Sprinting to $100M ARR 
in 3 years: CRO Stevie Case

Vanta CRO Stevie Case hyperscaled her team from 20 people and ~$10M to 300+ and $100M in less than two years. This week’s episode is a masterclass in how to change the trajectory of your business. 

If your company is between $5M - $20M ARR, you’l want tol hear the cheat codes to 

• Moving Upmarket: How to scale to enterprise customers without losing focus on your core SMB base
• Culture Building: Going all-in on enablement so your reps can grow their career as far as they want without leaving the company 
• Remote-First Structuring: How Vanta went against the conventional wisdom and achieved this hypergrowth with a fully remote sales team. 

The bar for startup growth keeps getting raised. The only way to keep up is to lead the way. Bravado CEO Sahil Mansuri brings you the insights to help you do just that every other Wednesday on The Bravado Pod.

Time-coded show notes:

00:00 — Introducing Stevie Case, CRO @ Vanta
06:55 — Success comes down to the people you hire. Who does Vanta hire?
23:24 — How to crush a Stevie Case interview - the exercise that makes or breaks it for candidates at Vanta
30:39 — Maximizing Productivity in a Remote-first team and the importance of face time
39:35 — It’s never too early to think about creating multiple revenue engines
49:47 — How to forecast accurately for success with the levers that drive pipeline
57:41 — The real ROI betting on SDRs
1:04:52 — Lightning Round: Sales as a Superpower, Professional Gaming to Sales

Full transcript:

00:00:00:00 - 00:00:09:01
Sahil Mansuri: I'm curious how you get confidence that you're getting maximum productivity out of your team from a remote environment. How do you gut check or pulse check that?

00:00:09:05 - 00:00:25:14
Stevie Case: I deeply believe that that sense that like, oh, maybe people aren't working hard enough does come from a sense of insecurity. And it's really easy when things aren't going well, to just point out that the problem is almost always something else. People want to work hard. They want to. They want to feel great about the work they do.

00:00:25:16 - 00:00:35:12
Stevie Case: And it's my job as a leader to create a team that they want to be on.

00:00:35:13 - 00:01:01:18
Sahil Mansuri: Hi, and welcome to another episode of The Bravado Pod. Today I have my dear friend, Legendary sales leader Chro at Vance. Stevie Case, formerly sales leader, rap turned sales leader at Twilio. So has a penchant for picking and building and scaling amazing companies and go to market orgs. Stevie, welcome to the Bravado Pod.

00:01:01:20 - 00:01:04:10
Stevie Case: Thank you. So excited to be here.

00:01:04:12 - 00:01:27:04
Sahil Mansuri: I'm so excited for this. So, as you know, today's topic is one that I think a lot of companies face challenges with, which is you have hit low double digit million RR. And maybe you've raised a series A, series B company has got, you know, 15, 20, 30 raps. You know, it's kind of in that infancy.

00:01:27:04 - 00:01:59:08
Sahil Mansuri: You have some product market fit but but hasn't really scaled yet. And you're trying to cross 100 million. You're trying to cross 200 million. It's time to really scale. Most companies fuck that up. Most orgs fuck it up and it gets fucked up for a variety of reasons. We're gonna talk about all of them attrition, churn, going up market, global teams, etc. and somehow some way you at van to have figured out how to navigate gate and successfully steer through around in between, up, down through those challenges.

00:01:59:08 - 00:02:12:13
Sahil Mansuri: And I want this to be a guide for every founder, everyone who's had a series B and be on stage and looking to scale, go to market, going from 20 to 100 and beyond. How you can do that? So, Stevie, you excited to dive in my friend?

00:02:12:15 - 00:02:19:12
Stevie Case: I am so excited. I lived through this pain myself and I cannot wait to share some of the secrets.

00:02:19:14 - 00:02:32:13
Sahil Mansuri: Cool. So maybe, you know, give us some context in terms of when you joined, van to, you know, what funding round were you, roughly in terms of revenue, etc.? Just so listeners can understand and then roughly where you are today?

00:02:32:15 - 00:02:55:12
Stevie Case: Yes. So when I joined van, the company was, roughly 180 people. We had, you know, crossed into double digit millions. So we were in this sort of low double digit millions and product had been flying off the shelves. I had about 20 people in my sales org. So I started with just, North American sales team, and that was kind of it.

00:02:55:12 - 00:03:13:08
Stevie Case: There was a post sales team. I didn't own it at that point. We had no global presence. It was just us only. And things were pretty single path. It was, kind of one bottleneck, one way of selling, no segmentation. And, that's where we started. We just had a really good product that a lot of people want it.

00:03:13:08 - 00:03:20:21
Sahil Mansuri: I saw an announcement last year, that you took that low double digit millions product. And this was in 2022.

00:03:20:22 - 00:03:23:22
Stevie Case: Is that right? Yeah, it was around April of 2022.

00:03:24:02 - 00:03:28:05
Sahil Mansuri: Okay. So April 2022 you joined and this is before the series B, right?

00:03:28:05 - 00:03:32:17
Stevie Case: Correct. Just before the series B, it was another couple of months before we raised.

00:03:32:20 - 00:03:50:19
Sahil Mansuri: Okay. So you join a series A startup, low double digit millions are, 20 people on the sales team. North America, only one product kind of path the sales machine, etc.. What is the team look like today? And what was that announcement last year that you guys had?

00:03:51:01 - 00:04:16:23
Stevie Case: Oh my goodness. So in January of 2024, we announced that we had crossed 100 million an R. So huge milestone we were really excited to announce to the world we of course don't announce revenue milestones past that. But I will tell you, we are really growing very quickly. We've grown quite a lot since January a year ago. So as you can imagine, the scale of that revenue and the scale of the team has grown quite a lot.

00:04:17:04 - 00:04:48:11
Stevie Case: My team today is a global organization at is everything and go to market except marketing. So I have sales rep, ops, SDR, customer success, account management channel, team partnerships, got all sorts of different folks in the org. It's about 300 people and we've got global presence. So I've got teams where remote first. So that's a unique thing about Manta is that contrary to the conventional wisdom, we are crushing it with a remote first team.

00:04:48:13 - 00:04:57:16
Stevie Case: We do, however, have offices. We've got offices in San Francisco, New York, London, Dublin and Sydney today, and I've got folks in all those places amazing.

00:04:57:16 - 00:05:28:23
Sahil Mansuri: So first of all, let's just do some math. So April 2022 low double digit millions and Jan 2020 400 million in revenue. That's what 21 months or so. So that's a hell of a two year run. And obviously continuing to grow much beyond that today. Tell me what what was that like in those 21 months that you got from, you know, double digit billion IRR to 100 million, what were the things that you did?

00:05:28:23 - 00:05:31:12
Sahil Mansuri: What were the problems you read into? What did the world look like then?

00:05:31:14 - 00:05:51:00
Stevie Case: I will tell you one thing that is probably not apparent from the outside, which is it was fucking hard. It was like really messy and hard. And I think that that's the thing that often gets lost with these success stories. You know, you look at these tech companies that are just rocket ships and they look so glossy and so clean on the outside.

00:05:51:05 - 00:06:14:09
Stevie Case: It is never as easy as it looks. We hit every challenge you could imagine. You know, we had incredible product market fit. And I will tell you that that is, like, deeply a thing that solves many problems. However, like many companies, we did hit a bit of a wall at one point. You know, we had a board member that even said that across his portfolio.

00:06:14:09 - 00:06:34:23
Stevie Case: He has seen this to be true, that there's this rut that happens, and it seems to happen when companies are in this sort of like 8 to $10 million quarter range. And when you hit that rut, companies just get stuck. And to your point, sometimes they stall out, sometimes they figure out how to get past it, but often they don't.

00:06:35:01 - 00:06:55:05
Stevie Case: And we struggled with that as well. Like we hit that rut and we have made 100,000 little changes. I wish I had a magic bullet for you. The truth is, it was a thousand little things with a few key themes that really allowed us to continue to grow past that point and diversify the way we drive pipeline, diversify the way we drive revenue.

00:06:55:05 - 00:07:18:04
Sahil Mansuri: Else, let's talk about the people first, because I think ultimately go to market orgs are the some of the people that are within, you joined at 20 at 20 people. You've scale to 300 plus today. If you talk to me a little bit about what the interview process looks like, the recruiting process looks like to ensure that you're getting the right level of talent into Vento.

00:07:18:06 - 00:07:37:22
Stevie Case: Yeah. I mean, the people are the number one. If there's anything I've learned and this is, you know, my mentor told me the same thing. It basically comes down to the people you hire. And for us, what that looks like is people who are highly resilient, with a ton of grit, who are typically first principles thinkers. They have a ton of urgency.

