20 Sales: How To Structure The Interview Process for All Sales Reps, The Must-Ask Questions When Identifying Potential Sales Talent & The 3 Biggest Mistakes Founders Make When Hiring Their First Reps with Lauren Schwartz, VP of Enterprise Sales @ Fivetran

Lauren Schwartz is Vice President of Enterprise Sales at Fivetran, the leading platform for modern data movement. She has helped scale Fivetran's enterprise business from its infancy to a team of nearly 100, while more than tripling enterprise revenues. Previously, Lauren spent close to 4 years at Segment where she started as the first female AE and ultimately built and led sales teams in enterprise and growth. Lauren earned an MBA from Stanford Graduate School of Business after 6 years at Google where her enterprise sales career began. In Today's Episode with Lauren Schwartz: 1.) How Being Rejected as an Eighth Grader Can Lead to World Class Sales Leader: How Lauren made her way into the world of enterprise sales with Google? Why, for a while, Lauren wanted to get away from the label of a salesperson? Why "salesperson" does not do the job of sales justice? Why does Lauren believe that one of the core traits the best salespeople have is being able to cope with rejection? How has Lauren been rejected? How did she respond? What changed their mind? 2.) The Sales Playbook: What, Who, When: How does Lauren define the term "sales playbook"? What are the nuances? Does Lauren believe the founder should always be the first sales rep? What are the core signs that a founder is now ready to bring in their first sales hires? What are the 3 biggest mistakes founders make when they hire their first sales reps? What are the core traits that the best early sales reps have? 3.) The Hiring Process: Building the Best Sales Team: How does Lauren structure the hiring process? What are the most unconventional but useful questions Lauren uses to determine the depth and quality of potential sales hires? What are the glaring red flags that Lauren looks for in this interview process? How does Lauren use case studies and deal reviews in the interview process to determine the quality of a candidate? 4.) Scaling the Machine: The Onboarding Process: What are the single biggest mistakes founders make when onboarding sales reps? How should sales team onboarding be structured? What materials should the founder have in place for the sales team to learn from on Day 1? How can sales leaders ensure new sales team members engage across functions?

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

• 0:00Harry Stebbings?

  20 Sales. This is the monthly show where we sit down with the world's best sales leaders to unpack how to build sales teams, how to scale revenues, how to create a reliable and a repeatable sales machine and playbook. And today, I'm joined by Lauren Schwartz. Lauren is Vice President of Enterprise Sales at FiveTran, the company that allows you to centralise your data in minutes, not months. Prior to FiveTran, Lauren spent close to four years as Senior Director of Enterprise Sales at Segment, and before Segment, Lauren spent an incredible six years in different roles within Google's sales. I do also have to say a huge thank you to Janja at Miro and Jordan at Monte Carlo. Some amazing questions today, it really did make such a difference. But before we dive into the show today, have you ever wondered how revenue intelligence experts Gong run their own revenue planning?

• 0:45Harry Stebbings?

  They use Pigment. Pigment is the integrated planning platform that allows you to make decisions you can trust, fast. Pigment integrates with your sales data, your CRM for your pipeline, your HRIS for your own open headcount, your financial data to give you accurate real-time reports and dashboards, and Pigment is designed to be used by leaders like you. From sales, to finance, to HR and marketing, Pigment's what-if analyses are a true game changer to model any type of scenario and understand what will happen to your target attainment if, say for example, you can't hire those 20 open reps, or if your cost of sales goes up by 20% or drops by 20%. Legacy tools make this painful and obscure, with you needing to ask third parties to take days or weeks to crunch the numbers for you.

• 1:29Harry Stebbings?

  With Pigment, you can do it all yourself in minutes and make the decisions you need. And that's why companies like Figma, Gong, Deliveroo, and many more trust Pigment. Visit gopigment.com/20vc to request a demo. What's more, if you use that link in the next 30 days, the team has promised me they'll run a personalised sales planning audit just for you. And next, we have SalesLoft. SalesLoft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace. It's the one place sales teams can go to prospect, manage additive deals, and get the insights they need to coach seller performance, forecast with accuracy, and find out what steps to take to close more deals. Some of the world's leading

• 2:10Harry Stebbings?

  Companies like IBM, Shopify and Stripe all love a new SalesLoft and so can you. It's the new way to sell. Find out more at salesloft.com. And finally, we have to talk about Chargebee. Chargebee is the subscription revenue and billing management platform that streamlines your revenue operations like never before. Chargebee automates the lead to ledger workflow across your revenue stack, so you can dream, deploy and enjoy the breeze while the MRR just keeps rolling in. But Chargebee goes so much further beyond just billing. One example, pricing alterations. They allow you the ability to change pricing models with one click. Grandfathering old pricing has never been so easy. That and for hundreds of other reasons is why the likes of Freshworks, Okta and Envoy all love and use Chargebee.

• 2:53Harry Stebbings?

  Simply head over to chargebee.com to find out more. But now I'm so thrilled to hand over to the one and only Lauren Schwartz, Vice President of Enterprise Sales at FiveTran.

• 3:07Speaker 01

  You have now arrived at your destination.

• 3:10Harry Stebbings?

