# How to Close Sales When Selling to CFOs How to Guarantee You Win Every Renewal, Core Questions All CFOs Ask Today When Buying, Why Revenue Operations is the Most Important Role in a Company with Steve Goldberg, CRO @ Salesloft 20Sales · Dec 13, 2023 · 50 min · 11,135 words Speakers: Steve Goldberg, Harry Stebbings Source: https://www.996.fm/episodes/20vc--ep-e47b92bc/ ## Cold open **Steve Goldberg** [0:00]: The market has changed from a nurturing market to a performance driven market. Yes, budget, everything goes to the CFO. But, no, they're not shut down for business. Every renewal is a new deal too. The first question my CFO asked me is something's up for renewal, what if you didn't have it? I think revenue ops is probably the most valuable role in the company. **Harry Stebbings** [0:19]: This is sales with me, Stebbings, and I started TwentySales because I thought there was so much trapped knowledge in the minds of incredible sales leaders, and so many founders would really benefit from hearing it earlier in their journey before they made classic mistakes that so many make. ## Intro **Harry Stebbings** [0:34]: Today's show is with a sales master, Steve Goldberg, chief revenue officer at Salesloft, the sales engagement platform that was acquired by Vista in 2022 for billion And prior to Salesloft, Steve was group vice president of enterprise at Yext, and before that was a senior senior VP at insidesales.com. but before we dive into the show today, ## Sponsor read **Harry Stebbings** [0:55]: static financial models with manually updated numbers, they just won't cut it anymore. Meet LiveFlow is the leader in financial analysis according to G2, two. 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But don't just take my word for it. There are 6,000 companies, including Zoom, Siemens, Okta, DocuSign, and many more who depend on Outreach to power their revenue organizations. To learn more, check them out at outreach.io. You have now arrived at your destination. ## Conversation **Harry Stebbings** [3:14]: Steve, I am so excited for this. I've got off a couple of reference calls now that just said what an absolute frickin' hero you are. So thank you so much for joining me today. **Steve Goldberg** [3:23]: Absolutely. I I was really looking forward to it, and I'm really curious to hear what you have to say, actually. **Harry Stebbings** [3:29]: Well, mean, listen, we'll save the 40th birthday party for later. I want to start. I think there's often a moment where someone, falls in love with sales. When did you first fall in love with sales, Steve? **Steve Goldberg** [3:39]: I didn't even know I fell in love with it. It just kind naturally happened. I was a psychology major in college, and I didn't realize how important psychology was in the business world until I actually got into sales. I always thought sales had a negative connotation when I was growing up. And when I first got into sales, I was afraid to say I wasn't sales because of that negative connotation. And then at one point, I realized that, you know what? I'm to embrace this because salespeople are problem solvers, and they help your customers solve their problems, which makes your customers at the end of the day look really good and hopefully get promoted and move through their career. And there was this one gotcha moment where I was actually working with Gateway Computers, and I was up there. I walked in there saying, know what? I'm I'm in sales, and I'm here to sell you something. But I'm here to help you solve your problem. At that moment, that salespeople are problem solvers, and they're psychologists. I just fell in love with it from that aspect. **Harry Stebbings** [4:31]: It's really interesting that, because actually David said to me beforehand that one of your greatest skills is knowing your customers. How do you get to know your customers so well? What questions do you ask? How do you unveil what they really need? **Steve Goldberg** [4:44]: Well, there's a business side and a personal side. You always have to understand everybody's business motivation and their personal motivation. And once you understand that, you really can help just relate to them and what they're trying to do and how you're to help solve their problems. And I just always look at, like, especially I always look at what their personal win is and what their professional win is. **Harry Stebbings** [5:04]: How do you find out what their personal and professional is? Do you ask them? **Steve Goldberg** [5:08]: You ask them. You just you have questions, you have conversations. Really quickly, I think one of the things that I've been able to do is I could pretty quickly tell, like, people's body language, people's kind where their head's at. Like, you do the research. You follow them. You research them. You understand what they talk about, maybe a little bit of their background, where they went if they went to college, where they went to college, did they play sports, what sports team do they like, they have kids, you know, where they're from, where people are from, where people grew up, you just of figure out how to correlate with them. And, you know, it's just one of those things where I've just naturally always been able to kind dig into it and get to the personal side of the relationship. **Harry Stebbings** [5:41]: It's funny. I had Chris Degnan on the show, he's CRO at Snowflake, recently. I can't remember the number. When you get to my age, Steve, memory is not quite what it used to be. But I think it was eight. But he's had eight calls with new prospects. It's all that you can do as a rep per week if you really want to be prepared. Do you agree with that, or do you think in the early days for young reps, it's about volume, it's about, at bats, reading as many people as possible, just go, go, go? How do you think about that depth? **Steve Goldberg** [6:13]: One thing, Chris Degnan's a really good friend of mine. Chris Degnan is my brother's best friend. He was the best man at my brother's wedding. And Chris has spent many many nights on my couch growing up when he was moving out to San Francisco. And and a perfect example of Chris, you know, Chris went to University of Delaware with my brother. Chris is from Massachusetts. He's from Lincoln Sudbury. I believe he played might have played lacrosse there. Him and I started off at AeroTech together, and then he went to EMC. And and so going back to your previous conversation, I don't know about how many you can make, because I think it's all about quality, not quantity. If you make two, but they're very quality, and the next week you make two more, but it's quality, it's really, really important. And so I just think you gotta be smart. You to do the research. You to understand who you're talking to to make sure that you're catching them at the right time. **Harry Stebbings** [6:56]: You also need to make sure that you're speaking to a buyer. How do you know if you're speaking to a buyer, Steve? And I did have a schedule, but, this is far too enjoyable. So fuck it. How do you know if they're a buyer, and how do you get there? **Steve Goldberg** [7:07]: So one one thing I always look at, especially when we're building our internal sales process and our structure around our is when you're selling to somebody within a large organization now if you sell to an enterprise company, like a large enterprise company, they're politicians. You sell to a smaller SMB commercial company, they're operators. And two