00:07:38:00 - 00:08:08:13
Stevie Case: So those are the things we are testing for. You know, one of the key changes we made to how we sell over the last two years, and this is not a quick change, but it is a change that takes time, is that we moved from really a transactional inbound sale to a much richer outbound value based sale. And so we have also had to really start to look for our sellers and people that can join the team that understand how to sell on value, that aren't just there to do that quick turn, you know, quick take in order.

00:08:08:14 - 00:08:27:00
Stevie Case: Like we need people who do incredible discovery and go deep. So when we're interviewing for folks to join the team, we are looking for people with a ton of curiosity. We are looking for people with grit. We're looking for people who will go to the second and third level questions, and that we truly believe have a lot of hustle.

00:08:27:00 - 00:08:49:18
Stevie Case: So, you know, you'll find some nontraditional questions in our interview process, like, we want to hear about things that people have had to struggle against for a long time, or things that have taken them a long time to achieve. Like I would way rather higher that like Cutco knives sales guy who has had to hustle and get out there and make it happen on their own, versus somebody that's got a really glossy tech sales resume.

00:08:49:22 - 00:08:56:08
Stevie Case: Because what I know is I've got somebody who's going to come do the work, really learn how to sell, and ask a ton of great questions.

00:08:56:08 - 00:09:22:19
Sahil Mansuri: I've heard that, you said the glossy tech sales resume. I've heard that a lot from, sales leaders in your position that somebody who is only been at post product market fit large companies doesn't understand what it takes to take nothing and turn it into something. And you need people with entrepreneurial backgrounds to be able to come in and bring that, like what's what's known in the Valley these days.

00:09:22:19 - 00:09:42:23
Sahil Mansuri: I guess as founder mode, you know, that that, that ownership, you know, the bravado, we call it getting stopped. Like, what does it take for you to get stopped if you get stopped easily, you're not going to succeed here. If you're the kind of person who never gets stopped, you're probably going to do really well. I'm curious how you test for that in an interview, because it's not really apparent on a resume.

00:09:42:23 - 00:09:59:03
Sahil Mansuri: I've met people who have had the glossy resumes who do have a lot of grit. I've met a lot of people with glossy resumes who don't actually know what the word means. And of course, the inverse of that. You know, I remember talking to the CRO of hop in, if you remember, hop in like meteoric rise back in the day.

00:09:59:03 - 00:10:33:12
Sahil Mansuri: And now one of the things he had told me was that the number one salesperson that hop in globally used to sell, laser tag like establishments to empty spaces in malls and basically, you know, that person was the number one sales person that doing that in, in, in California and then got to sell hoppin, which was obviously like the hottest of hot products at the time, but still applied the same level of rigor and ethic and at first principles kind of thinking, whereas everyone else was so, you know, found it so easy to just be an order taker.

00:10:33:12 - 00:10:37:13
Sahil Mansuri: I'm sure you've seen some of that in your career as well. I wonder how you assess for some of that.

00:10:37:15 - 00:11:03:15
Stevie Case: Yeah, it is the most important thing we look for because, you know, we talk a lot about this blessing and the curse of this incredible inbound lead flow. I mean, this is the tough thing. When you've got amazing product market fit, you've got a lot of inbound lead flow. You can have folks do relatively well without this level of hustle and grit, but if you're going to break through those walls and not get stuck in the rut, people have to have the urgency.

00:11:03:15 - 00:11:24:01
Stevie Case: So we look for it more as a personal attribute and something that's not necessarily domain specific. So we are looking for people that, you know, can look in a lot of different ways, either people that have come from nontraditional backgrounds and really had to work hard to be where they are and to to even be in the seat they're in.

00:11:24:06 - 00:11:49:09
Stevie Case: They've had to hustle against that kind of adversity, adversity. That's a green flag. If they have had to work a long time to achieve something that is typically another green flag. You know, we're looking for people that have got like insatiable curiosity and like this drive that will take them over the course of years. So one way we, investigate this is we ask people about their hobbies, like, what's something you're super passionate about?

00:11:49:09 - 00:12:08:08
Stevie Case: Tell me about that. You know, generally we find that people who have intense passion about one thing are super curious and like that, that curiosity and the passion carries over to selling and carries over to the conversations they have with prospect. So, you know, we are testing for that beyond just have you shown it in the sales contacts?

00:12:08:08 - 00:12:20:14
Stevie Case: We're really looking for people that just, like are in love with life and in love with people and like want to ask great questions and and just deeply want to understand things. If you've got that, you can learn the rest. And do you think.

00:12:20:14 - 00:12:45:05
Sahil Mansuri: That's true regardless of the complexity of product that you're selling? Because obviously Twilio pretty technical product selling into a very technical audience van to less technical of a product and a broader application. What lessons have you seen correlate between the two, or do you think there's a difference if you're like, selling cybersecurity or something that like the, you know, there's there's more nuance to it there?

00:12:45:07 - 00:13:06:20
Stevie Case: I actually don't think there's any difference. I think all of this is learnable. And actually one of my failure modes, early on in the history of answer was, you know, we kind of got some of that feedback, like we were moving up market and the feedback from, you know, folks in the space was, oh, you need to hire more people with domain expertise and they weren't necessarily wrong.

00:13:06:20 - 00:13:43:06
Stevie Case: But the way I applied, I was wrong. You know, I went out and I tried hiring salespeople with cybersecurity experience, and I hired sales leaders with cybersecurity experience. And unfortunately, what we saw is that those people did not typically perform well at Manta. And a lot of that had to do with the fact that we're taking a unique approach to the space, the the solution itself, the software itself, like, turns the space on its head and so if you come with like this legacy mindset, those folks tend to struggle selling it because they're like, this is not how it's normally done here.

00:13:43:12 - 00:14:01:22
Stevie Case: You know? And so there's this like barrier they have to overcome mentally to succeed. Whereas if you just get somebody who's really a learner and has a ton of curiosity and grit, they will learn the subject matter expertise. Now, I will say we built out the org now such that we have, a subject matter expert team, a Sony team.

00:14:01:22 - 00:14:22:08
Stevie Case: They actually report to our CISO and they support us and deals sort of like these. Is there like GRC experts, compliance security experts. So we do have those folks on the team. But by and large, our sellers are athletes. They are people who are curious, who did not come from a background here. And our top sellers almost universally did not come from this space.

00:14:22:10 - 00:14:47:04
Sahil Mansuri: Super interesting. You know, as a founder, I think there is a lot of VC advice that gets thrown around when it comes to this sort of thing of like higher, the higher the grizzly vet who's been there, done that and can break you into these accounts and has all this expertise. And it has been my experience that what you said is absolutely right, that raw, intangible, hungry talent, just tends to work better.

00:14:47:04 - 00:15:02:19
Sahil Mansuri: I wonder if some of that also has to do with your enablement. And I'd love to hear a little bit about if you're going to hire someone with less domain expertise, and someone who maybe doesn't come from the space, you do need to train them up because they do need to sound credible. Obviously, the product you're selling, I'm a happy customer.

00:15:02:21 - 00:15:23:00
Sahil Mansuri: Obviously the product that you're selling is something that like, you know, if you don't come off as really credible and trustworthy, I'm not going to buy from you, you know, because because at the end of the day, like, soc2 compliance, and other forms of security audit, are basically the, the, you know, you're it's a bottleneck to my revenue.

00:15:23:00 - 00:15:34:20
Sahil Mansuri: And so getting it wrong is never an option. And so like, how do you how do you build the right enablement in order to train up, perhaps less subject matter expert team to be credible to a prospect.

00:15:34:22 - 00:15:58:05
Stevie Case: This has really been the investment, and we have done it through a combination of really, really strong internal enablement plus third parties. So the way we've got our program built now, we bring folks in, they learn our product deeply, they learn our sales methodology deeply. You know, we have really gone deep into a value based framework. We teach them to build business cases.

00:15:58:05 - 00:16:22:12
Stevie Case: We teach them about the ROI of and to. They also learn the subject matter expertise. So we've ended up working with, really well-established organizations in our space, like OSA and IAP and others, and we enable our team to go out and do third party education and learn about GRC and learn about, compliance. And that has been kind of the magical unlock.

00:16:22:17 - 00:16:42:09
Stevie Case: So if you get great, smart, curious people and then you just arm them with great education, what we find is they become deep subject matter experts. And so it's not that the expertise doesn't matter, it's just that we believe you can acquire it in the building. We don't have to hire people that already have it. So we're going deep on that.

00:16:42:09 - 00:17:03:08
Stevie Case: We've got an incredible, enablement leader, Tara Sullivan, who has built a phenomenal program. And everybody goes through it. They go through it when they switch segments. So we also are big on internal promotion. So as folks move up the chain and they start selling to more savvy buyers, we are introducing a level up program. So we're teaching them how to sell in a different way.

