Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20Sales: Why You Should Not Do PLG and Enterprise Sales at the Same Time | How To Move Into Enterprise Sales Gradually | How To Make a Comp Plan For Sales Teams | Why Discounting is Good and Can Be Used with Stevie Case, CRO @ Vanta About this episode Stevie Case is the CRO @ Vanta where she oversees Vanta’s go-to-market team to support the company’s rapid growth. Prior to joining Vanta, Stevie was Vice President of Mid-Market Sales at Twilio, joining as one of their first account executives, Stevie helped to grow the sales team from a dozen to over 1,000 team members and played a pivotal role in establishing Twilio’s enterprise business with key Fortune 500 customers, generating more than $400 million in annual recurring revenue. If that was not enough, Stevie is also a Founding Operator @ Coalition Network and a prominent angel investor. In Today's Episode with Stevie Case We Discuss: 1. ) From World's First Pro Female Gamer to CRO: How did Stevie make her way from pro gamer to CRO? How did her career in gaming make her a better CRO and sales leader? In her early sales career, how did being a single mother with a child impact her approach to sales? What can founders do to make workplaces more inclusive for parents today? 2.) Enterprise or PLG: Which One To Choose: Why does Stevie believe it is not right to do both PLG and enterprise at the same time for startups? How can startups and sales teams move into enterprise selling gradually through testing and without committing a significant budget to an enterprise sales team? How do founders know when is the right time to move from PLG to enterprise? What are the signs? 3.) The Mythical Sales Playbook: How does Stevie define the term "sales playbook" today? What is it not? Should the founder be the person to create the sales playbook? If not them, then who? When is the right time to make your first sales hire? When is the wrong time? 4.) Mastering the Hiring Process in Sales Recruits: How should we structure the interview process for new sales reps? What is the right profile for these first sales hires? How do the best sales talent answer questions and perform in interview processes? How can we really test for grit and curiosity in the interview process? What are the single biggest mistakes founders make when hiring for sales? 5.) Discovery, Discounting, Deal Velocity: With sales cycles being so long, how do you know if enterprise sales reps are good? What is the difference between good discovery vs bad discovery? Should founders engage in discounting to get deals over the line? When does it work?
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Speaker 00 The most important in early hires is that person a hunter? Or are they used to taking orders? That grit that it takes to be somebody who can open doors and hunt? That person will succeed over others in every possible scenario.
0:16 Harry Stebbings? Welcome back to 20 Sales. This is the monthly show where we sit down with one of the best sales leaders in the business to reveal their tips, tactics and strategies to scaling sales teams today. And we're joined by a total rock star in this episode. Not only was our guest the first professional female gamer ever, but also an OG sales leader. And so I'm thrilled to welcome Stevie Case, CRO at Vanta, where she oversees Vanta's go-to-market team to support the company's rapid growth. Prior to joining Vanta, Stevie was Vice President of Mid-Market Sales at Twilio, where she helped to grow the sales team from a dozen to over 1,000 team members and played a pivotal role in establishing Twilio's enterprise business with key Fortune 500 customers, generating more than $400 million in annual recurring revenue.
0:59 Harry Stebbings? If that wasn't enough, Stevie's also a founding operator at Coalition Network and a very prominent angel investor. I want to say a huge thank you to the amazing Maggie Hart at Webflow, such an incredible person for the intro to Stevie, without which this episode would not have been possible. But before we dive into the episode today, finding your next customer is hard, but it doesn't have to be. If you're wondering how to drive more revenue and find the accounts that are looking for your solution right now, ZoomInfo is the answer. ZoomInfo handles the full revenue pipeline from marketing to sales, even ops, all based on the number one ranked business data. It's the single best way for B2B professionals to find their next customer, close their next deal and streamline their operations.
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2:57 Speaker 02 You have now arrived at your destination.
3:00 Harry Stebbings? Stevie, I am so excited for this. We were just chatting now. You have the most incredibly cool background, so thank you so much for joining me today first.
3:08 Speaker 00 Thanks for having me. I'm excited to be here.
3:10 Harry Stebbings? Oh, so am I. It's gonna be a great discussion, but I want to hear first you, now you're Ciara Vanta, how did you make your way into the world of sales first? And then most recently, maybe skipping a few steps, come to be Ciara Vanta.
3:22 Speaker 00 This is not the career I had envisioned for myself. This was very much a path that I happened on along the way. I had these grand visions of going to law school. I grew up in Kansas. Dad's a biologist, grew up on the prairie. I was going to the University of Kansas, pursuing law. I had some friends who were gamers and so I got really into games. And probably an understatement, I ended up as the world's first female professional gamer. This is late 90s, so dating myself a bit here.
3:51 Harry Stebbings? I'm sorry, that is such a cool title to have. The world's first professional female gamer is one I would live on forever, but sorry, go.
3:59 Speaker 00 That's my plan at this point. I'm gonna run with that. And it opened up this world of technology and computers. I learned to build my own PC because that's what you had to do to be competitive. It landed me eventually down in Dallas doing video games and then out in LA, working at Warner Brothers, making mobile games. This is pre-smartphone. I was a product manager at Warner Brothers. Making mobile games with their IP. And I had a vendor and he approached me one day and he said, hey, I need a junior salesperson. I think I could teach you to sell. I had no idea what that meant. I was very socially awkward. I thought this sounds deeply uncomfortable and I love a challenge. Let's go for it. That was the beginning of my career in sales and the company was Tira Wireless.
4:42 Speaker 00 Here we are nearly 20 years later. I'm a CRO, a role I had never heard of, did not know existed. Along the way, I've had some incredible people that taught me how to do it.