  Lauren, I'm very excited for this. I've heard so many things from Jordan, from Genia, from your time together at Segment. So thank you so much for joining me today.

• 3:19Speaker 02

  Well, thank you for having me and likewise your reputation precedes you as well.

• 3:22Harry Stebbings?

  That is very kind. They're forced to actually say nice things about me. It's the joy of my business. But I would love to start with a little bit of context on you. So we see the incredible companies you've worked with from Segment to now FiveTran. But how did you make your way into sales first? And then come to be an enterprise sales leader with FiveTran?

• 3:37Speaker 02

  I discovered sales at the age of seven when I became a Brownie Scout. That's when I fell in love with the art of cookie sales.

• 3:44Harry Stebbings?

  What did you love about sales then? What was it?

• 3:47Speaker 02

  We were selling cookies and there was an opportunity to create repeat purchasing by evangelizing the freezer lifespan of a cookie. So for me, it was really about the opportunity to compete with other brownie troops, but also to spread the love that I personally have for cookies.

• 4:03Harry Stebbings?

  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. Take me forward a little bit. What happened then?

• 4:11Speaker 02

  As I moved into my career after college, I spent six years in sales at Google, where I learned a ton from the machine that is Google. After about six years at Google, I went to business school, where I wanted to learn a little bit more about how to run a business. I actually spent a lot of time at Stanford trying to distance myself from being labeled as a salesperson. For me, it's like, nobody likes that word, nobody wants to be sold to. Pair that with a LinkedIn profile touting a college degree in psychology and a published thesis on persuasion. People start to think you're extracting something from them in every interaction.

• 4:43Harry Stebbings?

  Before I forget, I'm sorry, I'm just gonna like segment your career into a couple of different bits, but you mentioned the six years at Google. What was the biggest or one or two big takeaways for you from the six years at Google that really stuck with you?

• 4:54Speaker 02

  I think there is incredible value in learning how to sell something that people don't yet know that they want. The best skill you can develop in sales is an insatiable curiosity about what's possible and truly the instinct to ask for forgiveness rather than permission.

• 5:13Harry Stebbings?

  What does that mean, what does that mean, sorry, in sales? Ask for forgiveness, not permission?

• 5:17Speaker 02

  I think it's kind of like approaching rules as a suggested set of guidelines. I think it's thinking about outside of the box. 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. Nobody likes to sit in their moment of pain. 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. 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.

• 6:02Speaker 02

  But then you take them to a place that they can't get to on their own.

• 6:05Harry Stebbings?

  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?

• 6:20Speaker 02

  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 their current world looks like, feels like, and what frankly, the negative consequences of their current situation are. 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 understanding of what they're truly experiencing. 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. Imagine what a future state could look like for your business.

• 7:02Speaker 02

  If you could X, Y, Z, what would that unlock for you? 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 types of value drivers that you would want to make sure you're uncovering as an early sales rep.

• 7:33Harry Stebbings?

  My question to you at last, I have two questions. And this is why I told you the schedule is completely useless. One, like to get in that room, I straight away think of outbound. Does outbound still work today?

• 7:43Speaker 02

  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, providing them with something relevant. So for us at Five Tran, one of the ways that we go to market most effectively is with partners. In particular, when you're investing in data movement, which is what we do at Five Tran, 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.

• 8:24Speaker 02

  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 is really overlooked in sales. And a lot of salespeople grow up thinking, oh, partnerships, what are they really driving? What are they doing? They're setting up lunch and learns. But the reality is when done well, that's the best way to do outbound, as you describe it, going to market with your partners.

• 8:49Harry Stebbings?

  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. But my other final question before we move into actually what we have planned for the show is in terms of the data that you get back from those fantastic but uncomfortable conversations, great, you've learned a ton. What's the right way to feed back the data that you have and the stories that you have from the customers into marketing, into product, into customer success? How do you think about ensuring there's no information leakage and it's seamless across all functions?

• 9:22Speaker 02

  The role of the salesperson, especially in an earlier-stage startup, is equal parts sharing the story and the vision of your product, but also doing research and development. Give any salesperson an opportunity to give customer feedback to product and they will be chomping at the bit. So your question around consistency or breadth of exposure to that information, yeah, I mean, there are ways that you can make it more programmatic, right? You want to make sure you're capturing all of that in your CRM system like Salesforce. But we do a number of ways of communicating the experience, not just to other departments, but also to other sellers. So deal reviews, fireside chats, postmortems, any way of storytelling. I think the art of storytelling and using that as a data collection mechanism

• 10:05Speaker 02

  and a way to really move the product roadmap is incredibly valuable.

• 10:09Harry Stebbings?

  You said about repeatable there, and that instantly makes me think about the wonderful word of a sales playbook, which is just so, I think, mystic in its understanding. When you think about the definition of sales playbook, what does sales playbook mean to you, Lauren?

