20Sales: The 3 Profiles of a Sales Rep, How to Negotiate in a Sales Process, How to Sell to a CFO & How You Should Shift Sales Messaging in a Downturn with Frank Fillmann, CRO @ Salesforce Australia

Frank Fillman is CRO/Country Leader Australia for Salesforce where he is responsible for responsible for the overall strategy, execution, success, and growth of the $1B+ Australian market across all industries. Prior to Salesforce, Frank was SVP/GM @ Tableau where he was responsible for the strategy, execution, and growth of Tableau's Top Accounts. Over the last 10 years at Salesforce, Frank's accomplishments include $500M+ new revenue closed in 5 years and $1B+ revenue managed. As a result, Frank has been awarded #1 Sales VP of the Year, North America, 3 times! Huge thanks to Zhenya Loginov @ Miro for the intro to Frank today. In Today's Episode with Frank Fillman We Discuss: 1.) From Selling Kitchen Utensils to Leading $1BN Revenue Line for Salesforce: How did Frank first make his way into the world of sales selling kitchen utensils? Why does Frank believe, "how you handle tragedy defines you"? How did it define him? What does Frank know now that he wishes he had known when he started in sales? 2.) Build and Execute the Sales Playbook: How does Frank define what a "sales playbook" is today? What is it not? Literally, what are the first steps to building a sales playbook? Is it the founder who does it? What does a good playbook have? What does a bad playbook have? What makes the best? What tools should founders and sales leaders use to create their playbook? 3.) Enterprise Deal Dynamics 101: Why does Frank believe that you should never start with the price or "send over numbers"? How can enterprise sellers create urgency in a deal cycle? What works? What does not work? How does Frank advise sales teams on the use of discounting? How open should reps be in communicating the win for them as well as the win for the customer of closing a deal? 4.) Building the Bench: How does Frank structure the hiring process for all new sales reps? Why does Frank believe that all sales leaders want to be super reps? How does Frank rank high potential vs high experience when hiring reps? What matters more; the exec have experience in the sector you are selling into or the deal size? What are the single biggest mistakes founders and leaders make when hiring sales? 5.) Setting Quota and Deal Reviews: How does Frank advise founders on setting quotas? Why does Q1 set the tone for the year? How does Frank conduct deal reviews? How often? With who? What is the agenda? What is the one question that Frank always asks when a rep says, "the client told us it was not a priority and so it slipped into next quarter"? How does Frank advise founders and sales leaders on multi-threading large enterprise accounts? Items Mentioned in Today's Episode: Frank's Most Recent Book: The Go-Giver: A Little Story About a Powerful Business Idea

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  I think the biggest mistake is when you just send a price over and then you end up arguing about numbers. So if it's me, my preference would always be start with a blank canvas, find your buyer and spend some quality time. And I think you'd ask questions of her like this. Number one, how are you measured? What are the metrics that you as an organization, as individual are measured by at the organization level? And you start to really unpack how they define value and values and what their priorities are. And then you go like a level deeper.

• 0:25Harry Stebbings?

  This is 20 Sales and today we have a master of the sales world joining us. Our guest today has been awarded number one sales VP of the year for North America three times. His accomplishments include $500 million of new revenue closed in five years and a billion dollars in revenue managed. With that, I'm thrilled to welcome Frank Fillman, CRO and Country Leader for Australia Salesforce. Prior to this role, Frank was SVP and GM at Tableau where he was responsible for the strategy and execution and growth of Tableau's top accounts. But before we dive into the episode today, finding your next customer is hard, but it doesn't have to be. If you're wondering how to drive more revenue and find the accounts that are looking for your solution right now, ZoomInfo is the answer.

• 1:07Harry Stebbings?

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• 1:52Harry Stebbings?

  head on over to zoominfo.com/20vc to see for yourself and sign up for a free trial of the ZoomInfo platform. And speaking of tools we couldn't live without there, Salesoft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workflow. It's the one place where sales teams can go to prospect, manage, active deals and get the insights they need to coach seller performance, forecast with accuracy and find out what steps to take to close more deals. Some of the world's leading companies like Google, Shopify and Stripe all love a new Sales Loft and so can you. It's the new way to sell. Find out more at salesloft.com.

• 2:38Speaker 02

  You have now arrived at your destination.

• 2:41Harry Stebbings?

  Frank, let's do this, my friend. I've been excited for this one. We had such a good chat beforehand and I was like, shit, I wish we were recording this chat, but thank you so much for joining me today.

• 2:50Speaker 00

  Yeah, great to be here. Thanks for having me.

• 2:52Harry Stebbings?

  Not at all. As I said, excited and Jania said the most wonderful things. So I want to start with a little bit on you. You've run some of the most incredible sales orgs. What was the entry into sales for you, Frank?

• 3:02Speaker 00

  Look, I knew I wanted to be in sales straight away. In college, I worked for a company selling knives and people's homes, the opposite of the job you'd ever go for. I ended up running an office as a college student. I was 20 years old and 75 people working for me in Palm Beach, Florida. It was like getting a PhD in sales. So in undergrad, I'm in finance. It's an overloaded degree everyone's getting at. So I started to pick up some programming classes just to try to find some separation. And then IBM picked me up and I tell you one thing, as soon as I got to sales training, I realized most people didn't have any proper sales experience. And then my first role at IBM was a competitive sales rep. So every account I talked to didn't want to talk to me. So you get to kind of have this like bulletproof skin on you, which is a really great way to get into sales.

• 3:41Harry Stebbings?

  But I wanted to start there. And again, we said off schedule, I'm going straight for it. You said people get PhD in sales.

• 3:47Speaker 00

  Yeah.

• 3:47Harry Stebbings?

  What did you learn in that PhD of sales very early on?

• 3:51Speaker 00

  If I were to stack rate recruiting, the art and science of recruiting, a big part of it is how do you recruit a college student to go sell knives, you sell them to your mom, your aunt, their friend. And then at some point they end up fizzling out, but the ability to recruit, if you can recruit good people, you're going to have a lot of success. And that's carried on with me my entire career, which is if I get the best people and I treat them great. By definition, they hit their goals. I'm hitting my goals and the company's happy. The idea of recruiting the best people and it stuck with me. And then I was an intern for a recruiting firm and I enjoyed that a lot. That's kind of the bedrock of my. Whole approach as a sales leader.

• 4:21Harry Stebbings?

  I do want to start there. When we chatted before, you said how you handle tragedy defines you. I didn't know whether it was okay for me to ask this, but can you unpack this for me?

• 4:31Speaker 00

  We're going deep. We're going right in.

• 4:33Harry Stebbings?

  I can be out of it. I don't know if it's okay, but I'm going to anyway. Can you unpack this for me and how you feel on this one?

• 4:39Speaker 00

  Like, it's about resistance and persistence. I think my job every day is to solve problems. And I think if you have a problem with a problem, you're not going to persevere. If you're okay tackling something that's super difficult, how you respond to that is going to help define you. So like for me personally, when I was a kid, my father passed away when I was eight. My mom remarried. I picked up an incredible stepfather. And then years later, my brother passed when I was 30. But what it does is it makes you really grateful for what you do have, to look for the positive. But it always kind of produced a chip on my shoulder and a feeling of being unstoppable. And it's like, hey, I made it through that. Let's go. And that's just carried on with me through my professional career.