4:51 Harry Stebbings? We're going to dig into each of those chapters. I'm just too interested. Do you think you lost the insecurity around people and the, as you said, slightly withdrawn nature? Or did you embrace it and use it as a strength? Which one is it?
5:04 Speaker 00 Oh, I definitely did not lose it. I have embraced it. It is part of me. I will never be able to fully lose that, but I am deeply an introvert. It was actually Matt Golden, that initial mentor, who really opened the gates for me. We were in a meeting, a sales meeting, and we were meeting with some folks who were giving us a really hard time. He said, the best way to open people up is to give them comfort with your own vulnerability. He really taught me that being human and being flawed was the best way to give other people comfort with being imperfect. I thought that was such a powerful lesson. I've really embraced that over the years and it's changed the way I think about humans, but I am still that same girl.
5:47 Harry Stebbings? So I totally agree with you and I do actually, I use it a lot, don't laugh, in interviews to make people feel comfortable. Sometimes if they're a little bit cagey, I'll say, you know, I'm really shy, I'm glad I had an eating disorder and I'm sure really fat this week and just, and people open up more. In sales, it's a little bit of a different thing. You do slightly feel you have to project this kind of corporate air of confidence. Can you have vulnerability with clients in the same way?
6:09 Speaker 00 Yes, you can be both of those things. I believe that's the place I've come to, that I am deeply comfortable with who I am. I can still be confident. I can be knowledgeable. I can speak to you in depth about my product and its value drivers, but I'm also a human being and ultimately people still buy from people. You can be competent. And also just a flawed human being who is uncomfortable and unsure at times. If you can really embrace both of those things, that's the magic.
6:38 Harry Stebbings? I want to unpack a couple of elements. I spoke to Christina before the show, obviously, your founder and CEO, and she mentioned you're also a single mother, wonderful daughter. How has that impacted your approach to your sales career?
6:49 Speaker 00 It's really changed over time, and this is a very fundamental part of my life. I've been a single mom, full custody since my daughter was three. She's 18 now. So we've been at this a very long time. And early in my sales career, it was just me and her. Before I'd had any kind of liquidity events, I just remember early days of my sales career, taking sales calls and I'd be driving her back and forth to daycare or school. And I remember one in particular, I was trying to give a demo, but I was driving and I had to take her through a drive-through to get her the Frosty or Wendy's or something. And it's just always been in the mix. I think for the first half of my career, it really just made me so much hungrier because I have had something to prove, I've had somebody to fight for,
7:34 Speaker 00 I've had somebody that I had to achieve for, and I wanted to show her that I could do that. In the back half of my career, I don't have that same scarcity anymore. I'm really grateful. I've had great success and I'm in such a good, safe place. But it's really put me in a place where I don't take anything for granted. This whole ride, it's so hard some days. Nobody's got it easy every day in this business. This is hard. The bad days, the good days, the struggles. I really want to embrace it because I know that every minute I'm working, it's a minute I'm not spending with her. I'm thoughtful about that. So it just makes me very in the moment.
8:09 Harry Stebbings? Can I ask, take yourself back to those early days when she was four or five. Kids are not as self-sufficient as they are when they're teenagers. What drove you, when you're doing demos, when you're back-to-back with customers, and then you've also got a wonderful but also challenging four or five-year-old? What drove you?
8:25 Speaker 00 A combination of stubbornness and desperation and hunger to succeed. Some of the folks in my gaming life, when they found out I was pregnant, actually got an email from, one of them in particular, John Romero. Who was in that story, my ex saying, you're pregnant, you're never going to have a career. You're never going to be the person that you set out to be. You're making a huge mistake. This isn't it. You were meant for something different. I knew deep down, a lot of people thought that, and I deeply, one, wanted to prove them wrong and two, knew they were wrong. I've always been a little bit of an outlier. That's how I ended up on this weird path. I think in that moment of her being so young, the struggle felt so heavy, but deep down, the question in my mind was still, why not me?
9:10 Speaker 00 Why can't I have these things? Why can't I achieve these things? And I'm going to do everything in my power to make sure that I do.
9:16 Harry Stebbings? We're going down a rabbit hole, but I'm fascinated. Do you think people still perceive women post labor and with children the same? I've seen it before. Oh, Stevie's amazing, but now she's got a child. Can we really count on her for those late night calls and the travels? And it's not that you've changed, it's that the perception of you has changed. That's what I've seen. Do you think that's fair?
9:35 Speaker 00 Yes, it's extremely fair. It is still very real in many corners. I think the thing that has changed is there are now places that we can work, that we can go, where people are more enlightened. They understand that you can be both of those things. You can be in that world of being a parent, whether you're the mother, the father, or something else, a caregiver. You can do that and still be an incredible, successful professional.
10:00 Harry Stebbings? The joy of this show is just like the randomness. What advice would you have for women today? Not necessarily in sales, but in our world of innovation, who are really concerned that actually they will be viewed differently post having a child. How would you advise them and what do you know now that you wish you'd known?
10:16 Speaker 00 The single most important thing is don't apologize. Don't accept this narrative that it's a balance or a trade off, or you're giving something up somehow. It's up to you to define your own narrative and you don't have to accept that idea. Fully embrace everything in your life and make it a part of your narrative. Don't hide that you have to take your kids somewhere. It is okay. It does not make you less. And the more that we as individuals embrace the truth of our lives and can be honest about what we're going. Through being a parent is just one of those things. People are especially now struggling with so many things in life. And the more we can be honest about that and embrace that, the more we're all going to be able to achieve together
11:01 Speaker 00 and be a part of a team that is much more thoughtful and interesting and diverse.
