The Twenty Minute VCFivetran's Lauren Schwartz: Must-Ask Questions to Identify Potential Sales Talent | 20VC #939
EVERY SPOKEN WORD
95 min read · 18,993 words- 0:00 – 1:15
Intro
- HSHarry Stebbings
Lauren, I am very, very excited for this. I've heard so many things from Jordan, from Zhenya, from th- your time together at, uh, Segment, so thank you so much for joining me today.
- LSLauren Schwartz
Well, thank you for having me, and likewise. Your reputation precedes you as well.
- HSHarry Stebbings
That is very kind. Uh, 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 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?
- LSLauren Schwartz
Yeah. Um, well, I discovered sales at the age of seven when I became a Brownie Scout, and th- that's when I fell in love with the art of cookie sales. So, thinking back to that time in my life, absolutely-
- HSHarry Stebbings
Can I- can I ask, what did y- what did you love about sales then? What was it?
- LSLauren Schwartz
Oh. Well, we were selling cookies, and there was an opportunity to create repeat purchasing, uh, by evangelizing the- the freezer lifespan of a cookie. So, for me, it was really about the opportunity to compete with other Brownie troops, uh-
- HSHarry Stebbings
(laughs)
- LSLauren Schwartz
... but also to spread the love that I personally have for cookies.
- HSHarry Stebbings
(laughs) And so you're-
- LSLauren Schwartz
Um-
- HSHarry Stebbings
... seven, you realize the love of sales through selling cookies, which I'm sure you won this competition with other brownie providers.
- 1:15 – 3:10
Journey into Sales
- HSHarry Stebbings
- LSLauren Schwartz
No. (laughs)
- HSHarry Stebbings
Um, w- take- take me forward a little bit. What happened then?
- LSLauren Schwartz
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 in 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 would 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 (laughs) 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.
- HSHarry Stebbings
(laughs)
- LSLauren Schwartz
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-
- HSHarry Stebbings
I totally agree.
- LSLauren Schwartz
... s- right? (laughs)
- HSHarry Stebbings
Yeah. I agree. And then you have, like, car salesman, which I think really destroyed it-
- LSLauren Schwartz
(laughs)
- HSHarry Stebbings
... which is just terrible. Uh, I think, I think selling is like educating your buyer to the best solution for them.
- LSLauren Schwartz
Yeah.
- HSHarry Stebbings
But I don't think that is connoted in the word.
- LSLauren Schwartz
Yeah. For me, it's like no- nobody likes that word, nobody wants to be sold to. Imagine if you were using a word that makes people uncomfortable to describe your own professional work, your career, right? And then, for me-
- HSHarry Stebbings
I do. It's- it's called a venture capitalist, Lauren. (laughs)
- LSLauren Schwartz
(laughs) Um, right. And so, 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. (laughs) Um-
- HSHarry Stebbings
Lau- can I ask you before I
- 3:10 – 4:45
Biggest takeaways from working at Google
- HSHarry Stebbings
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. It ... at a very transformational time for you in your, like, career and development. What was the biggest, or one or two big takeaways for you from the six years at Google that really stuck with you?
- LSLauren Schwartz
It's really ... what I learned was the- the best skill you can develop in sales is an insatiable curiosity about what's possible.
- HSHarry Stebbings
Mm-hmm.
- LSLauren Schwartz
Um, and, and truly the instinct to ask for forgiveness rather than permission. Uh-
- HSHarry Stebbings
What does that mean? What does that mean, sorry, in sales, ask for forgiveness not permission?
- LSLauren Schwartz
I think it's kind of like approaching rules as a su- as a suggested set of guidelines. Um, I think it's, you know, thinking about outside of the box, what's possible for a c- 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-
- HSHarry Stebbings
How-
- LSLauren Schwartz
... 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.
- HSHarry Stebbings
So, help me out here.
- 4:45 – 6:40
What to tell a first day sales rep
- HSHarry Stebbings
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- how do I make it uncomfortable? When do I make them comfortable again? I- I- I'm first day on the job. Can you help me?
- LSLauren Schwartz
Well, I think it starts with an outside-in perspective. You ask about current state and you get the, um, potential customer to really define what it is they're h- 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 wanna lead with yes/no questions 'cause 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, 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, th- the implications on a 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 types of value drivers that you would wanna make sure you're uncovering as, as an early sales rep.
