#017 Unlocking Revenue Secrets with Jimmy Speyer

Thomas Miltschuh: Welcome to our new episode of Speak Revenue. Remember: revenue is not a goal. It's a result, but a result of what? In this show, we turn our eyes from the output towards the inputs. We speak to sales leaders and to entrepreneurs about their journeys. Join us on our quest to uncover and learn the root causes of success. Let's unpack what works for them and what didn't today with our guest, Jimmy Speyer. 

Jimmy Speyer: Hey Thomas. Great. to be here. Thank you for having me. 

Thomas Miltschuh: Great to have you here. Thanks for taking the time. Let's get started right away. Let us know who you are? What do you do? Why are you so successful?

Jimmy Speyer: Well I appreciate you taking time to chat with me, today. My name's Jimmy Speyer. I'm currently a CEO of a tech startup in the home services space. Very recently transitioning from being a revenue leader. I've been a SVP of sales, a VP of sales, a CRO, multiple verticalized software companies, in a couple of different spaces. Medical device technology, restaurant, hospitality. And most recently in logistics, I live in Nashville, Tennessee, and I am really passionate about revenue and growing, verticalized tech startups. 

Thomas Miltschuh: Awesome. Great. You're definitely the right person to talk about, the causes of results in the revenue space in the RevOps space. Can you give us a quick picture to, just for a start, what are your goals for this year and what about next year?

Jimmy Speyer: So as a startup, our goals are to really look at initial traction in the market. We're looking for that initial product market fit. We've set some revenue targets. They're year over year again. Nothing as a recent endeavor, but we are looking to really start to. Prove out the concept of what we're building. We've already partnered with beta customers, design partners. So now transitioning into that paying customer model and looking at scale in terms of going from that first 20 to 50 customers to that first 500.

Thomas Miltschuh: Great. So that will cover next year as well, probably.

Jimmy Speyer: Yeah. That plan is to take us through the end of 2024.

Thomas Miltschuh: Mm-hmm. Long journey to go, hopefully as short as possible. Could you step us through your sales process just beginning from lead generation, over closing to upsell.

Jimmy Speyer: Yeah, so I've been a student of Winning by Design, which is a sales process organization out of San Francisco. And they really talk about what you think of as a bowtie revenue model where the sale is the middle of the transaction. So you look at the expansion and adoption as the second half. So everything that goes into that customer acquisition is the first half. And you're measuring that usually in seven to 10 kinds of moments that matter. And then you also have additional moments that matter. Are they adopting the software? Are we able to expand them? Are they renewed? Do they come back for more? So I think about that in that regard. The best customers are the ones that you can not just sign, but that you can keep and that you can grow. So that would be kind of like a base level for how I think about a sales process or revenue model in general. 

Thomas Miltschuh: Right. So, of course I know Winning by Design. and you are building the whole thing from the beginning on. So, making sure that, at the early stage, adoption is high and retention is high as well. It

Jimmy Speyer: Correct. Speaking about our current company, but really the last three sales organizations, revenue teams that I've been a part of, how are you growing that 120, 130% NRR? There's, it comes from being able to identify the right customers at the beginning that have that propensity to grow. So it's understanding what is the value that you're bringing. I think another really important aspect to that is how you chop up a large solution or a multi-product approach. When you're really early in your growth stage as a business, it's usually, in my opinion, best and very easy to just be an all in one solution. Here it is. Take it, use as much as you want, as you kind of define and develop your ICP and your various segments that you wanna attack. Figuring out where those moments of inflection are, where different personas want different things, allows you to kind of go, not only target them on the front door, but then also figure out what can you upsell and how can you grow through expansion into that account. So understanding your product usage, understanding the value of those different pieces is really important. 

Thomas Miltschuh: .Understood. You've mentioned finding the right customers is very important. Can you elaborate on this a little bit? What's your secret there, regarding, go-to-market strategy in general?

Jimmy Speyer: I think it boils down to one really simple word, which is, no, no, we're not gonna go attack that part.

Thomas Miltschuh: Okay. 