• 5:12Harry Stebbings?

  Can I ask, because it haven't got you in trouble. Sometimes I felt unstoppable and I've done things that are too courageous.

• 5:18Speaker 00

  I do think that it creates a bold mindset and encourages you to go for jobs. For example, that you're unqualified for or go for deals that you're not in a position to win. But the best teams take three point shots and it encourages you to take three point shots. So yeah, you're going to take more risks. I would argue the outcome is going to be significantly better than if you have a more conservative mindset in your career. So I think it just encourages a lot of risk taking.

• 5:39Harry Stebbings?

  Boom. We've gone for an early sports analogy. Good to get the different demographics in there, Frank. Well done. I want to start there on one of my favorites because I go back and forth on this. People tell me I'm wrong. People tell me I'm right. I want to first understand, how do you define a sales playbook?

• 5:53Speaker 00

  Repeatable and relevant. So I think first it's client relevance. So clients don't care about you, your gear, your product, your organization. They care about them, their metrics, their firm. And so it's got to be client oriented. And then for the rep, it's really hard to ramp in a new firm, like probably 50% of reps out there. There's something new. It's a new company. It's a new team. It's a new client. It's a new industry. And so it takes six to 12 months to ramp up. If you can have something that's super relevant, it allows the client to get immediate interest in the firm. And it allows the rep to ramp way faster. So like for me, I always start with the money and I work backward and I focus on TAM. And then I start to build the playbook back from there. So at least I know if I'm on a treasure hunt and I've got a shovel, we've got. People digging, are they digging in the right spot? And I think that's the question that a lot of sales teams miss. They find it later in the year when it's a bit too late. Does that make sense?

• 6:37Harry Stebbings?

  I would love to actually just dig in there so I understand. So you said you start with the money and you work back from there. I'm a founder, help me out. What do I do? And what did you mean by that?

• 6:47Speaker 00

  I think a TAM, there's three elements to it. It's either near or far, right? It's either big or small and it's either known or unknown. That might be overly simple, but let's break that down. It's either near or far. So I'm either going to go on a 12, 18 month sales cycle for a larger deal. Or there's some creating close. Customer needs something and I'm going to go sell it to them. It's either big or small in the sense that I'm either going to take down something that helps my quarter. Or am I going to have a great year? I probably need to go for a transformational deal at my take a year or two. And I want to prioritize and run an and business where I'm at all times going for something big, but I'm chipping away along because you can't always count on a big deal. The third part is the part that I never hear people talk about. It drives me kind of nuts, which is it's either known or unknown. When Steve Jobs creates the iPhone, goes out and does the keynote, no one ever knew they had it and then they had to immediately have what he offered.

• 7:31Speaker 00

  And so it's about identifying problems a customer has that they don't know how to solve. Creating a vision and then encouraging them that you have an opportunity to solve that problem for them. And now you're hunting for a way larger pot of money. And you're actually aligned to what they're solving for. And you immediately differentiate because then it's not you versus a competitor. You're the only one that's going to solve it because you actually uncovered the opportunity for them. And you're bringing them along in a journey and building a vision. And I think that kind of goes back to the iPhone analogy of I didn't know I need it and now I can't live without it.

• 7:59Harry Stebbings?

  Do you have more patience with your sales team for that unknown element? Because you're also then engaging in a process of customer education, which is just traditionally another three to six months at least. Do you have more patience with that? And how do you think about the customer education as an additional challenge to, oh, I get it. I'm replacing something on my budget.

• 8:17Speaker 00

  When I think about an industry playbook, right? What I do is think about the first quarter as a sales rep. The first thing that you're asked to do is create an account plan. That's good. It gets you organized, gets the whole squad and team organized. I would argue that you want to have an account hypothesis and you want to go back and finish that in Q1. So let's take this apart piece by piece. First, you want to identify where the TAM is. Where is everyone going to mobilize and drive an and business? So where are the dollars? Known, unknown, big, small, near, far. From there, then you want to have a set of industry sort of assets. So if you want to drive client relevance and you're going to show up to an insurance firm and you're going to work with like an insurance claims adjuster. They don't want to see a demo of technology. They want to know, how do you make the life of a claims adjuster easier? How do you get to the scene of the accident faster? How do you detect fraud? How do you ensure payment comes faster?

• 9:01Speaker 00

  Like Rosetta Stone-ing everything from technology into the use case and the persona of the person. Now boom, you have an immediate set of client relevance where they go, well, this person really understands my industry. On the rep side, they're not thinking so much about the technology. They're immediately identifying, is there a problem? Can I solve it? And then you're ramping them in weeks instead of months and quarters. And now you jump to stage two in the sales process. So the funny thing is if you identified a TAM and you create a vision and you put an industry lens on it, the client gets engaged faster and the rep gets to go a lot faster. It actually compresses the sales cycle. And now you're finding where the dollars are in April, May or June, not in September or October. You actually have a shot at a good year.

• 9:39Harry Stebbings?

  So I totally get you. What is required there is a specialization of sales teams, the verticalization into industry specifics. So they are able to get up to speed with the customer problems, demands. How do you think about advising founders on how to specialize sales teams? When's enough customer demand? And if you were them, what would you advise them?

• 9:59Speaker 00

  So you ask the word patience. Yeah, that's a big part of it, working with them. But I think the fastest and easiest way to do it is let's say you're going to have an established team that has two or three people on it. You're going to get someone up front, leading like the quarterback that owns the whole process that's been there, done that. You're going to take the high potentials, put them inside that team. And then over time, they're naturally going to learn that process because they're following the leader and they're going to get there a whole lot faster. So doing it one by one as a sales leader would be really hard to like literally teach every seller. But if you selectively build teams in the right way, then you're having the team teach the team. And that starts to drive scalability and repeatability and you're not doing everything yourself. So I think that's the way that you do that at scale. And also if you get really good people that care about each other and they're competitive, even if they're not on the same team, they want to help each other. And you want to reward that and incent that and ask people to step up and help you.

• 10:43Speaker 00

  What you find is the best people, they want to teach. They're proud of their craft. They're proud of what they tried and worked. They want to help the new. Gal or the new guy.

• 10:50Harry Stebbings?

  Do you think that you should hire two reps at the same time? Jason Lampkin always says that you need to have two at the same time. Otherwise, it could just be a shit rap.

• 10:58Speaker 00

  Here's a challenge. If you want the environment where people perform at their best, you need safety. If you want safety, they have to know that you're trusting them, that you've got their back. And if you have two different people competing in the same environment, I don't know if that creates the right environment. I would prefer to go all in and have their back. And if need be, I'll go on sales calls. I'll do all the work with them until they're ready to go out on their own. And that takes a lot of effort. But if you get the right person with the right potential, absolutely, I'll invest in that person for a few quarters or a year, and then they're off on the round. So I would probably just go with one. That's just my gut.

• 11:27Harry Stebbings?

  You're like, what the fuck, Harry? You send a schedule. Hell, whatever. Do you see why I was like, don't bother preparing? It's fascinating you said about safety there, though, because especially in sales, I get it. But you also want a bit of, well, a lot of healthy competition. You want real quarters ending, efficiency, drive, urgency. You create safety with a little bit of fear of not hitting targets.

