The Sales Process is Stronger than the Outcome

Robert Simon 

Sure. So Now Vertical is a vertical intelligence software and services company, and the fundamental mission is to help a variety of different companies unlock the value that they have hidden inside their data, their stack, and their people by applying really specific industry expertise and technology to deliver solutions. And when you think about how theoretically, the points between data and decision should have shortened over the last ten years, they haven’t. Right? And there’s a number of reasons for that. And so we’re really passionate about enabling a number of different verticals to get really powerful with the data that they have. So, quite frankly, they can make decisions in the month, in the quarter, to do transformational change. 

Hessie Jones 

Okay, cool. I assume that you guys are taking advantage of all the generative AI stuff in order to make this possible. 

Robert Simon 

Yeah, we have a number of, like, machine learning, deep learning, AI models, an incredible tool set that goes all the way down from data discovery, it’s data illumination, insights, and analytics. So anything where there is a person or a process or technology that’s needed to extract value from data and develop predictive analytics or do a number of really sophisticated modeling. 

Hessie Jones 

Okay, see, that’s cool. And to me, that’s an example of a really good sales pitch, because within 10 seconds I understood exactly what you do. So let’s talk about sales from the perspective of an individual. It’s not for everyone. It’s hard. I do part of it in my job as well. And it’s arguably one of the most important roles in an organization because it’s tied directly to revenue. There are tons of benefits. People can make lots of money when they’re doing sales, but it can also be a role that has tons of responsibility. More, I would say, than what your average role would be in an organization. So for you as someone who’s actually been in sales for some time, what drives you? 

Robert Simon 

I mean, it’s an interesting question because there’s easy ways to answer that which are disingenuous. And I thought about this when we talked earlier. It really is the discovery of something and the potential in something. And so what I have always found fascinating about this career is the people that you get to talk to at any different state of where they are in the problem they’re trying to solve. They will share things with you. And if you’re good at your role and you build rapport, you get to learn things about a company or an industry that you would never learn without being inside that company or industry for decades. And so I find that fundamentally compelling. It’s like, why is it so broken? Explain it to me! And then they explain it to you and you’re like, ‘I had no idea.’ That was fascinating. That is just fascinating. So I love the discovery of where so many problems inside business are created by human inaction or human misalignment. And they know it, but they can’t get over their apathy and they don’t know how to solve it. And so being a part of that energy to say, ‘let’s do something really compelling and interesting,’ I think is just a great way to spend every day. 

Robert Simon 

And the money is good too. 

Hessie Jones 

It reminds me of what someone said to me, that even during the sales process, if you could speak less and listen more, you could probably be one of the best salespeople out there because you’re getting them to actually surface a lot of the problems that they’re saying. Right? 

Robert Simon 

Yeah. And I just got off a sales training where I had to coach them because they’re founders. And I said, ‘listen, you can’t talk for more than two minutes and 45 seconds and you’re going to put a watch in front of you, and when it gets to that 2:45, you’re going to stop talking. And if you don’t know how, then I just want you to say, I’m going to stop there and see if there’s any questions.’ Because if they don’t, they’ll talk for seven minutes. 

Hessie Jones 

That’s right. Ad nauseam, to the point that they don’t even know whether or not what they’re pitching is what the buyer wants. 

Robert Simon 

Very true. 

Hessie Jones 

Okay, so let’s talk about some of your first experiences in sales and how it’s actually changed because you’re selling transformation many years ago. Not that many, but years ago. And I’m sure sellin?G to a buyer then was much different. 

Robert Simon 

Yeah, I think that what has changed and I hadn’t really thought about how much it has changed from like if we go back to 2008, 2010, it was consultative invention, right.? They were as reliant and trusting on us as a sales organization to bring them insights and information as to how to get something accomplished because the toolkits didn’t exist like they do today from a development perspective, from a marketing perspective, analytics perspective. And so when someone wanted to do something transformational, they had to trust that you had both the consulting services, the application, the development services, to not only frame and understand the requirements, but to build confidence in it. Now, a buyer can find all different types of frameworks and case studies and past experiences in ways of having to accomplish similar goals. They can really do a tremendous amount of research in depth and build a level of confidence before they even engage a salesperson as to how they think their solution should progress. And then they’re going into market to vet everything that they’ve learned through a number of different channels. That’s completely different than the way it was when technology was just being brought into bear at scale. 

Hessie Jones 

So from that perspective, you as a salesperson may not necessarily get to control the conversation because you used to be the smartest person in the room when it comes to the solution. 