very different ways to sell to them. If you're selling in a large company, I try to put myself in not only their shoes, but the people's shoes that they're actually selling to within their organization to get something done, and if they're respectable enough that the people, like a CFO, would listen to them, and how they would be perceived within their company. And one of the questions I always ask my sales team is, the person you're selling to that you think is a buyer, typically, especially in this day and age, they're not a single sole buyer that they make all the decisions. They have to go to many different people. And when the CFO is putting pressure on them or their CEO is putting pressure on them, how are they to take to that? Are they to commit to it? Are they gonna say, I'm willing to commit to more because I'm to consume this technology or this service? And then you you role play with them. And you can very quickly realize in that process if they're truly a buyer or not, what part of the buying process they go to, or how they need to get to other people to help make decisions. **Harry Stebbings** [8:16]: What are signs that someone's not a buyer? Where would you be like, oh oh oh, Harry, we've got a sign that that we may need to go through someone else here? **Steve Goldberg** [8:24]: Well, one, if they tell you they're the buyer. People usually tell you they're the buyer. They they typically aren't. And and if they tell you, don't talk to anyone else. Just talk to me. I can I can navigate through this myself? Because you've gotta be able to work together. So let's let's talk about an enterprise company right now. A lot of enterprise companies at the beginning of every year, people switch roles. So if you're selling to a very large enterprise company, you could be the CIO one day, and then next year, you could be the CRO. They move roles quite a bit. Or if you're the CMO and you've been there for, say, four months and you wanna break some things, you wanna try some things, you're kind of in the honeymoon, you can actually take that chance. You gotta look at a company and how often they switch people's roles in the organization and what the tenure of of that role typically is. And if they're two years into a role as a CMO, they might not have as much power as they did when they were, like, a year into that role. **Harry Stebbings** [9:13]: Why is that? I thought you would have more power as time accrues because you establish yourself more. You're maybe more successful. You've proven yourself. No? We have to look at **Steve Goldberg** [9:21]: the culture of the company you're selling to and the typical time people are enrolled, role. There's always people that And remember, politicians in very large companies are always trying to find their next way up. So you've to find people that are on their way up, not on their way out. It's really important to navigate through that when you're selling to these larger companies. **Harry Stebbings** [9:38]: How do you find someone who's on their way up, not on their way out? **Steve Goldberg** [9:42]: You could tell by their behavior. You could tell by how they communicate. You could tell by how they talk. You could tell by their body language in a meeting. You could tell by if you're in a meeting with them and other people, are they actually showing authority in that? Are they controlling the conversation? Are they controlling the meeting? You know, if you think if most people out there, they they look at the deals they've done, the big deals they've done. They've always had a change agent in there that's driving through the process, that's navigating through their own process. And you gotta look at that person. I think what David told you earlier on was that I was able to always figure out where the true champion is in an organization and where the true change agent is in the organization. And that is really where the art it's hard to teach that to a lot of your salespeople. When you talk about MEDDPIC and you talk about MEDDIC, a lot of people check boxes there. You can't let them check boxes. You've to be able to ask the questions, like we're we're talking about right now, to ensure that that person really truly is a champion of change. **Harry Stebbings** [10:36]: Is the champion always the change maker? Is sometimes the change maker separate from the champion? Do they differ sometimes? Is that like a chief innovation officer and, like, a CFO, or are they often the same profile? **Steve Goldberg** [10:47]: No. It could be a director in certain accounts. You know, you may the economic buyer could be the CFO, but the change agent could be a senior director of revenue operations who wants to be a vice president or a senior vice president who wants to make a mark on something because they believe it so much that they're gonna drive it through the organization because that's their next promotion. **Harry Stebbings** [11:04]: Is it a good excuse if I'm one of your reps and I say, Steve, we nearly had it. Okay. We nearly had it, but then our champion left. I'm really sorry. It wasn't my fault. Our champion left. Is that not our fault and it's an externality? Or is that you should have known? Is it a good excuse to have a champion leave to lose a deal? **Steve Goldberg** [11:22]: No. It's not a good excuse. There's never just, like, one champion. There's multiple people as part of the process, and it's always never the seller's fault. We talk about why we do deal reviews, why we have first line managers to really coach and manage their people. You do that so you minimize the surprises that happen at the end. You've got to naturally always be looking and always have these conversations with people going back to what is their personal win. You've you go back and understand what this person's personal win is, you'll start to get a sense of how long they're gonna be at that company or not. If they trust you remember, salespeople, the negative connotation versus I'm a problem solver, I'm here to help you get to your next role. And if they trust you, they may open up to you and say, hey. Look. I'm not gonna be here that long. I'm thinking about moving on. you've to build that trust in these relationships. If not, you will get surprised. You will get surprised. And in that case, I never say it's your fault, but bad news never never travels better with age, like wine. You've gotta really, you know, sess that out early and go with your gut. **Harry Stebbings** [12:19]: I remember Dev at MongoDB, the CEO there, told me the best thing ever. He said, the different types of news travel at different speeds. Good news travels fast. Bad news is very slow. I thought that was really good piece of advice that I always remember. You mentioned deal reviews there, Steve. I'm a total novice here. I'm a first time founder. How should I do deal reviews? How often should I do them? What makes a good versus a bad one? Can you help me understand how to do deal reviews well? **Steve Goldberg** [12:47]: Yeah. So so one, it's it's really the the first line manager needs to own the deal reviews. They need to own the process. My job is to design and architect the overall system that people work within. So if I'm asking my second line and third line managers five questions, they need to be asking their teams the same five questions or the same 10 questions. Their deal reviews are different at different stages of a quarter, for an example, or different stages of a year. At the beginning