• 11:49Speaker 00

  Well, if you hire the right people that are just super competitive, it's like athletes on the field. They have the inner jive and the competitiveness that's going to far exceed any pressure that you could ever apply, full stop. That's just the way that I operate. And so for me, if you get the right people involved, a lot of those problems go away. So how do you find fast horses? You hire a fast horse and guess who they run with? They run with fast horses. Go find the best sales rep that you're going to go find and see who they hang out with in the office and socially. They hang out with top performers. They hang out with winners. And so whenever you're in the interview cycle, first question I always ask, full stop, is, hey, top rep, who are your friends? And should I have an opportunity to meet them? Because they're always going to know the best talent. And I think when you bring them in and you drive that competitiveness, all those problems go away.

• 12:30Harry Stebbings?

  How did I meet you, my friend? I went to Shania and I said, who's our sales rep? And he was like, oh, Frank. So I know your game. But you mentioned hiring many times. We're going to get back to playbooks and accounts, but I just want to touch on it because we're so on it now. How do you advise me on the hiring process for sales reps? Let's start that.

• 12:49Speaker 00

  For me, it depends on the account. And so you look at a spectrum of SMB to strategic sales. The answer is going to be wildly different. I'll probably talk about the enterprise. So for me, it's about fit. So if I've got an account that Has multiple reps on it. The team chemistry is really difficult, but I always want the closer up front because they have to carry it all the way from one end of the field all the way down. But I'm also going to want to bring in like a visionary. Sometimes they're more academic, they're super right brain, very creative, they can build a vision and bring the organization along. They may not be as comfortable closing. And then the third profile of people I want to pick up is the person that wants to go hunt and take down every deal. Let's see a bear shoot a bear. That's not something that I was like super talented at. I wanted to go big game hunting, but you, if you're going to run an and business, you need a collection of those different skills and you put them all together.

• 13:32Speaker 00

  You want to find those people and then at a chemistry level, figure out, can they work together? Or do you have two alphas? If you have two alphas, it's never going to work. And I've screwed this up a few times, by the way.

• 13:41Harry Stebbings?

  I want to talk to you on how you screwed up, but I just want to stay on the hiring specifically. So when you're interviewing reps, do you try and put them in a bucket and understand you're a visionary? You're a killer bear shooter bear, you're a closer. How do you advise me on hiring these three different profiles?

• 13:57Speaker 00

  If you ask them what their passions are, what they're most proud of, what's a deal where they created demand that never existed before? If someone's either going to get excited and passionate, or they're going to look at you like you've got two heads. You ask those qualifying questions, it's very easy to determine where do they fit in? If you're going to move into the enterprise and do material deals that are going to break records, you've got to have a closer that's super passionate. So I just ask those qualifying questions and people will make that answer super easy to follow.

• 14:21Harry Stebbings?

  You said create demand that's never existed before. And we chatted before, you said this was one of the most important skills you look for. Can you just explain what that means to me and how I should look for it?

• 14:31Speaker 00

  When we talked about the TAM example where demand is known or unknown, I think, how do you create money that doesn't exist? You go look at the demand that's inbound and then you look at the latent demand that doesn't exist. That's an immediate way to increase the TAM that you're pursuing without hiring any more people. And so when I think of creating demand that doesn't exist and you ask someone that, what problems does a customer have that they don't understand how to solve? Where you've created an answer to them. So go back to like the Frank Slootman example. He worked with different firms where he'd ask clients what they thought about the product and they were using it in very diverse ways. That surprised the organization. So at a product level, they're like, hey, we didn't design it that way, but customers are using it here. Lean in on that and ask them, well, how are you using it? Why are you using it that way? You go back and align that to the long range plans of the organization.

• 15:13Speaker 00

  Chances are there's a big gap in execution where they've got a big vision and a big target. They don't know how to get there. So how do you take a malleable platform and create a vision around that? It says, oh, you're trying to align and move up market. What if you had better insight into the customer profile that you're pursuing? And then you align a malleable platform and create a solution that says, we can help you get better visibility into how to pursue that. So you're chasing larger deals and you're moving up market to the enterprise segment. And now all of a sudden you're a consultant and you're not starting with tech. You're ending with technology. So for me, it's like every conversation starts through the lens of the customer and great empathy. What are they trying to do? And then how do we reverse engineer the product to fit it? It never starts with product.

• 15:49Harry Stebbings?

  Talk to me about negotiation in that process. People often think that comes first. Where does negotiation sit in that process of customer discovery, customer understanding for you?

• 15:59Speaker 00

  I think the biggest mistake is when you just send a price over and then you end up arguing about numbers. You ever see this? You send a proposal and whether it's a percentage savings or the absolute number, it's human nature and negotiation to look at that and then want that number to be smaller. And so sometimes you get lost on all the wrong details. So if it's me, my preference would always be start with a blank canvas, find your buyer and spend some quality time. And I think you'd ask questions of her like this. Number one, how are you measured? What are the metrics that you as an organization, as an individual are measured by at the organization level? And you start to really unpack how they define value and values and what their priorities are. And then you go like a level deeper. What's most important? Is it cash flow? Is it TCO? Is it year one fees? Is it exit fees?

• 16:41Speaker 00

  And you can start to kind of profile what financial levers do you have to play with that matter to them? Commensurately, you've got to be super transparent with your organization. Here's how we're measured. Here's how we report. These are the prioritized levers that we have. Here's what we want. If you do that and then you start to align on deal structure, whether it's like, is it a flat or is it a ramp? When you start to really categorize all the different ways to package a solution. If you do your job right and you're authentically looking for ways to create a win for them while being transparent about what a win for you looks like. Then by the time they get the first offer, it's going to land well because it's very predictable. And then when they counter or you counter, it should be very predictable because they've already told you. They're interested in, and so have you. And it takes something like the gammanship out of it,

• 17:23Speaker 00

  where you're just trying to find a win on both sides. When you start with price, it's really hard to get there.

• 17:28Harry Stebbings?

  You said communicate about what a win looks like for you. I've had founders say to me before, I never want to tell the customer what a win is for me because I always want them to feel I'm in hardship almost. I don't want them to think that I'm profiting. How does one communicate what a win is for them in a way that's beneficial for the progression of the deal?

• 17:44Speaker 00

  We talked a little bit about what sales tactics have changed over the last 20 years. Protectionism, I think things are a lot more transparent. Customers have access to all kinds of data about your organization, about products, about negotiation. The idea of being closed ended, like you have all the information and you don't want to share it. We're 20 years past that. It's about being really transparent. But if it starts with you, I don't think it's really authentic. It's got to always start with them. I was reading a book called The Go Giver, and it's like, how do I serve the person I'm working with and working for genuinely as the priority? And then you back into what's good for you. So I start with what are your priorities? What are the mistakes? What do you not want to see? What's really going to irritate you? If you're going to try to sell this internally, where are you going to catch a lot of flack? And then I say, great, now that I understand this, here's how we are generally measured,

• 18:26Speaker 00

  and here's some overlap. And then what I want to do immediately upfront, areas say, what are the friction points that we could acknowledge? We're probably going to bump heads here. So let's just identify it. We'll try to work through those with a very unique solution. And I think if you do that authentically, someone's going to say, all right, they're showing up, trying to help me out. And I don't know that every negotiation starts that way, but the best ones I've been involved in start that way.