- HSHarry Stebbings
My question to you, like, I, I have two questions. (laughs) And this is why I told you the schedule's completely useless. Um-
- LSLauren Schwartz
(laughs) .
- HSHarry Stebbings
One, like, to get in
- 6:40 – 8:03
Does outbound sales still work today?
- HSHarry Stebbings
that room, y- y- you know, with... I b- I straightaway think of outbound. Does outbound still work today?
- LSLauren Schwartz
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 m- investing in, in data movement, which is what we do at Fivetran, you're taking data from some place and sending it to some place. So, you would never buy, like, plumbing alone. You would only wanna 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 salespeople grow up thinking, "Oh, 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.
- HSHarry Stebbings
I
- 8:03 – 9:30
When do partnerships become viable?
- HSHarry Stebbings
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?
- LSLauren Schwartz
Again, it's like follow the path of least resistance in term... Like co- the, the term cold calling to me is like, I would so much rather a warm call, right? You're, you're, 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 a16z model, for example. Um, you're getting introduced to partners where you can go to market together. So, j- I don't actually think there is ever a time that's too early, um, in a founder's... in a, in a startup's life cycle to lean on the, the connections you have in your community to start developing those partnerships.
- HSHarry Stebbings
And if you have a really good rep, they, they could even do a, a very hot call, not just a cold call, actually. (laughs)
- LSLauren Schwartz
Indeed.
- HSHarry Stebbings
Um, but, um, I, my, my, my other final question before we move into actually what we have planned for the show, um, is in terms of the data that you get back from those fantastic but uncomfortable conversations, great,
- 9:30 – 11:00
How to turn sales insights into marketing
- HSHarry Stebbings
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?
- LSLauren Schwartz
Oh, wow. What an interesting question. 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, and development, right? So, we do... It's e- the question around how can you ensure there's no leakage of information, uh... (laughs) Give any salesperson an opportunity to give customer feedback to product, and they will be chomping at the bit, right? 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 wanna make sure you're capturing all of that in your CRM system, like Salesforce, but we do a, a n- number of ways of communicating the experience, not just to, um, other... not just to other departments, but also to other sellers. So, deal reviews, fireside chats, postmortems, anything you... any way of storytelling, I think, the, the, the art of storytelling and getting that... using that as a data collection mechanism and a way to really move, uh, the product roadmap, uh, is incredibly valuable.
- HSHarry Stebbings
You said about repeatable there, and that instantly makes me think about the wonderful world
- 11:00 – 13:06
How to think about the sales playbook
- HSHarry Stebbings
of a sales playbook, which, um, you know, is just, uh, so, I think, mystic in its understanding. When you think about the definition of sales playbook, what does sales playbook mean to you, Lauren?
- LSLauren Schwartz
I think that the, the word playbook is like a little prescriptive for super early stage startup. I think if, if what we're thinking about is first couple of hires and, 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. Um, like I said, the founder is the first seller. They were able to get funding to continue, uh, (laughs) continue running their company. And so using that, the, the founder's vision and the way that they tell the story of the, again, the, the positive business outcomes that they're solving with their, with their product, um, is how you start. That's this. The sellers need those at-bats. For me, um, the way that I learned... Like, when I started at Segment, I started as an SMBAE, and I, I mean, that to me, I, I'd been in enterprise sales at Google, then I went to business school, then I started as an SMBAE, and that was the best, uh, most humbling, but best decision I could have made in my career because...... the number of at-bats (claps hands) with those small, faster, h- higher velocity sales cycles that I got when I was learning a product that I'd never sold before. You know, I'd been at Google, I was selling media, then I came to Segment and I was selling SaaS data infrastructure. Uh, just a very different type of buyer and sales cycle and conversation and level of technical acumen. Um, and so for me, (snaps fingers) getting those at-bats, which ultimately allow you to build a sales playbook, uh, was critical for me to understand and accelerate my ramp as a seller.
- HSHarry Stebbings
I totally get you in terms of the acceleration there, giving you the velocity and the kind of increased level of learning. Can I ask, I- I'm always fascinated by PLG versus enterprise. Obviously, enterprise at Google, SMB at Segment, now enterprise at, um, Fivetran. When we think about, like, startups
- 13:06 – 14:25
PLG or enterprise, do startups need to choose?