of the quarter, you're gonna be asking a different set of questions because you're really gonna just try to get an understanding of what's happening. But the whole goal of deal reviews are to understand, like, why not something is gonna happen, but also understand how do we actually untie knots. Because managers my job and my job, my job is to help untie knots. **Harry Stebbings** [13:28]: Can I just pause on that? Just wanna make sure that I don't miss stuff, which is great. When you say at the beginning of the quarter, it's different. We to understand what's happening. What are we trying to understand, and why are we trying to understand it for forecasting, for projections? Help me understand our objectives on what we're understanding and why. **Steve Goldberg** [13:46]: Well, we're we're trying to understand power. We're trying to understand, one, do we truly understand the problem we're trying to solve? Do we truly understand what our unique value proposition is in that process? And has the buyer bought off on that? And then then you go through the MEDDPIC process and understand, what do we know? What don't we know? And MEDDPIC is really just a qualification process. And the goal at the beginning of the quarter is to understand what you don't know. You look at org charts. But by the middle of the quarter, at some point, what I usually lock in on, by the middle of the quarter, we have to have agreed upon mutual plans in place and alignment on how we actually get to the end of the quarter. And then we have to measure that nonstop to continue to track all the activities that needs to happen. But, obviously, you're gonna close business early in the quarter as well. But if you've got that process in place every quarter, then you're gonna have more consistency in actually closing business and not just waiting to the end of the quarter. **Harry Stebbings** [14:35]: What makes a bad deal review? **Steve Goldberg** [14:37]: When people aren't being honest. **Harry Stebbings** [14:38]: Do you know when they're not being honest? **Steve Goldberg** [14:40]: That's the goal of enabling that the first line manager is the most important kind of aspect of any process because they're the ones that have to be having the one on ones weekly and daily. They're the ones that have have to be able to understand that. So when I do deal reviews, not only do we do deal reviews with the sellers, but I also do deal reviews separately with the first line managers, and then you triangulate. How do they **Harry Stebbings** [15:01]: differ with the sellers versus the first line managers? **Steve Goldberg** [15:04]: Well, you talked about Dave Renicki for an example. Dave Vernitsky is the master at forecasting. The master for I've worked for Dave for probably ten years, and he had his forecast call every Friday at 10:00. You had to be prepared for that meeting because he would go through every opportunity, and he'd go through everyone. We'd have seller notes next steps and manager notes next step. And he'd like, alright, Steve. This deal, talk about it. Tell me what's going on. And I he'd go into so much detail. And if he figured out there was a gap, he would just dig into that gap, and then we'd move on. And so I would do the same thing with my team, and then they would do the same thing because I couldn't show up unprepared. So what it does was it really minimized surprises. He would go through the month, every deal in a month, in every deal in CTP, every deal in in best case, and every deal in long shot. **Harry Stebbings** [15:49]: How many chances do you give people, Steve? In an ideal world, and I don't mean this arrogantly, but everyone's like me and you, and what I mean by that is fucking machines. Sadly, not everyone is a machine or not everyone knows that 10:00 Friday, you gotta be on. How many chances do you give people when it's not quite there? **Steve Goldberg** [16:05]: The the market has changed from a nurturing market to a performance driven market, and that's happened probably over the last six to nine months. And it was really hard to drive that process in place because people would like to be asked questions, for example. But we still drove that process. And in my experience, when I grew up, I was at Siebel and I was at Salesforce. If you showed up once and didn't have it together, you maybe got invited back twice, but there was no third time if you didn't have it. And and that's just the environment I grew up in. Now the market's not like that as it is today, but the expectation, discipline that is getting back to that model. Like, the market is getting back to driving that process, and a lot of the people that have grown up in this industry over the past, say, five to ten, seven, eight years, they haven't seen this. **Harry Stebbings** [16:49]: Are they ready for it, Steve? **Steve Goldberg** [16:50]: I don't think they are. I think there's a set of people that are. I think there's a broader set of people that are not. And you could see it when it doesn't work out in your Glassdoor reviews, for an example. If you're saying you're gonna be a performance driven culture, you've gotta be a performance driven culture, and you're gonna get some challenging Glassdoor reviews out there. You're gonna get people saying some negative things, but you gotta commit to it, and you've gotta commit to that process. But if you're consistent with it and you have to have integrity, you treat people with the utmost respect in this process. But you've gotta be able to ask the questions because to your point earlier, it's really not okay when you get surprised towards the end. And if it happens once, okay. If happens twice, now you start to get some consistency in the same people that are missing it multiple times. You Then got start looking at the first line managers like, well, how are you missing this? **Harry Stebbings** [17:38]: Can I ask you, when it comes to those people who have what it takes in that performance driven culture, who thrive on that chase and the unwillingness to accept losing and that bloody grit, How do you test for that in interviews? How do you see it in someone before you hire them? **Steve Goldberg** [17:53]: One, you've got to really look for grit. And what we do in our interview process, one the most valuable things, we do top grades with everybody. And in a top grade, we'll spend two to three hours with you, and we'll have you walk us through your life. Walk us through the decisions you made in elementary school that you can remember. Walk us through, okay, now you went you got to be your freshman year and you, you know, you decided say you had a coach, You decided you were a quarterback. And walk me through, like, how'd you make that decision? And then, okay. So now you're in college, you went to this school. Why did you go like, you you had two decisions to make. Why'd you go here versus here? **Harry Stebbings** [18:25]: What do you want to see in asking those questions? **Steve Goldberg** [18:28]: I want see how people make decisions. I wanna see people's thought process for how they make decisions. I wanna see if people could be consistent, and they don't just give up. They're obsessed with winning, and they're very competitive. You naturally, you look for trends that people make throughout their life, and you look for consistencies. Then then you look at their career, and if they jumped around, like, tell me why you left this role to go to this role. Tell me why, okay, you started