• 18:46Harry Stebbings?

  So many people on the show have said before about the importance of like recording sales calls for training purposes. How do you think about the importance of that whilst also retaining the humanity and the truth elements, which often people will feel less comfortable sharing when there's a recording?

• 19:01Speaker 00

  I think the feedback loop, which is, I think, where you're going. It's less about recording and dissecting. It's also less about waiting a whole quarter and giving feedback. It's really hard and it never lands well. I like to do an obsessive in the trenches process with my team where we spend a lot of time prepping. We do a lot of time role playing. We go to the meeting together and the first thing we do when we're done is we go debrief. And the first thing is like, all right, give me some criticism. What did I do wrong? So it's not like me as a leader talking down to someone. All of us have an opportunity to We're all in this thing together versus like, how am I being evaluated or critiqued? Cause you go back to safety. If I feel like I'm being critiqued, I'm going to get defensive and I'm not going to get the best output. So I don't like the formal process. I like just to say, how do we get better at our craft? So next time it's going to land even better.

• 19:45Harry Stebbings?

  You mentioned before with the closers, the killer bash shooter bat and the visionary, that you've made some mistakes. What are some of the glaring mistakes that you made there?

• 19:53Speaker 00

  Yeah, I've certainly over my whole career. I'd say the biggest mistake I made was trying to team people together that were both alphas. I think being an alpha in sales is really good. You want the natural leader, but if they do it at the expense of other people and there's an ego involved, and then you have two of those together, it will crash and burn immediately. Stylistically, that's where the hair on the back of my neck stands up. And I say, I don't want to go through that again. And I want to be able to pair that person with someone who might say, you know, I don't have as much at bats, pair me with them. They're going to exponentially learn. They're going to get three years of education in a year when they get paired up with the alpha. So it's healthy, it's just not healthy together.

• 20:27Harry Stebbings?

  I totally get you in terms of not being healthy together. I'm thinking about like high alpha, high ego people. And I think about very experienced and also very high potential. When I hear that as a potential conflict, how, and this was actually from one of your friends, Matt, he said, how do you rank high potential versus high experience on the spectrum of importance when hiring leaders?

• 20:47Speaker 00

  That's an easy one for me. It's always hypo, one, experience, two. There's always an exception to that though. I think when you have like a big, mature customer and a big brand with a lot of visibility, you'll always have to take experience first. You don't want someone learning on the job in a very high profile environment, because then you might be setting them up for failure. And that's like not fair to them as a sales rep. With the exception of that, I'll always hire for potential. And I want to take someone who's got a tremendous amount of adaptability and future potential. Give them a job they might be a year away from. Watch them be a little bit nervous and stumble for a quarter. But what's going to happen is they're going to get there way faster. I'll always go potential first.

• 21:22Harry Stebbings?

  My question is, what's a stumble and what's a stumble too far?

• 21:26Speaker 00

  It's almost when you outsource to someone to say, hey, I think you're really good. You've got good potential. There's a big meeting coming up. You've got this. That's crazy. For me, what I want to do, whether it's me or one of my leaders, it doesn't matter who in the stack does this, someone who's more experienced. Get in the trenches with that person and say, look, you've never had a CEO meeting before. Let's figure out how they're going to operate and run the meeting. First off, they might run the meeting and you're just going to have to go along with it. So whatever you're going to plan for, you can just toss right out the window. And you don't know that until you go through it. During the preparation, the role playing, having that senior leader step by step with them to say, here's an experience I went through, but also ideally you have a senior leader go with them on that meeting and they play the role. So maybe they're teeing them up with a softball question that they can hit out of the park. Or they're there in case it goes off the rails, they can hop in.

• 22:10Speaker 00

  But I think having someone riding shotgun with you in the car and then giving the freedom to go take the wheel a little bit is really important. Once you get through that handholding process, you get a few at bats, you'll find the reps like, I think I got this. And then you go, great, you've demonstrated the experience, go. But I think if you start there, you're kind of leaving them out in the wind and that's not fair for them.

• 22:27Harry Stebbings?

  Speaking of like high potential, but maybe not quite there yet. One thing I do struggle with often in enterprises, like enterprise sales cycles are long and measuring rep effectiveness is naturally harder. How do you think about measuring rep effectiveness in strategic sales with much longer sales cycles?

• 22:44Speaker 00

  Let's take two examples. One example is you've got a big account that you're pursuing and you've got two or three reps. The first thing I do is grab the hypo and put them inside of that organization. So they're teaming along with it. If not, I think there's a level of babysitting, and I say that as a positive term, not a negative term, where I'm going to sit side by side with that rep. A big part of my day is I clear two to three hours that I have no plans for. Specifically so a rep says, hey, I've got a big account meeting coming up and I feel stuck. Or I have an account meeting coming up and I want you to join. I can immediately, I will immediately clear my calendar and say, let's get in the trenches. So I'm literally personally teaching them and bringing them along and never letting them out on their own until they're ready to go. I don't think there's any substitute for on handholding, on the ground training.

• 23:27Speaker 00

  And so the only way that you do that is personally getting involved. That's why we just run a super flat organization. I could care less what my title is or what yours is. We all have the client's interest in mind. Let's get together and go. I'm a rep, put me to work. And that's my mentality and I think the team appreciates that. Now you're not sitting in the ivory tower, like you're out there with them.

• 23:43Harry Stebbings?

  But six months in, I haven't closed a dollar. Are you going, shit, Harry's not great? How do we know whether I'm good or not? Cause the sales cycles are so long.

• 23:52Speaker 00

  That's a really good point. First off, you've got to set them up for success. If it's a big account and they're going to do a big buy every couple of years, you can cyclically understand what the odds are of that person coming in. And I think if it's a one to two year sales cycle and you have someone new, maybe it's more of an 18 to 24 month sales cycle. So if you put them in with the hope that they're going to land it in the first year, you're setting them up for failure. So I think you can prohibit some of that. So I think you either give that account to them in year two, or you don't give that account to them at all. I think measuring the effectiveness along the way is predicated on setting them up for success at the beginning of the year. But I also think that if you're a team and you're going on sales calls together, you know if they're doing the job or not. There's no escape from that if you're actually giving them ample time to prep, to go on the meeting with them and to debrief. Your job as a leader is to spot that it shouldn't be hard.

• 24:36Harry Stebbings?

  You said about setting them up for success there. It's one thing that I find a lot of families really struggle with, which is like new rep onboarding, especially when they haven't really done it before. I'm joining your team today. What does my rep onboarding look like for you in an ideal fashion?

• 24:49Speaker 00

  It's a little bit contrarian and we've talked about a couple of pieces, but let's take Humpty Dumpty apart and look at Q1. The first thing I want to do is I want to build an account plan, but let's call that a hypothesis. That way we're immediately starting to take action. We're mobilizing both the sales team and the extended team. But immediately from there, I'm going to pause and say, great, let's go do the TAM analysis. Where's the money? Where's the opportunity? From there, I'm then going to align the sales process to where that revenue opportunity is. And if I'm doing my job right, I'm running an end business. I'm going to pick off some of the small deals along the way. I'm going to go for the big bet and ideally there's a path to hit my quota both ways. So at the end of the year, if I intersect and both hit, I'm going to have a monster year. If one of the two hit, I'm going to have a pretty good year. From there, the third step is we're going to create like an industry playbook. I think playbook, it's sort of this ambiguous term.