• 10:22Speaker 02

  The word playbook is like a little prescriptive for super early stage startup. If what we're thinking about is first couple of hires and what they actually need. Their job is to go out into market and collect information about your addressable market, feedback from the customer that can inform the product roadmap. Like I said, the founder is the first seller. Using the founder's vision and the way that they tell the story of the positive business outcomes that they're solving with their product, how you start, the sellers need those at bats. For me, the way that I learned, like when I started at Segment, I started as an SMB AE. And that was the best, most humbling, but best decision I could have made in my career. Because the number of at bats with those small, faster, higher velocity sales cycles

• 11:07Speaker 02

  that I got when I was learning a product that I'd never sold before, which ultimately allow you to build a sales playbook, was critical for me to understand and accelerate my ramp as a seller.

• 11:16Harry Stebbings?

  I'm always fascinated by PLG versus enterprise. Obviously, enterprise at Google, SMB at Segment, now enterprise at Five Tran. When we think about startups, and again, you are advising me in early stage company, 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?

• 11:35Speaker 02

  There are companies who can succeed with just a sales-led motion. I think often companies wait too long. The founders and product are like, yeah, this product sells itself. Like, I don't think there's always an appreciation early on for the skill set that actually is selling. And so often I see startups going too long just relying on product-led growth. But the reality is in an enterprise product, it's not just a couple of users and then, then you're done, like you do your first deal with some big enterprise logo and it's just like really narrow land. 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.

• 12:19Speaker 02

  That like top-down sales combined with product-led growth is how you truly drive momentum.

• 12:25Harry Stebbings?

  When you think about kind of that wall-to-wall adoption and that expansion internally, we often hear about kind of multi-threading and finding 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?

• 12:42Speaker 02

  In enterprise, it's critical. Multithreading 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. And then what you do, you want to pull together current state, future state, negative consequences of current state, positive outcomes of future state. You don't just get that from one person and then call it done. You ask someone those questions, and then you ask someone else those 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 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 can actually make a decision, you have said, I've met with your entire team.

• 13:24Speaker 02

  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, you're not selling me. You're not persuading me. You're doing the research that I needed to do about my own company. And so it ends up being that you're not selling. You're helping them participate in their own rescue.

• 13:48Harry Stebbings?

  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?

• 13:57Speaker 02

  I would say, who at 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 our solution is what they need to solve it. So at FiveTran, we say, why do anything? Why do it now? Why do it with FiveTran? 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 when we really need to battle test, 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, taking a customer through a journey that's actually quite painful for them, thinking about their current state without your solution.

• 14:40Speaker 02

  It's only if we 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 you're going to get that deal done in the timeframe that you as a seller want to get it done.

• 15:01Harry Stebbings?

  In terms of like getting it done in that timeframe, sometimes it is urgent for them, but for whatever reason, they could just be bone idle. They could have 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. How do you think about creating urgency yourself as a sales leader and how do you advise your team?

• 15:28Speaker 02

  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. It's less about 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, 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 Q4. Okay, great. So in order for you to get that, let's walk backwards, right? It's a mutual action plan, but you do it in reverse. That's how you help accelerate urgency in terms of the timeline.

• 16:09Speaker 02

  But what you're not cheapening the outcome or the impact that your product is having. You're really just helping them participate in their own rescue.

• 16:17Harry Stebbings?

  I'm a founder in this hypothetical situation, very early stage company. Do I hire sales reps first? Do they do that 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?

• 16:31Speaker 02

  You talked a little bit about 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, kick down doors and ask the hard questions that will allow you to take that feedback and use it to improve your product or your messaging. And so like I said, you don't need it to be someone who is like a 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. A lot of times we say,

• 17:10Speaker 02

  Oh yeah, you can hire like a Renaissance A E or someone who's just like a more of an artist than a scientist and they're gonna go out. But the reality is, how are you gonna 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.

• 17:39Harry Stebbings?

  Do we hire two reps at once? Jason Lampkin at Saster always says, hire two reps at once and kind of play them off against each other like the Hunger Games for reps. Is that a good idea or not a good idea?

• 17:49Speaker 02

  I wouldn't call it the Hunger Games for reps. I would think of it as how to distill signal from noise. So I agree, you do wanna have multiple sellers going at the same time. Otherwise, let's say it's Lauren and Harry. And if it's just Lauren, and Lauren is a terrible salesperson, then you didn't really learn anything about your product or your messaging or your customers. You learned about Lauren. But if Harry comes in and actually gets completely different results, then you'll actually get signal rather than noise about a certain individual and their skills.

• 18:22Harry Stebbings?

  Yeah, it totally makes sense. But then I wanna unpack like how we actually discover these talents with someone. Cause everyone can present a good show in an interview process. Say we're gonna hire these two reps for our startup, we're co-founders. How do we actually structure the process for hiring these two sales reps? What does that look like?

• 18:38Speaker 02

  What's really important when you're interviewing salespeople is that you don't leave it open-ended for storytelling. 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 terms of structuring the process, it's really important not to just ask theoretical like, oh, how would you ramp in your first 90 days? 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 wanna be asking people like, hey, 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 could you have done differently? One of my favorite questions to ask is, tell me the name of the Logo of the deal that you're most proud of.

• 19:23Speaker 02

  And someone's like, oh, 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 comes behind that. Tell me about the deal you're second most proud of. And all of a sudden, it's like, oh, shit, I didn't prepare that deal for this conversation. And then you start to really get to the meat, right? Like, what did they actually do? They're thinking with you live. And that's more telling about what it's going to be like to work with them because it's raw and it's natural. And so making sure that you're identifying what their actual impact on the outcomes were, getting to the meat of it, and then trying to get past the questions that they prepared for. Because a seller needs to have a plan, but also needs to be able to pivot when the nature of the conversation shifts.