00:17:03:10 - 00:17:22:18
Stevie Case: We're going hard at SDR right now. We're actually, engaged in what we're calling the SDR triple down. So contrary to what a lot of folks are doing, we're actually hitting the phones and bringing in lots of junior folks who have never sold before. It's their first role. And we actually just launched SDR University to teach those folks how to be a ese as well.

00:17:22:18 - 00:17:26:14
Stevie Case: So enablement, I have found, has been one of our secret weapons.

00:17:26:16 - 00:17:53:14
Sahil Mansuri: It's funny how much that rhymes with what I hear from all of the top Cros and VP of sales, where they over invest in enablement in it because it allows them to do two things one, bring in more junior people that haven't learned bad habits yet, and they can teach them the right way to sell up front. And secondly, be able to create upward mobility within the team as people are progressing, such so that the ten year extends and people don't end up trading.

00:17:53:16 - 00:18:22:23
Sahil Mansuri: You know, it's I want to talk a little bit about that because, it can be such a problem for companies, I guess. Let's start with the hiring piece, front. I mean, what you're talking about sounds like a pretty big investment. You know, from from, screening to a number of calls you need to have, I can I know for a fact that, you know, while, the attributes that you're looking for are obviously really impactful, they're hard to spot on a resume.

00:18:23:00 - 00:18:39:11
Sahil Mansuri: You need to really invest time with someone to figure out if they've got them or not. That sounds like a lot of effort that you're trying to balance. At the same time as hitting quotas and closing deals, how did you weigh those two, and how did you kind of think about that from your perspective of your sales management, like front line managers perspective, etc.?

00:18:39:13 - 00:19:00:23
Stevie Case: You know, it's changed a lot over the last couple of years. I would say that the first year or two, you know, I felt, frankly, like we are fumbling in the dark a little bit, trying to figure out like, what is that magic formula of, of attributes and skills and background. And it took us a while. It also took us a while to understand deeply what is the business actually need.

00:19:00:23 - 00:19:22:23
Stevie Case: You know, one of the bigger mistakes that I made coming in initially is I did not have good data visibility. And in those early days, I believed that our biggest opportunity was selling to SMEs and startups. And that does remain a large part of our business. But it turned out there was a huge mid-market opportunity for us that I was not able to see in the data.

00:19:23:00 - 00:19:42:15
Stevie Case: Well, that fundamentally changes the nature of the type of reps that you're trying to bring in. If you're going to sell to a mid-market customer and the buyer is a CSO versus a founder. And, you know, as we sorted all that out, we definitely fumbled through a lot of different phases. We now have a hiring playbook that is absolutely nailed and it is efficient.

00:19:42:15 - 00:20:09:17
Stevie Case: And ramps are actually quite sure. We have like industry kind of well beyond industry norm ramps up like we have folks productive in three months or less. So they are getting on the team. They're getting productive very quickly. Now that we know what works and we have a hiring playbook that works, I consider the responsibility to higher and higher successfully equally important as hitting quota, because that is for a manager.

00:20:09:17 - 00:20:30:05
Stevie Case: That's their future capacity. So their ability to hire, train and get folks productive is fundamental to their success. So when we give them a quota now, it actually includes their hiring targets and includes the capacity they still need to bring on. And we see that as fundamental to how they run a successful team. And if they can do that, we can grow at the rate we need to grow.

00:20:30:07 - 00:20:32:16
Stevie Case: And so it's got to be equal to hitting target.

00:20:32:16 - 00:20:45:07
Sahil Mansuri: How much effort or time does your do the manager spend sourcing candidates themselves versus relying on talent team or inbound applications or other sources? Of of of candidate?

00:20:45:09 - 00:21:03:00
Stevie Case: I would say the honest answer is it depends on the time of year. You know, we have big hiring pushes, that we've got to do. You know, we're about to enter our new fiscal year, which starts February 1st. We are doing a huge hiring push right now. It is not possible for our recruiting team to do as much sourcing as we would like.

00:21:03:05 - 00:21:24:16
Stevie Case: So every one of my managers, everybody is out there. It's all hands on deck. Source, seeing working networks, getting referrals. And at the end of the day, I really do view that as the responsibility of the manager. So we've got a phenomenal, talent team. They do certainly do a lot of great sourcing for us, but our managers are equally responsible for that.

00:21:24:16 - 00:21:27:13
Stevie Case: And at some times of year, they are fully responsible for it.

00:21:27:13 - 00:21:49:01
Sahil Mansuri: It common themes that I'm seeing and something that I think, new managers can find really challenging because they haven't had that accountability or responsibility before. And trying to weigh that between the current team and closing deals and such. How do you set up enablement for managers to be able to scale up into balancing what what a scaling go to market Oracle looks like.

00:21:49:03 - 00:22:11:12
Stevie Case: You know, it really comes down to structure. We are a very metrics driven team and culture. And we really imprint that on our manager. So when a new manager joins us we are handing them a playbook. We are giving them a structure that really should help them understand what great looks like. And that structure applies to how they run their team, how their their coaching, their folks.

00:22:11:12 - 00:22:31:06
Stevie Case: It also applies applies to hiring. And we make it clear the expectations there are. So you know, we are not dropping them in and asking them to to figure all the stuff out for themselves. Yeah, we're telling them, here's the playbook. We have figured out what great looks like for Banta, which is very specific to our business, and we're asking them to go execute on that playbook.

00:22:31:12 - 00:22:58:23
Stevie Case: We've also really aspired to create a culture where there is taller pants for mistakes. We understand that like it's a learning process. We're not going to get it right every time. Every manager, especially new managers, they're not always going to get it right. We've created almost this like farm system for managers where, and just like we like to promote ease internally, we have a system where we can promote, new folks who have been eight years but not managers into a burst time management role.

00:22:59:03 - 00:23:17:13
Stevie Case: We give them a small team to start. Typically, they're starting with 3 or 4 reps. We're giving them a playbook. They're working under another manager who's getting a first time experience to manage another manager. So we've really tried to create a machine that gives them all the playbooks and ingredients they need to be successful. That way. None of it's a mystery.

00:23:17:15 - 00:23:23:22
Stevie Case: And then it's really hands on coaching from all of us in the tolerance to say, you know, if you get it wrong, that's okay. We're going to learn from it. We're going to move on.

00:23:24:00 - 00:23:42:02
Sahil Mansuri: You talked a little bit about, the interview process and what you've learned from that. Are there maybe 1 or 2 questions that come in for an interview for you really kind of make it or break it on someone that you think might have the potential to get there, but maybe it doesn't have the right expertise or background.

00:23:42:04 - 00:23:48:05
Sahil Mansuri: How do you try to assess for that? I love to, I'd love to hear what it takes to crush a Steve Case interview.

00:23:48:07 - 00:24:14:00
Stevie Case: You know, that most important thing is not actually a question. It is the exercise. And this has become the most important part of our hiring process. And that's true for pretty much every role we run. And we have really ended up customizing these exercises that go at the end of every one of our interview loops. And they have become the make or break thing.

00:24:14:06 - 00:24:33:20
Stevie Case: And I'll tell you what it looks like for a sales manager, for example, as we will, you know, of course, do their one on one interviews. Those are an important part of the process. Assuming they do well, they're we send them to the exercise and in the exercise they get a copy of our frontline manager playbook. They also get a copy of just some data.

00:24:33:22 - 00:24:56:18
Stevie Case: So it is data about performance of the team. Gives a little bit of insight into individual performance. We then also give them a call recording of what a real sales call sounds like at Banta. And what we ask them to do is put together a presentation based on all your conversations to date and those materials and tell us, like, what do you observe?

00:24:56:18 - 00:25:18:00
Stevie Case: Like what are our opportunities? What are we missing? What would you do if you were to be seated tomorrow? What would you change? What would you focus on? So they'll bring that presentation. It's not actually the presentation itself that does matter. But what we do instead is get them on a call with several of us and ask them a bunch of questions like, why did you why did you think about it that way?

00:25:18:00 - 00:25:34:12
Stevie Case: Why do you feel like this thing is important? That experience of asking them questions and having them defend their thinking has become the single most important part of the interview loop. If they crush that, we can go with high confidence that they are going to succeed in that role.

00:25:34:14 - 00:25:57:19
Sahil Mansuri: That's a really that's a really great exercise because it it's not just what you do, but but what you know, what you don't do that really matters. And how you think about operationalizing and prioritizing where to focus and such. And I guess it just gives you a really deep lens into what sort of critical thinker they are. That's a really cool exercise.

00:25:57:19 - 00:26:11:20
Sahil Mansuri: I haven't heard of another company doing such a broad based exercise, but I've heard pieces of it, you know, like, oh, we'll give you some data or we'll give you a sales call or we'll give you a copy of our Decker, our process. But to combine it all and then basically say, okay, based on this, what would you do next?

