20Sales: 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

13 Dec 2023 · 50 min

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In short

Podcast Summary: 20Sales with Steve Goldberg

Episode Overview Podcast Title: The Twenty Minute VC (20VC) Episode Title: 20Sales: 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 Host: Harry Stebbings Guest: Steve Goldberg, Chief Revenue Officer at Salesloft

Episode Description In this episode, Steve Goldberg, a seasoned sales leader and CRO at Salesloft, shares insights on navigating sales in today's market, particularly when dealing with CFOs. He discusses strategies to close sales faster, conduct effective deal reviews, and ensure renewals in a challenging environment.

Key Takeaways

  1. Becoming a Sales Leader
  2. Understanding Sales:
  3. Steve emphasizes that sales is more about psychology than techniques.
  4. He reflects on his journey, noting that he didn’t initially realize his passion for sales until he recognized it as a problem-solving role.
  • Mastering Buyer Psychology:
  • He highlights the importance of understanding both business and personal motivations of prospects to foster relationships.
  1. Closing Prospects Faster
  2. Building Relationships Quickly:
  3. Steve suggests asking questions that reveal personal and business motivations.
  4. Understanding body language and conducting thorough research are crucial to identifying true buyers.
  • Identifying Buyers:
  • He shares strategies on recognizing signals that indicate whether someone is truly a decision-maker.
  • Emphasizes the necessity of establishing multiple relationships within an account to safeguard against losing a champion.
  1. Conducting Effective Deal Reviews
  2. Characteristics of Deal Reviews:
  3. A good deal review includes understanding the deal's status and preparing questions that guide discussions.
  4. Steve elaborates on how the focus of deal reviews should shift throughout the sales cycle, with different objectives at the beginning and mid-quarter.
  • Addressing Slips in Deals:
  • He stresses that slipping into the next quarter is not an acceptable excuse for sales reps and highlights the importance of consistent communication.
  1. Ensuring Renewals
  2. Centralized Budget Control:
  3. Steve discusses the trend of budgets being controlled by CFOs and how this affects purchasing decisions.
  4. He argues that every renewal should be treated as a new deal, with an emphasis on showcasing the value provided to the customer.
  • Value Demonstration:
  • He shares insights on how to effectively demonstrate value to customers, particularly focusing on the long-term benefits rather than just immediate features.
  1. The Role of Revenue Operations
  2. Importance of RevOps:
  3. Steve believes that revenue operations is critical for analyzing processes and identifying blind spots in sales strategies.
  4. He emphasizes the need for data-driven decision-making to adapt to market changes and improve sales outcomes.
  • Hiring Strategy:
  • He recommends hiring skilled analysts early in a company's growth to optimize processes based on data insights.
  1. Navigating Market Challenges
  2. Changing Sales Dynamics:
  3. Steve notes a shift from nurturing markets to performance-driven environments, necessitating a more efficient approach to selling.
  • Responding to Buyer Pressures:
  • He discusses the importance of understanding and addressing the pressures faced by CFOs and other decision-makers.

Final Thoughts Steve Goldberg's insights provide valuable guidance for sales professionals, particularly in understanding the psychological aspects of sales, the importance of building relationships, and the necessity of adapting strategies to a rapidly changing market. His experience underscores the significance of continuous learning and adaptation in sales leadership.

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For more episodes and insights, visit [20VC.com](http://www.20vc.com).

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Transcript

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0:00The 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 is, what if you didn't have it? I think Remniew office is probably the most valuable role in the company. This is 20 sales with me, Harry Stebings, and I started 20 sales because I thought there was so much trap knowledge in the minds of incredible sales leaders and so many founders would really benefit from hearing it earlier in their journey.

0:31Before they made classic mistakes that so many make, today's show is with a sales master, Steve Goldberg, Chief Revenue Officer at Sales Loft, the sales engagement platform that was acquired by Vista in 2022 for $2 .3 billion. And prior to sales loft, Steve was group Vice President of Enterprise at Yaxxt and before that was a senior VP at InsideSales .com. But before we dive into the show today, static financial models with manually updated numbers, they just won't cut it anymore. Meet LiveFlow. LiveFlow is the leader in financial analysis according to G2. LiveFlow helps finance teams at Y -combinator, OpenFone, Landing AI, and thousands more forward -thinking companies to turn their spreadsheets into a real -time FPNA platform.