Jimmy Speyer: Because it's very tempting. It's very intoxicating to try and sell to everyone. Not everyone is your ideal buyer. And so if you don't take the time to identify the people you truly want to go after and work with, then you tend to be either be distracted by low quality opportunities that you're not going to win, or you start trying to force your solution into markets where you're really not Not very, like you're either not differentiated or you're not gonna be able to get the price you want, or the customers themselves, while willing to buy don't really get the value from what you're selling. So if you can't say no to anyone, then it's gonna be very hard to find the people that you really can say Yes to. 

Thomas Miltschuh: Yes. Yeah, that's right. How do you, or do we want to share, how to find the potential or the right prospects? Is there any approach you would like to recommend? Maybe depending on the different stages of a company even.

Jimmy Speyer: Well I think that is really gonna vary by what you're doing, right? Are you a horizontal software? Are you a verticalized software? Right? If you're horizontal, then picking a couple of industries where you have the best traction or the best fit, or it's the easiest process early, might be the best way to go. If you're a vertical software, you've already kind of constricted your tam down to a certain type of Buyer, a certain type of industry to begin with. So then it's about segmentation. verticalized software, and I'll focus on that 'cause that's my background. Every vertical should be able to be segmented. Is it by geography? Is it by size? Is it by the age of the business? Is it by their specialization? I was on a medical device. You could specialize by what type of medical device are, you know, class 3 devices that could, you know, really hurt someone? Or is it a tongue depressor? Right? Those are very different types of businesses and products. So I think if you take the time to within vertical software, figure out your segmentations, then you can decide over time where do we either want to go? where do we want to focus today based on the value of the market and your ability to address the key problems of that specific type of buyer. So it starts with segmenting. They should all be able to be segmented. 

Thomas Miltschuh: Right. right. So how do you recommend targeting? I often hear, cold calling doesn't work anymore, or cold emailing as well. Anything you would like to highlight there?

Jimmy Speyer: I think they, it depends a lot on who you're attacking, right? So if you are calling people who generally aren't getting called, so I've called into accountants, I've called into quality management, professionals. They're not getting as many phone calls, so phone calls worked. That was great. Now, if you are trying to cold call into CEOs and CFOs, that might be harder. They have a lot of gates in front of them. They've intentionally built and ringed themselves with ways to prevent you from finding them. So, first start out with who is your champion or your core buyer in your vertical, and then figure out what is the approach that's going to work best. The higher you go up the chain, the more relationships and introductions and being able to, you know, run what you would think of as a more enterprise sales motion come into play. If you are selling something that is really attacking problems for frontline members of the organization, then building a consensus from them might be a great way to attack that pro, penetration to your, into your market. And people aren't necessarily calling the frontline workers of companies as much as they think they want to call mid or above management. So start with who is your champion, then back into what's the best approach. Cold calling can work. Great. If your buyer is going to be receptive to it, content marketing, which everyone loves, that works great if you are the type of product where people are looking for education about it. If no one cares to be educated about your problem, you can pump on all the content in the world. It's not really gonna do you any good. 

Thomas Miltschuh: There is no standard solution for all SaaS companies, for example. Maybe we can summarize it with, understanding the target persona deeply. It seems like you're emphasizing, deeply understanding the target personas, right?

Jimmy Speyer: I'd say that's really true if you don't understand your buyer's problems and you don't understand how they buy software. So I'll say for instance, in having done multiple verticals in logistics, technology, selling to freight forwarders, they are a relationship sale to their clients. They might spend a year, two years, three years building that relationship to sell their service. And that's how they would prefer to be sold to. They would like you to get to know them. They would like to have multiple calls. If it could be in person, that's great. But selling medical devices is entirely different. They don't want that same relationship. They're really trying to make relationship free decisions about what's best for the health of the patient. 

Thomas Miltschuh: With this approach, it would be interesting to know a bit about your tech stack. Could you step us through this? What tools are you using?