00:26:11:22 - 00:26:17:16
Sahil Mansuri: I think that that's a it's open ended enough that it allows you to see a lot more of how the person thinks.

00:26:17:21 - 00:26:38:09
Stevie Case: Yeah, we really have tried to not be prescriptive. We're like, bring a dog, bring a deck. We don't really care. It's not necessarily the artifact. It's the thinking and the reality of the environment we're going to drop them into is that they're going to drop in and have to do exactly that. They're going to have to troubleshoot. They're going to have to figure out what to do about underperformance.

00:26:38:11 - 00:26:56:07
Stevie Case: They're going to have to figure out, you know, what to do next strategy wise, like what would really move the needle on results. And when they bring that, like, here's what I think matters. That is what can really help us see, like do they get it. Do they understand what can move metrics. Because there are a lot of people who can sell.

00:26:56:09 - 00:27:06:21
Stevie Case: There are a lot of people who can manage. There are not many people that can actually move metrics. And we need leaders who can move metrics. And that's really what we're inspecting for.

00:27:06:22 - 00:27:25:21
Sahil Mansuri: I want to touch on one more topic before I leave the people side of it, which is the you touched the third rail by saying your remote first. You know, it is the most popular, discussion, it seems these days about RPO and, whatnot. So first you said your remote first, but then you do have offices.

00:27:25:21 - 00:27:29:18
Sahil Mansuri: Maybe just clarify for me what that means. And how does that work for the sales team?

00:27:30:00 - 00:27:54:21
Stevie Case: Yeah. And this is actually evolving for us. So up until very recently, my entire team, was remote first by design. So everybody's hired as a remote employee. Now we do have a few exceptions to that. We built our teams in Europe and our team in Australia to be in office from day one. So those folks are three days a week in office, two days from home.

00:27:54:23 - 00:28:12:23
Stevie Case: We add flexibility on top of that. You know, we are still really trying to build a remote first culture in North America, which is our team that is crushing to the greatest extent. Those folks are remote first everywhere. We do have offices in New York and San Francisco, so if you happen to be nearby, you're welcome to come in.

00:28:12:23 - 00:28:38:06
Stevie Case: But nobody's required to come in. So that for us has just been from day one. That's the way Christina built the company. It's a it's a defining factor in how we have architected our teams. And I just deeply believe, look, we are all adults. My team works unbelievably hard. I have, no concerns that because they're from home, they're not doing what I need them to do.

00:28:38:06 - 00:29:03:19
Stevie Case: So this is a team that hustles. I think even harder because they're out there computers all the time. I know they're putting in hours well beyond. So that's just how we're built now. We are making one change to that right now, which is, I told you earlier, we're tripling down on SDR. We do feel we want to create like a world class SDR organization, and we think that there's a lot of value for first time starters of being in office.

00:29:03:23 - 00:29:22:14
Stevie Case: So we're building those SDR teams in our global offices. So they're going to be in San Francisco, New York, Dublin, London, Sydney. That way they can all sit together. We really want to give them a path to advancement and teach them to move into closing roles. We felt the best way to do that, because these folks are earlier in career, was to put them all in offices.

00:29:22:19 - 00:29:28:03
Stevie Case: So we'll have a nice blend going forward. But we will always be, by definition, a remote first company.

00:29:28:04 - 00:29:37:18
Sahil Mansuri: I've got three follow up questions. Let's go. In order of how you presented them, which is, first of all, why did you choose to do things differently in Europe and Australia if it's working so well in North America?

00:29:37:19 - 00:29:57:15
Stevie Case: You know, I think that the leaders who got those teams off the ground felt it was important because they already had the disadvantage of being far from headquarters, that they had everybody together in person. Now, what they did do is take some of the inspiration of the flexibility that we've got as a remote first team in North America, and they've introduced that there.

00:29:57:15 - 00:30:15:08
Stevie Case: So there are folks who are remote first. So we haven't limited ourselves. We can really hire the best talent regardless of where they sit. We haven't limited ourselves explicitly to people who can only be in office. So we got a good balance of that. But it was really about just doing what was best at that time for that team.

00:30:15:10 - 00:30:37:19
Sahil Mansuri: Makes sense. Second question, as you said, you know that your team is putting in the extra hours and they're working hard. I think there's a feeling amongst, sales leaders, that you especially when you get to hundreds of people in the org, that it's difficult to measure, that it's difficult to, to to check that and maybe some of that's built out of insecurity or lack of data or whatnot.

00:30:37:19 - 00:30:48:20
Sahil Mansuri: But I'm curious how you get confidence that you're getting maximum productivity out of your team from a remote environment. How do you how do you gut check or pulse check that?

00:30:48:22 - 00:31:14:04
Stevie Case: I mean, the truth is we are a winning team. Like this team is crushing targets, productivity is off the charts and ultimately, I deeply believe that that sense that like, oh, maybe people aren't working hard enough does come from a sense of insecurity. And it's really easy when things aren't going well, to just pointed that because it's an easy culprit to say, oh, well, maybe people just aren't working hard enough.

00:31:14:06 - 00:31:40:00
Stevie Case: I deeply believe that's almost never the problem. I the problem is almost always something else. There is something fundamental in your execution. There is something else that's leading people to be disengaged. You've got to get to that root cause. And, you know, I get to the level of confidence that people are working hard because we are a business that is well measured, well run, and we've got great control of what we're doing.

00:31:40:00 - 00:32:11:11
Stevie Case: We've got predictability. Our efficiency metrics are stunning. You know, we've got sellers who sell to startups. You know, they are often it's their first or second job closing. They are carrying $120,000 a month quota. And that team is rushing. They are delivering more than 100% of target pretty much every month. Wow. And so like I the idea that I would worry about whether or not they're working hard enough, it just it doesn't track for me.

00:32:11:13 - 00:32:17:00
Stevie Case: So I know they work hard, they're engaged, they're showing it in the results, and that's what matters.

00:32:17:02 - 00:32:48:18
Sahil Mansuri: I think. I think there's something really important that you said there which which is when things are going well, it's easy to start pointing fingers at work ethic as being the, the the culprit. When when often the challenge is much deeper within a business and almost the inverse of that being true, which is that when things are going really well out of business, people do lean in and work harder because everybody wants to be a part of something successful and ultimately the job that we have as leaders is to create a winning environment that people are energized by.

00:32:48:20 - 00:33:06:03
Sahil Mansuri: You know, I do think that there's there's a lot of wisdom to that, which is to say that like, is the reason why your your sales team isn't hitting quota, really because people aren't working hard, or do you actually just not have great product market fit, or are there like issues within the business that are holding it back?

00:33:06:05 - 00:33:24:07
Stevie Case: I, I deeply believe that to be the case. Like if people people genuinely want to be a part of a winning team, they want to succeed. And if you see folks disengaging, you got to look for the root cause. I deeply believe people want to work hard. They want to. They want to feel great about the work they do.

00:33:24:09 - 00:33:42:00
Stevie Case: And it's my job as a leader to create a team that they want to be on, and so also help them understand what the expectations are, what great looks like on our team. You know, we're trying to hire people that aspire to be great and then helping them understand what greatness looks like, and then it's up to them to execute on it.

00:33:42:00 - 00:34:01:04
Stevie Case: So, you know, if they disengage, I would start looking for a root cause, as in what we're doing wrong with execution, I wouldn't think, oh, let's pull them back in so I can lay my eyes on them like it's just not what it's about. So part of our thought on, you know, SDR is really aligns with this. It's not about, oh, we got to make sure they're productive.

00:34:01:04 - 00:34:18:16
Stevie Case: It's much more like, oh, we want this to be a world class SDR organization. We want to set them up for success in the best way possible. And we think having them sit next to other SDR and and at ease and really see what greatness looks like is the best way to do that for this early in career team.

00:34:18:21 - 00:34:21:09
Stevie Case: So it's really about that winning culture.

00:34:21:09 - 00:34:54:02
Sahil Mansuri: Totally makes sense. It's funny. I had Kyle Norton from owner.com on, the pod, and he was sharing the exact same thing, which is that he's has a remote only sales team, but it's bringing the SDR team in-house for many of the same reasons that you just described. And I think ultimately, if you think about an early career professional there used to being in the classroom environment, the dorm room environment, and it can be quite jarring to go from a world where you see your peers every day and you're in a really social environment, collaboratively learning and working together to suddenly being isolated at home.

00:34:54:02 - 00:35:17:05
Sahil Mansuri: And I think having a transition is, is, is probably really healthy, to, to train you to be able to do that. I mean, it was hard on all of us when we suddenly had Covid and and, you know, the world disintegrated. There were having to learn that on the fly is really hard. I think we as companies and as leaders have gotten a lot better at building remote cultures that are excellent and winning.