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3:12You have now arrived at your destination. Steve, I am so excited for this. I've got off a couple of reference calls now that just have one absolute freaking hero you are. So thank you so much for joining me today. Absolutely. I was really looking forward to it. And I'm really curious to hear what you have to say, actually. Well, I mean, listen, we'll save the 40th birthday party for later. I want to start. I think there's often a moment where someone that falls in love with sales. When did you first fall in love with sales, Steve? I didn't even know I fell in love with it. It just kind of naturally happened.

3:43I 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 going to embrace this because sales Those people are problem solvers and they help your customers solve their problems with makes your customers at the end of the day look really good and hopefully get promoted and move through their career.

4:13And there was just one gotcha moment where I was actually working with K -way computers and I was up there, I walked in there saying, you know what? 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 sales people are problem solvers and they're psychologists. I just fell in love with it from that aspect. It's really interesting that because as you David said to me beforehand that one of your The 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?

4:45Well, 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 going to help solve their problems. And I just always look at, like especially, I was able to what their personal win is and what their professional win is. How do you find out what that person is? Do you ask them? 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 of where they're heads at.

5:18You 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 to college, where they went to college, and they play sports, what sports seem to they like, their kids. where people grew up, you just kind of figure out how to correlate with them. And it's just one of those things where I've just naturally always been able to kind of dig into it and get to the personal side of the relationship. It's funny, I had Chris Dagnan on the show, you see our snowflake recently. I can't remember the number when you get to my age, Steve, memory is not quite what it used to be.

5:50But I think it was eight. But is that eight cools with new prospects? Is all that you can do as a rap per week? if you really want to be prepared. Do you agree with that or do you think in the early days for young raps? It's about volume, it's about at bants reading as many people as possible. Just go go go. How do you think about that? DEPT. One thing Chris Degna is a really good friend of mine. Chris Degna is my brother's best friend. He was the best man in my brother's wedding. And Chris has spent many nights on my couch when we were growing up when he was moving out to San Francisco. And a perfect example of Chris, you know, Chris went to University of Delaware with my brother.

6:27Chris is from Massachusetts, he's from Lincoln, Sudbury. I believe you played, might have played the cross there. Him and I started off at Arrow Tech together and then he went to EMC 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 gotta do the research, you gotta understand what you're talking to, and make sure that you're catching them at the right time.

6:56You 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 like, this is fall to enjoyable. So fuck it. How do you know if they're a buyer? And how do you get that? So one thing I always look at, especially when we're building our internal sales process and our structure around our process, is when you're selling to somebody within a large organization. Now, if you sell to an enterprise company, 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.

7:27If 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 soul 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 going to take to that?

8:00Are they going to commit to it? Are they going to say, I'm willing to commit to more because I'm going to consume this technology, or this service. And then you roleplay 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. What assigns to someone's not a buyer? Why would you be like, oh, oh, oh, Harry, we've got a sign that we may need to go through someone else. Well, one if they tell you they're the buyer. People who usually tell you they're the buyer, they typically are.

8:29And 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 got to be able to work together. So 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 so you can actually take that chance.

9:00You gotta look at a company and how often they switch people's roles in the organization and what the tenure 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. Why is that I thought you would have more power as time accrues because you establish yourself more, you're maybe more successful, That's where you prove a new self, right? You have to look at the culture of the company you're selling to and the typical time people are in roll. There's always people that, and remember, politicians in very large companies are always trying to find their next way up.

9:31So you've got 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. How do you find someone who's on that way, up, and on that way, out? 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 hearing 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 it, most people out there, they look at the deals they've done, the big deals they've done.

10:02They've always had a change agent in there that's driving through the process, that's navigating through their own process. And you got to 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 med -pack and you talk about medic, a lot of people check boxes there, you can't let them check boxes. You've got to be able to ask the questions, like we're talking about right now, to ensure that that person really truly is a champion of change.

10:36Is the champion always the change maker? Is sometimes the change maker sat put from the champion? Do they differ sometimes? Is that like a chief innovation officer? unlike a CFO, or are they often the same profile? 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's so much that they're gonna drive it through the organization because that's an expromotion.

11:04Is it a good excuse? If I'm one of your apps and I say, Steve, we nearly had it, okay, we nearly had it, but then on Champion Left, I'm really sorry, It wasn't my fault, I'll champion left. Is that not our fault and it's next -analysis? Or is that you should have known? Is it a good excuse to have a champion leave to lose a deal? No, it's not a good excuse. There's never just 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 happened at the end.