- HSHarry Stebbings
... And again, you are advising me an early stage company. Um, there's this kind of decision, like, are you gonna be PLG or are you gonna be enterprise? Do you need to make that decision? Can you be both or do you have to be one or the other?
- LSLauren Schwartz
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. C- 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 skill set 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 a s- your first deal with some big enterprise logo and it's just, like, really a narrow land. Um, the, the reality is there's ... Th- the only enterprise sales teams can actually expose and create recognition at 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.
- HSHarry Stebbings
Can I ask, when you think about kind of that wall-to-wall adoption and that expansion
- 14:25 – 16:10
How important is “multi-threading”
- HSHarry Stebbings
internally, um, we often hear about kind of multi-threading and finding, you know, s- 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?
- LSLauren Schwartz
It 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 w- reviewing deals with my team, we're, we're always asking about the different roles. Who is your champion? Who is the competitor's champion? Who is the champion for doing nothing? Right? That's even before you get to the economic buyer. There are ... Uh, the, the ... And then what you do, we talked about this earlier, when you're, um, you wanna 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 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 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, "Well, I've met with your entire team," or, "I've met with this person, this person, this person across all of the ... 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.
- 16:10 – 20:10
How to instill urgency in sales
- LSLauren Schwartz
- HSHarry Stebbings
I think the biggest challenge that I see today, honestly, is actually, you know, I sit on many boards and there's always, "Ah, you know, we missed, we missed this quarter because it, it ... D- the deal just fell to next quarter. It just slipped through to 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 (laughs) to you is like, if, if I said to you, "One of th- 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?
- LSLauren Schwartz
I would say, "Who at the company is telling you that this is the problem that they need to solve, that this is why they need to solve that problem, and this is when they need to solve that problem? And that your sol- 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 gonna 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, h- h- 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 gonna get that deal done in the timeframe that you as the seller wanna get it done.
- HSHarry 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, l- 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, eh, w- how do you think about creating urgency yourself as a sales leader, and how do you advise your team?
- LSLauren Schwartz
I don't really buy into discounting or relationship selling, personally. To me, I, 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 Q4." "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 gonna need to be live in production in this timeline. You're gonna need to be doing it in, uh, you're gonna... You might not even leverage, like, your production environment until this time," right? "We're gonna ru- roll out professional services. We're gonna 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 and, uh, 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're really just helping them, again, participate in their own rescue.
- HSHarry Stebbings
Can I ask, Lauren, what is that noise in the background? (laughs)
- LSLauren Schwartz
This is Dinah, the cat. I think it's really-
- HSHarry Stebbings
Oh, wow. Geez. The ca-
- 20:10 – 21:55
Hire sales rep or head of sales first?
- HSHarry Stebbings
the cat is here. I do have to ask it, you know, I think the big thing that I think about, uh, I'm a founder in this hypothetical situation, very early stage company. Do I hire sales reps first? Do they do that-
- LSLauren Schwartz
(meowing)
- HSHarry Stebbings
... 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?
- LSLauren Schwartz
Just depends. We talked a little bit about, um, s- 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 h- 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, 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. 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 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."
- HSHarry Stebbings
Can I ask, uh, before we dive into how to discover that,
- 21:55 – 23:00
Do you play reps off each other?
- HSHarry Stebbings
do we hire two reps at once? Jason Lamkin at SaaStray always says, "Hire two reps at once, and kind of play them off against each other like The Hunger Games for reps." Um, i- is that a good idea, or, or not a good idea? (laughs)
- LSLauren Schwartz
I wouldn't call it The Hunger Games for reps.
- HSHarry Stebbings
(laughs)
- LSLauren Schwartz
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, you know, 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 ha- gets completely different results, then you'll actually get signal rather than noise about, uh, a, a certain individual and their skills. Does that make sense?
- HSHarry Stebbings
So I... 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. So, um, how do you structure... Say we're gonna hire these two reps for our startup. We're co-founders.
- 23:00 – 25:25
How do you hire sales reps?
- HSHarry Stebbings
Well done, we have, we have new jobs. Um, uh, h- how do we actually structure the process for hiring these two sales reps? What does that look like?