00:35:17:10 - 00:35:36:15
Sahil Mansuri: And I'm curious if you have a couple of pointers for someone who maybe is leaning in to the idea of keeping their team remote or building out a large world class go to market organization that can get to 100 million in revenue that's remote only. What are some of your best tips, or maybe some of the biggest mistakes you've made or challenges you've had?

00:35:36:15 - 00:35:39:14
Sahil Mansuri: What have you learned about building a remote first go to market? Org.

00:35:39:16 - 00:35:58:18
Stevie Case: Yeah, I think there are a couple of key things. One is that base time really does still matter. So just because we're a remote first team doesn't mean we don't get people together. And in fact, we have you know, you can't you can't think about remote first as a way to save money. I would encourage you to think about it instead, as it is a different configuration.

00:35:58:18 - 00:36:15:20
Stevie Case: It's a different style of working. You still have to invest the dollars in putting people in the same place. So we are in two weeks, actually headed to New Orleans, and we're going to be doing our company kickoff, where we bring every vans in all over the world to New Orleans for a week to kick off the year together.

00:36:16:00 - 00:36:35:00
Stevie Case: That is going to be an incredible event, both from an enablement standpoint and a morale standpoint, and just getting aligned around what our goals are. And then as a go to market leader, I have implemented a QBR process and a cadence where we get, at a minimum, all of our people leaders together in go to market once a quarter.

00:36:35:02 - 00:36:53:01
Stevie Case: And we spent several days in a room and we all just sit together and we strategize. We plan, we hold each other accountable. We present. And those moments have ended up being incredibly impactful. I actually just did it with my direct last week. I took us all off site. We actually stayed in one house together under the same roof.

00:36:53:01 - 00:37:07:04
Stevie Case: It was an incredible experience. We had a blast and we got to have the kind of conversations and strategy discussions that are hard to do when you're just going zoom to zoom, to zoom. So you got to break it up, you got to invest and you got to put people together.

00:37:07:09 - 00:37:21:00
Sahil Mansuri: So your one big tip is remote first, doesn't mean that you can't invest in in-person events. And you must actually bring people together. Anything else in between the in-person events that you do or have found to be really valuable?

00:37:21:05 - 00:37:44:20
Stevie Case: Yeah, you got to overcommunicate in between. You know, slack is, both incredible and totally daunting. My slack is, like, just overloaded 24 seven. It becomes a really tough place to communicate. So you have to get very intentional. So, you know, Eliot has done a phenomenal job of this with our North American sales team. He actually does a Friday Night Lights update that he puts in slack every Friday night.

00:37:44:20 - 00:38:03:00
Stevie Case: That's sort of like summary of the week here. Some of the highlights we saw celebrating some of the great outcomes we had this week. You know sometimes he does a video with that. And you know we try to do a cadence like that on a regular basis. So we're telling the team here's what's going on. Here's what you should expect.

00:38:03:00 - 00:38:22:14
Stevie Case: Here's what we need from you. I send a weekly note this week in revenue to my entire team that's just sort of like, here's everything I'm thinking about this week. Here's what I think matters. And that alone has really helped get us a lot. And so overcommunicate overdo it. Repeat yourself. You have to repeat yourself as a leader way more than you would expect.

00:38:22:19 - 00:38:24:12
Stevie Case: That's how you break through the noise.

00:38:24:13 - 00:39:02:13
Sahil Mansuri: That's really great feedback. We struggled with this at bravado to where we're also a remote first company and, you know, weekly updates in slack, video loom updates, written updates, documentation, metrics, etc. and still people don't know what's going on, you know, and it's like it's it's like a constant in misinformation battle against your own company and your own team, because conversations can get siloed inside of a single slack channel or inside of a zoom call that someone wasn't a part of, and being able to, to to bring people together on a weekly basis just to be like, here's what happened this week and here's what we care about next week, even just the

00:39:02:13 - 00:39:17:14
Sahil Mansuri: simplest rhythm of that, is it's just so important we see productivity increased significantly at the company when when we have, more, when we overcommunicate and when we stop communicating, we see things slow down really fast as well. So it's a really good point.

00:39:17:18 - 00:39:29:22
Stevie Case: Absolutely. Yeah. We've seen the same. And that's we've seen it down from Christina as CEO. She does a monthly video. We do a lot of the same thing. So you add that to some in-person face time. And we found that works.

00:39:29:22 - 00:39:48:23
Sahil Mansuri: I want to talk a little bit more, at a higher level about the structure of how you think about this. And there were some questions, that I got from the bravado community of what people wanted to ask you, and get advice from as well. And one of the things that you mentioned at the beginning is that you started at a kind of a single product, single track, single motion.

00:39:48:23 - 00:40:07:22
Sahil Mansuri: Obviously today you have upmarket and and mid-market and SMB and etc.. When do you think is the right time to start thinking about these types of things? Territory management, you know, different tracks, different pricing models, etc.? When should a company start thinking about it, and how would you advise someone to try to think about that?

00:40:07:22 - 00:40:28:04
Stevie Case: So I would say it's almost never too early. You have to think about that from day one. And the core tenant at the heart of all the decisions you're going to have to make here has to be diversification. And I think about this both when it comes to pipeline and when it comes to revenue, but also on the post-sale side of the house.

00:40:28:04 - 00:40:56:17
Stevie Case: So I am constantly thinking about diversification and de-risking the way we go to market. Now, you can do this in a lot of different ways and succeed. You can force yourself into a new segment, a new vertical, a new ICP. You can force that. You just need to be aware if that's the choice you're making. One concept I've heard applied to this that I that really resonated with me was a concept of engines.

00:40:56:18 - 00:41:22:12
Stevie Case: And the concept of an engine is like an independent stream of revenue in your business that operates on its own, kind of has its own life cycle, and can be relied upon to have its own rhythm in a way that's independent from other engines. And a grizzled GTM vet once told me, he's been down this road many, many times in the past.

00:41:22:17 - 00:41:50:23
Stevie Case: He told me that by the time you go public, you really need to have minimum four engines and ideally more. There are companies that do it with less, but there is so much risk. So I would think of an engine as either an ICP, a geography, a new motion like expansion. So a lot of the way I'm thinking about this is how do I add more engines to the mix at any given time, and how would I staff it in such a way?

00:41:51:00 - 00:42:07:18
Stevie Case: It gets enough attention on you guys. The biggest mistake most go to market leaders make on this stuff is thinking, I'm going to try to add this other engine or this other motion, but I'm just going to ask my existing team to do it. So we sell into startups today. I'm just going to ask them to start trying to sell into mid-market as well.

00:42:07:20 - 00:42:13:12
Stevie Case: Almost always a recipe for disaster. You've got to have people have a clear lane that they operate in.

00:42:13:12 - 00:42:24:03
Sahil Mansuri: And you would suggest the way to do that is to hire a new team to go after it. Or would you suggest splitting your current team or having some people like how would you actually operationalize that?

00:42:24:05 - 00:42:46:18
Stevie Case: I like to do it by splitting my current team and then adding new people to the mix. So ideally, if you're doing this, you are first in a situation where you've got a team that could lose 1 or 2 folks and backfill them successfully. So that is sort of one is like, don't do it until you've already got one engine that really actually works and is durable and scalable.

00:42:46:23 - 00:43:08:22
Stevie Case: And to me, durable and scalable is like, you know, how to drive more pipeline. You could lose people from it, and it's not so fragile that it would fall apart. You have to be able to backfill and hire into it and know what works. So once you've got that one engine working, you can peel off 1 or 2 people for a new mission, add new people to the mix, because you also want to bring in some fresh DNA.

00:43:08:22 - 00:43:27:02
Stevie Case: You don't want to necessarily be weighed down by the way the company has always sold and then put them on that new mission, but it's critical that you give them clarity about what you want them to accomplish, and you give them the time and space to succeed. So that's the other place a lot of teams go wrong is you think, okay, we're selling into SMB today.

00:43:27:07 - 00:43:45:17
Stevie Case: We want to start to look at Mid-Market. We'll start a new team. Well, our ramp is three months. And you know our current team carries X quota. We'll just have the new team do the same. That rarely works. You really have to be thoughtful that you're asking them to essentially start a new business for you. Think about it that way.

00:43:45:17 - 00:44:00:15
Stevie Case: Give them the time and the grace and the clarity about what you want them to accomplish. Think about it like a 0 to 1. Give them targets that reflect that, and then set them off on that mission and have realistic expectations about it taking a little bit longer than you would like.

00:44:00:17 - 00:44:28:14
Sahil Mansuri: That makes all the sense in the world. And, and, and, you know, I think one of the things that, it starts to happen when, when you do move up market, when you start working on bigger deals, is people can tend to forget about what got you there. It doesn't seem like you've done that. How have you maintained a cadence and a rhythm such that the the early kind of startup SMB motion, which got vent on the map remains a core?