off as an SDR. You were there for nine months, and you went to another company. you'd be an SDR. Well well, didn't you wait? What happened? How'd you make that decision? Then you to look for trends, scenarios, and you could start to assess. What what you see is when you when you miss, you can look at backwards and people that didn't work out at your company, the same trends that you caught. They maybe admired the problem in the interview process, and you were just trying to fill street quota, and you didn't dig in deep enough. **Harry Stebbings** [19:14]: Steve, do you do case studies as part of the hiring process? **Steve Goldberg** [19:18]: Yeah. We what we do what we do is we we do mock case studies, for an example. So we'll have them come in and do discovery, because our business is very big on discovery and making sure you clearly understand the problem you're solving. Especially in this day and age, like, you have to be solving problems. People don't buy features. They solve problems. And it has to be the biggest problem, the top three problems a company has. So we go through a process where they have to do a discovery call with a sales leader, a couple sales leaders, and really go through that due diligence, and then come back and present the unique value problem, the business case, and also the how. A lot of people focus on the what, we also have them present the how. Like, how are you gonna help us get to that problem, and how are gonna help us solve that problem? Not just what you're gonna do to solve that problem. And so we we absolutely go through that as a big part of our process. **Harry Stebbings** [20:02]: You said there especially now you need to be solving a top three Everyone says two things. One, budget has completely retreated back to the CFO, and then two, CFOs just aren't buying new technology. Two questions. Has budgets completely retreated to CFOs, and are CFOs shut for business? **Steve Goldberg** [20:20]: Yes. Budget, everything goes to the CFO. But, no, they're not shut down for business. We actually just did one of the bigger deals in the company history just very recently. Back in the financial crisis in 2008, when I was at Salesforce, we did some of the biggest deals at the time in the company history at that point. Because when problem when you have problems and there's change going on, people solve big, big problems and they will solve it outside of their budget cycle. But you've got to really truly make sure that you're solving really big problems. And by the way, every renewal is a new deal too. You have to treat every renewal because every renewal is going to the CFO. The first question my CFO asked me is, something's up for renewal is what if you didn't have it? And that's what every CFO is asking. **Harry Stebbings** [21:01]: Does this mean that vitamins are dead and the only painkillers survive? **Steve Goldberg** [21:04]: Yep. Which is going back to the previous conversation around high performance cultures. Companies are doing more with less. A lot of companies out there have restructured. Big companies had tons of overlays that can help kind of talk about features and functions. They really don't anymore. Smaller companies have minimized their street quota and lowered their targets, but they're putting more emphasis on doing more with less and focus a lot on enablement. You have to be able to truly enable your teams. My CFO talks about this a lot is this year is about getting better. Next year is about getting bigger. And so you've got and you gotta get better with a core group because great people want be surrounded by great people. Great people wanna be around people that are like them. Building that culture and instilling it into them around making sure that we're truly solving the biggest problem a company has, number one. And number two, you found the change agents or in in an organization that to an make change. **Harry Stebbings** [22:00]: Do you not think they're slightly conflicting when you think about that? Say better this year, building a more efficient, more kind of high velocity machine better, and then bigger, more people, more revenue, more this, more this, they're kind of conflicting, aren't they? To assume you can maintain better while bigger is realistically impossible. **Steve Goldberg** [22:19]: Well, let me let me give you a couple of examples of that. So, you know, like, you ever been on a beach and it looks beautiful, the sun's setting, tides in, looking outside, it's like, it looks beautiful. Right? Then all of sudden, the tide goes out. And now you're looking at, wow. There's a huge reef over there. my god. There's a shipwreck over there. Like, look at all those rocks. I had no idea those were there. Well, that's what's happened this year. You have to change your process. What we found, for an example, two things that we did this year. So we have a commercial business, which is about one employee to 750 employees, and we had a hunter farmer model in that commercial business where we had sellers would sell a deal, and they would own it for a year, then pass it off to an AM who would just farm. And in the past, they were people were just adding on 100 licenses every year because they were growing at huge rates. But what happened in the past year was that these account managers were just hanging out with the same people that they sold the original deal to. And instead of buying nine 100 licenses, they're like, I only have 50 people at the company now. So we saw a lot of downgrades. So we shifted to a hunter hunter model, and we shifted our process. We had we had to change the profile of a salesperson of an AM to a hunter, and everybody had an interview for their role. And we opened it up to the outside, and and their job when we took the renewal away from the AM, we moved it to a renewal manager in CS, and we are now calling a account executive who owns new logos. Three months, they own it. Maybe a couple they can keep. Then right away, they pass it over to a client account exec whose job is to build relationships across the organization to sell find new use cases that they can sell into, not just hang out with the same people. So we went through this whole process change this year because the old old way was not working. We were just getting downgrade after downgrade, and a lot of it was because we were selling into other use cases. We were just hanging out with the people we sold to, and they were just they didn't have as many people to support. **Harry Stebbings** [24:08]: I love this detail. So we have this, you know, Hunter. They sell three months. Great. How do you do the handoff of, hey, meet enablement CS manager who you've never met before. They're gonna own this relationship now. Good luck. **Steve Goldberg** [24:21]: That's the second thing we changed. You have to bring the CS team into the selling process. Remember I talked to you about the what and the how? This is the s team is the how. So you bring them into the presales process so the customer can feel comfortable with the customer journey and how you're gonna make them successful. And they've got the confidence in that. So they know what they're buying into early on, and then we build these production environments because we're in a very competitive market. And everybody says they kind do the same thing with similar value props. So we have to go in there and say, all right, We're gonna build this production environment, and we're gonna align to a use