11:40You've got to naturally always be looking and always have these conversations with people going back to what is their personal win? 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 it sales people 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 look I'm not gonna be here that long. I'm thinking about moving on Like you've got 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 doesn't never travels better with age like wine You've got to really you know, set that out early and go with your gut I remember Dev at MongoDB the CEO there told me the best thing ever He said it's a 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 and the first time found out how should I do deal reviews?

12:40How often should I do them? What makes a good versus a bad one? Can you help me understand how to do deal reviews well? Yeah, so one, it's really that the first line manager needs to own the deal reviews. They need to own the process. My job is to design and architect the whole 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 example, or different stages of a year. At the beginning of the quarter, you're going to be asking a different set of questions because you're really going to just try to get an understanding of what's happening.

13:15But the whole goal of deal reviews are to understand like why not something is going to happen, but also understand how do we actually untie not because managers job in my job, my job is to help untie not. Can I just pause on that? I just want to make sure that I don't miss stuff which is great. When you say at the beginning of the quarter it's different, we want 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? Well, we're trying to understand power.

13:48We'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 you go through the med -pick process and understand like, what do we know, what don't we know? And med -pick 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 order 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 align in on how we actually get to the end of the quarter.

14:20And 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 and actually closing business And not just waiting to the end of the quarter. Well, maybe subon deal or if you when people aren't being honest Do you know when the no thing will miss? That's the goal of enabling that the first -like 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 to be able to understand that.

14:53So 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 time managers. And then you try and yield. How do they differ with the sellers for us as the first line managers? Well, you talked about Dave Rynitsky, for an example. Dave Rynitsky is the master at forecasting. The master at four. I've worked for Dave for probably 10 years. And he had his forecast call every Friday at 10 o 'clock. You had to be prepared for that meeting. Because he would go through every opportunity and he'd go through everyone and we'd have Cellar notes next steps and manager notes next step and he'd like all right Steve this deal talk about it Tell me what's going on and I'd 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 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 surprising he would go through the month every day on the month in every day on CTP every deal in best case, in every deal, in Lanshire.

15:49How many chances do you give people, Steve? In an ideal world, I don't mean this hang -in -a -and -a -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 o 'clock Friday, you got to be on. How many chances do you give people when it's not quite there? 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 a seabull and I was a sales force 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 that's just the environment I grew up in now the market's not like that as it is today But the expectation the 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.

16:49Are they ready for it, Steve? 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 can see it when it doesn't work out in your glass door reviews, for example. If you're saying you're going to be a performance -driven culture, you've got to be a performance -driven culture, and you're going to get some challenging glass door reviews out there. You're going to get people saying some negative things, but you've got to commit to it and you've got to 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.

17:20But you've got to 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, and I start to get some consistency in the same people that are missing in multiple times, then you guys are looking at the first -line managers like, well, how are you missing this? Can I ask you when it comes to those people who have what it takes in that performance driven culture? You thrive on that chase and the unwillingness to accept losing and that bunny grit. How do you test for that in interviews? How do you see it in someone before you hire them?

17:53One, you've got to really look for grit and what we do in our interview process, one of the most valuable things that 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 to say you had a coach, you decided you were a quarterback and walked me through like, how'd you make that decision? And then, okay, so now you're in college and you went to this school, why did you go, like, you put you at two decisions to make?

18:24Why'd you go here versus here? What do you want to see in all of this question? I want to see how people make decisions. I want to see people's thought process for how they make decisions. I want to 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 look for trends that people make throughout their life, and you look for consistency. And 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 then you went to another company, and being an SDR, well, why didn't you wait?

18:55What happened? How did you make that decision? Then you started to look for trends, scenarios, and you could start to assess what you see when you miss, you can look at backwards and people that didn't work out of 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. Steve, do you do case studies as part of the hiring process? Yeah, what we do is we do case studies for an example, so we'll have them come in and do a 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.

19:31People don't buy features. They solve problems and they, it's 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 going to help us get to that problem and how you can help us solve that problem. not just what you're going to do to solve that problem.

19:59And so we absolutely go through that as a big part of our process. You said they're especially now you need to be solving a top three problem. 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. It has budget has completely retreated to CFOs, and our CFOs shut for business. 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 a sales force, we did some of the biggest deals at the time in the company history at that point because 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.