00:44:28:16 - 00:44:33:18
Sahil Mansuri: You know, piece of the business instead of everyone's eyes kind of drifting toward mid-market in enterprise.

00:44:33:20 - 00:44:59:15
Stevie Case: It really comes down to that dedicated resourcing and the cadence and space that supports it. So our startups business remains the heart of Valentine. It is a monthly business. It is high volume, high velocity. And we have not only kind of continued to invest in it, I would say we have gotten just radically better at serving that market over the last several years.

00:44:59:17 - 00:45:20:20
Stevie Case: You know, part of that comes down to product innovation. We've continued to invest in the product in that part of the market. It also just comes down to the fact that we've got dedicated leaders in our startup business, and they know founders inside now. They are like invested in that community. We measure that business separately and we celebrate that success separately.

00:45:21:02 - 00:45:44:16
Stevie Case: We don't treat it as like lesser because the companies are smaller. It is core to our business. So, you know, I over time have had to diversify the way I run my forecast and my whole cadence. So we create enough space to run our operational cadence for startups and give equal air time to that as we give to mid-market, as we give to enterprise.

00:45:44:16 - 00:46:07:07
Stevie Case: That means we've gone from I used to run in the early days, one 30 minute forecast every week to think as we enter the new fiscal year, I'm going to be at about six hours a week of forecast cadence, and that's across my entire team, all the geographies, all the segments, sales, post sales and everything in between. So that inspection really matters and you have to create enough space for it.

00:46:08:08 - 00:46:10:15
Sahil Mansuri: Six hours of forecast meetings is a lot.

00:46:10:17 - 00:46:11:18
Stevie Case: It's a lot. It's a.

00:46:11:18 - 00:46:26:09
Sahil Mansuri: Lot. It's a lot of it's like I said, what? Maybe just quickly how have the way that you've run forecast meetings changed over the last 5 or 7 years of your career? And what have you learned about what it takes in order to run an effective forecast meeting?

00:46:26:11 - 00:46:51:02
Stevie Case: Oh my gosh, it's changed a lot. It's changed a lot. You know, and I learned a lot here at Twilio. I think, you know we had a great crew there. Mark board at ski and a CFO who, who are very metrics driven but also had great sales acumen and like did that great deal inspection and, you know, I view a great forecast as one that is both top down and bottom up.

00:46:51:07 - 00:47:10:20
Stevie Case: Like I want to do that spot inspection. I want to hear about the details of the top deals, but I also want the math. And I'm looking for leaders who can give me that and build confidence in their forecast. So I would say that lake forecast for me is a living, breathing thing. Like we're iterating on it about every three months and we are redoing our cadences.

00:47:10:20 - 00:47:30:12
Stevie Case: And you know, the example of the move I'm in right now, I've probably changed it ten times since the early days. It back into the forecast we run today is very functional, so I'm bringing in a team and getting their forecast and looking at their deals. I'm bringing in my startups team. I'm bringing my enterprise team. I'm bringing my European team.

00:47:30:15 - 00:47:49:16
Stevie Case: I'm bringing my case team, my account management team. What we're actually transitioning to is a segment based forecast. And this is how we'll start our next fiscal. And this is what a mature forecast should look like, which is we'll look at a segment at a time. So we'll look at the the the startup segment. And we will look at it top to bottom.

00:47:49:16 - 00:48:10:14
Stevie Case: So everything from top of funnel all the way through renewals and expansion and step by step inspecting that will allow us to have greater appreciation for the customer journey, the challenges, the pains and the opportunities that are specific to that ICP. So it's a fundamental shift in how we're going to look at the business, but I think it's going to drive some great results.

00:48:10:16 - 00:48:30:15
Sahil Mansuri: Yeah, makes makes it makes a ton of sense. And the evolution makes sense as the business gets more mature to look at it as, as kind of individual lines of business as opposed to looking at it through a function by function basis. So in the early days, it probably makes more sense to go function by function, because each one is somewhat independent of the others.

00:48:30:17 - 00:48:33:22
Sahil Mansuri: When you're still kind of building each each of the stages out.

00:48:34:00 - 00:49:00:01
Stevie Case: That's right. Yeah. And I mean, for me, at the heart of it, you just need to really have a forecast cadence that drives it, drives inspection and drives like these moments where you realize something is happening that you didn't know was happening. You know, a bad forecast is a read out where you're getting yelled out by your sales leader, like we've all been a part of those, where they are just like kind of name and share and bring your number and they'll be told it's not good enough.

00:49:00:07 - 00:49:25:04
Stevie Case: That is not helpful. And if I was spending six hours a week doing that, I would I hopefully be like, just put put out of my misery. That sounds terrible. I think a great forecast is one that identifies pattern, that brings it brings in KPIs, gives you the chance to identify what's going really well in our business, that we could double down on what's not going well, that we can address are there anti-patterns that we need to be aware of?

00:49:25:09 - 00:49:30:22
Stevie Case: It's really about building a learning machine in your forecast rhythm, and that's what we aspire to do.

00:49:31:00 - 00:49:53:02
Sahil Mansuri: So ton of sense makes a ton of sense. Learning is a big a big theme. And I feel like forecasts can be a lot of, accountability driven as opposed to curiosity driven. Let's shift gears once again. And for the for the last kind of 15 or so minutes here, I want to talk a little bit about your role as CRO managing up.

00:49:53:04 - 00:50:18:13
Sahil Mansuri: Because this tends to be a thing that comes up a lot. The, the two most common issues. Let's just start with the biggest one, which is, managing forecast and quota target for, for next year. So, you know, you walk into a low double digit million, are our business. I'm pretty sure the target by the end of 23 wasn't 100 million in revenue.

00:50:18:15 - 00:50:35:19
Sahil Mansuri: And so, you know, I'm sure there are some overachieving of the target, but sometimes, crows can feel like they're in the opposite band where, you know, they walk into a ten, $20 million business and they're told, okay, we only go from 20 to 40 next year. And they don't. They don't understand how to get there. And then there can be contention with the CEO and with the board.

00:50:35:19 - 00:50:49:18
Sahil Mansuri: So maybe share with me how you and Christina work together in order to think about what the targets should be next year and how to kind of model that out, and then maybe how you work with the board at van to in order to deal with that as well.

00:50:49:20 - 00:51:14:17
Stevie Case: Yeah, this has been really an evolving science, I would say in those early days, like the first year, really working with Christina, working with the board, it was just me and her and the C-suite at the beginning, we didn't have a CFO. You know, we we didn't have a lot of great measurement. We were really, you know, just getting our hands around what what is happening in the business, how do we measure it, what can we reasonably expect?

00:51:14:18 - 00:51:41:19
Stevie Case: And so for that first year, so much of our practice was how do we deeply understand what's happening and articulate it accurately. So we partnered a lot there in the early days. And, you know, we had targets. But I would say there was, you know, a reasonable amount of tolerance for getting it wrong just because we all knew we didn't yet really have great measurement in the business.

00:51:41:21 - 00:52:04:03
Stevie Case: So, you know, post that first year, once we got our hands around it, we sort of knew what we were working with. Then it started to be about benchmarks. Since like, what kind of company are we trying to be? And this is often as you get bigger, the discussion at the board level, the CEO level, it's like, what is the what is the reasonable level of growth that we want to shoot for?

00:52:04:06 - 00:52:23:07
Stevie Case: What kind of company are we trying to be? How does that play into how much cash we have on hand, and what next milestone we're trying to hit? So it's a more strategic discussion about what do we want to spend, how efficient are we? What can that get us? And then what kind of capacity do we have to put in the field to be able to deliver on that?

00:52:23:09 - 00:52:46:12
Stevie Case: So then in year two, this is you know, I'm now entering my my year three, but in year two it was really about like those things like okay we can get to that agreement. Can we execute on it. Can we be accurate in our reporting of it. And once we got past that, now we're at a much more nuanced point where it's like, okay, we've got our hands on the levers, we know exactly how to dial it up or down.

00:52:46:16 - 00:53:10:15
Stevie Case: We could get more growth. We could slow down growth. Then it comes back to what is the multiyear journey. And now I'm so grateful. I actually have a CFO partner in the mix, David Eckstein, who is just phenomenal. Best CFO in the business, and he is a true partner for me and with me in that journey of deciding like, what kind of growth do we want to aim for, what does that mean strategically for us as a company?

00:53:10:15 - 00:53:27:21
Stevie Case: What does it mean in terms of our burn and our runway and everything else? So he's really my thought partner there. And then he, Christina and I along with Jeremy, our CPO, and Ari, who's our chief legal people officer, we bring that to the board as a team, but at this point, we have it dialed in. So the board is more blessing.

