#032 Sales Unwrapped with Jon Rydberg

The Sales Maestro's Playbook

Guest & Host

Jon Rydberg & Thomas Miltschuh

Welcome to Speak Revenue, the podcast where we emphasize that revenue is not just a goal; it's a result. In this show, we shift our focus from the output to the inputs. We engage in conversations with sales leaders and entrepreneurs about their remarkable journeys. Our mission? To uncover the true root causes of success. In this episode of Speak Revenue, join us as we sit down with Jon Rydberg, VP of Sales at Valcre, a commercial real estate software company. Jon shares his extensive experience in technology sales and his journey through various sales roles, providing invaluable insights into what makes a successful salesperson and leader. Discover the importance of having a common language and a qualification framework across your organization, and learn about the power of mutual action plans to achieve transparent, successful outcomes. Dive into the nuances of sales processes, tech stacks, and the art of developing a winning sales team.

October 31st, 2023


Thomas Miltschuh: Welcome to our new episode of Speak Revenue. Remember, revenue's 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 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, Jon Rydberg. Hi John. Welcome. Thanks for taking the time. 

Jon Rydberg: Absolutely, Thomas. Excited to be here. Looking forward to the conversation.

Thomas Miltschuh: Awesome. So let's get started right away. Tell us who you are.

Jon Rydberg: Yeah.

Thomas Miltschuh: What do you do? Why are you so successful?

Jon Rydberg: Absolutely. I appreciate it. So John Ryberg VP of Sales at a company called Valcre. We're a commercial real estate software company focused on appraisers. So valuation software, report writing software to really simplify and streamline it for our prospects and customers. My background has been the last 15 years in technology sales from SaaS and project management to Intuitive Surgical, so the Da Vinci Robot medical device sales with the software and technology there all the way through the senior living space to Cisco, to a Microsoft partner and on. And so the last three roles have been VP of Sales roles in the commercial real estate space, and the past focusing on lenders, law firms, title companies. And then moving into the leasing asset management world with property owners and commercial estate brokers, and now to valuation professionals. And yeah, so that's the background there.

Thomas Miltschuh: Awesome. That sounds like a lot of experience you can share. Just recently we've had a podcast guest. He mentioned what he would have done differently in the past looking back is, forward early enough to move forward. Don't use too much time for a specific role because you might miss gaining enough experience and regret it later.

Jon Rydberg: Yeah. No, I think if I had to do something different, I would probably have... So I look at everything in buckets, right? So people, processes, and tools. So those are the three things with which I evaluate certain segments of the business or my go-to-market strategy. And I think if you really look at the people side in the past when I was a newer sales leader, I didn't really have a scorecard framework for hiring to really map who we're looking for to meet the profile of someone that would be successful in that business, specifically to that market, to that ICP. And now that I have one, I can see where I missed when things didn't go so well or maybe a hire didn't work out. And so if you look at things like coachability, grit, passion, curiosity, communication, energy, all of those things are really important. And you can ask questions to test for that in the interview process on the front end, and ensure that there's an experiential component of it where not just their background because… Being a successful sales person, that's table stakes, right? To recruit someone that's an A player or someone that's good at the role, but finding someone that's coachable, finding someone that has grit, that can really push through and persevere. That's something that's really important to me. And so having that scorecard always ensures that the framework is on point.

Thomas Miltschuh: Awesome. Let's talk about the framework in a minute. Maybe you could give us a quick overview first on your sales process, how does it look from lead generation over closing to upsell?

Jon Rydberg: Yeah, sure. So we have, obviously we have an inbound component with our marketing team. So we do a lot of things around white papers, ROI calculators, various things they can download on the website. We have an Opinions of Value podcast focused on valuation professionals, so certainly we have a good influx of inbound visitors there. Then our BDR team is really focused on an omni-channel approach to filling the top of the funnel. So emails, LinkedIn phone calls are the normal scenario there. And then we have, we take a very customized approach to our demos. We're not gonna do a generic sort of, high level demo. Everything's tailored, right? So we'll have a discovery call at least 30 minutes, uncover goals, challenges, pains, things like that. And we have a custom tailored demo. Given the nature and the complexity of our platform, because it's for value, commercial real estate valuation, there's a lot of components to it. We leverage a solution engineer, one that's a former appraiser that understands the domain and really can help sell the value of the platform. And then from there, it's either a pilot for the larger enterprise groups or for SMB. Sometimes it can be a three touch close where maybe there's just a few stakeholders that have to make a decision. So you might have a secondary demo and then we close for an annual contract.

Thomas Miltschuh: So it's a few steps. Is there, so there's a BDR somebody, like a presales consultant, if I understood it correctly?