Robert Simon 

Yeah, I think that is where it has evolved from. You need to be incredibly valuable to people at every stage. It doesn’t mean you’re the smartest, it doesn’t mean you know everything. But it means as a salesperson, you understand when there is a gap and you can fill that gap with valuable information that’s either proprietary to what you do as a solution or it’s just part of the industry that they’re not aware of. So being valuable is incredibly important more than given the appearance of being the smartest person and engagement, you ultimately want to listen to deliver value back. 

Hessie Jones 

Okay, so for you in your career, what do you think is one of the key drivers of your success? Because there’s a lot of people out there that have done sales and everybody has a different driver in terms of what makes them stay in sales,m what makes their job important. What is it for you? 

Robert Simon 

The way I’ll answer that is think about what do I think is important for when you’re hiring new salespeople moving forward? Based on what I have felt has made part of that success, I think that you should be looking at any salesperson inside your organization today or you’re bringing in intellectual curiosity and resilience. I don’t think anything else is going to matter in the next two to three years. They have to be intellectually curious because the nature of change and disruption is so rapid. The sources of information in order to understand where value can be controlled and manufactured and delivered are so diverse and they have to be resilient because you are going to need to be in a number of different channels, repeatedly in different avenues and fail at a much higher rate than succeed than ever before. And the market just seems to do crazy things every year, whether it’s because there’s a global actor who’s decided to transform the market for us or there’s something that we did collectively that was stupid, that decided to transform it. I don’t think that’s going away. But the impacts of that we feel constantly. 

Robert Simon 

So the lack of resilience in your salesperson/salesforce is going to ultimately hurt you tremendously. 

Hessie Jones 

Where does, I would say, compensation as well as competitiveness play when it comes to motivation with respect to what you’ve already mentioned, curiosity and resilience? Do you think those things are sustainable? 

Robert Simon 

Yeah, I mean, absolutely. So the best sales organizations create really good opportunity to deliver on your OTE, right? You’re on targeted earnings above your base. So having a great base that’s competitive is going to be table stakes. But having a sales commission structure that isn’t punitive, that isn’t loaded with 50 variations of a claw-back, that pays enumeration in a period that is logical and makes sense, is going to be competitive when you’re looking to hire people. Eight out of ten salespeople have no idea how they get paid. By the time you get to the middle of the year, your compensation structure has likely changed so much that you’re not really sure what the multipliers are over on top of. You just know roughly you’re trying to make an additional X on top of your base. But I would argue that most salespeople you talk to at some point in the year have no idea how they actually are going to get paid when it comes above their base and their variable. 

Hessie Jones 

Okay, so let’s talk about things like, I guess from a startup perspective because they are our audience and they’re developing tons of these new and different technologies all the time. In the early days before you actually have a salesforce, it is the founder or founders who are probably the most effective at delivering the sales message as they start to grow their company. What are some of the things that they should take into consideration when they’re starting to sell their solution to some of these larger organizations? 

Robert Simon 

I’ve dealt a lot over the years of founder-led sales transitioning to a professional sales organization. And there’s a couple of things that I think that as a founder you can do immediately that are sales methodologies, that are just going to apply a different outcome for you. So one, really get clear on your ICP, your Ideal Customer Profile. And so this is an understanding of how they view the sector, the sector pain, and their company pain. So why they fundamentally need to buy something. Not you. Right? The mistake and I just went through this a few weeks ago. They gave me their ICP profile and it was all about buying them. That’s not what they show up to do. Your buyer never shows up to buy anything. They show up to do their job. So the reason they need to buy something, you have to be really clear on and understand what the pain is driving that. Get that codified or written out and then understand how your value proposition maps to that or doesn’t. It may not be perfect, but you need to understand where there is a really good connection between where you see pain in the sector with your particular buyer and how you think that you can resolve that. 

Robert Simon 

That starts the core of what your messaging and your outreach and your conversation should be about. The mistake that I think that almost any founder will make is they think that their founding story is really interesting and it is for maybe a couple of slides. And then it’s really important to stop talking about yourself and start talking about how you can be a solution to a problem that you built the company for. Right? So stop talking about the company and start talking about the problem and why you’re interested in solving the problem and then get that person across the table from you to explain the problem back to you in a way that makes sense and is meaningful to them. That’s how you need to start to transform a lot of your sales process from the very beginning. 

