#034 Trust in Tech with Jeremiah Chambers

Steven Morell: 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 input towards the output. We speak to sales and revenue leaders and entrepreneurs about their journeys. Join us on our quest to uncover the root causes of success. Let's unpack what worked for them. What didn't. Today with my guest, Jeremiah Chambers from DigiCert, do I pronounce DigiCert right?

Jeremiah Chambers: DigiCert. You almost got it!

Steven Morell: I almost got it. It's a name that has become so familiar over the years. I wanna say decades, but I don't think I ever said it out loud, ever.

Jeremiah Chambers: I know. We're like the best kept secret in tech is what we like to call ourselves. 

Steven Morell: Yes. For our listeners, real quick Jeremiah. Who are you? What do we do, and why are you guys so successful?

Jeremiah Chambers: Yeah. I'm Jeremiah Chambers. I'm a VP of Sales over here at DigiCert, leader in Digital Trust. And if you don't know who we are, look up your browser and you see a little lock. That's probably us, TLS and SSL certificates. Why are we successful? Pretty simple from top to bottom. We are very much customer obsessed. We are very obsessed with what's important to them, and that's not just our external customers, but our internal ones as well.

Steven Morell: You are obsessed with your customers' internal so many things to unpack. Let's start with who are your customers?

Jeremiah Chambers: Yeah, so our customers are primarily gonna be CIOs, CISOs at organizations that range really in size. We're talking about all the way from SMB to the largest enterprises you can think of, and pretty much, you know, if you name it, if it's a big name. In the business market, something that's in the Fortune 500, we most likely work with them. But that's primarily who we 

Steven Morell: Let's intersect here real quick because I think we both are tech guys. And we have this 19 inch conversation and we assume everybody knows what a certificate is. Let's explain to our listeners that they are not so techy. What exactly is a certificate? What does it do?

Jeremiah Chambers: Yeah so basically you think about a certificate like this is, you want to send me a message and that message, we'll think about it as a unique key. And for me, I have the other side of that key. I've got that lock that's unique to that key to make sure that only you can receive that message and boil it down. That's what a certificate is. It's that one kind of secure layer that we make sure that the connection we're trying to make, whether it's a user, a device or accessing a website that is secure and just a one-to-one relationship between whoever's the user and whatever they're trying to access is protected and secure. 

Steven Morell: I think the 25 year old example is when you do online banking, then you can be sure if you see this little lock on top in, in the address bar, then you can make sure this is really the website of the bank.

Jeremiah Chambers: Absolutely.

Steven Morell: And today all websites have that. And if they don't, you get a warning usually from your browser, there's something not right and just don't go there because we encrypt everything and we, is encrypt the right word?

Jeremiah Chambers: Yeah. Yeah. encrypts the right word. We, yeah, we do that from websites to email addresses to again, think about your device. If you walk into your office and you automatically connect to the wifi. Even that connection is something that we work on now. And then of course, with IOT it's a really big deal these days.

Steven Morell: And it's interesting because this technology was introduced. At a time where we would transmit data quite openly over the internet. Most websites were not encrypted and most data communication was open. Very easy to sniff in and listen into and tap into. And I feel, I know, how long has your company been around? 25 years?

Jeremiah Chambers: Yeah, around 25 years. Yeah.

Steven Morell: 25 years. This technology has been around for 25 years. We have secured all the communication channels at the same time. We are putting out our private lives everywhere. I see what people have for breakfast on LinkedIn and they post their kids on Insta. So we have more secure communication lines, but we are more, I don't know if we trust the internet more. Talk to me a little bit about what trust is and how that has evolved.

Jeremiah Chambers: Yeah. Yeah. So when you think about digital trust, it's like you said just there. I'm gonna put part of my private life on the internet because I trust that wherever I'm putting it is gonna be safe. But it extends beyond that, especially in B2B applications. Something that we like to talk about specifically is we work with a lot of medical device manufacturers and think about if you had an insulin pump. And you're a diabetic that is connected to the internet. Do I trust this device to regulate the insulin in my body? Do I trust my smart home device to open my garage door or close it when I'm not at home? 

Steven Morell: That's very different from telling my smart speaker which song to play

Jeremiah Chambers: Yeah. 

Steven Morell: It gets wrong all the time.

Jeremiah Chambers: Yes, it's like that, but it's really the connection because you think your smart speaker, it's connected to your home network. What else is connected to your home network? If you're an entrepreneur, you might have proprietary information that's on your laptop that's also connected to that network and. Just a one untrusted device and specifically, the US government's actually put out this initiative, this regulation for what they call it cyber trust mark on devices to make sure it says, Hey, this device does not have the vulnerabilities that may be present in other IOT devices so that you can trust it to connect and not have to worry about whatever network you're on, whether it's an office network or a home network having a significant vulnerability because of that device.

Steven Morell: Is that a topic that had its own boost due to the Covid pandemic and everybody starting to work from home?

Jeremiah Chambers: It's actually, it extends beyond that. Prior to my time at DigiCert, I was actually with Verizon and IOT devices. I think we're approaching 30 billion devices now. Across the globe. It's almost five devices for every human being on the planet that we have right now. And because of that explosion, a lot of it has industrial applications or medical applications, or even in aviation, very important things that we, again, trust every day. You trust that we get on an airplane, that everything's gonna work okay, and you're gonna get to your destination in a reasonable time. You trust that if it's an oil and gas company that you know everything is gonna work. All the sensors are gonna work correctly so that we can avoid any kind of danger or potential event that could be catastrophic. And that is where really this extends from and the home side of things has only made it a little bit more relevant to us as consumers because we don't think about all the industrial things that are going on around us. But we do think about, as you said, the home speaker that doesn't always pick up on the song I'm trying to play, or the smart fridge that I have that tells me when I'm out of milk. That's what we do think of. So that's kind of brought it more into the forefront for everybody.