- LSLauren Schwartz
You know, what, what's really important, uh, 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, y- you really don't know what you're getting. So, in, in the process, in terms of s- 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, th- 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. Y- you wanna 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 wanna talk about Bank of America. Tell me about your second, the, the deal that you're, that comes behind that. Tell me about the s- 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 didn't prepare that deal-"
- HSHarry Stebbings
(laughs)
- LSLauren Schwartz
"... for this conversation." And then you start to really get to the, to the meat, right? Like, what, what do 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, um, because it's raw and it's natural. And so, um, yeah, making sure that you're identifying what their actual impact on the outcomes were, um, getting to the meat of it, and then trying to get past the questions that they prepared for because, um, a seller needs to have a plan, but also needs to be able to pivot when the nature of the conversation shifts.
- HSHarry Stebbings
I, I, when I had Jordan on the show, um, he said something fascinating about sales attribution. He was like, you know, 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, um, in terms of, you know, 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.
- 25:25 – 28:49
How do you define attribution in sales?
- HSHarry Stebbings
So I guess my question is like, how do you really define at, or, 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, out of proportion. How do you really tell if it's someone's work?
- LSLauren Schwartz
Yeah. Well, 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, um, maturity phase or where in the company's phase of growth they were employed and they were successful. Because, you know, 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, uh, one of the, the pieces of feedback was, "Well, you came from Google. We don't think you're, you're likely to be that scrappy and you know, you're used to, uh, a breadth of supporting resources." And I was sort of like, "Oh, okay. Well thanks for that feedback. Here are 10 examples of scrappiness or working..." Right? So the, the point I'm making is you need to think about... And they were right to be asking those questions. The conclusion they came to ultimately was wrong. But then we, we sorted that out. I think the, 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're, 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, you know, roadmap." Or, "My champion left." Or whatever it is. Like I, what, what you want to look for is that type of instinct. Like, hey, accountability. 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.
- HSHarry Stebbings
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, ooh, that's a revealing one of character?
- LSLauren Schwartz
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-
- HSHarry Stebbings
Gotcha.
- LSLauren Schwartz
... 'cause 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 about 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 did they say about you? Okay, great. Can I reach out to them?" And if you're a candidate, you're not gonna say no. You know? You want... But then that's when you really get clarity into what the experience is i- to buy from them.
- HSHarry Stebbings
Ooh, yeah. That is a good one.
- 28:49 – 30:48
Do you do case studies when interviewing?
- HSHarry Stebbings
I like that a lot. Um, can I ask, do you, do we do a case study at all? We've got a, 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?
- LSLauren Schwartz
I've done it both ways. Uh, w- I've spent a lot of time hiring people with where 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 faced on their last call and the candidate's like, "I don't know. I..." You know, and you sort of lose, uh-
- HSHarry Stebbings
(laughs)
- LSLauren Schwartz
... (laughs) the ability to tell if they're actually good because you're like, "Ah, stumped them. They're not good." Right? So-
- HSHarry Stebbings
(laughs)
- LSLauren Schwartz
Um, the, the pitch is a, is a tough one. Um, I actually like, aga- 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, l- 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, I'm procurement, let's go." And then I, I just walk th- do it live off the cuff. Again, this is about being able to, being s- so prepared to listen to a, to a customer and to...... be able to bring any conversation back to the, the business outcomes that you're driving for them, that they should be able to pivot along the way on that conversation.
- HSHarry Stebbings
Can
- 30:48 – 32:11
Biggest mistakes you’ve made in hiring
- HSHarry Stebbings
I ask you a question that's quite direct?
- LSLauren Schwartz
Okay.
- HSHarry Stebbings
What's the single biggest mistakes you've made in hiring when you reflect on them?
- LSLauren Schwartz
Uh. 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, the important work of, like, really diving deep into deal-level experiences. This was, like, really early in my sales leadership career. A great lesson.
- HSHarry Stebbings
That's tough. Yeah, that's a mistake. I've, I've made many mistakes hiring, don't worry. I'm terrible at hiring, so have no fear. Um, I, 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. Um, I, I don't know what I'm doing. You
- 32:11 – 35:45
How do you do onboarding?
- HSHarry Stebbings
do, luckily, which is why you're co-founded with me. Um, how do we do onboarding? Like, I've... They turn up on day one? What now? Wh- what do I... What do we give them?