Hessie Jones 

Okay, now before we even get to that, let’s assume when you’ve identified, let’s say, what your ideal customer profile looks like from a channel perspective, once you start to identify what the profile looks like, how does that look like tactically? Let’s say when you go out to a sales navigator. 

Robert Simon 

It’s a great tool. 

Robert Simon 

Yeah. Okay. So from a tactic perspective, there’s three things that you always want to have and let’s call it a cadence. Your cadence is orchestration of sales activities over time where the number one goal is never to sell the company, but it’s to sell time with you. So when you are doing outreach, you are literally trying to convince someone to spend 15 to 30 minutes with you to talk about the potential of what you can do as a partnership, not to explain everything that you do. So from that perspective, you are going to build out a list of people and you’re probably going to look at maybe 150 to 200 to keep it manageable. The reason when you do that is you want to do elements of personalization when you send them a LinkedIn inbox request or you send them an email because you’ve procured their email through another third-party platform. And then you’re also calling. So you are doing a mix of email, manual, and automation. You’re making calls, hopefully calls based on triggers and I’ll come back to that in a second. And then you’re also doing social outreach generally on LinkedIn where you’re asking to make a connection with them, and then you’re following up to hopefully book time together through an email request or furthering the conversation once they’ve connected in with you. 

Robert Simon 

Phone calls work and work tremendously well. It’s doubtful as a founder that you’re going to spend 3 hours dialing and making 90 calls. So this is where having a platform like an outreach or an Apollo, where it can tell you who inside your list is creating actions, who’s transitioning from being a lead to an MQL, who’s opened it and clicked on it because those are the ones you want to partition out and call. Those are the ones that you want to jump into and trigger on social media as well. So you’re going to use the type of engagement platform against your list to say the limited time I have as a founder to generate activity should be really directed by action that’s coming from the prospect. So make sure that you set up that capacity so that you can use your time effectively. 

Hessie Jones 

Okay, so it seems like it’s a repeatable process that you have on a day-to-day basis to say I’m going to reserve X amount of time for outreach and then follow-up is going to be here. Is this the kind of cadence that you’re talking about? 

Robert Simon 

Yeah. And you’ll basically run a cadence over, let’s say 19 to 20 days. So in your mind you’re saying, “I have found 200 people that I absolutely want to talk to and I’m going to spend the next 20 days probably touching them eight or nine times over that 20 days across different channels to try to get them to say yes, to take a meeting with me.” And then once that goes through, you cycle into the next group and the next group and then you can come back. But the mindset is finding that initial set of really tightly aligned prospects, thinking about what I said earlier about understanding the pain that they have and the value prop and your messaging is based on that to really compel them to take action and to spend 15 or 30 minutes with you. 

Hessie Jones 

Okay, so let’s get into the pain. Tell me more about the discovery and understanding the clients pain points. 

Robert Simon 

Yeah, there’s a lot of methodologies that you can apply to the sales process, but let’s assume you’re just working instinctually. There’s still things that you can pull in from like a medic or a sandler that can be really effective. So when I talk about this with new people who are leaning into sales as founders, I say there are three things that you want to know about any deal, right? And when you think about paying one, why do they have to buy anything? What is the fundamental driver? Why should they buy you? Right? How does that connect into what you provide or service? More importantly, why buy now? And why buy now comes a little bit into deal orchestration and moving it through, but focusing on the first one when you’re building the pain is you want to understand what’s working, what’s not working, what are the impacts of what’s working and not working. And the advancement in your deal qualification and sales process will come not just when you ask the questions like, ‘Hessie, I see that you’ve been struggling to acquire customers within this particular market. What’s been holding you off?’ And then you tell me, and the smartest way to really build the rapport, the relationship, and the value of peace and discovery is to say, ‘well, what does that cost you?’ 

Robert Simon 

You say that you struggled. Is that a percentage-based question or is it a revenue-based question? So what you want to understand about the pain is not just the way they articulate it, right? Do they run towards it saying, ‘I can’t wait till we can solve this. If we can crack this market, it’s going to be amazing?’ Or are they like, ‘I just want to get through this quarter, it’ll be behind us, and then we can move on to a different I just need it done’? So understanding how they feel about the pain they want to solve is important, but more importantly, you have to get them to quantify it. The more metrics they will share with you early in discovery will help you shape the conversation in a meaningful way at every single stage, because then you start dealing with the practicalities of the business and what they’ve been assigned to do. 