• 20:03Harry Stebbings?

  Well, when I had Jordan on the show, he said something fascinating about sales attribution. He was like, if you go to the Twilio salesperson who sold Airbnb, Uber in 2008, when it was like product led growth, maybe a little bit of handholding, but not really. They're probably the greatest sales rep in history in terms of attainment and dollars attached to their name. But it probably was not actually that complex, given the stage of maturity of the companies and the sales cycles. So I guess my question is like, how do you really define or look to discover attribution? When my numbers could be amazing, but honestly, it was kind of easy, or the companies just grew so out of proportion. How do you really tell if it's someone's work?

• 20:42Speaker 02

  A couple of things. First of all, you're making a good point about the time that they were at the company that they worked at. So where in the company's maturity phase or where are the company's phase of growth? They were employed and they were successful because a lot of times, I mean, this happened to me. When I was interviewing at Segment, I was actually rejected when I first interviewed at Segment. Because one of the pieces of feedback was, well, you came from Google. We don't think you're likely to be that scrappy. And so you're used to a breadth of supporting resources. And I was, oh, okay, well, thanks for that feedback. Here are 10 examples of scrappiness or working. Right, so the point I'm making is, and they were right to be asking those questions. The conclusion they came to ultimately was wrong, but we sorted that out.

• 21:24Speaker 02

  I think the type of questioning should be around, okay, when were you at this company? When did you have this impact? Who else was involved in the deal? What was your actual contribution versus their contribution? And then I do this a lot when I ask about, tell me about a deal that you lost. And the reason I want to learn about that is because you get a really good signal about someone's locus of control. Either they have an internal locus of control and they're taking responsibility for their role in a loss, or they have an external locus of control and they're saying, oh, well, the product didn't deliver, we couldn't prioritize this on the roadmap, or my champion left, or whatever it is. Like, what you want to look for is that type of instinct, like, hey, accountability.

• 22:06Speaker 02

  I had this role in this outcome that wasn't ideal, and here's what I learned from it, and what I'm going to do next time. Those are the types of indicators that will, at least at FiveTran, make sure that they're successful.

• 22:17Harry Stebbings?

  Are there any other questions that I should ask? Are there any others where you're like, oh, that's a revealing one of character?

• 22:23Speaker 02

  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? Ultimately, trying to get some validation outside of just, 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 did 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, but then that's when you really get clarity into what they experience is to buy from them.

• 22:57Harry Stebbings?

  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?

• 23:08Speaker 02

  I've done it in both ways. I've spent a lot of time hiring people where they had to come pitch their product. That's not usually that valuable because often the people in the room, like on the panel, 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. I've done it where they need to pitch your product, which also has its own implications, like, everyone in the room is like, ready to ask them the tough questions that they just faced on their last call, and the candidate's like, I don't know. You sort of lose the ability to tell if they're actually good, because you're like, ah, stumped them, they're not good, right? So.

• 23:51Speaker 02

  The pitch is a tough one. So we talked about it's really important to identify the actual material impact in previous performance. But when we're talking about trying to recreate real life scenarios, I often will just do a role play with them that they're not prepared for. 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. I just do it live off the cuff. Again, this is about being so prepared to listen to a customer and to be able to bring any conversation back to the business outcomes that you're driving for them, that they should be able to pivot along the way on that conversation.

• 24:32Harry Stebbings?

  What's the single biggest mistakes you've made in hiring when you reflect on them?

• 24:36Speaker 02

  Making assumptions about their experience. I hired someone once we were doing pitches and his pitch was so smooth and I was like, oh, great. It was very comfortable, 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? 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 it turned out what I thought was enterprise experience was actually commercial experience and different companies call segments different things. And I hadn't done the important work of like really diving deep into deal level

• 25:18Speaker 02

  experiences, like really early in my sales leadership career. A great lesson.

• 25:22Harry Stebbings?

  I do want to kind of move the post hiring process because now we've hired these two reps. And again, we're co-founders. I don't know what I'm doing. You do luckily, which is why you're co-founder with me. How do we do onboarding? They turn up on day one? What now? What do we give them?

• 25:35Speaker 02

  Are we talking about first sales rep or just anyone that we're onboarding?

• 25:38Harry Stebbings?

  First and second sales rep.

• 25:40Speaker 02

  I was talking earlier about how valuable it was for me when I started a segment to be getting those at bats. It helped accelerate my ramp. I think the most important thing you can do when you're starting your sales role is getting exposure to customers. So whether it's listening to recorded calls, whether it's joining the founder or the hiring manager on sales calls, we did something taking A call that a BDR would normally take so we can just get some at bats to get someone ramped is something that I did back at Segment. It really helps because it's like lower risk, right? You don't want a new hire to take that call with First Republic and say, hey, right? That's not the time when you're hiring people in enterprise. It's tough because it's like few and far between opportunities. And each of those at bat in a long enterprise sales cycle is actually a very high impact, high leverage.