11:04 Harry Stebbings? Can you help me? I am a hypothetical founder and CEO. I want to create this inclusive environment for my team. How can I do that? What can I do proactively and deliberately to make all people, men and women, feel that children can be a net add, not a net subtraction?
11:19 Speaker 00 Step one is genuinely caring about the people that work for you and asking them about their lives, whatever those lives include. If you show a genuine and ongoing interest in the human beings on your team, that acceptance and that inclusive environment ultimately will be created. People just want to be seen. This is one thing. Parenting is one thing. There's so many others, but people want to be heard. They want to know they can be themselves. If you just open the door, you don't have to understand. You don't have to do anything very specific other than see them as a full human being in everything they're dealing with in life.
11:56 Harry Stebbings? Getting out of the rabbit hole, otherwise I could get out there a long time. If we think about it, obviously Twilio had the self-serve developer-led motion. And then you and George really pioneered and brought in the traditional enterprise sales motion. I often see startups today thinking they can do both from day one. Can you do PLG and traditional sales, enterprise sales from day one? Or does it have to be in a staggered motion?
12:18 Speaker 00 You can, but I would caution you against trying to do both right away. Think in the early days of sales, you have to be very clear on what is the value prop for the customer? And what is that experience? When you try to combine PLG and a sales motion, often what happens is customers get confused and sales reps and your sales team more broadly get very wrapped around the axle about the mechanics of who gets credit. That's one of the harder things when you're trying to piece apart PLG and sales. Who really gets credit? If people sign up on the website, but then a salesperson closes a deal with them, should they get credit? Should they get comped? How do you work that out? When you introduce both too early. You introduce the risk of complication.
13:02 Speaker 00 A much more effective model. If you're going to start with PLG, you've got to focus instead on customer enablement and customer success. And it might include elements of selling, but it's got to be success first. It's got to be engagement first. Otherwise, if you're just trying to go at commercialization from two different angles, everything gets messy.
13:22 Harry Stebbings? There comes a time when you do want to layer on traditional enterprise sales. Respectfully, it sounds like you waited quite a long time with Twilio. It could have been done a little bit sooner. My question to you is, for founders listening who have the PLG model that's working, how do you know when is the right time?
13:38 Speaker 00 I am a big fan of testing. Sales should be approached in an iterative way that is similar to software development. And when you've got a PLG motion, one of the things you can start to test is, if you put somebody on that relationship, you put a human being in the mix, can they actually get more revenue from the customer in a way that the customer also is happy with? Can they solve a problem that can't otherwise be solved? If you can add those two experiences together and get a better outcome, then that's when you should do it. And the only way to know often is to start to experiment with that and put somebody in the mix and see what you can drive. I think a lot of it too comes down to who's your ICP? Who are you selling to? If it's SMBs, you can be PLG all day and they're going to love it as long as you make their life easy.
14:23 Speaker 00 But if you're trying to sell into an enterprise, you've got to have some sales folks to back it up as well because they always have means that cannot be automated away.
14:31 Harry Stebbings? Do you struggle in terms of that expansion into the enterprise on the value prop perspective? Because the value prop changes incredibly when you're selling from an SMB or a startup to Cisco or Chase or First Republic. It's very different. How do you think about what changes when making that transition? And how you deal with that as a sales leader?
14:50 Speaker 00 It is really a fundamental shift in the story of the problems you're trying to solve. That doesn't necessarily mean that the product has to be radically different. In this mix at Nanta right now, in that we have been historically SMB focused. Well, this year, we made the move up market, but the value prop is very different. The underlying product is The same. We're an automated compliance platform. But our SMB customers are solving the problem of addressing compliance for the first time, getting their first SOC two, the first time they've ever done it as a company, and standing up a security program. Our enterprise and mid-market customers are solving something very different. They want a single pane of glass for compliance in a much more complex, larger organization. The way they measure success against that is very different.
15:35 Speaker 00 So an SMB is measuring, how quickly can I complete this process to prove I'm compliant? And a mid-market customer is really measuring, how much time can I save? How much risk can I reduce? Underlying all that is one product, but we have to tell the story and talk about the value drivers in very different ways for those profiles.
15:54 Harry Stebbings? Why did you decide to make the move into enterprise? I always think a big mistake that startups make is they move too quickly into enterprise. And we always forget just how huge SMB is. I mean, HubSpot, fuck.
16:05 Harry Stebbings? So why, when it was working so well in SMB and startups?
16:10 Speaker 00 So for us, it's additive. But the truth is, we are being led there as a business. We are seeing success that we didn't pursue but came to us in those segments. This is another opportunity for us to start to experiment. We started seeing, for example, mid-market customers and a couple of enterprise customers come in. So in the middle of the summer, I created a team just to go after those mid-market and enterprise opportunities. Because it is, it's a very different cycle. Put that team on a different comp plan, gave them a little bit more space and time to experiment, ran it as an A/B test, and right out of the gate, they killed it.
16:46 Harry Stebbings? That's really interesting because that feels like a little toe-in-the-water test to see if it worked. But I always hear that you've got to be fully committed to enterprise or fully not. And I'm like, oh, that sounds quite scary. Do you not have to be in? For founders listening, can you test it in a more gradual way?
17:02 Speaker 00 You can test it with the caveat that these things are radically different. The way that I'm testing that in our business was to inch up market. It wasn't necessarily to cut over from SMB to suddenly we're going to go do deals with companies 5,000 employees plus. It was, okay, let's look The patterns of success we've had with companies over 200 employees. What is common among them? Can we take a small group of folks and see what they can make happen? The thing that was not toe in the water about it is that I actually pulled the resources out of our core SMB team. And their job 100% of the time was mid-market and enterprise.