• 25:33Speaker 00

  So I don't mean like the PhD version of a playbook. What I mean is I'm a sales rep, I'm about to go on a call. What I don't want to do is go prepare all the materials. I just want to go out and make the sales call. So let's say you're walking out, like I've got four kids. So one of my kids is walking out in the morning to go to school. They don't want to prepare their meal. They don't want to pack the lunch. They want to get the Capri Sun, the apple, the sandwich, put it in a Paper bag, go out and they want to eat. And so if I'm a new rep, I don't want to go figure out everything about my product, everything about the industry and the customer. And go build this whole thing that by the way, all of their peers did. You got to drive a level of repeatability. So what we do is we build industry playbooks. So if we're covering an insurance company and the insurance adjuster, that example we used earlier, we're going to put together five slides. In the industry with 80% accuracy, these are the problems they're faced with.

• 26:18Speaker 00

  These are the solutions where we fit. These are examples where it works. These are the outcomes of customers who have solved the problem with our technology and the outcome of it. And then here's a success plan to get there. And what it does is it doesn't replace discovery, but it gives them a framework to say with 80% accuracy, you're probably going to land well if you use this process. So number one, you know where the money is, you're making the right sales call, you're talking to the right person, you're pursuing the right opportunity. And when you show up, you're talking the love language of the client. Immediately you're relevant, immediately you get ramped and you've qualified out, the opportunity isn't worth pursuing. Or it is, and you've jumped along in the sales cycle. Now you race back at the end of the quarter and you rebuild your top account playbook, you rebuild your account plan. And then now you've got three quarters to find and close the revenue versus finding out in Q2 or Q3.

• 27:03Speaker 00

  And now you're in a race to the end of the year. And I think when you're in a race, it's really hard to perform. How do you ramp them and give them some space to run? That's how you do it. So I think what you do in Q1 completely determines the success of your year.

• 27:15Harry Stebbings?

  How do you create the slides? I know this sounds stupid, but is this like Google slides? And then how do you share them across the team? Cause I love that in terms of a way to run people efficiently, it's fantastic. But what do you use in practice?

• 27:26Speaker 00

  So first off, I drive people crazy. So like I did this personality test a few years ago with my coach. And what I found out is I'm full blown left brain and right brain at the same time. And the absence of focus, I'm everywhere. And so what I have to do is get really focused on what's the idea? How do we prioritize, say on message and then execute with focus? So that's one of those learnings as a leader that I've tried to get better at over time. So a big part of what we do as a team is we want to bring the creative energy and we want to bring the right people. Not to conform to our group, but bring in a lot of diverse set of experiences and personalities and perspectives. So we do a lot of right brain, creative whiteboardy stuff to come together on, hey, we Try these five different points with a customer, three fail, two work. Let's go in on those two. So it's very much trial and error. Mistakes, very encouraged in our group.

• 28:11Speaker 00

  So if you screwed up and the client meeting went poorly, great, tell us so we don't go do that again. And so whenever we build the playbook, don't end up in slides. But the way that we build it, we call it by the people for the people. I'll literally bring in my industry team, my sales reps, my engineers, me. And we'll sit down and say, let's bring together the last six months of learnings. And let's go rebuild the industry playbook based on what's actually working. What's monetizable, even with COVID, the world's changed a lot in two years. If you're not adapting your cycle, it's going to be stale. So you have to do that. And then we put together five very simple point and shoot slides that a fifth grader could read and understand. And then you take that and you say, this isn't the end all be all. It's a template. Make it yours. Make the questions yours, but let it inform the discovery.

• 28:55Speaker 00

  So when you're asking questions, the buyer is like, wow, they did their homework. I appreciate that. I want to lean in and help this person.

• 29:01Harry Stebbings?

  We're moving to the end of the cycle. People are slow to convert. We both know this. How do you create urgency in a sales cycle where there might not be urgency on the buyer's side?

• 29:11Speaker 00

  I think if it starts with you as an organization and what's in the interest of the firm trying to sell it. They're going to see through that. I don't think it's going to work. I think it's got to be through the lens of the client, full stop. So let's take an example. I'm a customer. I'm trying to stand up a new program. That's always going to require people processing tech, but tech's got to enable something to get set up. And they go, hey, we have to go live next July. We don't need it yet. This is Q4. Come back in six months. Well, we go, great. You need it in July. When do you do user testing? Well, we're going to do user testing at bay. So when do you need to administer the technology? Well, we'd probably do that in February or March. Great. So when would you need to stand up the technology and have a contract in place? Well, maybe like January, February. And if you actually take that very logical objection of not now, we're six months away. And you programmatically work back and you create a success plan based on their timeline.

• 29:56Speaker 00

  Chances are they need to get going right now. But you can't make the assumption that they understand it because this is what your job is, not theirs. So you've got to build out this, here's a success plan over the next six months and requires you to start now. And by the way, take advantage of your enterprise buying power at our fiscal year end to get the best technology financial deal. That aligns to your success. And if you focus on their success and their outcomes and a faster ROI table, then they might believe you and want to lean in and buy earlier. But I think if you do it based on what's in the best interest of the firm that you're representing, I don't know that it's going to land as well.

• 30:28Harry Stebbings?

  So the biggest reason I'm on many boards, the biggest reason for companies not hitting targets is, hey, they loved it. They're super keen, but it just slipped into next quarter. That happens all the time. What would you say if you were on the board of that enterprise sales company?

• 30:41Speaker 00

  Yeah, I'd say two things. Number one, in this environment, the first question is, have you adapted a lens on the buying cycle for the CFO to review it? Is there a quant element of value inside the proposal that a CFO who's never met with you, who will never meet with you, who's never used a technology could look at, understand and say, I like what I'm seeing financially? Because we have a new buyer in the cycle that was never there. That's the CFO. And they're probably going to get personally involved in an enterprise deal that's material. And if you haven't evaluated that and haven't like role played that, then you're going to fail. That's number one.

• 31:11Harry Stebbings?

  So we do it at the time. Do we need to do that? Like create a doc specially for the CFO that says, I love you CFO?

• 31:19Speaker 00

  Yeah, no, here's the way I would do it. I was like, after you go through, what are your value and values? What is the problem we're solving? What is the solution? What is the success and roadmap? What is the value? And then what is the pricing? And what is the next step? Like, that's the logical process. Before you get to pricing is the value. And I think the value slide has a few different pieces to it. If you're being really specific here, it's a Google slide. But you've got to think through a few lenses. One is the economic value of buying. Are they getting a good deal? Are they avoiding costs? Are they saving money? And part of that is fee reduction as an example. Another part is, how do you consolidate and do cost reduction in this cycle? Where, hey, I have 15 vendors. How do I standardize on one? So cost reduction or cost savings has a lot of different pieces. The other piece of that is value.