case. We're gonna build out the business case, and then we're gonna put it in production and show you exactly how we're gonna do this. So you're gonna understand what it's like to work with us even before you're a customer. Our win rate and attach rate to that is is pretty pretty incredible as we go into this year. So we made all these changes this year, and I've heard some of, you know, other CROs talk about, you know, the handoff, and they do it after the implementation. You got do it as part of the early selling process. What makes us unique is our ability to make our customers successful, meaning they get to the specific outcomes they're looking for. But it's so hard to show that in a sales process, so you've got to actually show that. You got they gotta see what it's like to work with you. **Harry Stebbings** [25:29]: Dude, you ever chatted to Chris Degnan about CS? He goes, you know what I did when I came into Snowflake? I got rid of all CS. No more CS. I don't believe in it. What do you think of that? **Steve Goldberg** [25:40]: talked to him about this actually a while ago. Look, I think that the skill set of a CS person is different. When we we were at Salesforce back early on in the day, we created this customer success manager. We were the only we're the first companies to do it. It hasn't changed since then. A lot of customer success organizations are are really a first line for support because they're hanging out with the people. Remember I told you about? They're hanging out with the people that they sold the first product to, and they're just answering questions. They're not able to be proactive. They're not able to get strategic. They're not able to help them get to these outcomes because they're just solving how to problems with, like, the admins and the operations people. And so I think what Chris is talking about doing is that he he probably believes, and I believe this as well, a lot of times when things aren't when you're losing customers is you lose access to the buyers. You you lose access to the people of power. Because you do a deal, you're up here. All of sudden, you're implementing it. Now you're down here. And then when it's implemented, now you're down here. You've gotta stay up here. You've gotta stay across the organization. So in that How do you how **Harry Stebbings** [26:38]: do you stay up there? **Steve Goldberg** [26:39]: You gotta change your process. You gotta change your profile the people you're bringing in. The way I was explaining to you is that you've gotta change the profile of the people you're putting into those into those roles. **Harry Stebbings** [26:48]: Do you still need CEOs to close big deals? You said about coming in up here. The CEOs need to come in to close large seven, figure deals or eight figure deals? **Steve Goldberg** [26:56]: One, CEOs should never be RVPs. They should never be the ones that are actually closing deals. That's my job. What they CEOs should give the customer the confidence about our vision and what we are doing as a company. I never like to put my CEO in a position where he's actually having he he or she is having a closed business. Their job is to align with others, maybe CEO and other executives, to give them comfort that they're making the right bet on the right company. They should not be closing business. But I strongly believe when you do big deals, they buy into your company. They buy into your culture. They buy into your innovation. They buy into what you're doing. And you've got so many tentacles within your organization that they buy into you. And it's kind of called the shiny penny in a way. You become the shiny penny of each other's companies, and everybody rallies around them. So it's not just the CEO. It's multiple people in the organization. It's aligning CFOs. It's aligning chief technology officers. It's aligning chief product officers, and it's aligning CEOs. And that's the job. It's the connections. **Harry Stebbings** [27:53]: You'll you'll understand after this question why I'm asking. What's a sales playbook to you, Steve? **Steve Goldberg** [27:58]: I think it's different in each segment. It's different in terms of if you're selling into a commercial business or you're selling into an enterprise business. It's gotta be designed and architected into those businesses. It is the kind of gravitational pull that you wanna drive within your process to make sure that the sales process is set up so it's on your wheelhouse, so everybody's competing with you. And it's gotta be consistent in how you do it, and it's gotta be very tactical and very strategic. My job is to architect those across an enterprise business and across a commercial business and make sure that, you you wanna give people some of the flexibility, like their manager, some flexibility, but they've gotta work in your framework. **Harry Stebbings** [28:34]: Steve, I need your help on this one. I believe strongly something. Many others disagree with me on this. Very very different views. The founder should create the sales playbook. Do you agree with me, or do you think the sales leader should create the sales playbook? The first one. **Steve Goldberg** [28:48]: The first one, mean as a startup company? **Harry Stebbings** [28:51]: As a startup company, they need to create the sales playbook. What's your messaging? Who's your ICP? How do you sell to them? What's the pricing? **Steve Goldberg** [28:59]: I had a conversation with our previous founder, Porter, and he was so passionate about our company and our product and our features. And him and I would talk about this a lot, and he'd say, Steve, what I realized when you and I met was that I can convince one person to do anything about my product. I can convince one person that our product is the best product ever. But what you help me do, help us do as a company, is convince multiple people in a company that we can solve their problem, and it's great for them, and they got move down a process. That was kind of an moment when I got here. We were about, you know, 50,000,000 in revenue. And, you know, we got there early on by just being so passionate about what we do. And but we didn't have a process. We were really great about talking about our product, and we were a product company at that point. We weren't a platform, and we shifted now to be more of a platform, and it's a very different sell. So when you sell a product, what I found is most founders are so passionate about it, and passion gets you to a point. But at some point, you gotta get to a point that you need a you need a process. And I think most founders are very passionate what they do. Maybe they're more on the product side or more on the marketing side, but not many have, like, the experience in a go to market and like, building, like, an enterprise company, an enterprise process. And I think that's a much different world where you need, like, RevOps and enablement, you need to put, like, infrastructure in place. And I don't think that most founders have that experience. **Harry Stebbings** [30:19]: I know it's different for different segments. I know it's different for different companies, but just baseline bastardize it for me. RevOps enablement, when's the right time to hire your first in each? 10,000,000 in revenue, your first massive logo, when's that trigger? **Steve Goldberg** [30:34]: So I think revenue ops is probably the most valuable role in a company, and you're to start to see the evolution of RevOps be moving into