Jon Rydberg: Yeah, so there's a BDR, so they're doing the prospecting and filling the top of the funnel for the AEs. Certainly the account executives are filling the top of the funnel, but they're the most expensive form of demand gen. So we really want to use their time on quality qualified demos and conversations with prospects, advancing and closing deals. And so we really leverage the BDRs for, call it 80% of the prospecting.

Thomas Miltschuh: How is it going with the BDR approach? Differences compared to a few years ago. Apparently a lot has changed in the last few years, especially when it comes to BDR work.

Jon Rydberg: Oh yeah, absolutely. So I think ultimately buyers are more informed than ever. With privacy concerns and privacy regulations, it's more difficult to get ahold of people over email, for example. We're still seeing a lot of success with drip campaigns, like we use HubSpot sequences over email. But in my opinion, nothing beats the cold call. I realize it's all. Tied to the ICP, different ICPs might be able to reach in different ways. For us, calls are really effective right now, but you see that change, so every business is different. And with a persona, there's a different way of getting a hold of them. For example, in the brokerage world, in my previous role, brokers were really easy to get a hold of because they always think it's a deal, so they're gonna answer their call, right? Where asset managers are sitting at their desk and they're probably not gonna answer their phone. They may peruse the email, but then not respond. So it all sort of depends.

Thomas Miltschuh: Yeah. I regularly see advice on social platforms like LinkedIn. Saying cold email doesn't work anymore. Cold calls don't work anymore. But it seems like it really depends on the individual, there's no general result on this.

Jon Rydberg: Yeah, I think a lot of that's click bait, right? They're trying to get you to click in and read the or blog. So yeah, you're spot on. It all is contextualized right? For us, calls, cold calls are dead? Calls work great for setting up prospect appointments here.

Thomas Miltschuh: Awesome.

Jon Rydberg: Email's pretty strong too!

Thomas Miltschuh: Nice. So what does it look like after the closing? Maybe have quick information about the onboarding and upselling process.

Jon Rydberg: sure. Absolutely. So what we have is we use HubSpot workflows. So let me take a step back, even before that, we have a weekly onboarding AE and CS team joint call. Hey, these are the ones that are close to closing so that knowledge transfer isn't happening last minute where there's a scramble. They're very informed in terms of the CS team on who their prospect is, their challenges, pain points, goals, use cases, all of that, because, hey, this is coming down the pipe. We're about two weeks away. So we have that knowledge chancellor ahead of time, which we find to be really helpful in that way. Again, we're not scrambling. And then the onboarding process, we do have a quick sync, like a 30 minute sync for knowledge transfer. Usually we only need about 10 to 15 minutes because the information's all there and a form that we fill out pings the CS team and the deal can't officially close or release the training times until that form's been filled out. 

Thomas Miltschuh: What's the average sales cycle?

Jon Rydberg: Absolutely. So call it 12 to 18 months for enterprise for us, and about 2 months for SMB.

Thomas Miltschuh: All right. So the whole range

Jon Rydberg: The whole range. We're covering everything and about a call six months ago, we really focused on the market. Our core cohort segment is SMB and the majority of commercial real estate appraisers are SMB. So we're really servicing the broader market. So we have large enterprise customers and also a one person shop, and so in a lot of ways we're democratizing valuation software for the smaller groups all the way up to the larger enterprise.

Thomas Miltschuh: Alright, Maybe just a quick elaboration on onboarding and upselling any specific methods you are approaching there.

Jon Rydberg: Yeah. So just in general, we try to tee up upselling on the front end. So understanding, hey, what does your go forward strategy look like? Are you acquiring other businesses? Do you plan on growing the team? So we have a general sense of what add-on upgrades could be coming. And then also just getting insights from the product. What does the utilization look like? Open support cases, where are they struggling? Where could maybe our platform help fill gaps? The CS team does an incredible job of understanding use cases, challenges as their needs of the business change. How can our platform meet them where they are to get them to the outcomes that they want? So then of course, QBR is a great way to go over stats, usage, monthly active users. Where are we missing? Where can we be more optimized and help out with our product? So we're constantly having conversations to really have a joint collaborative effort with our customers to help them get where they need to be.

Thomas Miltschuh: Alright, so there's a really close relationship?

Jon Rydberg: Very close relationship. And a regular cadence. And you want to get that cadence on the front end, Hey, what's our touch point? You don't want to be reactive in the approach and in our opinion. And that, I think, made us really successful.

Thomas Miltschuh: Definitely. So I know you are really passionate about team development and process optimization. So let's talk about how you make sure you have a winning team working on your pipeline? And, also what tech stack you are applying to get an overview to know how you make sure your team is as successful as possible?