00:53:27:21 - 00:53:48:06
Stevie Case: Things. They're not like, oh, you guys are totally wrong. They are. Generally, when we're bringing something to the board, we've had good discussion and it's on point. So, you know, as in terms of managing that board, the one of the best pieces of advice I've gotten from another Chro, that I thought was extremely on point was never market to the board.

00:53:48:07 - 00:54:10:20
Stevie Case: You should never be going in there being a marketer, telling them things are great if they're not great. One of the most important duties that I have is the CFO is to be honest about performance, good or bad, and to just tell it like it it is. And if I believe I can deliver on a number, I will say that if I believe I can't, I will say that too.

00:54:10:20 - 00:54:32:00
Stevie Case: And it's really important to take that pain upfront and just be honest about what you can and can't do or what you see versus trying to tell them, like, everything's rosy, it's all great. I'm going to hit the number no problem, when really you're not sure how you're going to do it. So never market to the board. If you do that, hopefully you've got a great positive board who has your back and they can help you work through how to get to the other side.

00:54:32:02 - 00:54:55:03
Sahil Mansuri: There was a lot of really good advice there. Let's go back to your one really quickly, because I think that's the stage that most companies are in that I talked to where they don't really know what the levers are. It's a little bit of a guessing game. It's a lot a bit of a guessing game. And the feeling can be I've heard a few different problems kind of creep up.

00:54:55:03 - 00:55:10:09
Sahil Mansuri: One of the most common ones I hear is, you know, I don't know that we can get to this number. You know, we're at ten today. We're trying to get to 30 next year. I don't know that we can get to 30. I also don't know that we can't get to 30. You know it's not it's not that I do it don't.

00:55:10:14 - 00:55:32:11
Sahil Mansuri: So my inclination is let's try to set the target at 20 because I know we can get to 20 and I feel confident about it because I don't want my. And then if we get to 23, I've overachieved as opposed to if we set the target at 30 and I get to 23, we've underachieved. But then you're kind of sandbagging the business a little bit and it's not really the job in venture to try to like, you know, incrementally win.

00:55:32:14 - 00:55:34:01
Sahil Mansuri: How do you think about balance like that?

00:55:34:02 - 00:55:56:17
Stevie Case: It is an art to get this balanced. Right. You know, we we toyed with this a lot in that year one. And one of the challenges we faced in there is that we set a very aggressive target in year one. And there's a thing that happens when you set a target that is too aggressive, and that is going back to our earlier discussion about people disengaging.

00:55:56:18 - 00:56:19:23
Stevie Case: You know, if people feel like there's no path to success and there's no way to hit the target, they do give up. Like people psychologically, just so like, you know, you'll start to see people throw their hands up, they'll complain about quotas. They won't go search for ways to hit it. If it's too far away from real, they will just say, nah, not for me, and they'll find another place to go.

00:56:20:02 - 00:56:35:06
Stevie Case: So you do have to be careful you don't set things way too far out. But to your point, you also don't want to sandbag. You don't want to aim too low. So I would say that in those early days, the one of the most important things is recognizing that trying to forecast a year out is probably not realistic.

00:56:35:06 - 00:56:56:01
Stevie Case: Like it's it's not really possible if you can't measure your business, you don't have any real segmentation, you barely got a handle on your capacity. You kind of know where your pipeline comes from, but not really. It's if you're making up a number for a year from now, you're making it up. There's just no real command of those numbers.

00:56:56:03 - 00:57:17:21
Stevie Case: So to start to work back into a plan, the first thing you should start with is pipeline. Where does my pipeline come from? Where do I find opportunities and can I generate more on demand? That is the number one thing, because if you don't have pipeline, you will not hit the number and there's no right or wrong answer to that.

00:57:17:21 - 00:57:39:01
Stevie Case: Like it can come from search engine marketing. It could be all outbound. It could be it could be billboards, you know, it could be anything. But you have to be able to deliver it repeatedly. Once you've got a handle on that, then you can start to speak to what the future might look like. But if you don't have a handle on those levers that drive pipeline, everything else is just a finger in the wind.

00:57:39:01 - 00:58:02:06
Sahil Mansuri: Let's come back to pipeline, because you're talking about the year of tripling down on the SDR, highly unconventional in a world in which, many companies are exploring AI, SDR is and trying to cut SDR teams and such. And more more than that, you said your cold calling which like what a what a what a relic from the past, brought back, you know, to to the future.

00:58:02:08 - 00:58:11:05
Sahil Mansuri: It tell me more about that. I'd love to. I'd love to hear more about your thinking and why you think it's working when other companies are not having success. I would love to hear more.

00:58:11:07 - 00:58:33:04
Stevie Case: Yeah, I mean, my question on AI at SDR is why not both like we are big believers, that yes, absolutely there is great tech out there that can make SDR more efficient, that can drive all sorts of automation. We are investing in those things. So we've bought a bunch of those technologies. We are leveraging them. But fundamentally the why is that?

00:58:33:04 - 00:58:55:17
Stevie Case: It works. It absolutely works. And when you look at the math, you know, we're at that stage where we're really well measured. We know what's going on in our business. The, customer acquisition cost for opportunities via an SDR versus the other mechanisms we've been using in the past. It's about 30% the cost to drive an opportunity with an SDR.

00:58:55:19 - 00:59:23:17
Stevie Case: And, you know, it's the things that are working there are the things that, frankly, have always worked. They're just not easy. It's picking up the phone. It's driving a culture of excellence around having those cold call conversations. It's intense personalization, really thoughtful messaging. It's quality. You know, it is quality and human conversation and well, I'm a big believer in AI.

00:59:23:18 - 00:59:45:21
Stevie Case: One thing that is happening is that so much of the written outbound now has become noise, because it is happening at such high volume, and that's made it harder to break through. So you have to do the other things. You have to pick up the phone, you have to go to video, you've got to work. Social networks like, and that stuff is working for us.

00:59:45:21 - 01:00:04:22
Stevie Case: So others are saying it's not working for them. I don't know what to tell you about that, but I can tell you it's working for us and it's efficient and it's an area we are really excited to invest in. We actually just opened a brand new extra office in San Francisco to temporarily house our brand new, SDR team.

01:00:05:03 - 01:00:24:11
Stevie Case: We're hiring dozens of people over the next 60 days. It's really exciting times. And, you know, we're excited not just because we're gonna have a great SDR team, but those folks, we're setting them up with SDR University to become closing ease. We want to set them on a path to joining our startups team, to closing deals and having a great career in sales.

01:00:24:12 - 01:00:32:06
Sahil Mansuri: What is the, expected ten year life cycle of an SDR before they graduate? Obviously it's going to depend on the person, but but generally.

01:00:32:08 - 01:00:53:21
Stevie Case: One year minimum, two years maximum would be the ideal. Like we want it to be quick. We want people to have a great experience. I absolutely want them in that SDR seat for a year. I don't really probably want them in it for more than three. I would love for them to see a path to being a closer within that sort of 1 to 3 year time horizon.

01:00:53:21 - 01:01:28:20
Sahil Mansuri: You know, one interesting tactic that I've heard of startups using is they will look at who who has been an SDR and, for like ten months or 11 months, and we'll reach out to poach those people because they know that they are probably coming up on the timeline and, but don't have certainty yet that they're going to get it, and they can offer that certainty to that SDR and basically say, come here as an SDR for three months and we will promote you, assuming you have your number and people make that bet, it is a tactic that I myself have used to poach some really successful people from companies.

01:01:28:22 - 01:01:44:11
Sahil Mansuri: And so I do think that that's like an interesting sort of lens. But again, to your point, I think that's where the in-person culture really will help, because if they have those friendships and they have those relationships, it's a lot harder to say goodbye. And you can have a lot more faith that it is really going to happen.

01:01:44:11 - 01:01:56:16
Sahil Mansuri: I think sitting behind a computer screen as a 22 year old, it's easy to get jaded and, and skeptical, you know, of, like, whether anyone's paying attention to what you're doing and how much it really matters.

01:01:56:21 - 01:02:22:02
Stevie Case: I think that's very true. And like that culture aspect is so important. We also really felt like, and this is all credit to, Willie, our head of SDR, who's phenomenal, Willie Pearson, he is building this SDR university program. And this was all fundamental to the investment. So when we decided to do this triple down on stars, it was also a recognition that we're not just going to hire a bunch of people and sit them.

01:02:22:02 - 01:02:42:11
Stevie Case: They're like, we got to provide them with the structure to have the confidence you're talking about that they will get that promotion, that there's a path to it and that they can learn how to close. We will teach them how to close, and then we will give them the opportunity to move up. So we're trying to provide that level of certainty, the surrounding culture that backs it up.

01:02:42:12 - 01:03:04:08
Stevie Case: And, you know, it's like it's a it's a tough environment out there. I think that I like I deeply believe that we can build an incredible, like, winning sales culture, Amantha, and have it be the kind of place that people stay for a decade or more. You know, that is my aspiration. So we hope to start that with our SDR program and give people the chance to move up.