the CRO world when you start bringing data and science together. I think you wanna hire an analyst, like a really good analyst early on at about, say, 5,000,000 to really start to analyze your process. Because a great CEO, passionate, but they gotta be able to make decisions based on data, not just based on gut. And you're by million, you're to start to use some data and some AI that you can start to incorporate some AI. So you to hire really smart analyst And as you grow to million, maybe two analysts, when you get to million, you're going need someone who's got some management experience kind seeing that ship around really building a strong kind of RevOps organization. RevOps, I couldn't survive without a great I've got an incredible RevOps leader. What do you think RevOps gives you so much of? The blind spots. They're constantly looking at the data and analyzing the data to understand where their blind spots are. **Harry Stebbings** [31:30]: Can you can you give me an example? Sorry. I know it's detailed, but I'm just trying to understand what is an example of a blind spot that a good RevOps team would give you? **Steve Goldberg** [31:37]: One of the reasons that we changed our processes that I just talked to you about earlier is that we were starting to see, based on our data, that we were seeing more churn because of the way our processes were set up where the AMs were seeing more downgrades, but they weren't seeing cancellations. They were seeing more downgrades of users just downgrading in certain segments of the market. So in, like, companies that we were selling to, tech companies that sold to other tech companies. So we saw that, and we had to stop that trend right away. So we started to change our process around a set of customers, a set a set of data that we saw in the market quickly. That's that's one example. **Harry Stebbings** [32:10]: On enablement, I had Henry Schuck, the CEO of Zoom info on the show, and he said that actually kind of aligned to what you were saying there about kind of downgrades but not cancellations. He was saying, years past, people just upgrade more, more seats, more, more seats. Great. Wonderful world to live in. Now, not only do they not upgrade, but they want data on usage. Prove to me that you're valuable in my org. Show me usage, show me whatever that is, transactions, requests, whatever we want. Are you seeing a change in how you structure your team to service the requests of buyers? **Steve Goldberg** [32:42]: Yeah. You have to be very proactive about it. It goes back to the skill sets you put in the the post sales side so they can start to look at data to show their customers the insights and the value that you're creating for them. And remember, the CFO is the buyer now for every renewal. If you don't if you're not showing them insights around business value, then you're not to be renewed. Do you **Harry Stebbings** [33:00]: do that continuously throughout the year? **Steve Goldberg** [33:02]: Oh, yes. We've changed our whole adoption strategy to outcomes versus adoption because nobody cares if I come to you and say, here's how many logins you have. Here's how many activities you had. What you to know is what is my pipeline metrics been and how am I coming in every quarter to my pipeline targets, and what are my outcomes around revenue that I'm driving with your platform. And so we've changed our whole adoption metrics to outcome metrics, and we know all the leading indicators that get the outcomes. And we design health scores around every single one of our customers. And we could see be proactive when it triggers from a green to a yellow and what created that, that will all of a sudden start to drive leveraging our platform workflow and and activity and thought leadership and content out to them, and the CSM will follow right up once we see something change. **Harry Stebbings** [33:46]: You said activity, thought leadership, content. Is that ABM, like, hey. Here's actually, like, marketing material that kind of fits you and kind of could be interesting, or is this, like, deep analysis on your business use case? **Steve Goldberg** [33:59]: It's deep analysis on their business use case, and it's deep analysis on if they get stuck on a three step cadence, but they're not running it through a five step cadence. And we see if that's happening. If we see some integrations are off, we can get really proactive and fix them proactively. And then we have these EBRs that we run every quarter with our customers, and we have process in place on how we do that. We meet with that's how you get higher in the organization. We meet with, you know, the leaders in the organization and show them the insights of what they're doing with recommendations on how to improve. **Harry Stebbings** [34:27]: What's your biggest advice? As you mentioned with Salesloft, bluntly, it's a noisy landscape, and there's a lot of people who say they do the same thing. The product messaging and marketing is quite similar in a lot of cases. What would be your biggest advice to founders who are in noisier markets where a lot of people say the same things? **Steve Goldberg** [34:44]: You to focus on the how, and you to stay maniacally focused on the how. A lot of companies focus on the what. There's a lot of what out there. Here's what we do. Here's our value prop. Here's how we do that. Focus on, like, what you're delivering for them and how you're to help them. But you to prove it. You to show them every single day. And you've to be maniacally focused on showing them the how. And you gotta it goes back to solving the right business problem, but you to constantly be in front of them, showing them how you're helping them, how you're helping them hit these targets, how you're helping them solve the problems, not only when you get the deal done. When you get the deal done, the relationship just starts. **Harry Stebbings** [35:17]: Steve, I get you. I love the how. I love the how. But, you know, ex competitor, they're to give me a 20% discount. matters nowadays. My budgets are tight. How do you feel about discounting? Is there a right time, or should it be a flat no always? **Steve Goldberg** [35:31]: So, no, it should never be a flat no, but I care more about what's in the contract than how much they're paying us. Meaning, like in our business, being a workflow platform, there's consulting capabilities that we need to bring into the process. There's support and services pieces in there. And I to make sure that the relationship is set up so they can be self sustaining and that we can integrate truly into their workflow. I care more about that, and procurement cares a lot about I to see what my per unit price is. They to understand, like, what their per unit price is. So we can work with them on making sure we fit within their budgeting cycle, but I care a lot about making sure the customer is set up for success because we're negotiating many, many deals right now or all the time. And my point to them would be, yeah, you may look good because you got this per unit price down. But in six months from now, when your business unit comes to you and says, well, I'm not getting any value out of the product, then how are you gonna feel then? We've to figure out and meet somewhere in the middle because, yeah, we'll make sure we give you the right structure that's in place. I always try to get, and I coach my team on, you don't want any winners or losers in these negotiations. You really wanna try