17:42 Speaker 00 I think the thing that goes wrong is when you've got a team focused on one segment and you ask them to dip a toe in the water of another segment. It's very hard for any one person to both do high velocity, bottom of the market deals and also do strategic deals. They're always going to go to whatever is going to have the best results for revenue and comp and whatever they know how to do best. So you have to have this division of labor for folks who focus exclusively on that experiment.
18:08 Harry Stebbings? We're going to get to hiring a team. You mentioned the word repeatable earlier, which really ran out to me because everyone says about playbooks and sales are repeatable. So tell me, does the founder need to be the person to create the sales book? Or can it be an experienced sales leader that's brought in?
18:22 Speaker 00 I think the elements of the early playbook a founder should develop initially, the story. That founder has to be storyteller in chief because there's an element in early sales of trust. You're trying to sell to someone and they know they're coming on as one of your first customers. They need to believe in the vision. They need to buy in with that founder. So the founder has to be the first salesperson. They have to be able to talk about the story, those early value drivers and the why behind why someone would work with this product. What's the real value? That part of the playbook has to be built by a founder. When I think of a playbook, I think much more, all right, we've got product market fit. We know what it is.
19:06 Speaker 00 Somebody's got to write down on paper, what are the mechanical steps that every new rep has to know and master to succeed at selling this product? If you try to ask a founder to do that too early, it puts you in a position where you can't iterate as much. And you maybe feel you're committed to something without really knowing yet if you've got the right ICP, if you've identified the right value drivers and you're on the right path.
19:26 Harry Stebbings? So say we do have a playbook. I am fascinated again by the kind of. Idea of testing a little bit the expansion up. When we think about structuring our team, moving from a PLG motion to a more traditional motion. I'm the founder, you're my angel investor and advisor. Do I hire a head of sales first? Do I hire two SDRs, two AEs? How do I structure my first foray into the world of sales?
19:49 Speaker 00 If you're going after enterprise customers, you likely just need one to two really great enterprise salespeople who are creative and understand how to open doors. If you're going after SMB, a little bit of a different story. You want somebody who understands the mechanics of scale and velocity. In that case, I think it becomes more of a player, coach, an athlete, somebody who can do some of those first deals, but really starts to understand how do you build a machine that can do this with speed? In between, you've got to have a founder who stays engaged. That is going to shift between the time of that first sales hire and when you get to the point of actually scaling a sales team.
20:32 Speaker 00 Your business will radically change multiple times. The biggest mistake folks make in there is thinking, oh, I'm going to make a great sales hire. They get bamboozled by a really sexy resume, somebody who's succeeded at a great brand name company. They bring them in, they sit them at a desk and like go sell. They fail because the founder has delegated something that is so core that is not yet baked to somebody who may be very bright, but isn't in the weeds enough.
20:57 Harry Stebbings? What should that engagement be like then? Me, the founder, sitting next to the person every day, them joining calls with me? How would that look in an ideal world to you to prevent that mistake from happening?
21:07 Speaker 00 I think the single most important thing in that is that that first sales hire has to be glued at the hip with the founder. It's a matter of joining every call with the founder. It's a matter of the founder sitting down at a whiteboard and whiteboarding the vision and telling the story. Because your first sales hire has to be able to speak as if they were a founder of the company. That is typically the most successful model. When you get that first person in the door and they're now basically in a seat where they sound like a co-founder and they can speak to the why and the vision with enthusiasm. Theatism and passion, that's how you get success. And the best way to do it is just to model it. Let them hear what it sounds like to tell the story. And I think the mistake people make, especially when they think about the playbook and like,
21:50 Speaker 00 I've hired the salesperson is they try to write it out in a document. Here's how you do it. Go do it. No human being can recreate that storytelling and the passion of a founder if they just read it in a document. They've got to be there. So default to including that salesperson in every conversation and not just sales conversations. Let them listen to when you talk to investors, when you talk to partners, when you're talking broadly about your company and why you built what you built. They need that whole story so they can be fully audible ready and they can sound like a co-founder of the company.
22:23 Harry Stebbings? If you were to choose between someone who's got domain expertise in your domain that you're selling into, so being a previous history with it selling to that customer base, or history selling that ACV size, that contract size, which is more important?
22:37 Speaker 00 Neither.
22:38 Harry Stebbings? I wasn't sniping that at all.
22:40 Speaker 00 Of those two, I'd go ACV. It's actually much more important that somebody understand the profile and they understand the mechanics of doing a deal of that size with that profile. They can learn the subject matter expertise in many cases. The most important in early hires, is that person a hunter? Or are they used to taking orders? That grit that it takes to be somebody who can open doors and hunt, that person will succeed over others in every possible scenario. So you got to look for somebody who is comfortable with that and does not expect business to come to them.
23:13 Harry Stebbings? Do we ever want someone to take orders? If we think about those two motions, the enterprise versus the higher velocity, is the hunter one and the take orders the other? Do we ever want someone who takes orders? How should we think about that?
23:24 Speaker 00 Yeah, I think there's a place for people who take orders. And I think particularly early career, when you've got a velocity business and you've got a playbook and it's very clean and you know exactly how the math works, there's a lot of value in somebody who can just very efficiently take those orders. I don't think that's the world we live in anymore. I think with the shifts we've seen in the macroeconomic environment, we are no longer in a growth at all costs world. We are no longer in a world where Business is just going to come to anyone. I think that we're in a world where everyone now has to be a hunter. And every member of your team has to be accountable for cracking doors and breaking down barriers. And grit is going to become infinitely more important over the next 18 months.
24:07 Harry Stebbings? We won't talk about Gen Z entitlement because I might just get on a high horse. So we'll just move on from that. You mentioned grit there being a characteristic. We're going to build the team together now. What non-obvious characteristics and attitudes make incredible 10x sales hires from your experience?