Jon Rydberg: Oh yeah, great question. So I think it starts out with recruiting, right? We went over like the scorecard of getting that profile, someone that will be successful selling in this business to this ICP with this platform. I found you can't just plug and play. You can't just take the Oracle or Salesforce or Cisco rep and just place them in a certain role, right? There's certain nuances to the business and there might be a gap with skill or domain expertise that you need that's unique to this environment. And so it really starts out with understanding a, what profile is successful? And you can see that even with your first couple AE hires, right? What's working, what's not? Who's more successful? What does their background look like? Reverse engineer that coupled with what's important to you to be successful in the business as an AE, individual contributor, and then hiring for that. So then having a scorecard that really maps to that profile. So you put them in a good position for success and then tech stack. If you want me to go there. HubSpot's our CRM. We use Chorus for AI call intelligence to understand challenges, objection handling, what went wrong on the call, what went well. And you ease that for coaching one-on-one. So that's been really helpful as well. We use Notion internally as an organization that's really helpful. A LinkedIn Sales Navigator wouldn't go anywhere without it. And just LinkedIn in general is extremely helpful to our business. ZoomInfo for business intelligence and getting the right contact information and org charts is also really important for us.

Thomas Miltschuh: Okay. Pretty comprehensive tools cover all aspects of activities, right? 

Jon Rydberg: Exactly. 

Thomas Miltschuh: Yeah. How do you make sure your team is progressing efficiently? How do you see things go well or maybe goals might be missed? Are there any methods you are approaching?

Jon Rydberg: Sure. A couple things. One, we use HubSpot dashboard, so we have a personalized rep view, where they can see it. We also give access to the entire company to that view. And then we have a team view. So you can see the leaderboard, you can see AE activity per person, you can see their pipeline. All of that is super important to get a 30,000 foot view. And also you can drill in as needed to understand things. And also with one-on-one coaching it's pretty clear, right? You have, you talk about performance, right? Hey, how are we doing against quota? If performance is struggling, let's look at the pipeline. That's the next level down. What is your pipeline? Good. What does your pipeline look like? Do you have good pipeline coverage right to quota? And if the pipeline's anemic, that's a whole nother conversation. Now you need to drill down into activity. Are you making enough outbound dials? Emails? Connects? To create enough opportunities to build enough pipelines to cover that number. And really, we're shooting for a 4 x pipeline to quota ratio.

Thomas Miltschuh: How is acceptance of those measure methods and transparent dashboards in your team?

Jon Rydberg: Yeah, that's a great question. No, so it's accepted because again you're really recruiting for the profile that's competitive, that wants to get better, that wants coaching, transparency, competition. So the people that we bring on to Valcre have that DNA, right? And so they're wanting to compete. They're wanting to see where they stack ranked to their peers, and that's really important. Also, we try to map to individual goals, right? So we have an activity tracker where you can put in your quota, your average deal size, your win rate, and you can figure out working backwards, just an Excel model of exactly how many demos you need weekly, how many discovery calls, how many connections, et cetera. To get to that goal. And it's more effective in my experience and in my opinion, to map not just to the company goals, but their personal learning goals because sales reps are competitive and they're coin driven, right? So if you can make it about them, they wanna buy a new house or whatever the case may be, whatever that earning goal is.

Thomas Miltschuh: Yeah. Very individual. So you really look into personal motivation.

Jon Rydberg: Very much and one other thing Thomas to mention there, even our Monday standup, it's like, Hey, we'll go over the housekeeping stuff and then we go straight into what are your top two key priorities for the week? And then we follow up, Hey, how are you against those priorities? What are your objectives? What are you looking to focus on? So it really dials in. The focus and it gives the broader team an understanding of what people will be focusing their efforts on that week. So there's the qualitative piece and the quantitative in terms of dashboard, metrics, everything else.

Thomas Miltschuh: Nice. Seems like that's really developed. machine you're working on.

Jon Rydberg: We try. 

Thomas Miltschuh: Like a sales machine. There must have been some things that didn't work out in the past. Maybe you can give us one or two examples, something that just didn't work.

Jon Rydberg: Yeah. I would just say in general, over engineering, doing too much, too much internal training, too many internal meetings or calls during the golden hours of customer conversations. So we really try and prevent anything from nine to five as best we can, so they can be focused. AEs can be focused on creating opportunities, advancing opportunities, and closing opportunities. So I think having too many meetings, too many places to update, like spreadsheets and all these other areas outside of HubSpot, try and just make HubSpot, our CRM, the single source of truth. And try to extract value from that and allow that to inform us so there's not too many tools outside of that for them to do so they can focus on selling. So I think too many meetings, too many areas of reporting outside of the core CRM. I think that was a mistake in the past for sure.