- LSLauren Schwartz
Yeah, I mean, early in the, in the growth of a company, a lot of this is pretty, um, grassroots, where it's, like, the first manager, they're their first hiring manager. You're s- Are we talking about a first sales rep, or just anyone that we're onboarding?
- HSHarry Stebbings
I mean, kind of first and sales r- first and second sales rep.
- LSLauren Schwartz
So, I was talking earlier about how valuable it was for me when I started at 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 y- 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. Um, we did something where, uh, we, where, like, a BD... Taking a call that a BDR would normally take so we can just get some at-bats, um, to get someone ramped is something that I did back at Segment. Um, 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," you know?
- HSHarry Stebbings
(laughs)
- LSLauren Schwartz
Right? That's not, 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... Each at-bat in a long enterprise sales cycle is actually a very high, um, high-impact, high-leverage. And so, the onboarding process needs to be, uh, 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. Um, so learning that... Yeah.
- HSHarry Stebbings
And so, and so w- what's right for us there? 'Cause 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?
- LSLauren Schwartz
Yeah. Recorded sales calls. Having, like, a library of recorded calls is really, really valuable as people ramp. Um, and then just, just capturing postmortems. Lessons that we learned from a win, lessons that we learned from a loss. I'm really big on, on running deal reviews and making sure that we capture learnings that we can then amplify when people are, are joining the organization.
- HSHarry Stebbings
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, uh, the decks that we have from fundraisers. Is it like two weeks in, or is it like three months in? This is enterprise.
- LSLauren Schwartz
Yeah, I th- I think it... Again, it depends on your organization and where you are in terms of your, um, of your customer base and the types of c- buyers that you're working with. But y- 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 Fivetran, 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 wild.
- HSHarry Stebbings
We're gonna talk about deal reviews, because this is like a nerdy
- 35:45 – 38:03
Indicators that a new sales rep isn’t performing well
- HSHarry Stebbings
passion of mine, which is one of the many reasons why I'm single. Um, but, uh, before we discuss deal reviews, I, I do have to ask, like, 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. (laughs) Are there any ways to understand or determine the quality of a new joiner, a rep, w- without dollars brought in?
- LSLauren Schwartz
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 won deal hitting the wins Slack channel every 30 days. You get the long and sustained satisfaction of a strategic full team coordinated game, play by play.And so when you're try- 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, what is the follow-up? When they are, um, when they move a customer into a trial, for example, have they earned the, the right to expend our resources on that trial or are they handing out trials like candy, right? We... That's not, 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 the- so these are early in the sales cycle. There's no win yet, but you're really getting a sense for process and accountability.
- HSHarry Stebbings
I, I totally get you there. Uh, how long do you think it takes before you know if someone's actually any good?
- LSLauren Schwartz
I'd say in the first 30 days you can get a sense of whether they're going to be successful, because you're looking for things like what are they doing to... 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, right? What, h- what are they actually doing with their team? Have they, uh, ingratiated themselves with cross-functional folks so that they can learn together, right? They're, are they attaching themselves to our top sellers and learning from them? And, you know, there are a lot of leading indicators you can see.
- HSHarry Stebbings
Let's talk deal
- 38:03 – 41:49
Deal reviews
- HSHarry Stebbings
reviews because otherwise I could talk all day. Um, deal reviews, you mentioned, like, your liking of them in terms of the process. How often do you do them? How do you structure them? Who sets the agenda? W- again, if we're starting from scratch, how should we do them?
- LSLauren Schwartz
I think deal reviews should be conducted very frequently and there, there are different levels of depth, right? We can do more of, like, a storytelling at your, your all hands for the whole company. You have a sales rep come up and, 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 sort of like, "Hey, we got this logo. Everyone appla-" You know, there's no learning for everyone. Um, in, in... So th- there's like, that's more, uh, broad strokes, but it's important to sort of bring the rest of the company along with you. In terms of the, um, the real specific deal reviews, um, I mean, I, I think it's really good to run them weekly. Um, maybe y- 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, um, to step up and lead it and bring... 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 m- like, just so that we can get, um, all perspectives, all angles so that we can uncover where are the gaps and work together to close those gaps. But, um, I think 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 s- baby step along the process really matters.
- HSHarry Stebbings
What's a good answer to lose a deal? What's a bad answer?