Hessie Jones 

Okay, so give me an example. Let’s say you’re talking to somebody and you want to sell a specific solution and they’re not ready for it. They’re saying, ‘well, we have this installation that we want to do in the next 30 days. Let’s get back to that. I can touch base with you in the middle of, let’s say, six months from now.’ How do you deal with, I guess, the balance of customers who may be ready today versus the ones that may not be ready in the future? Because you have a portfolio or a hit list of the number of target accounts. 

Robert Simon 

A couple of things. So one, it’s always good to dig into when they do that deferment. They’re like, ‘well, maybe we’ll do….’ Find out why it’s okay. And ways to do that is, ‘you know the last three conversation I had. They really felt they needed to move this particular initiative forward because of X, Y and Z. So what’s different about what’s going on inside hessiejones.com that you feel that you can put it off six months? Are you seeing success somewhere else? Is it just not a priority?’ 

Robert Simon 

And then they’ll give you more information. And that’s the information that you can then use to build the nurturing communications, the reconnection point, because it gives you the understanding of why. Or you may find out that really they honestly just don’t care about solving your problem. And this is the thing founders need to understand. A great conversation does not make it a deal, right? Sure, you met someone compelling and they loved you and loved you do. That doesn’t mean it’s a deal. Did they share a problem that you can solve? Did they share metrics around the problem? Did they agree to set a next meeting on the same call? 

Robert Simon 

Did they confirm that this is something that they are looking to solve actively? They’ve assigned budget to it and it is a problem they want to solve. Have they talked about other players inside the organization who need to be a part of this solution? None of those things happened. It’s not a deal. Right? It’s not a conversation. And so part of what you’re saying is there are some things that I would encourage founders to just unqualify. Put it into a nurture and come back to it later. And then spend that energy on qualifying the deals that you actually need to. So don’t waste energy on people that don’t want to solve problems the way that you do. When you’re building a company, spend your energy on those that want to solve the problem and who are interested in hearing what’s different about the way that you do it. 

Hessie Jones 

Interesting. 

Robert Simon 

The trick is qualifying those out because you will get suckered into people who just want to drag you along for weeks and weeks and weeks. And unless you get really diligent on qualifying those deals out, you will waste time on them for no reason at all. 

Hessie Jones 

Now, have you ever been in a situation where you have a solution to a specific problem, but the client identifies a different use case that you may not necessarily be ready to do today? It may be something that almost requires building some kind of customized, I don’t know, feature for them. How do you handle those kinds of things without actually putting your own product and service at risk? 

Robert Simon 

Yeah. So without knowing the specifics, my advice is don’t do the deal. Right? Because it is a horrible feeling to know that you’ve sold in a deal that’s based on a feature roadmap. That’s as precarious as can be. You are just waiting for the moment for someone from product to call you and tell you, ‘you remember when we said we’re going to do it in Q1? It’s actually going to be Q4 now.’ And you brought in a deal where they mapped all of the roadmap delivery on their end to Q1. So don’t do it. You will build trust, respect, and you will absolutely close that deal when that feature is ready, right? They will always come back to you if you say, ‘Hessie, listen, the product team is working on that, but they feel that they’re four to eight months away. So if you to ask me when is the best time for us to do this deal and start the service, and I am going to tell you it’s going to be August.’ And you say, ‘you know what, Robert? That works, that’s totally fine.’ And you’re like, ‘okay.’ 

Robert Simon 

I mean, there’s ways to stay engaged or there may be ways to partition the deal and advance it, but my advice is do not bring in a deal based on a future that does not exist. 

Robert Simon 

Your job as a salesperson always is to sell the best version of the company that exists today. Right? You have no ambition for the future. You don’t care about it because it doesn’t exist and you can’t sell it. You only care about what exists on the plate today that can be monetized, commercialized and made value to somebody else. Nothing else is a reality to you. 

Hessie Jones 

And that makes sense. I think the one thing that some founders do also, it’s really hard, is revenue is revenue, right? Revenue pays the bills. And if it has to move us a little bit away from what we’re doing, then so be it. But I think you’re absolutely right. Okay, so what other words of wisdom do you have? 

Robert Simon 

Well, I’ll expand on that because you raised a really smart point, is that, yes, you can get clients that can help you build features into your product and pay for it. We’ve all been through that cycle. Well, not all of us. And it does work and it’s helpful. However, almost every company that I’ve been to that’s been through the startup phase or is in the startup phase and has done that recurringly year over year, they have incredible technical debt and complexity that they then need to unload. 