24:23 Speaker 00 It's about a couple of things. It is about grit, number one. And grit is not necessarily just being a hustler or somebody who pushes really hard. Grit is about hanging with something hard over a longer term and actually making it happen. When I look for grit, I'm looking for somebody that has picked something hard to accomplish and stuck with it through adversity.
24:46 Harry Stebbings? How do you test for grit? I'm a candidate. I want a job with you at Banter. How do you test if I have grit?
24:52 Speaker 00 You've got to get to the heart of what are some of those accomplishments that person is very proud of? And they don't have to be at work. I think there are people who are very early career, who have tremendous stories of grit. Whether it's something they accomplished in their pursuit of a great education or something they accomplished on a human level that was really hard. Asking about those things, you want to see passion. You want to hear stories of overcoming. If you can get those stories out of someone, those are the kind of people that will be resilient in a really dynamic workplace and they will figure out how to win, even as things change.
25:29 Harry Stebbings? I always want to see discipline that means sacrifice. And it could be like incredibly grueling exams, which mean you have to study so hard and you lose a load of social. It could be doing ultra marathons, meaning you miss birthday parties and great food. Pain as a result of discipline.
25:45 Speaker 00 That is real. When I think about why I have been successful, some of those things are really at the heart of my story. I actually dropped out of university all those years ago to go be a pro gamer. I made my My way into tech, into sales in my early career, there were lots of places I could not even get an interview because I didn't have a degree. I couldn't even get in the door at like Google or Meta or these places that were so aspirational. They wouldn't even speak to me because I did not have the pedigree. I decided over time that it was really important to me to complete the degree. Over the course of 25 years, I basically did a class at a time and I take breaks and then I come back to it.
26:27 Speaker 00 And even as I was a single mom, I was doing a class at a time at night. And I actually graduated and got my undergrad degree during the pandemic. That is the kind of stuff I'm looking for in people I hire is just the determination.
26:39 Harry Stebbings? Can I ask you a really rude question?
26:42 Speaker 00 Of course.
26:43 Harry Stebbings? Why did you do that? It's wonderful and it's amazing, but you're a proven sales leader with immense success. You don't need a fucking undergrad degree now.
26:52 Speaker 00 It's very true. It is very true, but I wanted to know I could do it. It was a personal challenge for me. It became such a part of my story and identity. Oh, I'm a college dropout. I didn't do that. It started to bother me. I wanted to prove that I could overcome this thing. It wasn't about proving it to somebody else. It was about proving it to myself. In the end, it doesn't change anything about my career, but it just felt so good to get it done.
27:18 Harry Stebbings? I think you are so awesome. By the way, I would not be the same. I've dropped out after three weeks, two refreshes. We don't have any desire to go back. And life is good.
27:26 Speaker 00 Hey, that's fair. Everybody's got their own goals.
27:28 Harry Stebbings? We're going to get back to the hiring. How do you structure a process? Do I hire after one interview? Do we do case studies together, Stevie? How do we go through structuring hires for sales teams?
27:39 Speaker 00 Yeah, this is so tough and I've seen it gone wrong so many times. Definitely not one interview. I think you need a number of perspectives. I think it's actually extremely valuable to get the perspectives of folks who are not salespeople in that process. You've got to have a combination of functional interviews. Can this person check the basic boxes of doing the job? And then you've got to get to the heart of what is going to make them succeed. If grit is the thing, which it is for me, you've got to have a full interview dedicated to testing for grit and hearing those. Stories. The second one for me is curiosity. In the sales cycle, what this comes back to is really discovery, but curiosity is at the heart of that hustle that it takes to learn and change with a
28:21 Speaker 00 business. It's also at the heart of closing really hard deals because you've got to do great discovery. You've got to ask great questions. So for curiosity and discovery, I actually really love to do a case study, a role play and get folks to walk through what it looks like for them to do discovery in the room. And this is often where I see that you've got a candidate who may look really good and they answer questions well, one on one, when asked directly, but you put them up at a whiteboard and ask them to do discovery in an uncomfortable situation. That's where a lot of them fall down.
28:51 Harry Stebbings? Can I ask, what does good discovery look like?
28:54 Speaker 00 Oh, my gosh. It's dynamic. It's rooted in genuine curiosity. So bad discovery looks like checking boxes. You might know the right framework, whether you're going through med pick or something else, you may have your list of questions. Bad discovery is checking the boxes of that list. Good discovery is really about curiosity and listening, allowing the person you're asking questions of time to speak. And then rather than checking the box and then going to the next question, it's about looking for those nuggets that are going to be the things you can put your hooks in that they care about to get your deal done. So you may have a 30 minute set of discovery questions and you're walking through that with a prospect. They might say one thing in that 30 minutes and that's your thing that you're going to tie your deal to,
29:39 Speaker 00 but you've got to be able to listen and iterate and get to the heart of what do they really care about? What are they trying to do? Why are they even talking to you?
29:46 Harry Stebbings? How do you know what's that nugget? How do you know what's that one thing?
29:49 Speaker 00 Well, you got to be curious and it's going to be custom to whatever your business is. And often that one thing is connected to why they're talking to you. Why does this matter? People are extremely busy. Everybody's on Zoom 24/7. Now, nobody wants to take an extra meeting. There's got to be something compelling at the heart of why this person has agreed to spend time with you. Deeply listen and understand what that thing is. And once you get a hold of it, then quantify it. You can keep coming back and use that as Your hook to get your deal done and maybe it'll be some kind of ROI they need to deliver. Maybe it'll be a problem they need to solve, but you've got to get to that why at the heart of the thing.