- LSLauren Schwartz
I think it's really valuable if, if it turns out that we don't solve the problem that they're trying to solve, that means we missed on qualification and qualific- qualifying them out of our pipeline, and that's a huge, huge miss. So on one hand, as a sales leader, it would be wildly disappointing for me to know that, uh, my sales team had invested cycles on, uh, uh, trying to provide a solution for a, frankly, a problem that we're not intending to solve, right? It's- it's- it's in- incredibly valuable for us at Fivetran to be very, very hyperfocused on the problems that we do solve. And so, um, if we've missed that in qualification, that's, that's a painful loss of, of time and resources, but it's something that we can coach. And so for, for me, that's like, it's painful, but it's, it's solvable in teaching people how to better qualify.
- HSHarry Stebbings
Lauren, they went with a competitor. I'm really sorry. They, they were cheaper than us. I, we know they're a shit product, but they were cheaper than us. What do you say then?
- LSLauren Schwartz
I think it depends on the competitor. If the competitor is do nothing, which is often a competitor, then no. What-
- HSHarry Stebbings
Yeah, no, I'm, I'm totally with you, but I- I- I'm-
- LSLauren Schwartz
Yeah.
- HSHarry Stebbings
... just worried that do- do nothing, doesn't that fall into your, well, they don't really have the pain then?
- LSLauren Schwartz
Then they don't... Exactly. So if the, if the competi- 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, uh, 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? Because 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
- 41:49 – 44:40
How do you create an environment of safety?
- LSLauren Schwartz
data as a competitive advantage and how can we help them?
- HSHarry Stebbings
Can I ask, where do you think you're exceptional, truly world class as a sales leader? Where are you like, "This part, I'm the best"?
- LSLauren Schwartz
Transparency and direct communication. For me, it's about being the... I- I try and create a culture and an environment where people feel safe talking about mistakes that they've made, and it's important to me that people are comfortable owning those, owning their learnings and, and sharing learnings with other people on the team. So, um, you know, I've never-
- HSHarry Stebbings
How do you make people feel safe? I- I've been told that I shut people down before and I'm cynical, which is a (laughs) wonderful description and very accurate. Um, wh- how do you make people feel safe?
- LSLauren Schwartz
... 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 and, um, and, yeah, that I value people being honest about where they're struggling and where they want to learn, and, um, yeah. That's... I mean, I've gotten that feedback too, Mary. Like, I, I, I'm a pretty direct communicator and have certainly gotten feedback that, uh, you know, 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 got was, "Hey, I don't know what your agenda is, but you're freaking me out." (laughs) And what I learned from that was, it's really helpful to share the agenda, right? "Hey, I'm asking this question because of X. 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- that's something that I've learned over time as a sales leader, is really explaining the why, when you ask someone.
- HSHarry Stebbings
I don't mind to do that because then you can guide that discussion.
- LSLauren Schwartz
Mm-hmm.
- HSHarry Stebbings
If I know the why to yours, I can tailor my answer to tell you what you want to hear.
- LSLauren Schwartz
Mm-hmm.
- HSHarry Stebbings
"Ah, you're wo- you're worried that actually I need too many resources 'cause I came from Google. Well, I'm gonna 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, 'cause I- I don't want to lead the witness.
- LSLauren Schwartz
Yeah. I, I mean, I... 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, um, transparent and demonstrate and model accountability so that people feel safe taking accountability themselves.
- HSHarry Stebbings
Yeah. No, I get you totally. Big difference. Um, that's why you're a brilliant sales leader and I'm not. Um-
- LSLauren Schwartz
(laughs) Yeah.
- HSHarry Stebbings
Uh, uh, I do want to move into a quick fire round though, Lauren. So I say a short statement and you give me your immediate thoughts. Does that sound
- 44:40 – 45:25
What deal are you most proud of?
- HSHarry Stebbings
okay?
- LSLauren Schwartz
Sounds great.
- HSHarry Stebbings
So, uh, a very wise person once asked this question. Um, what deal are you most proud of, Lauren?
- LSLauren Schwartz
(laughs) What deal am I most proud of? Uh, I would say, you know, nothing makes me prouder than bringing really incredible talent onto the team, so 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, um, I'm, I'm most proud of some of the sales leaders that I've hired and, um, and helped enable to, to achieve their own career outcomes.