• 26:25Speaker 02

  And so the onboarding process needs to be driven by three things. One is exposure to customers so they can really understand the impact and the value that we're having with customers. Two is exposure to what has worked and what hasn't worked so far.

• 26:39Harry Stebbings?

  What's right for us there because you're the sales leader? Have we recorded all of our sales calls? Do we have like deal review papers that they can go through? What materials can we give them to make sure that their ramp is easier?

• 26:51Speaker 02

  Yeah, recorded sales calls, having like a library of recorded calls is really valuable as people ramp. And then just capturing postmortems, lessons that we learned from a win, lessons that we learned from a loss. I'm really big on running deal reviews and making sure that we capture learnings that we can then amplify when people are joining the organization.

• 27:10Harry Stebbings?

  Okay, so we have talking to customers. We have the library of resources. When do we actually let them speak to customers? Because 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 fundraises. Is it like two weeks in or is it like three months in? This is enterprise.

• 27:27Speaker 02

  You will have some of those early customers that are more than happy to talk with new hires, right? In terms of like a specific period of time, it really just depends on how quickly they ramp. So in a past life, we did practicing with the pitch and then you would go through a certification. Right now at Five Train, 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. And then just depending on how quickly you can ramp up, we get you out in the wet.

• 28:00Harry Stebbings?

  We're going to talk about deal reviews because this is a nerdy passion of mine. But before we discuss deal reviews, I do have to ask, in enterprise sales, it takes six to nine months before you can close sometimes a big customer. You may not know that I'm crap for six to nine months. Are there any ways to understand or determine the quality of a new joiner, a rep, without dollars brought in?

• 28:19Speaker 02

  There are a number of important leading indicators. I think that's one of the things that's so fun about enterprise sales is it's a collection of small milestones. And truly, you need to build an acquired taste for that. You don't get the adrenaline hit of a closed one deal hitting the win slot channel every thirty days. You get the long and sustained satisfaction of a strategic, full-team coordinated game, play by play. And so when you're trying to assess whether someone is doing well, you're looking at early indicators. It's not just, hey, how much pipeline did they build? It's, hey, when they took that first call, did they progress the deal? Did they get follow-up, right? What is the follow-up?

• 28:58Speaker 02

  When they move a customer into a trial, for example, have they earned the right to expend our resources on that trial? Or are they handing out trials like candy, right? That's an investment from our company, from our sales engineering team, to actually do a proof of value. And so you look at that type of thing. Did they get alignment with the economic buyer before they invested more of our resources in it? So these are early in the sales cycle. There's no win yet, but you're really getting a sense for process and accountability.

• 29:25Harry Stebbings?

  How long do you think it takes before you know if someone's actually any good? It's like with a show. Someone asked me this about shows the other day. I was like, I can tell in the first two minutes whether a show is gonna be good. Funny.

• 29:34Speaker 02

  How can you tell?

• 29:35Harry Stebbings?

  Oh, it's so easy. Can someone tell a story? Do they have intonation in their tone? Is there rapport between us? Do they come alive with certain topics? Can I read them fast? My job is to read you, to see where you light up and where you don't, to move to where you light up and move away from where you don't. Same as sales.

• 29:51Speaker 02

  I'd say in the first thirty days, you can get a sense of whether they're gonna be successful. Because you're looking for things like, what are they doing to get organized? What are they doing to start to learn about your product? Are they as curious as they sounded in the interview? What are they actually doing with their team? Have they ingratiated themselves with cross-functional folk so that they can learn together, right? Are they attaching themselves to our top sellers and learning from them? And there are a lot of leading indicators you can see.

• 30:19Harry Stebbings?

  Let's talk deal reviews. You mentioned your liking of them in terms of the process. How often do you do them? How do you structure them? Who sets the agenda? If we're starting from scratch, how should we do them?

• 30:30Speaker 02

  I think deal reviews should be conducted very frequently and there are different levels of depth, right? We can do more of like a storytelling at your all hands for the whole company. You have a sales rep come up and talk about, hey, this is what we did. This is how we won. Here are the things we learned and here's what we would do differently next time. Those are the two most important things. Otherwise it's, hey, we got this logo, everyone applaud. There's no learning for everyone. There's like, that's more broad strokes, but it's important to sort of bring the rest of the company along with you. In terms of the real, specific deal reviews, I think it's really good to run them weekly. You don't need to be reviewing the same deals over and over again at that kind of cadence, but great opportunity for the sales rep to step up and lead it and bring it.

• 31:13Speaker 02

  I would never expect it would just be the AE alone. I would expect them to bring their cross-functional selling team. So the sales engineer, for example, if they're working with a partner, someone who's helping them, like just so that we can get all perspectives, all angles, so that we can uncover where are the gaps and work together to close those gaps. But that frequency is important so that you're constantly making progress. Like I said, enterprise sales, it's not a high velocity deal, but every baby step along the process really matters.

• 31:41Harry Stebbings?

  What's a good answer to lose a deal? What's a bad answer?