Robert Simon 

Yes. Be opportunistic you’re right. Right. Like, let’s be practical, right? If Bell comes to you and says, Hessie, we love what you’re doing in your software company. We want to do a deal, half a million, and you’re going to build a completely new version, a branch of what you do as a software. But it’s valuable and you’ll be able to commoditize it later. That’s great. But if you do that five times and then what you have is this completely fractured sense of who your product is, a completely different sustainment and selling culture against each of them, you haven’t bought anything else other than a nightmare. And you’re just waiting for that nightmare to hit, which is like ‘Hessoe, you now need to grow the company 50% over the next two years. And you’re like how? Which lane? I built five lanes. They’re kind of all valuable, but I don’t know how.’ So you’ve made a huge mess to yourself, and technology is a huge mess. So evaluate seriously when someone does want to say, ‘you know what, we love what you’re doing as a company. I want to give you a ton of money to get you there and help build that.’ That works great. Just don’t get addicted to it. As a management team, as a founder, don’t let the salespeople convince you it’s the best way to go because it’s an astronomical commission for them. 

Hessie Jones 

Wise words from a salesperson saying ‘don’t let the salespeople convince you.’ Okay, so anything else that we missed in your words of wisdom? 

Robert Simon 

No, I mean, what I would wrap up is if you were a founder and you’re getting serious about ramping up your sales, get serious about understanding how to qualify deals. Because that’s where you are going to save and build your businesses. Your time is more important than your actual intellectual capacity when you’re building your pipeline. So get really diligent about how to understand how to do that and get really diligent about targeting where you’re going to spend your time. Make sure you understand who these people are, who they are as buyers, as professionals, so that your outreach can be as effective and optimized and do it in a platform. So you get some metrics, right? Even some base-level metrics to help you key in and trigger. It’s all about managing, your go-to-market, your time allocation, and the time that you’re going to spend when you think you have a prospective opportunity, but really you don’t. 

Hessie Jones 

Okay, now so you’re going through this process and you’re measuring success. How do you know when you are finding these increments of success within each of these stages? 

Robert Simon 

Okay, yeah, that’s a good question. Lots of ways to answer that but I think from the very beginning, if you’re starting, you want to look at how much of your outreach is converting to first meetings. So keep it simple. I reached out to 200 people. That’s really maybe 2200 communication touches throughout a month, and I got five meetings. All right, that’s great. How many of those five meetings move to the next stage, meaning they’re really opportunities? Was it just one or was it three? If it was three, that’s great. What worked? Can you replicate it? And then the next thing I would stop is at stage two is how many of those deals died at stage two, whatever that is for you. Demo, qualifying, because if you start to focus on just those three things, net new meetings, stage one conversion, stage two conversion, you’re going to understand how good of a job you are doing at outreach and qualifying without getting lost through the whole deal cycle, which doesn’t matter yet because you’re still getting dropout at stage two. So I think focus on understanding the dropout from net new means to stage two, and you’re going to find a lot of forensic evidence to improve your deal qualification and your outreach. 

Hessie Jones 

You might have already answered this based on what you said. So you have a winning formula when…… 

Robert Simon 

Oh, I would say your forecast accuracy. You have a winning formula when you are confident in your forecast at the end of the month, when you know that you have maybe eight deals or 18 deals that are sitting at different stages, the ones that you’ve committed to bring in revenue. If you feel 100% confident in whatever that deal allocation is and that repeats, you got a winning formula. The number one job in sales is forecast predictability. No one ever talks about that, but that’s the value to the organization. Whether it’s an investor or whether it’s shareholders, they absolutely want to know that revenue is predictable, which means your forecast is predictable, which means you have the right formula from targeting to qualification to deal flow to get to a predictable revenue forecast. That’s the big thing. If you don’t trust your forecast, you don’t trust your revenue. Okay, you’re in a lot of trouble. 

Hessie Jones 

Thank you so much, Robert. I can’t believe it’s already like half hour, so we’ve flown through this really quickly. So thank you for being with us today and I truly appreciate your expertise in this because this is something that a lot of founders need and there is no process in the beginning when you’re a startup, but to be able to set that up in the beginning is really great. So thank you for coming. So, for our audience, if you have any topic that you’d like us to cover, so please contact us at [email protected]. We are accepting applications now for our incubator and investor readiness program, so please go to our website, altitudeaccelerator.ca for more information. We’re also on podcast, so find us wherever you get your podcast. This is Tech Uncensored. I’m Hessie Jones, and until next time, have fun and stay safe.