thought was enterprise experience was actually commercial experience. And I just different companies call segments, different things. And I hadn't done the important work of like really diving deep into deal level experiences, like really early in my sales leadership career, a great lesson.

AI assessment note: “I would say making assumptions about their experience. I hired someone once.”

Q Yeah, no, I'm, I'm totally with you, but I, I'm just worried that do, do nothing. Doesn't that fall into your will? They don't really have the pain then.

A Then they don't know exactly. So if the, if the competition, if we lost to the competition, it's always important to know is like one of the main competitors is don't change at all. Right. And that inertia can be really challenging to compete with, but to your point, exactly. Right. If that happens, my reaction is what was the, the identified pain, how painful was it? Did we miss an opportunity to attach to a bigger business problem? Cause a lot of times when you're selling technology, you're like, oh, I found a practitioner who wants this thing because they're doing this project. And then all of a sudden it's like, oh, actually they deprioritize the project. Okay. Well, that wasn't the biggest business problem that you could have attached to. And so where can we go back into the company to understand, well, what are the things that they're really trying to solve? How are they trying to use data as a competitive advantage and how can we help them?

AI assessment note: “If that happens, my reaction is what was the, the identified pain”

Q My question to you, I have two questions, and this is why I told you the schedule is completely useless. Um, one, like to get in that room, you know, with, I'm sure do I think of outbound. Does outbound still work today?

A I think outbound has a bad rap. And it's sort of a limited way of describing engaging with customers in a way where you're meeting them where they are and providing them with something relevant. So for us at Fivetran, one of the ways that we go to market most effectively is with partners. Um, in particular, when you're investing in, in data movement, which is what we do at Fivetran, you're taking data from someplace and sending it to someplace. So you would never buy. Like plumbing alone. You would only want to buy it in association with a destination for that data. And of course you have data sources. And so we work really closely with a number of our partners, Snowflake, Databricks, GCP, AWS, and go to market with their sales teams. So I think actually the value of co-selling with sales teams at other businesses that are in your ecosystem, where a customer would benefit from the compilation of what we call a modern data stack. Um, is, is really overlooked in sales. And, you know, a lot of sales people grow up thinking, ah, partnerships, you know, what, what are they really driving? What are they doing? They're setting up lunch and learns. But the reality is when done well, um, that's the best way to, to do outbound as you describe it, going to market with your partners.

AI assessment note: “when done well, um, that's the best way to, to do outbound”

Q easy to just like Pop on Slack or pop on email just quickly. It was just half an hour a day, but then you're kind of in and you're kind of out and it's kind of tough for your team then. And is that right or is that wrong? How do you think about that? Like fully in, fully out, checking in, not checking in. What's the right answer there?

A Yeah. I think it's a choose your own adventure for everyone. What makes them most comfortable? Uh, so I'd say for me, I really tried to honor the fact that it was, uh, A once in a lifetime experience to, or multiple times depending on, on your family structure, but, um, to experience that time with my newborn and really just expand the scope of what life means. And every time I thought about it with that level of gravity, it was, um, really easy for me to say the slack and wait or, uh, you know, empower someone else on the team to make a decision. Ideally what I've done is Create a team that can function in my absence. And so, um, yes, of course, always tempted to engage and, you know, folks reach out sometimes, uh, and that's really, really hard to, to, to create that boundary. But, um, for me, it was, you know, setting out times where I was like, okay, I'm going to devote this hour to thinking about what's going on in the business. And then after that, I'm going to sign off. No guilt. I assigned myself a schedule. I'm following the schedule and I'm going to refocus on This, again, really magical, once in a lifetime exhausting experience.

AI assessment note: “I think it's a choose your own adventure for everyone. What makes them most comfortable?”

Q Lauren, I'm intrigued. How did you think about this kind of potential career pause and that aspect of parental leave?

A Yeah, I think it's, um, and it's critical that, and what Maggie just said at the end there, um, the non-birthing parent and the birthing parent, right, we want to expand the scope of policy design to any type of family unit that's bringing a child into the world, and so, uh, it, it, frankly, it's critical to be inclusive of every approach to whether it's adoption, whether it's same-sex couples, but whatever it is, um, we, we need to create an environment that doesn't treat people differently. Because it's outside of their control. So what I thought about, and I didn't think of it as putting my career on pause. Really what I thought was, well, how do I continue the momentum while I'm out? Uh, so for me, it was critical to invite folks on our team to step up. Great opportunity for them to step up, put leaders in place who can keep momentum going. And really that requires setting clear expectations for what will be accomplished before you get back. So that's a lot of work. I know I don't want to make light of it because you really have to take responsibility to make sure You know, while a leader is on leave, how can a team be successful and what are the expectations and what kind of accountability are you going to put in place? Um, because the business continues whether you're in there or not. So it's, it's your choice whether you want to put a blueprint in place to ensure your te…

AI assessment note: “I didn't think of it as putting my career on pause.”

Q Enterprise. Obviously, Enterprise at Google, SMB at Segment, now Enterprise at, um, Fivetran. When we think about, like, startups, and again, you are advising me in early stage company, um, there's this kind of decision, like, are you going to be PLG, or are you going to be Enterprise? Do you need to make that decision? Can you be both, or do you have to be one or the other?