• 31:45Speaker 02

  If it turns out that we don't solve the problem that they're trying to solve, that means we missed on qualification and qualifying them out of our pipeline. And that's a huge miss. So on one hand, as a sales leader, it would be wildly disappointing for me to know that my sales team had invested cycles on trying to provide a solution for frankly, a problem that we're not intending to solve. It's incredibly valuable for us at Fivetran to be very hyper-focused on the problems that we do solve. And so if we've missed that in qualification, that's a painful loss of time and resources, but it's something that we can coach. For me, that's like, it's painful, but it's solvable in teaching people how to better qualify.

• 32:23Harry Stebbings?

  Lauren, they went with a competitor. I'm really sorry. They were cheaper than us. I, we know they're a shit product, but they were cheaper than us. What do you say then?

• 32:32Speaker 02

  I think it depends on the competitor. If the competitor is do nothing, which is often a competitor, then no.

• 32:38Harry Stebbings?

  I'm totally with you, but I, I'm just worried that do nothing, doesn't that fall into your, well, they don't really have the pain?

• 32:43Speaker 02

  So 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. That inertia can be really challenging to compete with. But to your point, exactly right. If that happens, my reaction is what was 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 deprioritized 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?

• 33:23Harry Stebbings?

  Where do you think you're exceptional, truly world-class as a sales leader? Why are you like this part? I'm the best.

• 33:30Speaker 02

  I think I'd say transparency and direct communication. I try and create a culture and an environment where people feel safe talking about mistakes. And it's important to me that people are comfortable owning their learnings and sharing learnings with other people on the team. So.

• 33:45Harry Stebbings?

  How do you make people feel safe? I've been told that I shut people down before and I'm cynical, which is a wonderful description and very accurate. How do you make people feel safe?

• 33:53Speaker 02

  I try and be really honest and transparent about mistakes that I've made and share them with the team. So taking accountability, modeling accountability. When I could have done something differently so that it's clear that I value people being honest about where they're struggling and where they want to learn. And I've gotten that feedback too, Barry. Like I'm a pretty direct communicator and have certainly gotten feedback that when I first became a sales leader, I remember I was practicing deal inspection and I'm asking question after question. I'm thinking, I'm really getting to the meat of this. I'm really helping this seller. And the reaction I thought was, hey, I don't know what your agenda is, but you're freaking me out. And what I learned from that was it's really helpful to share the agenda. Hey, I'm asking this question because of X.

• 34:36Speaker 02

  I've run into a situation like this before and this outcome happened that was less than ideal. So I'm asking you to help make sure that we don't have that outcome. Right. So that's something that I've learned over time as a sales leader is really explaining the why.

• 34:47Harry Stebbings?

  I don't like to do that because then you can guide that discussion. If I know the why to yours, I can tailor my answer to tell you what you want to hear. You're worried that actually I need too many resources because I came from Google. Well, I'm going to definitely tailor my story to this customer where I did it very lean. I didn't bring anyone else in. I'll forget about the nine others here where I absolutely did spend a lot of resources. And so I like to like, keep the mystery to myself. I don't want to lead the witness.

• 35:13Speaker 02

  What you're describing is an interview environment where you absolutely don't want to share the answers. I think that's spot on. What I'm suggesting is as a sales leader with my team, it's really important to be transparent and demonstrate and model accountability so that people feel safe taking accountability themselves.

• 35:28Harry Stebbings?

  Now, final element before we move into a quick fire round. Lauren, tell me, why do you love getting rejected?

• 35:37Speaker 02

  Well, here's what I'll say. As it turns out, sales is a great career path for people who thrive on pushing the limits of what's possible. You get rejected so often, you start to expect getting rejected. And while the sting of getting rejected never lessens, it's important to remember that happiness is actually defined as reality minus your expectations. So if you expect a no, asking for what you want isn't scary anymore. Getting comfortable with rejection came from starting to expect it. And I think that's really important, not just for salespeople, but especially for women in sales. Getting really comfortable, asking for something that you know you might get a no to. And that's okay. The first no is usually an opportunity for you to ask why and uncover the hesitation

• 36:21Speaker 02

  and really get behind what's holding people back.

• 36:24Harry Stebbings?

  Does that not, does that not mean you enter with a negative mindset? I worry that if you go in with the no, it almost leads them there. Do you know what I mean? And it just comes out subtly in the way that you ask questions.

• 36:34Speaker 02

  I agree with what you're saying around confidence being critical. And I'm not suggesting that, in fact, I think in sales, a really important lesson I've taken away in my career is either you believe what you do matters, or you don't believe what you do matters. And if you do believe what you do matters, that enables you to persist when the pressure of carrying a quota and the burnout from the roller coaster of wins and rejections causes you to question, hey, is it all worth it? But if in, if in sales, you believe what you do matters, selling is actually curiosity about your customers and their problems, and less about persuasion. And actually, buyers, you're talking about coming in super confident, they're going to say yes. Buyers will resist sellers who attempt to persuade them.

• 37:17Speaker 02

  Instead, in sales, if you're asking insightful questions and you try to solve your customers' biggest business problems, the buyer's going to persuade themselves. So ultimately, that's what comes back to why believing what you do matters is critical in this business. And it's liberating. It gives you the confidence to ask for something you don't think you're able to get.

• 37:35Harry Stebbings?

  Do you think most sellers today and most salespeople are good storytellers?