to avoid that, and you don't want any take it or leave it. You wanna work with them to figure out, at the end of the day, how you can both feel good about the relationship. Because when procurement leaves and the buying leaves, you're focusing on helping them be successful. You wanna kind of get through the contract, but you don't want a bad contract dictate a a bad relationship. **Harry Stebbings** [36:49]: You focus a lot on relationships. Like, you hear this time and time again in the way that you speak. Something that I find goes against is, like, how do we encourage urgency in a deal cycle? How do we encourage urgency, like, close, close, close? And it kind of just feels like it goes against the solving Steve's problem. How do you balance between that needing to close an urgency of closing in a quarter with, I get it, Steve. It may not be optimal for you to sign right now. You've got this big thing happening. Have another week. How do you balance that urgent with the personal? **Steve Goldberg** [37:20]: I think there's a respect component of that where you build relationships, and you're working towards a moment in time where you gotta have a tough conversation. You you don't want have it to be a surprise. You don't wanna ever do anything unnatural. But at the end of the day, you know, we do work in months and quarters. And there's going be time throughout the relationship that you're going ask me for something, and I'm going to ask you for something. Right now, what I'm asking you for, not to do anything unnatural, but if you can do it in this timeline, we'd appreciate it. Now, you don't have to, but we would really appreciate it. But that's why the mutual plan is so important. So you're not just having to do something unnatural and throw a hail Mary at the end of the quarter, end of the month. I mean, that happens in certain cases. But if you align on the deal reviews and the process and the structure, you're having these conversations and you're aligning towards a plan to be able to do something in a timeline that works for both of you. Talk about compelling events and how do you back into compelling events, and, you know, I think that's also really important. But at the end of day, that's I do think relationships matter because a procurement person, if they're told what to do by the buyers, they'll work towards those dates. I think you've gotta have those relationships because you're gonna win and lose a deal 100 times before you actually win it. You're gonna feel like you've lost. The deal done. You to be okay with that. But you gotta pick it up every day, and you got figure out how bring it back together because you're gonna lose it three or four times during the day. You know, you've just gotta be able to pick it up. And if you don't have those tentacles, you go back to CEOs. Do they have to close business? What's really important is that you're not single thread in an account, and you've got your managers and all the different people. I call selling selling is a team sport. Our organization, I've never been in an environment where it's, here's here's your territory. Go read me the news. We make the news together, and so it's a team sport. We sell together. So very rarely do we have a deal that we only have one person in there because there's to be a point that you've gotta go and have the tough conversation, and you can't be afraid you can't admire You can't be afraid of it. And in some cases, things need to get uncomfortable before they get comfortable. **Harry Stebbings** [39:07]: Are you comfortable having uncomfortable conversations, Steve? **Steve Goldberg** [39:10]: Very. My job is to untie knots. That's my job. **Harry Stebbings** [39:13]: Have you always been that way, or did you learn it over time? **Steve Goldberg** [39:16]: What I've learned was that you can't be afraid to have the tough conversation. You just you can never be afraid because if you don't have it, then some somebody else will. This And is where you gotta balance things out. Like, I've had some of the best sellers in the world when I was a first time manager. They were the best relationship people, the best, but they couldn't close because they couldn't have the tough conversation. So my job as the RVP in that case was to have those tough conversation and to leverage their strength and leverage my strength. And so you you need that balancing act. You need to team. **Harry Stebbings** [39:45]: Can you learn to have hard conversations? **Steve Goldberg** [39:47]: I mean, look. Some people will never be able to have those tough conversations. Some people will won't wanna have it. And it doesn't mean that they're not good at what they do. It's just this is where you may need to tee it up so someone else can have that tough conversation. **Harry Stebbings** [40:00]: Steve, listen, I could talk to you all day. I do wanna do a quick fire, so I'm gonna pepper you with questions. You're gonna give me your thoughts. How does AI impact the future of sales, Steve? **Steve Goldberg** [40:09]: AI is gonna make people smarter, and it's going bring information to them so they have better insights on how to have smarter conversations with their customers. **Harry Stebbings** [40:17]: Will AI replace reps, RevOps, enablement? **Steve Goldberg** [40:20]: I think there'll be parts of the market that it does replace, like, maybe more some of the transactional business, maybe some of inbound capabilities, but I think we're a bit away from that. I think people are gonna be over rotating in some cases, and they're gonna learn. Kinda like the IVR. Remember we used to call an IVR? You'd be like, press one and you'd speak into the the phone, and it wasn't the best experience. I think there's gonna be some of that, but I I do think over time it will. But our philosophy and my my view is it's gonna give you better insights on what to do next. **Harry Stebbings** [40:48]: What sales tactic has not changed over the last five years? **Steve Goldberg** [40:51]: Solving business problems. You still have to be able to always had to be able to solve business problems. **Harry Stebbings** [40:57]: What sales tactic has died a death? **Steve Goldberg** [40:59]: I think the adage of let's go golfing and hang out on the weekends and go and and all those things are just, like, not as I think people look at their time and that's changing a bit in terms of, like, the different lunches and the golfing and those things have changed. **Harry Stebbings** [41:13]: Tell me about a deal you've closed, but you've had to do something creative to get it over the line. **Steve Goldberg** [41:18]: Oh, there's so many. Creativity could be that someone's on vacation, and you need to figure out how to find the person on vacation so they will sign the contract, because their timeline might not be your contract. But I've had times where people have been skiing, and this is where it gets it gets a little you want to balance out not being, like, creepy, but, like, you find out where they are on vacation, you might just send them flowers and just, hey. Just remember them. You know? I'm out there. You know? Just remember me. You know? I've had reps do that where they might find out not in a creepy way because they built the relationships where they've someone might have been on a ski trip, they when they got back to the room, had a bottle of wine there for them or something just to remind them. Someone says, thanks. And they come up for air, and they're