20:45But 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 The first question my CFO asked me is, something's up for a renewal is what if you didn't have it. And that's what every CFO is asking. Does this mean that vitamins are dead and the only pain killers survive? 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 talk about features and functions they really don't anymore.

21:19Smaller 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 to get better with a core group because great people want to be surrounded by great people. Great people want to 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 an organization that want to want to make change Do you not think they're slightly conflicting when you think about that say better this year building a more efficient More kind of a high velocity machine better and then bigger more people more revenue more this more this more that kind of conflicting on it to assume you can maintain better while bigger is realistically impossible.

22:19Well, let me give you a couple examples of that. So, you know, like you've ever been on a beach and it looks beautiful, the sunsetting, tides in, looking outside, it looks beautiful, right? Then all of a sudden, the tide goes out. And now you're looking at, wow, there's a huge reef over there. Oh my god, there's a shipwreck over there. Like, look at all those rocks. I don't know, those are 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 with sell a deal, and they would own it for a year, and then they'd pass it off to an AM who would just farm.

22:58And in the past, 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. Instead of buying a hundred 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 to change the profile of a salesperson of an AM to a Hunter. And everybody had an interview for their all. And we opened it up to the outside and their job.

23:30When we took the renewal away from the AM, we moved it to a renewal manager in CS. And we are now calling the Count Executive, where one's new logo's three months, they all own it, maybe a couple they can keep, then right away they pass it over to a client of Count Executive 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 way was not working. We were just getting down great after down great, and a lot of it was because we were selling into other use cases.

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24:03because we were just hanging out with the people we sold to, and they were just, they never had many people to support. I love this detail, so we have this hunter. They sell three months great. How do you do the handoff of, hey, meet an Abelman CS manager, who you've never met before. They're gonna own this relationship now, good luck. That's the second thing we changed. You have to bring this CS team into the selling process. Remember I talked you about the what in the how? This is the S team is the how. So you bring them into the pre -sales process. So the customer can feel comfortable with the customer journey and how you're going to 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 of do the same thing with similar value props So we have to go in there and say all right We're going to build this production environment and we're going to line to a use case We're going to build out the business case and then we're going to put it in production and show you exactly how we're going to do this So you're going to understand what it's like to work with us even before your customer our win rate and to that is pretty incredible.

25:05We go into this year, so we made all these changes this year, and I've heard some of the other CROs talk about the hand -off, and they do it after the implementation. You've got to 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. They've got to see what it's like to work with you. Dude, you have a child that's Chris Dagnan about CS. He goes, you know what I did when I came in this snowflake?

25:34I got rid of all CS. No more CS. I don't believe in it. What do you think of that? I talked about this actually a while ago. Look, I think that the skill set of a CS person is different. When I was, we were at Salesforce back early on in the day, we created this customer success manager. We were the only, we were the first companies to do it. It hasn't changed since then. A lot of customer success organizations 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.

26:05They'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 probably believes, and I believe this as well, a lot of times when you're losing customers is you lose access to the buyer. You lose access to the people of power. Because you do a deal you're up here, I'll send you're implementing it now you're down here and then when it's implemented now You're down here. You've got to stay up here.

26:35You've got to stay across the organization So how do you how do you stay up there? You've got to change your process You got to change your profile the people you're bringing in the way I was explaining to you is that you've got to change the profile The people you're putting into those into those roles. 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 -six figure deals or seven figure 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 of what we are doing as a company.

27:09I'd never like to put my CEO in a position where he's actually having a, 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, and the way you become the shiny penny of each other's companies and everybody rallies around them.

27:41So 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. You'll add the sign off to this question while I'm asking. What's the sales playbook T -Steve? 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 got to be designed and architected into those businesses. It is the kind of gravitational pull that you want to 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.

28:18And it's got to be consistent in how you do it. and it's got to 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 want to give people some of the flexibility like their managers some flexibility, but they've got to work in your framework. Steve, I need your help on this one. I believe strongly something, many others disagree with me on this. Very different views. The founders should create the sales playbook. Do you agree with me or do you think the sales lead to should create the sales playbook?

28:47The first one. The first one you mean as a startup company? As a startup company, they need to create a sales playbook. What's your messaging? Who's your ICT? How do you sell to them? What's the pricing? I had a conversation with our previous founder Kyle 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 we were 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 helped 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 to move down the process.