• 37:39Speaker 02

  I think what makes a good storyteller is someone who has the combination of, again, believing what they do matters, having customer proof points that they can actually use to illustrate what they do, and is a really good listener, so that they actually understand the type of story that's going to resonate with the person that they're talking to. A bad salesperson just gets out there and says, hey, this is my favorite feature of the product. No one cares what your favorite feature of the product is. Is it aligned to the problem that the customer is trying to solve? Oh, it is? How have you done it differently than other companies? Oh, great, where have you done this before? Tell me a story about that. Now, as a buyer, I'm imagining myself in the shoes of this incredible, iconic, aspirational business

• 38:21Speaker 02

  who got to the solution that they wanted with your product and with your team. And now I want to be like them.

• 38:26Harry Stebbings?

  Is there anything with rejection that you would like to add that we haven't added?

• 38:30Speaker 02

  My career has been a, a stream of rejections. I mean, even just back to. When I was in eighth grade, I wanted to go to a specific high school. I applied to five private high schools in San Francisco, got into four, didn't get into the fifth, was waitlisted. As an eighth grader, I was like, well, all right, I'm going to give them another opportunity. Marched into the admission office and said, hey, I think there's a great fit here. Long story short, I ended up at that high school. Same thing happened when I applied to business school. I applied to several schools, got waitlisted at Stanford, got into Harvard, got into a number of other schools, but I really wanted to go to Stanford. And so gave some feedback to the Stanford admission office. Thank you for giving me the opportunity. It's encouraging to do a better job sharing with you the impact I'd like to have at Stanford.

• 39:14Speaker 02

  Long story short, ended up going to Stanford instead of the other schools. And again, when I interviewed at Segment, I got rejected. And for me, this is where it comes back to like what's holding you back from asking for what you want, not being afraid of getting rejected. In particular, I, when I was, when I interviewed at Segment, the feedback that I got was the recruiter actually didn't want to give me the feedback. You know how it goes. When, when she called, I interviewed at Segment on Friday, and that next Tuesday, this poor recruiter called me to relay the bad news and I asked her why. I can just feel her physically squirming through the phone, trying to provide as little concrete information as possible.

• 39:58Speaker 02

  And I gathered what I could, thanked her for the feedback, and then I asked, hey, can I speak with the hiring manager so I can help him understand what he missed? And that's met with audible squirms and some more back and forth, and she agreed to relay my request. So in the meantime, what I did was I wrote an email called Take a Chance on Me. In that email, I shared that while I was disappointed, I found the feedback to be very encouraging because I frankly believe that the team's concerns were quite addressable. And so I explained, here's what I think you're looking for, here's how I'd recommend that you test for it, let's do another, another interview with a more intentional structure. And so I went back in and actually met with Jenya. Who then introduced me to Jordan and that's how I ended up at Segment.

• 40:40Speaker 02

  The rejection turned offer is something that I have continued to experience throughout my career. It also happened when I went from leading a growth business team into leading enterprise team. Again, at that time, I'd been in enterprise sales at Google and I just hadn't done that segment. And I really wanted to get back into enterprise. They were like, listen, you're in SMB, we need someone to lead enterprise. I was like, all right, well, we talked about deal reviews earlier. Let's do a deal review, except I'm the deal. So here's what we're trying to accomplish. You're trying to hire someone to lead the enterprise sales team. Here's what I can offer to lead that team. Here are the gaps between what I can do and what you're looking for. And here's how I propose that we solve those gaps. It's just like doing deal inspection and really understanding how to solve those gaps.

• 41:25Speaker 02

  Long story short, I moved into the enterprise sales leadership role.

• 41:28Harry Stebbings?

  I do want to move into a quickfire round there, Lauren. So I say a short statement and you give me your immediate thoughts. Does that sound okay?

• 41:33Speaker 02

  Sounds great.

• 41:34Harry Stebbings?

  So a very wise person once asked this question. What deal are you most proud of, Lauren?

• 41:38Speaker 02

  Nothing makes me prouder than bringing really incredible talent onto the team. I think I'll punt that question and say, in terms of bringing someone into the fold, where a deal can be bringing a customer into your account base. I'm most proud of some of the sales leaders that I've hired and helped enable to achieve their own career outcomes.

• 41:57Harry Stebbings?

  I mean, expertly done. You have a career in politics, safe after this. Tell me, what sales tactic has not changed over the last five years? What is still going strong?

• 42:06Speaker 02

  I mean, we talked a little bit about qualification before. I think tactics, maybe not the word I would use, but instincts and skillsets, a curiosity. There is no substitute for deep curiosity, which drives relentless discovery and ruthless qualification.

• 42:23Harry Stebbings?

  What sales tactics have died a death?

• 42:25Speaker 02

  Pricing that's not aligned to value. Black box, subscription, shelfware, licensing. That model is moving in the past.

• 42:32Harry Stebbings?

  What one piece of advice would you give to a sales leader starting a new role today?

• 42:37Speaker 02

  This goes back to what I said before about listening. The best thing you can do, then there's nothing more important than listening to customers.

• 42:43Harry Stebbings?

  How would you most like to change the world of sales?

• 42:46Speaker 02

  Like to increase the diversity in sales leadership.