Thomas Miltschuh: Okay. Sometimes it's not easy to find the right balance and you. I don't know, maybe you have some tools or you have a gut feeling of the right moment to steer in the other direction.

Jon Rydberg: Yeah.

Thomas Miltschuh: But was there a specific case of realizing there's too much distraction? And when and how did you realize?

Jon Rydberg: Yeah. So the easy way is top performers tell you exactly how they feel. So that's a nice poll. Through one-on-ones, it's Hey, what could we be improving upon? What could be optimized? I feel like I have too many meetings during the week and even company meetings. So sometimes you have to go to the executive team and talk to your peers, my peers, and say, here's what we're seeing. Here's a snapshot of the calendar. Hey, did you know that we're in 6 hours of internal meetings a week? And think about how that could be used to fill the top of the funnel or advance and close deals. And so I think just from a calendar perspective, it's very easy to see. Where the reps are spending their time and when you have too much time spent on internal things. And again, some things are important, like company wide all hands, there's certain things also that could be better used that are better focused in terms of the best use of an individual contributor's time. So both feedback from a rep, through one-on-ones, and just looking at the calendar analysis of how people are spending their time.

Thomas Miltschuh: Yeah. Seems like it's a bit similar to making good progress with your clients to develop them further. The closer you are connected and the more transparent you're sharing information, the more efficient you can develop the whole team further.

Jon Rydberg: I agree, absolutely.

Thomas Miltschuh: Awesome. Maybe you could tell us If you've done it at the beginning of the call a little bit. If you look back and maybe give some advice to anyone new in the business what lessons learned you would like to share?

Jon Rydberg: I would say, a, have a common language across the organization, so you know, understanding what, whatever it is, whether you're using MEDDIC, MEDDPICC or whatever. SPICED is another one. From Winning by Design, whatever that is, right? Have that set in stone. Have the common language across the team, have the entire organization, even if it's founder-led sales, train on that. So everyone can use the same language. It helps you go fast. I think that's extremely important to have a common language, a good qualification framework. It really sets people in the right direction. So I think that's definitely something that I would advocate for. Anyone that you know doesn't have that now, definitely get that. It'll set you up for success. The other area, mutual action plans or mutual success plans are really important, particularly for enterprise deals. Having those milestones, dates, timelines, commitments in a visible way for both the prospect and the AE, super important. It's Hey, we're at risk of not meeting this deadline. Is this still important to you? Hey, we need to go through the procurement vendor risk process. We need to go through legal red lines. All of those dates and milestones are mapped out and that document is shared with the prospect. So that allows you really to have full insight into where things stand and to honestly just do a better job of forecasting, right? Because you can see exactly what's missing, where the deal is in terms of status. So that's another thing that I think is really important, and I would've done that in the past.

Thomas Miltschuh: Are you using HubSpot for this or maybe any additional tool?

Jon Rydberg: That is a, that's a great call out there. That's the other piece, right? Because if it's too cumbersome, reps won't fill it out. If they view it as busy work, particularly top performers, they're not gonna do it. So you have to do it or operationalize it, or they're already working. We build that right into the sales process, so there's certain gates and entry and exit criteria for each deal stage, and some of that is filling out that qualification. Those answers and those will change over time, but you can't even get to the next stage without filling out the certain aspects of it.

Thomas Miltschuh: Yeah. I think that's really important because it shows a commitment of the AE to the deal, to the prospect.

Jon Rydberg: Absolutely.

Thomas Miltschuh: We need commitment on both sides, right?

Jon Rydberg: A hundred percent.

Thomas Miltschuh: Make sure it goes forward in a professional

Jon Rydberg: Yeah. And you're being a good teammate, right? Because now when you make that handoff to customer success, all that information is captured, right? So you're not having to regurgitate things. You're not gonna be in a position where the customer doesn't feel understood. It's Hey, we've gone through this whole sales process and you're asking these redundant questions. Everything is captured, everything is qualified. And the weighted probability of the ideal stage is tied to the qualification diagnostic questions to ensure that it's not just a gut feel, but it's objectively understood of how well qualified that is and what stage it's at.

Thomas Miltschuh: Nice. So I feel like we could talk about those topics, maybe hours, several hours more. But unfortunately we need to come to an end of this episode. So this brings us to the end of this episode or Speak Revenue. I want to thank our guest, Jon Rydberg, 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 us full transcript and additional resources. And if you join 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 and Instagram or on YouTube. We'll be back soon with another great guest. Until then, stay curious and keep listening. 

Copyrighted © 2022-23 Jaxx Technologies, Inc.

Copyrighted © 2022-23 Jaxx Technologies, Inc.