29:26That was kind of an aha moment when I got here. We were about 50 million in revenue and we got there early on just being so passionate about what we do. 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 a more of a platform and it's a very different cell. 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 got to 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 of the product side more of 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 and and you need to put like infrastructure in place and I don't think that most founders have that experience.

30:19I 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? Temmeling and revenue, your first massive logo, when's that trigger? So I think Remnoo Apps is probably the most valuable role in a company and you're gonna start to see the evolution of Revops, be moving into the CRO world, when you start bringing data and science together. I think you want to hire an analyst, like a really good analyst early on at about say five million, to really start to analyze your processes, because a great CEO, very passionate, but they get to be able to make decisions based on data, not just based on God.

30:57And by five million, you're gonna start to use some data and some AI that you can start to incorporate to AI. So you want to hire a really smart analyst, and as you grow to 10 million, maybe two analysts, when you get to 20 million, you're gonna need someone who's got some management experience, kind of 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? The blind spots. They're constantly looking at the data and analyzing the data to understand where their blind spots are.

31:30Can 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. 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 process were set up where the AMs were seeing more downgrades but they weren't seeing cancellation. 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.

32:00So 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 of data that we saw in the market quickly. That's one example. On Enablement, I had Henry Schuck, the CEO of ZoomInfo, on the show. And he said that actually kind of aligned to what you were saying there about kind of downgrades for not cancellations. He was saying, years passed, 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.

32:31Show 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? Yeah, you have to be very proactive about it. It goes back to the skill set you put in the post -seal 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're not showing them insights around business value, then you're not going to be renewed. Do you do that continuously throughout the year? Oh, yes.

33:03We'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've had. What you want 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. 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 They will all of a sudden start to drive Deliveraging our platform workflow and activity and thought leadership and content out to them and the CSM will follow right up once we see something change You said activity thought leadership content is that a BM 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?

33:59It's deep analysis and their business use case And it's deep analysis. 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, and 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, and we meet with, that's how you get higher in the organization. We meet with the leaders in the organization and show them the insights of what they're doing, with recommendations on how to improve.

34:27What's your biggest advice, as you mentioned with sales loft? Blondie, it's a noisy landscape and there's a lot of people that you say they do the same thing the product messaging and marketing It's 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? You got to focus on the how and you got to stay Monetically 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 gonna help them but you got to prove it and you got to show them every single day and you've got to be maniacally focused on showing them the how and you got it going back to solving the right business problem but you got 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 you get the deal done the relationship just starts Steve I got you I love the how I love the how but you know X compared it they're gonna give me a 20 % discount matters nowadays my budget's a tight how do you feel about discounting.

35:28Is that a right time or should it be a flat -nosed? So no, this never be a flat -nosed, but I care more about what's in the contract than how much they're paying us. Meaning, again, our business is 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 want 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 Here's a lot of what I want to see with my per unit prices. They want to understand what their per unit price is.

36:00So 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 I'm 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 the business unit comes to you and says, well, I'm not getting any value out of the product, then how are you going to feel then? We've got to figure out a meat somewhere in the middle. Because yeah, well 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 want to try to avoid that and you don't want any take it or leave it You want to 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 when the buying leaves you're focusing on helping to be successful You want to kind of get through the contract, but you don't want a bad contract to take a bad relationship You focus a lot of on relationships Like, you hear this time and time again in the way that you speak.

36:54Something 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? I think there's a respect component of that where you build relationships and you're working towards a moment in time where you've got to have a tough conversation.

37:29You don't want to have it to be a surprise. You don't want to ever do anything unnatural. But at the end of the day, you know, we do work in months and quarters and there's going to be time throughout the relationship that you're going to 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. You don't have to, but we would really appreciate it. But that's why the mutual plan is so important. And so you're not just having to do something unnatural and throw a hail marry at the end of the quarter end of the month.

37:54I 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 allying to or to 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 the day, 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 got to have those relationships because you're going to win and lose a deal 100 times before you actually win it And you're going to feel like you've lost the deals that you've got to be okay with that But you got to pick it up every day and you got to figure out bring it back together because you're going to lose it three or four times during the day You know, you've just got to be able to pick it up And if you don't have those tentacles you go back to CEOs today at the closed business What's really important is that you're not single threading an account and you've got your managers and all different people I call selling as a team sport our organization I've never been in an environment where it'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 gonna be a point that you've got to go and Have the tough conversation and you can't be a fr - you can't admire You can't be afraid of it and in some cases things need to get uncomfortable before they get comfortable Are you comfortable having uncomfortable conversation Steve for very my job is to untie knots.