A There are companies who can succeed with just an enter, like a sales led growth, sales led motion. I think, um, often companies wait too long, you know, founders and product are like, yeah, this product sells itself. Like, I don't think there's always an appreciation early on for the skillset that actually is selling. Um, and so often I see, uh, startups going too long, just relying on product led growth, but the reality is in an enterprise, Product. It's not just, you know, a couple of users and then, um, then you're done. Like you do your first deal with some big enterprise logo and it's just like really a narrow land. Um, the, the reality is there's the only enterprise sales teams can actually expose and create recognition and a market for a product across the whole enterprise. So. That like top-down sales combined with, uh, product-led growth is how you truly drive momentum.

AI assessment note: “top-down sales combined with, uh, product-led growth is how you truly drive momentum.”

Q Can I ask you a question that's quite direct? What's the single biggest mistakes you've made in hiring when you reflect on them?

A Oh, I would say making assumptions about their experience. I hired someone once. Who did this was back when I was doing, we were doing pitches and his pitch was so smooth. And I was like, oh, great. You know, he's very comfortable, um, off the cuff, blah, blah. And I had asked, but I hadn't done the work of digging deep into what are the types of deals that you've done before? What, how, how did you drive the outcomes that you drove, right? The specifics that I was talking about earlier, I ended up hiring this person and, uh, it turned out. What I thought was enterprise experience was actually commercial experience. And I just different companies call segments, different things. And I hadn't done the important work of like really diving deep into deal level experiences, like really early in my sales leadership career, a great lesson.

AI assessment note: “Oh, I would say making assumptions about their experience.”

Q Yeah, no, I'm, I'm totally with you, but I, I'm just worried that do, do nothing. Doesn't that fall into your will? They don't really have the pain then.

A Then they don't know exactly. So if the, if the competition, if we lost to the competition, it's always important to know is like one of the main competitors is don't change at all. Right. And that inertia can be really challenging to compete with, but to your point, exactly. Right. If that happens, my reaction is what was the, the identified pain, how painful was it? Did we miss an opportunity to attach to a bigger business problem? Cause a lot of times when you're selling technology, you're like, oh, I found a practitioner who wants this thing because they're doing this project. And then all of a sudden it's like, oh, actually they deprioritize the project. Okay. Well, that wasn't the biggest business problem that you could have attached to. And so where can we go back into the company to understand, well, what are the things that they're really trying to solve? How are they trying to use data as a competitive advantage and how can we help them?

AI assessment note: “to your point, exactly. Right. If that happens, my reaction is”

Q What does that mean? What does that mean, sorry, in sales, ask for forgiveness, not permission?

A I think it's kind of like approaching rules as, as a suggested set of guidelines. Um, I think it's, you know, thinking about outside of the box, what's possible for, I mean, when you're having a conversation with a potential customer, you're spending time helping them really realize the pain that they feel today without you and without your product, which Is an uncomfortable conversation and, uh, nobody likes to sit in their moment of pain. Um, and so as a salesperson, you really do need to be comfortable Taking someone to a place that makes them very uncomfortable, but then it is your responsibility to catch them when they're falling. And that's the opportunity to ask for forgiveness because you've helped them through a challenging conversation and really sitting in what their lives would look like if they didn't take any action or do anything. Um, but then you take them to a place that they can't get to on their own.

AI assessment note: “I think it's kind of like approaching rules as, as a suggested set of guidelines.”

Q I agree. I think it's fantastic, especially when you have the partners that you do. The challenge is as an early stage startup, you don't have the ability to have high quality partnerships with such incredible companies. And so I guess my question to you is at what point do partnerships become a viable option? And does one do traditional outbound before then?

A Again, it's like follow the path of least resistance and turn like the, the term Cold calling to me is like, I would so much rather a warm call, right? You're an early stage founder. You have been selling your product from the beginning. You've earned some funding round and you have investors who can create introductions for you, right? You have Your YC cohort or whatever community you've built, um, of founders to, to introduce you, right? Take the A-sixteen Z model, for example, um, you're getting introduced to partners where you can go to market together. So I don't actually think there is ever a time that's too early, um, in a founders in, in a startup's life cycle to lean on the connections you have in your community to start developing those partnerships.

AI assessment note: “I don't actually think there is ever a time that's too early”

Q Okay. So we have talking to customers. We have, uh, the library of resources. Um, when do we actually let them speak to customers? Cause like day one, we can't let them speak to customers. They have to listen to like recorded calls, read the decks that we have from fundraisers. Is it like two weeks in, or is it like three months in this is enterprise?

A Yeah, I think, I think it's, again, it depends on your organization and where you are in terms of your, um, of your customer base and the types of buyers that you're working with. But You know, you, you will have some of those early customers that are more than happy to talk with new hires, right? You'll, um, in terms of like a specific period of time, it really just depends on how quickly they ramp. So we've done, uh, in, in a past life, we did. Uh, practicing with the pitch and then you would go through a certification. Right now at Fivetrain we have like a full 90 day plan of onboarding where you come in and you have like very structured. These are the things you're learning about the company. This is what you're learning about our pitch. This is what you're learning about our customers, our value drivers, et cetera. Um, and then just depending on how quickly you can ramp up, uh, we get you out in the wet.

AI assessment note: “in terms of like a specific period of time, it really just depends”