30:29 Harry Stebbings? So we've gone through this now. We've tested for curiosity. We know that they're great at discovery. They've got grit. We want to make them an offer. When it comes to compensation packages for sales teams, what's your biggest piece of advice and lessons and why do you think many go wrong? Again, I've never done this before, so treat me like a simple person.
30:47 Speaker 00 We've got it.
30:47 Harry Stebbings? That's really hard to do.
30:49 Speaker 00 Of course. The key in these early stages, as you do want to bring on people that are amenable to risk, they have to be willing to take a little bit of a leap of faith. And I think this is where early founders can go a little bit wrong. They get bamboozled by a great resume, somebody who's coming from a bigger company, and that person is going to want more guarantee of outcome. So they might be asking for more of a minimum guarantee or a draw that is pretty lengthy or reassurance that they're going to make their variable compensation. Somebody who indexes too hard on those guarantees probably is not a fit in a startup. At the end of the day, what you want out of a great comp plan, early days as a founder, something that is so clear that if a salesperson reads it,
31:33 Speaker 00 they understand exactly what they should spend their time doing when you're not in front of them. Ultimately, that's what a comp plan is. Those are your marching orders. That is your job description for a salesperson. And if it's not aligned, if you build a comp plan that isn't clear or incentivizes them to do something else, you're not going to get the results at the end of the day. People are very attuned to what those things drive. And because startups are very dynamic, the important other side of that is you've got to be willing to iterate on it. You've got to be willing to work together with the salesperson to talk about what you're incentivizing them to do, understand their feedback on if that makes sense to them, if it's aligned with what they are thinking it means they should accomplish. And then you got to build it together.
32:16 Speaker 00 Let go of traditional ideas of what a comp plan is supposed to be and really just focus on those incentives and the outcomes you're trying to drive.
32:23 Harry Stebbings? As a sales leader today, we're looking at a different 2023. How do you think about managing morale around sales comp? In your team, when people are going, oh shit, what if we don't sell as much? And what if comp isn't where it was last year? How do sales leaders manage that?
32:37 Speaker 00 There are strategic things and there are tactical things. I think strategically, you have to be really honest with the team. You cannot make false promises. Nobody knows what the world is going to look like over the next 12 months. We know it's probably going to be rough, but we don't know exactly what it's going to look like. Being honest about that, really getting a team on board and bought in on the mission of what you're working to accomplish, building trust with them in that environment. You're going to do right by them as long as they're doing the right things that you're in it together, really number one. And then tactically, we've got all kinds of levers as sales leaders. And while we enter tough environments and things may be dynamic, you've got to find ways to identify the wins that underlie the big numbers.
33:23 Speaker 00 When you're in a situation, which everybody at some point in their career is going to be, where reps are not hitting the top line number, you've got to look for ways to incentivize them to get other wins that matter, whether that's spiffs or other mechanics or gamifying the experience. And you've got to go further back in the funnel. An example of this would be if team's not making the top line number, your diagnosis is they're not outbound enough. Nobody loves outbound and you can hound them all day and you could do a spiff to say, oh, anybody who does drive more revenue gets spiffed. The better thing to do is to go back to the basics of what is the first thing they have to accomplish to succeed at this? Build spiffs and a game around those first things, around the activities, around the first thing lead to revenue and incentivize them there so they can get an early win.
34:06 Harry Stebbings? A spiff in the UK is generally cannabis. What's a spiff in your world?
34:11 Speaker 00 The spiff is very different, very different, hopefully. It's a special incentive. So essentially it is an incentive outside of the typical compensation plan. Spiffs are generally rolled out with a limited timeframe around a specific, unique goal. People will do spiffs around end of quarter, or they might do a spiff around a specific activity. So it may be that you've got a quota and you're executing against a revenue quota, but maybe at end of quarter, we want people to do a specific. Kind of deal on a specific vertical. We may say every deal that comes in, you're going to get a 1.5x multiplier on those deals in that vertical.
34:47 Harry Stebbings? But the SPIF always has to be tied to revenue, correct? It couldn't be tied to outbound leads.
34:52 Speaker 00 It can be tied to anything, and I think it should be tied in many cases not to revenue. The quote on the compensation plan should address revenue. A SPIF is going to work best when you tie it to something else that might not be directly tied into how they're incentivized in the comp plan, but it's something you need them to do and is important to the business.
35:11 Harry Stebbings? What's an example of a SPIF? Is it like cash? Is it like a day away? Is like a massage? And two, do people really give a shit unless it's cash?
35:19 Speaker 00 Generally speaking, I am a fan of cash for SPIF. And those things, you can do it any way you want. The other things I think do work are things that involve recognition. I like to do SPIFs that are if you win, you get to go out to dinner with the CEO and have a special session or you get special access to somebody. It's that kind of leaderboard aspect of competition that you want to drive because you also want it to be fun. People want to come out on top. One of the most successful programs I've ever run around this was trying to drive outbound on my mid-market team at Twilio. We did a whole week of activities called it Pipe Week. We really just wanted them creating pipeline, going outbound, and came up with a gamified version of Pipe Gens.
36:04 Speaker 00 You get points for a certain kind of outbounding. You get points for creating new contacts in CRM. And it was all these activities that lead to opportunity. The end of the week, they scored themselves and they turned in their score sheet and the top prize winners got cash in that case. And then we also had some other fun prizes that went along with it.
36:23 Harry Stebbings? I love that. I think that's a great idea. Going back, you mentioned effectiveness and SPIFs can help effectiveness. If we're actually just looking at new hires going, I don't know if they're any good. The hard thing with enterprise I always find is the sales cycles are so long. How do you measure effectiveness of new hires when the sales cycles are so long?