Jimmy Speyer: We've decided to go with HubSpot, for our CRM system. I think if you'd asked me that question, even three or four years ago, I would've said Salesforce defacto. But I think HubSpot has made a lot of big jumps and they really can take a company to $30, $40, $50 million in ARR before you really have to consider the integrability of a larger system. So that's the direction we're going in. There's a lot of lead generation tools out there, ZoomInfo likes and the alikes. I find that with those tools, I like to rotate through them if I can every once in a while because they tend to grab different data sets over time and You know, it also kind of depends again on your vertical. Some of them are stronger and more B2C or B2B. So that's a little bit of a commodity in my book. I'm really in favor of having a recording tool, whether it be a Gong or a Chorus, or there's a couple of other, tools out there Now CL just bought one that is pretty good as well, but whichever one you're gonna use, using it religiously and really using it for coaching the team. I think it's super important. I like Gong's interface. I've tried a couple of them. I think it's pretty easy to use as they all go. What else? There's so many tools nowadays, and that would be the thing I would say is there's so many tech tools for sales and marketing teams is being able to figure out what do you actually need versus, you know, what do you want? And I actually made a declaration about a year and a half ago to my team and my revenue operations director. I said, you're not going to be approved to put in a new tool, unless you tell me the one we're taking out.

Thomas Miltschuh: Mm-hmm.

Jimmy Speyer: Because the bloat is, telling a 25 year old, whatever age SDR nowadays, here's 15 or 20 different tools to use every day. It's a big ask for them to be able to actually learn, manage, and effectively run a process. So I've actually gotten to the point of believing that less is a little bit more sometimes when you think about your tech stack, picking the things that really make an impact versus what is just kind of nice to have. 

Thomas Miltschuh: Hmm. Right. Yeah. I think, um, the really great, the justice, it's all often underestimated how much effort it is to get used to a new tool in addition to all the other tools that are already in use. How do you realize you need to change something in a tech stack? Are there any signals or, do you just do it, after a specific time range? Continuously. 

Jimmy Speyer: So I'm looking at those on an annual basis as contracts come up, right? What is our usage? I'm really looking at who is using the software and most of the good ones nowadays will let you go in and see who logged in, how much, and what their usage is. 

Thomas Miltschuh: Mm-hmm. 

Jimmy Speyer: If a tool is only as good as adoption, so I can put the greatest in my opinion tool in front of my team, and if no one uses it, it doesn't really add any value to the business. And I can keep, you know, driving or harping on why they should use it and do more training. But ultimately if it's not getting utilized, then it's not getting any value into the business. And then you just ask people like, I'm a big proponent of if you want to know, ask. 

Thomas Miltschuh: Yeah. That really makes sense. What about customer success? Any tools or general advice and tools you could recommend there.

Jimmy Speyer: So I definitely think you should put in a CS or CX layer into the business. Gainsight is the market leader. Churn zero is, I think, a really strong player in that space as well. But having a tool that helps, and again, this will depend on how you define customer success. Are they doing upsells? Are they doing cross sells or are they doing renewals? What is their role and their responsibility? If it's mostly ticketing and support, then I would be looking at ticketing, Zendesk and things like that. If they are being tasked with really more of an account management or ownership role of that account, and now you're probably talking more about 20,000 plus annual contracts in the us if that's where you'd start to see that role of responsibility, then I want a tool that's managing relationship and managing renewals, and it's also tied into their usage. You have to tie that thing back into your application to truly drive value for that CS manager to be able to understand patterns and reach out if there're red flags. 

Thomas Miltschuh: Okay. Any single source of truth you prefer there? Is it HubSpot?

Jimmy Speyer: I'm gonna take the CRM as my single source of truth, as my de facto. So, that has often been Salesforce in my experience. HubSpot, like I said, I think has evolved to the point where it can handle a lot of that for many businesses. Depends on your complexity, but I do think you have to have one place where everything connects and aligns. So that we can go and agree. I have experimented with Data Lakes and using Tableau and other tools to kind of aggregate multiple data points. If you have a large IT department, a lot of technical acumen, you can build and manage drone snowflake instances and things like that. I think that can be a strong solution. You're probably $20 to $30 million plus run rate before you can justify that type of data team though, it's a big lift. 

Thomas Miltschuh: Yeah, that's right. I think the next question is, really interesting look, looking forward to your answer. especially because of your experience and your impressive track record. What have you tried that didn't work? Anything, you would like to mention that comes up?