• 32:03Speaker 00

  How do they drive value to the organization? Now, if you've done your homework right and you've asked the questions, you know how they're measured, you've read the 10K, you know what is important to that organization financially, and you've built a value framework that either says time to value is faster, ROI is there, this is going to drive shareholder value in these meaningful ways? And then I think the qualitative value, which I don't think a CFO Really going to buy into is as a side benefit, you might raise sales as a side benefit. You might have happier people as a side benefit. You might reduce your carbon footprint because you've moved to the cloud. Now, these are things that like a CFO would look at and say, first, they've done their homework. Second, my team has validated this. Third, now I want to lean in and not object to it, but maybe ask some questions.

• 32:44Speaker 00

  You're avoiding all of these inhibitors to a sale and maybe enlisting the support of someone that all they care about is financial value. So if you skip it, it's going to be problematic to a sales cycle.

• 32:53Harry Stebbings?

  Do you notice the language and the priorities of your buyers is changing in a new economic cycle? Whereas before they would care about ESG, they would care about team collaboration and morale. And now it's like save me dollars.

• 33:06Speaker 00

  Absolutely. They want to do more with less. Costs matters, efficiency matters. This is when you're going to get more financial buyers as part of the process. If you haven't organized your story around these new evolving priorities, shame on you because their their priorities have shifted. Your messaging and your value prop should absolutely be shifting in alignment with them. Or you're going to be irrelevant and that's your fault.

• 33:25Harry Stebbings?

  The other question I have to ask, kind of given the very influx times, really planning and forecasting, who fucking knows? As a sales leader today, and I know it's very different for different segments, different go to market motions. But just for you, how do you think about forecasting where it's like, I don't know, there might be war. There might be hyperinflation. England may have a new prime minister tomorrow. How do you plan with such uncertainty?

• 33:50Speaker 00

  I think there's three pieces. One is you need a very left brain math model that looks at all the historicals and says, on an average ratio, this is our close rate to pipe. Like there's basic math that everyone should include as part of the cycle. Number two, everyone should be layering in AI to be able to at a predictable level. If you're a big organization at scale, understand trends, because if everyone else in the organization is seeing a downfall in forecast, technology is going to pick that up where if you've got a team of five people in a small territory, you're not. You don't have a chance to pattern match because you're not talking to a thousand reps, but the tool is. The third is I think you need to have like a right brain qualitative review of everything in your cycle. So what we do is we do a bottoms up deal by deal analysis and then we go back and compare it to the math model.

• 34:33Speaker 00

  And whatever AI says and we go, do we believe the truth of this? And I think if you're really involved in your business, if you're like out talking to customers and listening to them and asking qualifying questions, I think between those three or four dynamics, you should be able to call your business. But I think when you look at the Wall Street Journal, you can tell when there's going to be more cost pressures. So like, we spend a lot more time forecasting and truing up and doing like checks and balances now, as you should in this cycle. So you're never going to remediate all of the other risks. But I tell you what you can do is you can microwave it a little bit and take it out of the cycle and have a more predictable forecast.

• 35:07Harry Stebbings?

  It's so funny, you said that kind of about kind of the reps. I remember before the show when we chatted, you said even the best sales leaders want to be super reps. And I thought it was kind of confusing because I thought the point was that reps wanted to be sales leaders and sales leaders didn't want to go back down to being super reps. Why do the best sales leaders want to be super reps, Frank?

• 35:24Speaker 00

  Well, there's two kinds of super reps. There's the good and the bad. So just go up there. So I think if you're a controller oriented leader where you've always got to be the person in the meeting, or hey, I did this, or I'm going to get overly involved, or I'm going to micro this person, that's not great. But I do think if you want to understand how to drive success in the field, if you look at your job as internal and the sales rep is external and you're too far removed from the customer, that's terrifying to me. All of our big deals, we do a weekly review, full stop every single week. What are the biggest deals in the week or the quarter of the month or the year? And what I'm going to do is I'm going to get really involved. And the second I see something go off the rails, great, I have a two hour block in my calendar, cancel whatever you got, let's get on the phone and we're going to spend time rebuilding your entire value prop. And then next week, I want to see how that goes.

• 36:06Speaker 00

  And so I think that's the way that I get sort of micro, but it's in the interest of the rep. And the first question I ask on a big deal review is, what's your goal? Not your quota, what's your goal? What do you need to be financially successful this year? Great, now how do we get there? Here's this proposal. You're not going to get there with this proposal. Let's work together to bridge the gap so you hit your goal. And I think if you do that authentically, you're helping that person and you're not being critical, you're not looking over the shoulder, you're just trying to drive increased odds of success. But in so doing, you've got to be like really in there with the rep. So you got to be like a leader and a sales rep and you just have to be able to fluctuate back and forth.

• 36:40Harry Stebbings?

  You said about the weekly review that I really want to dig in on this. When do you do it? How long does it last? Who sets the agenda? Who's invited? Just walk me through it again. I'm an angel investment of yours. I have no idea about weekly reviews.

• 36:54Speaker 00

  It's an hour and a half a week. The first 30 minutes is free form. Maybe it's because there's an urgent deal and we just need to pivot into whatever senior leadership might need that week, or I have a house on fire we need to solve. Great, let's identify it and swarm. The second hour is very structured and it's a little bit more looking forward. So I might have an hour broken into 20 minute slots and I've got three reviews. Maybe that's this quarter or next quarter. And what they're going to do, very programmatic, is show me two slides. One is the why slide and one is the big deal review slide. In the why slide, what I'm going to do is say, I want you to tell me exactly through the lens of the CEO's long range priorities. Maybe it's a CIO or a CDO or a chief operating officer, but let's take the CEO for the example and say, what are their long range plans? And then you say, great, what's going to inhibit them from hitting that?

• 37:38Speaker 00

  What would be the value of accomplishing those goals? How would you quantify the value of solving that problem? And you kind of go left to right where what's important to them is paramount. And far off on the right, if you have views your binoculars, is the technology that solves the problem, but it forces the rep to think through the client problem through the lens of the customer, not the lens of product. And so it's going to force to say, if you're going to build a vision or a story to solve a problem for them, let's start with what's important to them. Great news, it's a public firm, grab their 10K, do some discovery. This isn't hard. The second thing I'm going to do is a big deal review template, which is going to be a slide that's going to tell me all the mechanics. Who are the players? What's the solution? What's the product? What are the needs? Who's involved? What's the next step? You get the point. And I can true up the right brain, artistic, industry oriented lens of how do we solve

• 38:23Speaker 00

  a big scary problem? And then you true that up to the fundamentals of what they're doing day to day in the field. And the third component is I want the entire team on that call. The industry team, the value team, the solution team and the sales management. And we don't go in picking away at this. We go in as peers saying, how do we elevate our game? And I think taking the fear out of that call and saying, no one's judging. Come in with crappy ideas, like bring all of them, where people genuinely know you're trying to help them hit their goal. You can drive criticism and provoke people in a really good, healthy, competitive way that. Elevates everyone's game.

• 38:55Harry Stebbings?

  You said about the variance of inputs there from your side, from the seller side.

• 38:58Speaker 00

  Yeah.

• 38:59Harry Stebbings?

