YouSaid · the spoken record

Stevie Case

lines on the record: 57
first: 2023-01-25
most recent: 2023-01-25
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“That was Clearly 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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I'd love for it to just be more human, higher empathy. It's still so agro in so many corners. And I think that there is a world where folks can be extremely successful in sales and also kind.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Oh my gosh, ask all the questions. No question is stupid. Ask everyone questions. Get time with your executives. Proceed without fear.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, that was another random CV 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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“It's so 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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“A high volume cold outbound at scale. It just is brutal. You've got to personalize. People are constantly hit from every angle. You got to give them something meaningful”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Ultimately, sales is the same as it has always been. It goes back to the Rudnitsky playbook People Buy from People. They want to have an authentic experience that is rooted in real value. That will never change.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yet we do a little bit and look, Atvanta, 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 much more efficiently with less spend and less time.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 advance, I want to avoid the key decision maker. I want to avoid the CISO. I 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, 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 out.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Discount pushed the deal over the edge and procurement got it done at 4 p.m. 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. Its terms, it's pricing, but it's also like the risk and attention of not getting it done.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I'm definitely not against it. I think that there's so much urgency you can create at the end. If discounting is your only strategy, then you're in trouble. It's not a great sign. If you're 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. 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,”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 factor. 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. It's like, oh, they're missing something in their discovery.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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. Like, oh, the whole thing fell apart. That's unfortunately very common, whether it's the founder or a sales manager. 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?”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Generally speaking, I am a fan of cash for SPIF. If there's 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. You get points for a certain kind of outbounding. You'd get points for creating new contacts in CRM. And it was all these activities that lead to opportunity. At the end of the week, they scored themselves and they turned in their score sheet and the top.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Can be tied to anything, and I think it should be tied in many cases not to revenue. The quota on the compensation plan should address revenue. A spiff 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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“It's 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 SPFs 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 a 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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Other winds 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 teens not making the top line number, your diagnosis is they're not outbounding enough. Nobody loves outbounding and you can hound them all day and you can do a spiff to say, oh, anybody who does drive more revenue gets spiff. 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 in 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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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. 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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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. 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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 fitness startup. At the end of the day, what you want out of it a great comp plan early days as a founder, something that is so clear that if a salesperson reads it, 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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 medpic 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, but you 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?”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, this is so tough. And I've seen it gun 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 business. It's also at the heart of closing really hard deals because you 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”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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. 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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I think the single most important thing in that is 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 the seat where they sound like a co-founder and they can speak to the why and the vision with enthusiasm 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. I think the mistake people make, especially when they think about the playbook and I like 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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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, 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 succeeded.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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. 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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 S&B to suddenly we're going to go do deals with companies 5,000 employees plus. It was, okay, let's look at 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? A thing that was not tow in the water about it is that I actually pulled resources out of our core SMB team and their job 100% of the time was mid-market and enterprise. 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”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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, 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”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 Atvanta right now, in that we have been historically SMB focused. Well, this year we made the move upmarket, 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 to, 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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 to 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. 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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“You can, but I would caution you against trying to do both right away, thinking 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 compt? How do you work that out? When you introduce both too early, you introduce the risk of complication 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”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 and be a part of a team that is much more thoughtful and interesting and diverse.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 my mind was still, why not me? 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.”
2023-01-25 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source