Jimmy Speyer: One that sticks out to me always when I think about this, is I tried to have player coaches, team lead managers who also sold when I was a first time vp, first time, revenue leader, and I'm scaling a team and as I was scaling the team, I kept thinking like in small jumps and small gaps, like, oh, we'll go from me managing five people to these people carrying a quota and managing two people and then that will keep dividing like cells in the body. But it's not necessarily how a sales organization really works. It's not the same as cells. Most people need to have specialization in the job they're doing, right? So being a player coach is incredibly difficult. The idea that you're gonna find multiple people in your organization that are both promotable and are going to be good at that role. Hybrid as it is, incredibly unlikely. You should either be promoting from inside with a mix of outside bringing outside talent, but letting them do the management job when you're ready to have a full-time manager versus having them try and do two jobs at once. that was probably one of the things that I found was. The biggest, that was one of the biggest mistakes I made along the way. 

Thomas Miltschuh: Mm-hmm. When did you realize it doesn't work properly and how? Especially

Jimmy Speyer: I've realized fairly quickly, maybe a quarter or two into the experiment, and it was pretty easy to tell because of the performance of the individual reps on the teams. Wasn't really keeping up with the expectation of that pod. Right? still I was interrogating the organization, like, what's working, what's not? I'm interviewing people and I kept hearing from the reps themselves. You know, my manager is really more concerned with their deals than my deals. Like my manager isn't really a manager, they're just here kind of like as an advice because they have their own set of priorities. They're in sales, they're in revenue. They have a number to hit. They know that they're gonna be judged on that. And it, so it was fairly easy to learn that mistake from the evidence on the field. I wish I'd been able to foresee it and avoid it in the first place. Though

Thomas Miltschuh: What was your solution?

Jimmy Speyer: We went to dedicated managers, it did require a larger span. It both required and enabled a larger span of control, though. So instead of having

three team leads doing both jobs. I was able to have two managers and they had more people that they were supporting 'cause they weren't having to sell entirely on their own. It also meant I could specialize in each of those people's jobs. Though the managers got more management training and less how to be in AE training, the AEs didn't have to worry so much about who's gonna be there to help me if I need it. 

Thomas Miltschuh: Okay, you were able to avoid this error or this mistake sustainably, right?

Jimmy Speyer: Yeah, I mean, I made it the first time. So as a first time VP, you know, coming up through my very first organization, actually myself, growing from AE to manager, to director to Vice President. Right? Probably every mistake you make along the way. So the point is not to never make them, it's to not make them twice, right? So I've subsequently put that in my playbook where we really don't do that anymore. If we're ready to have a manager, we get a manager until we're ready. We don't have one. 

Thomas Miltschuh: Okay. Nice. talking about, I think that's already a lot. Nice lesson learned. Maybe you could give us two or three more lessons you've learned, during your career. You would like to share with the audience.

Jimmy Speyer: For sure I get asked fairly often from, especially like brand new account executives or people who are very early in their career, they have either aspirations or goals about getting into leadership often. And so I get this question fairly often. One of mine is that you have to be willing to take relatively large risks in your career, and be willing to fail at times, right? I've gone from restaurant hospitality technology, and then I took that into medical device technology and then that into logistics. And then most recently, you know, starting my own software company, and those are big jumps across multiple verticals and then into different levels of leadership. And I have made plenty of mistakes along the way, but being too safe and too comfortable will often kind of prevent you from being willing to take that next jump. That might be the one that takes you to a better opportunity for future and further growth, right? Just being a little complacent can be, it's safe, but it's maybe not gonna get you where you want to go if your goal is ultimately to get to a certain place with your career. of the others I'd say is in revenue. Sometimes just being different is what is really required. So everybody wants to create a new category. Everybody wants to create a new type of solution or solve a new pain problem. you're in a competitive market, you don't have to be better at everything. But what is your core differentiation? What are you best at and focusing on? That will also lead you to trying to find those buyers who care the most about what you actually excel at, right? So focus on your differences. And use those as your strengths. And then the last one would be, especially for anybody who wants to grow their career or you're in leadership, surround yourself with people who can teach you something, right? So go out and find other people that know things that you don't know. Podcasts, books. I'm a big believer in reading. I see you've got books in your background there. My whole bookshelf down here is full of 'em, so. They can't all be right, so take 'em with a grain of salt, right? I've got about 150 different sales books I've collected, and they can't all be right about everything, but as long as I'm going back and reviewing them and thinking about them, I can apply their different lessons to the different problems that I experienced along the path. If I never read them or never listened to them, then I wouldn't have the knowledge to bring up at the  appropriate time. Just don't stop learning. Even if it's not relevant today, it might be relevant tomorrow. 