39:12That's my job Have you always been that way? Or did you learn it over time? 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 somebody else will. And this 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 conversations and to leverage their strength and leverage my strength.

39:41And so you need that balancing app. You need to do this team. Can you learn to have all conversations? I mean look, some people will never be able to have those tough conversations. Some people won't want to 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. Steve, listen, I can tool you all day. I do want to do a quick fire. So I'm going to pat you with questions. Yeah. You're going to give me your thoughts. How does AI impact the future of sales, Steve? AI is going to make people smarter and is going to bring information to them so they have better insights than how to have smarter conversations with their customers.

40:17Will AI replace wraps, revelps, and abulant? I think that will be part to the market that it does replace, like maybe more than some of the transactional business, maybe some of inbound capabilities, but I think we're a bit away from that. I think people are going to be over -rotating in some cases and they're going to learn. Kind of like the IVR. Remember we used to call an IVR and you'd be like press one and you'd speaking to the phone and it wasn't the best experience. I think there's gonna be some of that, but I do think over time it will, but our philosophy and my view is it's gonna give you better insights on what to do next.

40:48What sales tactic has not changed over the last five years? Solving business problems. You still have to be able to always have to be able to solve business problems. What sales tactic has died of death? I think the adage of let's go golfing and hang out on the weekends and go and kind of all those things are just like not as, I think people look at their time and that's changing bit in terms of like the different lunches and the golfing and those things have changed. Tell me about a deal you've closed but you've had to do something creative to get it over the line. Oh, so many. Creativity could be that someone's on vacation and you need to figure out a person on vacation so they will sign the contract because their timeline might not be your contract.

41:29I've had times where people have been skiing and this is where it gets a little. you want to balance out and not be in like creepy, but like you find out where they are in vacation, you might just send them flowers and just, hey, just remember them, they know I'm out there, just remember me, you know, that 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 and they, when they got back to the room, they had a bottle of wine there for them or something, just to remind them, and someone says, thanks and they come up for air and they're like, hey, remember me, hey, oh yeah, that's right, I forgot, sorry, I was with my family.

42:02Tell me what one piece of advice would you give to a new sales leader? Someone's starting a new sales leadership role. What would you tell them the night before? This kind of a crazy thing that just kind of came to mind. I saw this quote the other day. So, well, someone gave me advice and I'll tell you what this is. Someone gave me advice when I was in college, same advice. And I walked into 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 up dinner, where I was just graduating college. And this guy was sitting at a bar and he looks to me and he says, I can be any advice, know your trade before you're ready to move to the next role.

42:33And 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 moved in. I was an SDR. And what he meant was like, know your trade. So when you're an SDR, give really good at being an SDR before you're ready to go into sales. And then give really good at enterprise sales or sales or whatever you're selling before you're ready to move in a management. And I wasn't ready to move into management until I started having kids and I got married because my life changed Like the way I thought about things changed.

43:03I 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 want to do anything to be a second -line manager But they're not ready for it. And I've seen sellers who want to be first -ly managers, but they're not ready for it. They're not in a good headspace. Do you think they agree with you that they're ready for it?

43:29Most often they think they are when they're not. 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. I'll 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 learning. And there's this quote I heard the other day is 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.

44:11They need to be incess with improving and when I see people do deals Big deals is because they're obsessed with the customer or they're obsessed with the relationship, and they're maniacally focused, and they're gonna do it every day, possibly get a win. There's people that need to lose, but there's not many of you that really know how to win. You gotta be obsessed with winning. 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 what? Well, that's sales people are selfish.

44:36They'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 gotta do is think about myself, my schedule, my time, my schedule, that's all I cared about. But when I started out with kids, my personal schedule changed. I had to be a little more organized. I had to think for other people. I had now three kids. I had to think about them and my family. And it started to get me thinking, you go from catching the ball on the end zone as a seller to be on the sideline coach and the team and being able to be having kids.