  In terms of buyer side, like multi-threading, brilliant word, I love how kind of intellectual it sounds. But when we think about multi-threading, often I hear this as, oh, we said about slipping deal cycles. It's like, oh, our champion left. And you're like, well, build multiple champions. How do you think about the right way to multi-thread, at what stage it makes sense, and often mistakes that you see?

• 39:18Speaker 00

  How do you do it? I think it starts with customer obsession. If you really want to understand what the customer needs, I think a traditional sales cycle of thoughtful discovery in a few meetings and being single-threaded into like one buying unit or one person, that's scary. What if someone leaves the organization? Or like you said, what if the sponsor leaves? Like, that drives problematic approaches. So if you really want to get to know the account, you've got to be obsessed. Buy the share. If you're selling to a cellphone organization, go buy the cellphone, go into the store, talk to the retail sales associate. You get to really understand broadly the challenges across the organization in a multifaceted way. Number two, you want to start threading in conversations from like IT to data to the line of business all the way across. The other thing you want to do is have really good top-to-top alignment.

• 39:59Speaker 00

  And I don't mean when it's deal time. I mean like before it's deal time, where there's a thoughtful conversation of aligning, whether it's the CEOs together, or the CIOs together, or line of business executives together. If you take this customer-obsessed mindset, you're going to have that entire organization wired top to bottom. But it's not in your interest, it's in theirs. If someone's stuck, have the bat phone to call your peer, who's my boss? That drives transparency, because at all times, they know they have ultimate access to your organization. When that happens, and there's risk in the cycle, you don't have to worry about it, because you've got the entire place wired. And so I think if you've got like an obsessed mindset, you're going to have every angle covered. And when one predictably falls astray, great news, you remediate that, but everything else is going to stay in place.

• 40:39Harry Stebbings?

  When you think about the set of alignment there, selling into very strategic larger accounts takes a lot of challenges from a product perspective, whether it's SOC two or any of the security requirements. Where do you think are the biggest, not misalignments, but alignment gaps that sales faces? Is it with product? Is it with legal? Is it with design? Where are the biggest misalignments that sales has with other functions within the organization?

• 41:04Speaker 00

  As my career has grown, what I've noticed is a big part of my job is dealing with all of my parallel, my peers, the extended team. Like that's in some cases, the majority of my job. By the way, the first question I always ask every time I meet with those leaders, how are you measured? What do you need from me? And this is, these are the three things I need from you. And do we have agreement and alignment on what those priorities are for both of us and what the expectations are? So every time we talk, I don't want to go through everything else. Let's start there and then we'll cover the rest of it. So I think like an area where it's really hard right now is customer success because the customer might beat them up. The sales team has very different goals than they do. And what I find is a lot of time, the sales team doesn't understand how success is measured and paid. They don't appreciate the challenges of how hard it is to be a success manager because everybody wants something from you and you've

• 41:48Speaker 00

  got to be everywhere. If you're measured against everything, you're measured against nothing. And so I think one way to kind of make that problem smaller, bring success on the sales calls with you. Make sure they're client facing. Have them come in and don't do a quarterly business review. Have a success review and elevate them, put them on a pedestal, put a spotlight on them, make them successful. The client's going to appreciate that because you're not just trying to sell, you're trying to drive value. And now they're critical path in the cycle. And what otherwise would be a lagging function that's trying to run and chase up and make everybody happy. Now they're critical path. And if you have a big customer and they do a big buy, now you're going to have to otherwise go grab the success person and bring them in and say like, I need you to do all this stuff. And they don't like, I don't even know what they bought. And so how do you make them successful? You bring them along during the process and treat

• 42:31Speaker 00

  them like a teammate and make sure they know that you're helping them hit their metrics. And that's going to be one way to help them.

• 42:36Harry Stebbings?

  Final one for you, which we stuck so much to the schedule. I'm so glad about that. I literally spent hours on these schedules. I don't know why I literally bother anymore, but anyway, it informs my mindset or some bullshit. Compensation wise, how do you think about constructing the right sales comp plans? I have a lot of early first time founders that are like, I hit like five to one. How do I think about the right sales comp plan for my sales team?

• 43:00Speaker 00

  The biggest challenge you want to solve is alignment with how the company reports to their shareholders, whether that's a private or a public company. How is the company measured? And then make sure there's alignment all the way down to how the sales rep is paid. I think in the absence of that, there's going to be a tension point where what the customer Wants and what the rep wants is wildly different from what leadership wants. And then you take the salespeople, whether it's a first or second line manager, they're in the middle getting squeezed. Where the people above and below them want wildly different things. And that creates a lot of tension in the cycle. If you've got full alignment, that this is how the organization is being measured. This is how the reps being paid. You're driving aligned incentives and then everything starts to work a lot better. So I think if that fundamental principle is there, the other problems start to work themselves out.

• 43:38Harry Stebbings?

  Was you a hardest job today? What's the biggest challenge you were offering?

• 43:42Speaker 00

  When you think about talent, bringing the right people in. Okay, let me ask you a question here. You ever bought a house, apartment? So you go through the process. When I bought my house, it was nice foundation, terrible color, terrible decoration. And so what happens is most people go through this process of buying a house. And they look at it and if they can't see the end state, they don't have the vision to do so, they're not going to buy it. So I literally told my agent when I bought my house, I was like, I'm so glad this color of this house was rust red. She goes, no one else said that. I'm so surprised to hear you. I said, well, if it was white, it would have been sold a year prior and I wouldn't have been able to afford it. So quite literally, the idea that people that can visualize the end state, that's a very powerful tool. And it's very rare to be able to do that. And by the way, customers have a hard time doing that. They're busy, they're stressed out, they've got a million things to do.

• 44:25Speaker 00

  Finding people that can be visionary, that can imagine the end state and then creatively reverse back engineer through the lens of the customer, the challenges that they're going to see and then how to remediate that. And then bring that to life and take the customer on the journey and inspire them and excite them. And then get them to the state mentally where they believe you and they see what the outcomes can be. That is an art that is extremely difficult to find. And when you can find someone who has it, you grab them, you bring them over and you just give them all the resources possible and you try to retain them as long as possible. That is a skill and a value that's very difficult to find. That and teaching people to communicate with senior executives, hard to find skills. And so I appreciate that when I see it.

• 45:04Harry Stebbings?

  All of my career, I've been told I'm not experienced enough. I haven't put the yards in. And I'm like, I get it, but what if I can? What if you're wrong and I'm right? And it's like the visualization of, I get you, but let's see like in my mind, what it looks like if I'm right. And I think I am seeing what others don't in terms of the uncapped.

• 45:22Speaker 00

  And here's the deal here, that's a competitive. Manage, right? And so you recognize that like very few people do that. What they want to do is just hire more people. The ability to capitalize on that is rare. If you get really good at something other people don't pay attention to, I think. That's probably one of the things that makes you great.

• 45:36Harry Stebbings?

  I could talk to you all day. I want to move into a quick fire round. So I say a short statement, you give me your immediate thoughts. Does that sound okay?

• 45:42Speaker 00

  Let's go.

• 45:43Harry Stebbings?

  So what sales tactics have not changed over the last five years?

• 45:46Speaker 00

  Listening, discovery, personal relationships, face to face.

• 45:50Harry Stebbings?