• 42:48Harry Stebbings?

  What can be done to do that?

• 42:50Speaker 02

  I think it comes down to building community and building pipeline and promoting from within and creating opportunity for people to see people that look like them and sound like them in leadership roles. And we haven't done a great job of that historically. So it's an important area that I spend a lot of time.

• 43:05Harry Stebbings?

  Having done twenty sales now for ten episodes, I definitely see that. Tell me, what is the hardest element of your role with Five Tram today?

• 43:12Speaker 02

  It's ironic a little bit because one of the things that Five Tram does so well is our product is really simple. It solves a really hard problem and behind the curtains, it's complicated, but it's a simple user experience. And as a sales leader scaling a sales org, 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 the biggest challenge I have. Because you're looking at, 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 try to solve with a comp plan becomes very complex and you lose focus. So what's really important to me is to drive simplicity and focus for the team.

• 43:54Harry Stebbings?

  Penultimate one, what's the secret to a successful comp plan?

• 43:58Speaker 02

  Alignment with the business outcomes that you're trying to drive as a company.

• 44:02Harry Stebbings?

  Do many comp plans have that?

• 44:03Speaker 02

  Often they do not.

• 44:05Harry Stebbings?

  How not?

• 44:06Speaker 02

  We're in a consumption business and so it's really important to align compensation structure with the best outcomes for the customer, which are also aligned to the outcomes of our company. So a traditional bookings quota and variable compensation structure, what that does is it drives someone to land a deal and nothing else. When you start to align compensation with the actual adoption of the product and consumption of what you sold as a salesperson, all of a sudden, the incentives of the AE and the incentives of the customer and ultimately the company are much more aligned.

• 44:41Harry Stebbings?

  Should customer success not be part of this comp plan on expansion?

• 44:45Speaker 02

  Really depends on your philosophy and enterprise. The account executive in enterprise is the CEO of their franchise. And so it is important that the account executive remains intimately involved with their customer throughout their lifecycle. So it's not like in a more of a transactional business where you're signing a deal and tossing it over the fence.

• 45:04Harry Stebbings?

  Final one for you, what sales teams do you think are the best and why?

• 45:09Speaker 02

  I think the best sales teams are people who have had to be in a category creating environment. The real hustlers that I've seen be successful are people who are selling products where there isn't already an identified budget. And it creates an opportunity for us to really tie value to the product that we're selling.

• 45:29Harry Stebbings?

  Lauren, I've so enjoyed doing this. Thank you so much for putting up with me. I'm so glad that we didn't stick to the schedule. But this has been a total joy, so really appreciate the time.

• 45:37Speaker 02

  Well, thank you so much for having me here. I had a great time.

• 45:42Harry Stebbings?

  I so love doing that episode and I just cannot get a picture of Lauren as an eight-year-old storming into the principal's office at a school she wanted to go to and doing a deal review on herself and why she should get in. I absolutely love that story and think it's testament to the resilience and persistence. So I love that. If you'd like to see more from us behind the scenes, of course you can on 20vc.com. But before we leave you today, have you ever wondered how revenue intelligence experts Gong run their own revenue planning? They use Pigment. Pigment is the integrated planning platform that allows you to make decisions you can trust fast. Pigment integrates with your sales data, your CRM for your pipeline, your HRIS for your own open headcount, your financial data to give you accurate real-time reports and dashboards.

• 46:24Harry Stebbings?

  And Pigment is designed to be used by leaders like you. From sales to finance to HR and marketing, Pigment's what-if analyses are a true game changer to model any type of scenario and understand what will happen to your target attainment if, say for example, you can't hire those 20 open reps, or if your cost of sales goes up by 20% or drops by 20%. Legacy tools make this painful and obscure, with you needing to ask third parties to take days or weeks to crunch the numbers for you. With Pigment, you can do it all yourself in minutes and make the decisions you need. And that's why companies like Figma, Gong, Deliveroo, and many more trust Pigment. Visit gopigment.com/20vc to request a demo.

• 47:04Harry Stebbings?

  What's more, if you use that link in the next 30 days, the team has promised me they'll run a personalized sales planning audit just for you. And next, we have Sales Loft. Sales Loft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue New workspace. It's the one place sales teams can go to prospect, manage additive deals, and get the insights they need to coach seller performance, forecast with accuracy, and find out what steps to take to close more deals. Some of the world's leading companies like IBM, Shopify, and Stripe all love a new SalesLoft, and so can you. It's the new way to sell. Find out more at salesloft.com. And finally, we have to talk about Chargebee. Chargebee is the subscription revenue and billing management platform that streamlines

• 47:47Harry Stebbings?

  your revenue operations like never before. Chargebee automates the lead to lead your workflow across your revenue stack, so you can dream, deploy, and enjoy the breeze while the MRR just keeps rolling in. But Chargebee goes so much further beyond just billing. One example, pricing alterations. They allow you the ability to change pricing models with one click. Grandfathering old pricing has never been so easy. That, and for hundreds of other reasons, is why the likes of Freshworks, Okta, and Envoy all love and use Chargebee. Simply head over to chargebee.com to find out more. As always, I so appreciate all your support, and I cannot wait to bring you an incredible episode this coming Friday.