Thomas Miltschuh: You don't need to invent the wheel every time, right? But take the right knowledge, the things out of the knowledge issues you can find like books and combine it together in the right way that fits for you. I think that's really important. Yeah. And surrounding people, talking about surrounding them with the right people, looks like it's really important, especially if you would like to start with a sales leader role to have people that embrace failure, right? And, really see the positive things in it and try to continue and start something new and learn out of it, right?

Jimmy Speyer: Absolutely, you're gonna be the best. You know. Baseball, I've always said the best baseball players in the world are wrong twice as much as they're right. The same goes for sellers and revenue leaders. A great close rate is 20-30%. It means you are going to lose twice as much as you win. So if you're focused on that all the time, it's a miserable experience. So the people who can focus on that 30% to get excited about it, those are the people who can usually keep going through and deal with the other two thirds of the time where it just didn't work out.

Thomas Miltschuh: Mm-hmm. Exactly. Cool. Sounds great. So, talking about books, do you have maybe one or two recommendations you would like to highlight right now?

Jimmy Speyer: Absolutely. I just spent this past summer setting myself a challenge to read a dozen new ones, and go back to a couple of tried and true ones as well while I'm at it. so this is very top of mind for me. "Amp it Up" by Frank Slootman. He's the CEO of Snowflake, multiple times CEO. Datadog, ServiceNow. Um, anybody who's serious about building a high performance culture, whether you're in one or you want to be designing, one should read that book. It's fantastic. He is proof of what he's produced, right? So he's really keen on setting up a specific set of processes and circumstances that lead to good results, good results, or that come from a good process and I think he really believes that. I also just read "Shoe Dog" by Phil Knight. I thought that was really a great book for anybody who's going on a hero's journey, as we say, or an entrepreneur's journey about kind of how it always takes longer and it's always harder than you think. 

Thomas Miltschuh: Mm-hmm. 

Jimmy Speyer: And if you're a brand new seller or brand new to revenue and you wanna start thinking about how to do an educated process or how to teach your buyers how to buy, "The Challenger Sale" is a classic. It never, some things never go outta style, and I would say that one never does. It's one of the ones I give to new sellers. As soon as they ask me, or as soon as we hire them, we usually ship them a couple of books, and that's almost often one of them. 

Thomas Miltschuh: Nice. So we even have some recommendations for people in our audiences with, in different stages of their career, different phases. Sounds great. Thanks a lot. 

Jimmy Speyer: For sure. There's so many out there. I would just say, you know, be willing to invest the time in learning. And like I said, these are tools you'll employ at different stages of your growth trajectory. Just like a mechanic, they have all the tools in the wall, in the shop. They pull out the one they need at the right time. They don't go to the store and buy one every time. They need a new one. 

Thomas Miltschuh: Yeah. Yeah. You can use it like a verge work better actually. Yeah. 

Jimmy Speyer: Absolutely. 

Thomas Miltschuh: Great. Thank you very much Jimmy. I think we can come to the end of this episode. So all, all right everyone, it brings us to the end of the episode of Speak Revenue. I want to thank our guest, Jimmy Speyer, for joining us today and sharing such valuable insights. A huge shout out to all our listeners. Your support means the world to us. Remember to check out our website: speakrevenue.com for a full transcript and additional resources. And if you enjoyed the show, please leave us a review on Apple Podcasts or wherever you go for your listening needs. It really helps get the word out. Also, follow us on LinkedIn at Instagram or YouTube. We'll be back soon with another great guest, until then: stay curious and keep listening.