36:42 Speaker 00 In those cases, you really have to have someone engaged with that salesperson that knows what good looks like. That can weigh in on whether those deals are progressing or not. Because what can go wrong when you've got a long sales cycle? If you just leave a salesperson to their own devices, some will report out accurately on deal progress and some will report out very inaccurately. And the most common thing that happens is you'll hear from that sales rep, "Oh, we're making great progress. We're aiming towards a signature by Q3." Then you get to Q3, you'll talk to the sales rep and be like, "Oh, actually, I haven't heard from them in 60 days." Be like, "Oh, the whole thing fell apart." That's unfortunately very common. Whether it's the founder or a sales manager,
37:25 Speaker 00 someone has to be close enough to the work of that salesperson to understand and deeply inspect the deals and know if they are progressing. If you can analyze that, that will tell you, is this person on track? Are they getting it? In enterprise cycles, things can happen. They can fall apart at the last minute. Somebody who knows what's up needs to be close enough to diagnose.
37:45 Harry Stebbings? Things can fall apart on the last minute. I'm on many boards and the most common thing that I hear, Stevie, and I want your advice because I don't know what to say to this one. It just slipped to next quarter. It was so close, but it's just slipped to next quarter. And I'm like, "Did it okay?" I'm not sure. How would you respond to that if you heard that from a founder?
38:02 Speaker 00 So many great salespeople suffer from this. Ultimately, this is a failure of discovery. When this happens, you can almost always trace it back to the beginning of the conversation in that deal and a lack of understanding of some key factors. Some dots did not get connected early on. Either that founder or that salesperson doesn't have a full grasp of if this matters to their buyer and why. When that happens, you get in these scenarios where it's, "Yeah, they're saying good things. It feels like it's going to happen, but you haven't actually nailed the mechanics of a closed plan and understanding of all of the factors happening inside your buyer's business." It's true for enterprise salespeople too, is you'll see deals slip.
38:46 Speaker 00 It's like, "Oh, they're missing something in their discovery."
38:48 Harry Stebbings? You also see things fall apart often at the end of quarters. One thing that we see often is discounting. How do you feel about discounting to get deals done?
38:56 Speaker 00 I'm definitely not against it. I think that so much urge You can create at the end. If discounting is your only strategy, then you're in trouble. It's not a great sign if your your one go to is discounting. But it can really matter. And you know, I think back to one of the first big deals that I did at Twilio with a major US airline. And it was one of our first kind of Fortune 500 deals. We got close to the end of this deal. We had pitched to them a product that was really a bundle of features that hadn't existed before and didn't have a price on it. But we bundled it up and we said, okay, it's $15,000 a month. Random made up number. We know you need all this stuff. These are enterprise features. It's 15 grand a month.
39:38 Speaker 00 And in the end, we pushed them to get the deal done at the end of Q4. Literally on December 31st, we ended up offering them a discount on that $15,000 a month bundle. We gave them 15% discount. And in the end, that discount pushed the deal over the edge. And procurement got it done at 4:00 PM on December 31st. Like, it's free money. That package didn't even exist before. If you can do discounting that way, it can be really powerful. But you've got to understand there's so many other levers to create urgency. It's terms, it's pricing, but it's also like the risk and attention of not getting it done.
40:13 Harry Stebbings? Speaking of risks of not getting it done, two more things before a quick fire. One is we're seeing multiple buyer infringements, I'm calling it now, which is in a much more capital constrained world. The CFO's role is much more prominent in all buying decisions. How does that change your role today, leading sales teams and educating sales cycles?
40:32 Speaker 00 The most important thing in an environment like this is that your sellers pull those people into deals much earlier. The junior sellers approach in these kind of environments is I want to avoid the CFO at all costs. In the world of Vant, I want to avoid the key decision maker. I want to avoid the CISO, want to just keep it to my champion. He says, we're going to get it done. We're just going to like barrel through and get it done. That's how you end up with deals that fall apart at the last minute and slip at the last minute because you did not uncover all of the possible requirements and objections. And to do that, you have to get multi-threaded. Earlier, you can go multi-threaded and give your champion An excuse to bring in a CFO, their head of security. All the folks who might object.
41:15 Speaker 00 It gives you a chance to work through those objections early and set your champion up to help get the deal done and look like they've got it together. You're putting them in a bad position if you don't help them bring that CFO in earlier. You've got to go at it head on and make the case. That is the only way to win in an environment like this where you're going to have these last minute objections show up. So you got to discover the whole landscape.
41:37 Harry Stebbings? Final one, we're also seeing people wanting to see the value a lot more, especially on renewal. Are you changing the structure of your org to equip these people in your customer bases with the data that shows how powerful Vanta is? Cause now they want it before it was like renew. Now it's like, well, show me, show me the ROI. Do you have to change what you do to tailor that?
41:58 Speaker 00 Yeah, we do a little bit. And look at Vanta, we do value based selling. We are talking in every conversation with our customers about those value drivers. To date, our number one value driver has been growth. The thing that does have to shift as we move forward now in this new environment is that the value drivers that matter are a little bit different. We're going to have a little more emphasis on cost savings and efficiency. And yes, growth still matters. Everybody's still got to grow, but it's a flipping of that cost savings and risk reduction from the bottom of the list to the top of the list. So it really changes about how we sell or how we present our value props, but we are emphasizing other values so we can help our customers get compliant
42:42 Speaker 00 much more efficiently with less spend and less time.
42:45 Harry Stebbings? I want to move into a quick fire round now, Stevie. So I say a short statement, sound good?
42:49 Speaker 00 Sounds great.