  Covid, that changed a little bit, no?

• 45:52Speaker 00

  Well, it changed, but the need for it didn't change. So now that we're cycling back to face, what I'm finding is it's really difficult to build relationships when you're remote. It's easier to retain them over time. But I think what I'm finding is the absence of face to face, something is missing from the cycle. You've got to find a way to recreate that, acknowledging that it wasn't there for a while. We've got to bring that back.

• 46:12Harry Stebbings?

  How did your sales approach change remote with Covid?

• 46:16Speaker 00

  I'd say there's two things that I learned in Covid. One is if you're a hunter rep, if you're like an SMB, it's really hard. You're trying to build a relationship from scratch. Fortunately, we were in the enterprise space, so we didn't have that. But in the enterprise space, I think one thing that we would do is we build like a big executive briefing. And we would send Uber Eats gift cards to everyone who would be a part of that briefing. And we would have like a really nice digital experience. And we were trying to bring in the events team and get really kind of clever and crafty and make it fun and exciting for the customer. And then on the internal side, we would do a lot of virtual happy hours at the very beginning when people were scared. How do you kind of bring morale up, get people connected? But I think now that we're on the back end of Covid, the value of face to face, when you can do it and it's safe, we need to bring that back.

• 46:56Harry Stebbings?

  Tell me, what sales tactics have died a death, Frank?

• 46:59Speaker 00

  Hiding information, the idea of solution selling, which is I have information, you don't, and I'm going to tell you what. People have wild access to information on your firm and the organization and the product. I think recognizing that and being super transparent and coming in saying, tell me what you know about it and being really authentic with that. I think hiding information and trying to be protective, that's 20 years ago.

• 47:19Harry Stebbings?

  Love that little body motions. That's brilliant. For people on TikTok, they'll love it. For those listening to the podcast, I think, what the fuck is going on? What would you say is the biggest mistake founders make when hiring sales teams?

• 47:30Speaker 00

  I think there's a maturity curve of an organization going from a few customers to really big in scale. And I think as you start to hire the sales team, you're going to get to a maturity point where you want to move up market. Customers have a different expectation. And I think trying to train folks that don't have the enterprise experience and convert them over, I don't think it's setting them up for success. I think you need to be able to find folks that have done this before, that bring in the top end of the game, and then having really good segmentation, SMB, commercial, enterprise, and then alignment by industry. You need to hire the proven team that's got experience doing that. Your customers expect it, but you still want the other team to be able to manage the lower end of the business because they really know the organization of the product. So I think it's a compliment to those two things.

• 48:10Harry Stebbings?

  What's more important, my friend? Experience on deal size or experience on industry specific?

• 48:16Speaker 00

  I think everything starts in with the customer. If you understand their needs, I think everything else is going to work better. I do think in some particularly large deal cycles, you don't want to give someone an at bat where they've never really been in the big game before. That's not really fair. But if I had to stack rank that, industry experience and driving client trust and relevancy, you can reverse engineer everything a lot easier than having big experience on a deal, but not understanding what's going to make your customers successful.

• 48:41Harry Stebbings?

  What advice would you give to a sales leader starting a new role today?

• 48:44Speaker 00

  It's not about you, it's about your team. So I always think that you want to put the customer first. I think you got to put the employee first before the customer. It's always been kind of wild to me that folks would be self-focused as a sales manager because by definition, you're as successful as your team is. And so like I was just reading the book, The Go-Giver, I want my team to be more successful than I ever have been. I want them to be able to create wealth for their families. And so I think the more that I work for them, I serve them, and they know that, and I'll do anything they need for me to do. So I think just running a very flat organization, being very selfless and driving their success, what I've found is not only do they end up producing, it creates a level of incredible loyalty that you really weren't planning on. Sometimes they don't want to leave the nest even when they need to. So it's kind of simple, but I don't see it enough.

• 49:26Harry Stebbings?

  What would you most like to change about the world of sales today?

• 49:28Speaker 00

  Empathy. I think we need to really remember how Hard it is for our team. Go look at the last two years. How hard is it to be a sales rep who might have joined an organization and after two years never actually went into an office? To be able to like get in the mindset of a sales rep who's never actually been in, they haven't met their comrades, they haven't met the customer face to face and remembering just how hard that is. And as you go farther up in the organization, more and more of our job as sales leaders is internal. But if you get too far away from the customer, you get too far away from the rep, you forget how dang hard it is to do their jobs. And so being empathetic and spending quality time with them keeps you humble, keeps you relevant. So that's probably the one thing I change.

• 50:03Harry Stebbings?

  Final one for you, Franco. Love this. What one company sales strategy have you been most impressed by recently?

• 50:09Speaker 00

  For me, it's Miro. Now that everything's been remote and of course, we're trying to like ramp that back. I'm super right brain, super creative. I like to grab a whiteboard in an office and work through stuff. I'm super visual. It's really hard to do remote. I put like a whiteboard up my office, my wife throws it away. And so Miro is like the technology that enables the ability to feel connected as a team, have a connected sort of set of tools that bring all these disparate ideas together. And allow the team to rally when you're remote. And then that's now in digital format that you can bring into the office and extend it when you're in person. So that's really been something that's helped us in the last couple of years.

• 50:41Harry Stebbings?

  Frank, I've loved this. You are a hero. You put up with so much shit from me. I honestly really love this. It shows like this, which make me love what I do. So thank you for being amazing and you were fantastic.

• 50:51Speaker 00

  Yeah, well, listen, I've never done this before. I've been like not anxious, but I'm excited to see what the outtakes look like.

• 50:59Harry Stebbings?

  I have to say, Frank, you're just such a fun person to hang out with. I absolutely love doing that show. If you want to see more from us, of course you can on 20vc.com. Likewise, you can find us on YouTube by searching for 20VC. But before we leave you today, finding your next customer is hard, but it doesn't have to be. If you're wondering how to drive more revenue and find the accounts that are looking for your solution right now, ZoomInfo is the answer. ZoomInfo handles the full revenue pipeline from marketing to sales, even ops, all based on the number one ranked business data. It's the single best way for B2B professionals to find their next customer, close their next deal and streamline their operations. Best of all, it's all in one place. So your revenue team. Can collaborate easily and close deals faster.

• 51:44Harry Stebbings?

  Customers include the likes of Snowflake, Workday, PayPal, Dropbox, and thousands of startups and growing companies. Now 30,000 customers and growing. And ZoomInfo is making their go-to-market playbook available for free for anyone to try. So if you want to find out how you can use intent data to target key prospects, or how to revive a stalled deal by expanding your buying committee outreach, head on over to zoominfo.com/20vc to see for yourself and sign up for a free trial of the ZoomInfo platform. And speaking of tools we couldn't live without there, SalesLoft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace. It's the one place where sales teams can go to prospect, manage active deals,

• 52:30Harry Stebbings?

  and get the insights they need to coach seller performance, forecast with accuracy, and find out what steps to take to close more deals. Some of the world's leading companies like Google, Shopify, and Stripe all love a new SalesLoft, and so can you. It's the new way to sell. Find out more at salesloft.com. As always, I so appreciate all your support, and I look forward to bringing you an incredible episode on Friday with Yub Kim at CalPERS.