01:03:04:08 - 01:03:31:05
Sahil Mansuri: That's, that's a really cool aspiration. I want to I want to tell you something. I've done a bunch of these, both in the podcast. I probably done hundreds of conversations with crows, kind of, you know, what I do is with, bravado, you mention your team by name more than any other crow I have heard, whether it's Elliot or Dennis or Willie or, you know, like, I'm getting to, like, meet these people almost.

01:03:31:05 - 01:03:45:12
Sahil Mansuri: And it strikes me how many people will say, oh, we have a great head of SDR, we have a great head of Bob's, we have a great head of sales. I hear that a lot, but I don't hear them mention the person's name in the way that you do. And I think that's really cool.

01:03:45:13 - 01:04:07:06
Stevie Case: Thank you. These are this is my crew. Like I am really passionate about this team that we've built like I have got truly, I believe like the best team in the business. And, you know, I'm sure there's a certain amount of protectiveness among crows. They don't want their folks to get poached. But I also believe that we built something really special.

01:04:07:08 - 01:04:27:02
Stevie Case: You know, we've got I had them all at my house last week hanging out. And these are people that I deeply believe in. I am in it with them and they deserve the recognition. They're are the ones doing the hard work. You know, I've got, Kelly Bray running my post sales org who is just absolutely phenomenal. Best post sales leader I've ever worked with.

01:04:27:02 - 01:04:39:05
Stevie Case: She's got customer success and account management like these people are the ones building this greatness. So I am very fortunate to get to represent the company, but really they're the ones doing the work.

01:04:39:05 - 01:04:56:08
Sahil Mansuri: I just think it's really cool and, and, and speaks a lot to how I think you've been able to build a winning culture even remotely. Is, is that people feel like you've really got their back. I think that's really awesome. Okay. We are at the end of time, but I can't let you go without playing our lightning round.

01:04:56:08 - 01:05:18:08
Sahil Mansuri: So we've got a little lightning round and a little bit of fun to add. So my first question is sales, I deeply believe I'm sure you do as well, that sales is a superpower. And it extends far beyond our capacity to close deals. What is it time that you have used your sales superpower for your own personal benefit in a way that you think is cool?

01:05:18:09 - 01:05:40:19
Stevie Case: You know, I'm so bad at this, too, because I always just use it like I feel so much empathy for other salespeople. So I would say less for my own personal benefit. But I what I do instead is anytime anybody is trying to sell me something, I just try to like, comfort them and like give them the best experience of selling to me that I possibly can because I know how hard their job is.

01:05:40:21 - 01:05:48:21
Stevie Case: You know, I try to just, make it less, less painful for them and give them great feedback and, help them close the deal.

01:05:48:21 - 01:05:58:10
Sahil Mansuri: That's going to be a huge mistake when 300,000 salespeople listen to this podcast and go, okay, well, Stevie's promised me a soft landing for my sales.

01:05:58:12 - 01:06:02:17
Stevie Case: That's only when I buy. I will say I'm quite good at saying no these days as well.

01:06:02:18 - 01:06:32:03
Sahil Mansuri: Immediately pulls the invitation back. Sorry. The Bartow community. Okay. Next question is what is some great advice that you've we didn't get to touch on your background, which I wanted to do, but I was so worried that I would just spend like 45 minutes on it and I wouldn't get anywhere in the actual conversation. But you've got such a cool background, from gaming and, I'm curious how that has translated to sales success.

01:06:32:03 - 01:06:39:15
Sahil Mansuri: And if you feel like there are, any learnings from competitive gaming that you've brought with you to sales that have been influential?

01:06:39:20 - 01:07:02:11
Stevie Case: Oh, hugely. So I feel like there's a ton of overlap. You know, I just the fundamentals of what it means to be a gamer. You know, the strategy, the resource management, all of that, the urgency there. That all comes into play in my role as CRO in a way, when I was a close, like same thing like it really is a game at the end of the day.

01:07:02:11 - 01:07:21:20
Stevie Case: And you know what I love about sales and this, this comes back to the superpower thing is I feel like this, it's this incredible fusion of humanity and feelings with like, technology and math, like it's all of that all balled up into one thing. And, you know, I see games a little bit the same way. It's the psychology of it.

01:07:21:20 - 01:07:45:16
Stevie Case: It's the structure, it's the math, but it's it's the people as well. So, you know, I do feel like that overlap is there. I also think I spent a lot of my early career as the only woman in the room. You know, I was always an outlier. And so I got very comfortable early in my career being contrarian and standing alone with an opinion.

01:07:45:16 - 01:08:05:11
Stevie Case: And that is something that has served me well as a sales leader. You know, I think that, part of why I, I have had the success I've had in the CRO role is that I didn't just show up and run somebody else's playbooks. You know, I stood alone and I ran really first principles investigation of what needed to happen.

01:08:05:13 - 01:08:12:08
Stevie Case: And I built strategies from scratch. And I think those are skills that came with me from my gaming days.

01:08:12:08 - 01:08:31:17
Sahil Mansuri: I really I really love that answer. You know, it's funny because there's so much you even use the word you said. You know, our our sales team are athletes and there's this whole thing around, like hiring people who played sports. But it turns out that many of the underlying heuristics that make an athlete desirable, you can find in other places as well.

01:08:31:22 - 01:08:52:09
Sahil Mansuri: And I think gaming is certainly one where like to be really good, you gotta you gotta fucking grind like thousands and thousands of hours playing something like, I there's this game called Astro. I don't know if you know it. It's like a, it's like a, it's a PS5. It's like the game that's installed on the PS5 as a default.

01:08:52:09 - 01:09:17:16
Sahil Mansuri: And it got it won like game of the year. And whatever. Even though it was just like this like free game. So they created like a new version of it. And there's people, they try to speedrun it and you watch people speedrunning it. And like the level of perfection that it takes in order to shave a 10th of a second off of the time and get up the leaderboard, like, you just have to play the same level, you know, like literally 5000 times.

01:09:17:16 - 01:09:41:20
Sahil Mansuri: And, and in order to learn every pixel of where you need to land and to have that much grit and determination to achieve something that has no monetary reward, you're just doing it because you want to be the best, right? You are competing against the entire world to be the best at something that requires just the utmost level of meticulous detail orientation.

01:09:41:20 - 01:09:45:18
Sahil Mansuri: Like it makes sense why someone like that would be really good at sales. You know, like it.

01:09:45:18 - 01:09:46:09
Stevie Case: Makes a lot.

01:09:46:09 - 01:09:46:23
Sahil Mansuri: Of sense.

01:09:46:23 - 01:10:06:05
Stevie Case: So 100% that competitive nature is like, I just thrive on that. And, you know, in the times when things have felt harder or we felt stuck like that is what has kept me going. You know, we did we still joke about it because in the early days when I joined bands on the leadership team, we did these strength finders.

01:10:06:07 - 01:10:29:03
Stevie Case: And, you know, it gets your your characteristics and rank order and mine. Of course, number one was competitiveness. So like tell surprise. Yeah she's competitive. I like to win and and I will find a way to win. And that is a through line in my life when, you know, my background might look somewhat odd and disconnected. And it's like, how do you tie these things together?

01:10:29:08 - 01:10:40:12
Stevie Case: Thing that ties them together is that I love to win and I bring that to work every day with my team. I want to build a winning team. I want to be on a winning team, and I'm going to figure out how to get us to victory.

01:10:40:12 - 01:10:58:16
Sahil Mansuri: Gosh, that was such a good answer. And I'm so I we can't end on a higher note. So I'm going to I'm going to say if there's one thing you should make sure your CRO or VP sales has it's ultra competitive desire to win, because that that's going to get you through a lot of shit that might otherwise get you stopped.

01:10:58:18 - 01:11:19:19
Sahil Mansuri: Then, Steve, this has been amazing. Thank you so much for taking the time, to share your knowledge, with founders, with sales leaders, with, sales reps who are trying to learn and level up their career. If people want to ask you further questions or follow up, what's the best way to, to to get in, get in touch with you?

01:11:19:21 - 01:11:25:21
Stevie Case: I would love for them to find me on LinkedIn. I post on LinkedIn pretty regularly and would love to connect there.

01:11:25:23 - 01:11:44:08
Sahil Mansuri: Amazing. All right, so we'll drop a link through the magic of editing here. To your LinkedIn. And we'll have people connect with you. Steve, I, I want to do this, like, once a quarter with you, like, you just do it. Whatever is the latest learnings you've got. You are you you're you're fucking awesome. And I love you.

01:11:44:08 - 01:11:45:09
Sahil Mansuri: And it's just the best.

01:11:45:11 - 01:11:47:22
Stevie Case: Thank you. I love you, too. Thank you for having me.