like, remember me. Hey. Oh, yeah. That's right. I forgot. Sorry. Was with my family. **Harry Stebbings** [42:03]: Tell me, what one piece of advice would you give to a new sales leader? Someone starting a new sales leadership role, what would you tell them the night before? **Steve Goldberg** [42:10]: This is kind of a crazy thing that just kind came to mind. I saw this quote the other day. So well, someone gave me advice, and I'll tell what this is. Someone gave me advice when I was in college. Same advice. And I walked into a a restaurant. I was sitting at the bar with another person who was sitting next to me. And I was waiting for my parents to meet me to go have dinner, I was just graduating college. And this guy was sitting at a bar, and he looks to me, and he says, I can give you any advice. Know your trade before you're ready to move to the next role. And I had no idea what he was talking about. I'm like, what do you mean know my trade? Like, what does that really mean? And then it hit me. Like, I started my career. I was in recruiting, and then I I moved in. I was an SDR. And what he meant was, like, know your trade. So when you're in SDR, get really good at being an SDR before you're ready to go into sales. And then get really good at enterprise sales or sales or whatever you're selling before you're ready to move into management. And I wasn't ready to move into management until I started to have kids and I got married because my life changed, like, the way I thought about things changed. I took that advice, and I would say, don't move until you're ready to move. Some people move too quick because if I did that too quick, I couldn't give the advice I give to people because I've lived their roles. I lived I lived in those roles, and I think it's really important that people try to move on too quick. I've seen so many first line managers just wanna do anything to be a second line manager, but they're not ready for it. And I've seen sellers who wanna be first line managers, but they're not ready for it. They're not in a good headspace. **Harry Stebbings** [43:27]: Do you think they agree with you that they're ready for it? Most often, they think they are when they're not. **Steve Goldberg** [43:31]: Most often, they think they are. I think something in some cases, like, that's a change within your life. Like, if you go, you get married. All of a sudden, you have to think differently. You're thinking about you and somebody else. You start to have kids. You're thinking about your thought process changes. So I would give that same advice is that study. Be obsessed with what you're trying to do and be obsessed with with learning. And there's this quote I heard the other day. It's like, why is a lion the king of the jungle, if you think about it? Like, why? They're not the strongest. Like, the elephant is the strongest. They're not the fastest. The cheetah is the fastest. There's many animals that are smarter than them in the jungle, but they're obsessed with winning. And I think that's what people they need to be obsessed with learning. They need to be obsessed with improving. They need to be obsessed with improving. And when I see people do deals, big deals, is because they're obsessed with the customer. They're obsessed with the relationship, and they're maniacally focused, they're gonna do whatever they possibly can to win. There's people that hate to lose, but there's not many people that really know how to win. You gotta be obsessed with winning. **Harry Stebbings** [44:25]: I always say you have to earn the right to do the next thing, and I think that's very similar to the know your trade. How did having children change your operating mindset towards work? **Steve Goldberg** [44:35]: a lot of salespeople are selfish. They're selfish with their time. I don't think there's any better job than being an enterprise salesperson with a great company and a great market with a great product. All I had to do is think about myself, my schedule, my time, my schedule. That's all I cared about. But when I started to have kids, my schedule, my personal schedule changed. I had to, like, be a little more organized. I had to think for other people. I had now I have three kids. I had to, like, think about them and my family, and it started to get me thinking, you go from catching the ball in the end zone as a seller to being on the sideline coaching the team and being able to, like like, having kids. Like, I'm trying to, like, teach them and help them, and it just changed me to think, I wanna help coach people and coach salespeople to get them to be the best of them. Like, now I love watching people improve. I love watching people get promoted. I love I love if I say something and all of a sudden I see them put it in action or they tell me what they did and through through a coaching initiative, I love that. I wasn't thinking like that before I had kids. It was all about me. **Harry Stebbings** [45:31]: Now our final one, otherwise, I can just keep going all day, but it's what company sales strategy around you that you've seen? Do you go, that's really impressive. I'm impressed by that. **Steve Goldberg** [45:42]: I've worked at many companies. Back in the day we were at Salesforce, I think Salesforce did it so good. Like, I spent almost 10 years at Salesforce. I know that you had a a listening interview with Marc Benioff, and he cultivated such a culture of perfection that people wanted to win for him. He cultivated so many incredible leaders, and that company just had such an incredible sales process. Because if you think about our market, you could say, well, at that point, Siebel and Oracle were the big PeopleSoft, SAP, Microsoft, they were the they no one even knew about Salesforce. He just created so much talent around a process that we built a process around helping companies be more agile, be more flexible. Put your data in the cloud. Were you crazy? Put your day in the our sales process was around trust us. We'll show you our security. We'll show you our uptime and downtime in the market, and we would be very transparent with our customers. And we just had such an incredible sales process designed and built around what made us great you what made us unique that nobody could compete. **Harry Stebbings** [46:41]: Steve, I didn't send you the schedule before this show, which was very uncharacteristic of us. Normally, we do. I'm really pleased that I didn't, because you would have gone, that was not what we agreed upon in the schedule. These shows are really why I love doing what I do. It's so great to have such a natural discussion. Thank you so much for being so brilliant, and I've just loved this. **Steve Goldberg** [47:00]: No, I loved it. I appreciate the conversation, and it just flowed nice, and I appreciate your curiosity, by the way. **Harry Stebbings** [47:07]: That was so much fun to do with Steve. I love the way the conversation just flowed so naturally. As I said, I'm super pleased that he did not see the schedule beforehand because none of that was intended, but it was so much fun to do. If you to see more from us, of course, you can on YouTube by searching for 20VC. That's zero I to see you there. But before we leave you today, ## Sponsor read **Harry Stebbings** [47:25]: static financial models with manually updated numbers, they just won't cut it anymore. Meet Flow. LiveFlow is the leader in financial analysis according to G2, two. 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