- HSHarry Stebbings
I mean, expertly done. You have a career in politics
- 45:25 – 46:04
How have sales tactics changed over the last 5 years?
- HSHarry Stebbings
safe after this. Um, (laughs) uh, tell me, what sales tactic has not changed over the last five years? What is still going strong?
- LSLauren Schwartz
I mean, we talked a little bit about qualification before. I think, uh, tactics may be not the word I would use, but, um, instincts and skill sets, uh, curiosity. Like, there is no substitute for deep curiosity, which drives relentless discovery and ruthless qualification.
- HSHarry Stebbings
What sales tactics have died a death?
- LSLauren Schwartz
Pricing that's not aligned to value. Black box subscription, uh, shelfware licensing. That, that model is, is
- 46:04 – 46:15
Advice for new sales leader starting today
- LSLauren Schwartz
moving in the past.
- HSHarry Stebbings
What one piece of advice would you give to a sales leader starting a new role today?
- LSLauren Schwartz
This goes back to what I said before about listening. The best thing you can do, there, there's
- 46:15 – 46:55
How to increase diversity in sales leadership
- LSLauren Schwartz
nothing more important than listening to customers.
- HSHarry Stebbings
How would you most like to change the world of sales?
- LSLauren Schwartz
I'd like to increase the diversity in sales leadership.
- HSHarry Stebbings
What can be done to do that?
- LSLauren Schwartz
Oof. How much time do you have? I think it-
- HSHarry Stebbings
(laughs)
- LSLauren Schwartz
... it comes down to building, uh, building community and building pipeline, and, um, and promoting from within, and, 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. Um, so it's- it's an important area that I spend a lot of time.
- HSHarry Stebbings
You know, having done 20 sales now for ten episodes, I, um, I, I definitely see that. Yeah.
- 46:55 – 47:53
Hardest part of role with Fivetran today
- HSHarry Stebbings
(laughs) It's a, it's a real problem. (laughs) Um, uh, tell me, what is the hardest element of your role with Fivetran today?
- LSLauren Schwartz
You know, w- it's, it's ironic a little bit because one of the things that Fivetran does so well is our product is really simple. Uh, it solves a really hard problem and be- and, um, behind the curtains, it's very, it's complicated, but it's a simple user experience. And, um, as a sales leader scaling a, 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
- 47:53 – 49:29
Secret to a successful comp plan
- LSLauren Schwartz
to me is to drive simplicity and focus for the team.
- HSHarry Stebbings
Penultimate one. What's the secret to a successful comp plan?
- LSLauren Schwartz
Alignment with the business outcomes that you're trying to drive as a company.
- HSHarry Stebbings
Do many comp plans have that?
- LSLauren Schwartz
Often, they do not.
- HSHarry Stebbings
How not?
- LSLauren Schwartz
(laughs) Um, for example-
- HSHarry Stebbings
I would be such a good salesperson. I am great at this customer discovery. (laughs)
- LSLauren Schwartz
For example, uh, we're in a consumption business, and so it's really important to align compensation structure with, with the best outcomes for the customer, which are also aligned to the outcomes of our company. So, a traditional bookings...... quota and, uh, 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.
- HSHarry Stebbings
Should customer success not be part of this comp plan on expansion?
- LSLauren Schwartz
Really depends on your philosophy in enterprise. We ha- w- the account executive in enterprise is th- the CEO of their franchise. And so, it is important that the account executive remains intimately involved with their customer throughout their lifecycle. So, we- it- it's not like in a- more of a transactional business, where you're signing
- 49:29 – 50:20
What makes the best sales teams?
- LSLauren Schwartz
a deal and tossing it over the fence.
- HSHarry Stebbings
That was a real grenade at the last minute, wasn't it? Uh (laughs) ... uh, final one for you, what sales teams do you think are the best, and why?
- LSLauren Schwartz
Um, I think the best sales teams are people who have had to be in a category-creating environment. So, people who l- like, the- the- the real hustlers that I've seen be successful are- are people who are selling products where there isn't already an identified budget. And it's- it creates an opportunity for us to really tie, um, value to the product that we're selling.
- HSHarry 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. Um, but this has been a total joy, so really appreciate the time.
- LSLauren Schwartz
Oh, well, thank you so much for having me here. I had a great time.
Episode duration: 50:40
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