45:08I'm trying to teach them and help them. And it just changed me to thinking, I want to help coach people and coach sales people 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 a coaching initiative. I love that. I wasn't thinking like that before it kids. It was all about me. Now I 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, huh?

45:39That's really impressive. I'm impressed by that. I've worked at many companies back in the day where we were at Salesforce. I think Salesforce did it so good. Like, that's been almost 10 years of Salesforce. I know that you had a, and I listen to your interview with Mark 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 you think about our market. You can say, well, at that point, C -Bull and Oracle were the big people -soft, SAP, Microsoft. They were the, they know and even knew about Salesforce.

46:15Do you just create so much talent around a process that we built a process around helping companies be more agile, be more flexible for your day of the cloud? Were you crazy for your day in the cup? Well, our sales process was around trust us. It will 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 and made us unique, that nobody could compete. Steve, I didn't send you the schedule before this show, which was very uncharacteristic of us.

46:46Normally 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 loved doing what I do. It's so great to have such a natural discussion. Thank you so much for being so brilliant and I just love this. No, I loved it. I appreciate the conversation and that just This flowed nice and I appreciate your curiosity, by the way. That was so much fun to do as 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.

47:17If you want to see more from us of course you can on YouTube by searching for 20VC, that's 20VC. I loved to see there but before we leave you today, static financial models with manually updated numbers they just won't touch it anymore. Meet LiveFlow. Liveflow is the leader in financial analysis according to G2. Liveflow helps finance teams of Y -combinator, Open Phone, landing AI, and thousands more forward -thinking companies to turn their spreadsheets into a real -time S -P -N -A platform. You might be wondering how does it work? You're likely using Google Sheetter itself for your financing modelling, right?

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48:28So let LiveFlow shoulder that burden for you, tap into their library of 100 plus expertly crafted templates, such as 13 week cash flow forecast, which you can access and customize for free. Don't wait, head over to LiveFlow .io ford slash 20 sales, and elevate your financial game today. The first 10 people who sign up via the link will get 20 % off for 3 months. And, speaking of incredible products like Liveflow there that change how we work. Outreach is the only AI -powered sales execution platform that unlocks seller productivity to help sales teams efficiently create and close more pipeline, from prospecting to deal management to forecasting, their platform leverages automation and artificial intelligence to help revenue leaders increase efficiency and effectiveness of all go -to -market activities and personnel across the revenue cycle.

49:20An outreach is the only company to offer sales engagement, revenue intelligence and revenue operations functionalities in one unified platform. But don't just take my word for it, there are 6 ,000 companies, including Zoom, Siemens, Octo, Doc Hussain and many more who depend on outreach to power their revenue organisations to learn more. Check them out at outreach .io. As always I so appreciate all your support and we've got an incredible app so coming you on Friday with Henry Ward, founder and CEO at Carter.

From the publisher

Steve Goldberg is the Chief Revenue Officer at Salesloft, the sales engagement platform that was acquired by Vista in 2022 for $2.3BN. Prior to Salesloft, Steve was Group Vice President of Enterprise at Yext and before that was a Senior VP @ InsideSales.com.

In Today's Episode with Steve Goldberg:

1. Becoming a Sales Leader:

  • When did Steve first fall in love with sales?
  • Why does Steve believe sales is more psychology than anything else? What can sales reps do to master the psychology of their prospects?
  • What does Steve know now about sales that he wishes he had known in the beginning?

2. How to Close Prospects Faster Than Ever:

  • How does Steve build relationships with prospects very fast? What questions does he ask?
  • How does Steve know if he is really speaking to a buyer? What are the signals?
  • How does Steve advise sales reps on getting multiple relationships within an account to prevent the potential of losing your champion?
  • How does Steve feel about discounting? When is the right time to do it?

3. How To Do The Best Deal Reviews:

  • What makes good vs great deal reviews? Who is invited? Who is not?
  • Who sets the agenda? Who is responsible for what?
  • How do deal reviews change throughout the quarter and throughout the year?
  • Is a deal slipping into the next quarter an acceptable excuse for a sales rep to give?

4. How to Ensure Renewals in a World When They are Not Guaranteed:

  • Have all budgets centralized back to the control of the CFO?
  • Are people right to say that no CFOs are buying new technology today?
  • What is the best way to show to customers the value you provide?
  • Why does Steve believe revenue operations is the most valuable role within an org?

More from The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

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20Sales: 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 @ SalesloftThe Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · 50 min
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