42:50 Harry Stebbings? Tell me, what sales tactics have not changed over the last five years?
42:54 Speaker 00 Ultimately, sales is the same as it has always been. It goes back to the Radnitsky playbook. People buy from people. They want to have an authentic experience that is rooted in real value. That will never change.
43:08 Harry Stebbings? What sales tactics have died today?
43:10 Speaker 00 Oh, high volume, cold outbound at scale. It just is brutal. You've got to personalize. People are constantly hit from. Every angle, you gotta give them something meaningful.
43:22 Harry Stebbings? What is your single biggest challenge as CRO today?
43:25 Speaker 00 Adapting to unknown conditions and doing that with enough foresight that I don't have to change course quickly. The pace of change is so rapid, but I need to plan a year out. It's the hardest thing.
43:39 Harry Stebbings? It's also like, how do you plan resource allocation for an unknown destination? Do you cut things massively and then overcut and then that's not good? Or do you undercut and then have to do multiple? Well, that's not good. Basically, it's fucking hard.
43:51 Speaker 00 It's so hard. So much change. And who knows? We might be in for a mild recession. We might be in for a very significant recession. And I've got to put forward an annual plan that would accommodate either of those things.
44:04 Harry Stebbings? December next year, are we going to be in a better or a worse place?
44:07 Speaker 00 Plan for worse, be prepared for better.
44:10 Harry Stebbings? Suing your high school? Not normal, Stevie. Why?
44:14 Speaker 00 Yeah, that was another random Stevie backstory. So I sued my Kansas school district because they banned a book. I grew up in Kansas, outside of Kansas City. The school board banned a book because it was an award-winning book, but it had homosexual theme. I did not feel that was either right or constitutionally correct. And it turns out that the Federal Circuit Court agreed with me and I won my case against the school board. They had to put the book back and pay the legal fee.
44:43 Harry Stebbings? You are such a rock star. Tell me, what one piece of advice would you give a new sales leader joining a new role today?
44:49 Speaker 00 Oh, my gosh. Ask all the questions. No question is stupid. Ask everyone questions. Get time with your executives. Proceed without fear.
44:59 Harry Stebbings? What would you most like to change about the world of sales?
45:01 Speaker 00 Oh, I'd love for it to just be more human, higher empathy. It's still so aggro in so many corners. And I think that there is a world where folks can be extremely successful in sales and also kind.
45:17 Harry Stebbings? Tell me, final one, what one company's sales strategy have you been most impressed by recently?
45:23 Speaker 00 Oh, Clary. I just bought Clary and the sales experience, the best I have had. I think selling. To salespeople is incredibly hard.
45:32 Harry Stebbings? Why was it so good? Because Maggie Hart said it was amazing, too.
45:36 Speaker 00 Clary's sales process is very human. It's very high quality. Every touch is quality and thoughtful. And my sales rep engaged with me as a human being. He didn't just cold outbound me. Tactically, for salespeople, he commented on my LinkedIn posts in a human way. He engaged me as a person and it made me want to help him win. And it made me want to help him get the deal done. Of course, the tool had to be amazing. There had to be all the value there. They had to prove that value. They showed us so much value before we signed the deal. And then they gave us a great offer we couldn't refuse at the end of the quarter. And we got it done, even though we had a budget freeze, we bought it.
46:13 Harry Stebbings? That's so good to hear. Stevie, I love doing this. Thank you so much for being so great on the show. You are a star and I've so enjoyed having you on.
46:21 Speaker 00 Thank you for having me. It's been a blast.
46:24 Harry Stebbings? Now, as always, you can check out more from us by heading on over to YouTube and searching for 20VC. I'd love to hear your thoughts on our YouTube channel. But before we leave you today, finding your next customer is hard, but it doesn't have to be. If you're wondering how to drive more revenue and find the accounts that are looking for your solution right now, ZoomInfo is the answer. ZoomInfo handles the full revenue pipeline from marketing to sales, even ops, all based on the number one ranked business data. It's the single best way for B2B professionals to find their next customer, close their next deal and streamline their operations. Best of all, it's all in one place, so your revenue teams can collaborate easily and close deals faster.
47:06 Harry Stebbings? Customers include the likes of Snowflake, Workday, PayPal, Dropbox, and thousands of startups and growing companies, now 30,000 customers and growing. And ZoomInfo is making their go-to-market playbook available for free for anyone to try. So if you want to find out how you can use intent data to target key prospects or how to revive a stalled deal by expanding your buying committee outreach, head on over to zoominfo.com/20vc to see for yourself and sign up for a free trial of the ZoomInfo platform. And speaking of tools we couldn't live without. Sales Loft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace.
47:47 Harry Stebbings? It's the one place where sales teams can go to prospect, manage, active deals and get the insights they need to coach seller performance, forecast with accuracy and find out what steps to take to close more deals. Some of the world's leading companies like Google, Shopify and Stripe all love a new Sales Loft and so can you. It's the new way to sell. Find out more at salesloft.com. As always, I so, so appreciate all your support and I cannot wait to bring you an incredible episode this Friday with Cliff at Canva.
Previous 20VC: USV's Albert Wenger on What Elon Musk Should Do with Twitter | The State of Crypto Today; The Impact of SBF and Why Now is the Best Time To Invest in Crypto | Are We Too Late to Save The Climate and Why Civil Disobedience is Required | Will TikTok b Next 20VC: Canva Co-Founder, Cliff Obrecht on The Journey From 100 VC Rejections to a $40BN Company, Why Good Enough is Not Good Enough, The Secret to Hiring Non-Obvious Talent and Relationships to Money and Why They Are Giving Away Billions Page updated September 29, 2026 · transcript and summary are machine-generated