Steven Morell: Interesting. Let's talk a little bit about your sales motion. You mentioned earlier that you're targeting the CISO , that's the Chief Information Security officer. Or the CSO, that's not the chief sales officer. That's the chief security officer, right?

Jeremiah Chambers: Yep. Or yeah, CIO as well. Yeah.

Steven Morell: I think that's a regional difference where they call themselves CSOs and CISOs, but they're the same folks I know from personal experience. They're usually not the type of person that likes to get cold called Or talk to anyone at all. I think it's, I would say it's a difficult audience to make contact with. Tell us a little bit about your lead gen motion. Are you doing inbound? Are you outbound? How you're building this.

Jeremiah Chambers: Yeah we're doing both and for the inbound, the outbound motion, there's a lot of things that we have that flow into that. Specifically as you mentioned, DigiCert has been around for quite some time, so fortunately we have a very strong brand reputation. Many of these organizations that we're dealing with. They have at least interacted with us because they have certificates, they have public certificates. It's on their website and that's how they maybe started with us, but, that's earned us the right to maybe get in front of them a little bit more. But the way that we've been working, the inbound and outbound motion really starts with significant investment in events and making sure that we are spending time not only educating the market of CIOs and CISOs, but giving them a voice to talk about what is going on in their world specifically related to something called PKI or public or private key infrastructure. That's our bread and butter, that's where we relate to, and that's been allowing us to get some things to the forefront that are issues that they're facing. That we solve for. And when it's an organic discussion that starts with this group of CISOs or CIOs, it really does help get that thought planted of how can we do this better? How can we protect ourselves from vulnerabilities, increase our security posture? And that's where we do see a significant amount of inbound traffic coming from our website. Where people are reaching out specifically asking about what we can do with certificate lifecycle management or software code signing and helping them with a software supply chain. And then from an outbound motion, where we go is very specific, very targeted, using the use cases that our solutions actually solve for us. Talk about that customer obsession. We really partner with our customers and study what is the use case. Why is it so important to them? And if they don't solve the problem that we're solving for, what are they worried might happen? Because as you said, the CIOs and CISOs , they maybe don't wanna talk much, but something that they don't like is they really don't like having this lingering feeling that they have a vulnerability out there that they haven't addressed. And that's where we expose that we talk about that with them. And then through our outbound motion, it's really specifically targeted to, Hey, this is your industry. Here's a use case that we typically see within your industry. Here's an example of how we've solved that for someone else. And that will typically help us get some pretty good return rate on our investment of time and effort and touches to be able to get those meetings so that we can have valuable conversations.

Steven Morell: I think I heard you saying that you are essentially running a community of those people. When you say you listen to them, did I get that or how do you listen to them? How do you let them speak and listen to what they have to say?

Jeremiah Chambers: Yeah we've partnered with quite a few other organizations to be able to host round table discussions. We're very close to something called the CAB forum. Is basically a regulatory committee that regulates all of the policies and everything that we see around certificates. And because of that, that gives us a little bit more credibility, a little bit more access than we may see. And, even, coming up here next week, we've got what they call a Trust Summit coming up in Las Vegas. Where we have all these CIOs and CISOs coming in to be educated, to learn and to have that discussion. That's not a sales pitch, but a true, here are issues that we're facing. Here's some problems that are coming with post quantum cryptography and being able to, really talk about that in more of a safe setting where they're hearing from their peers. And fortunately. We're able to use that and say, if we could solve this for you, what would that do for your business? And luckily it's been turning out quite well. We've been able to solve this problem for quite a few people and it's gaining kind of a snowball effect if you will. 

Steven Morell: I think It's easy to picture how you as a company with that standing in the market and with that brand awareness how you generate inbound leads. How do you do outbound? Do you cold call them? Do you email them? How do you get in front of them in your outbound motion?

Jeremiah Chambers: Yeah so our outbound motion is something that when I say it's perfected, no, but it is something that you said, do we email them? Do we cold call them? The answer is yes. Yes. We also do LinkedIn , and quite frankly, I will go knock on the door if I'm in town to say hello to somebody because.

Steven Morell: That was my first sales job.

Jeremiah Chambers: Yeah. Yeah, I've been there too. Yeah. But really it's not just about the touches, it's not just about the cadences. It's not about having really good email copy and content and partnering with our marketing teams to get that put up. It's about the intense belief that we all have, as an organization that we really can solve these problems for our customers and that conviction that we are the best and that conviction that we do this and good things happen for the end customer. We're not selling shelfware. We're selling something that is really important and we do a lot of product education that flows into that outbound motion. So it's not just the fact you're talking to somebody that says, Hey, Steve, do you have a few minutes for me to tell you about why I called? It's them truly and genuinely feeling this is important for you. I think you should hear me out and you can hear it in their voice.

Steven Morell: Yeah, I can see that working. Okay, so let's talk about how you organize this. Do we have, it sounded to me like marketing is responsible for outbound messaging. That's interesting. Do we have an SDR / BDR team? SDR handling the inbound? Qualifying the inbound and a BDR team setting appointments outbound?

Jeremiah Chambers: Yeah so our SDR team is actually flexing. We do have an SDR team. The ratio right now is roughly about one to every 3 or 4 account executives. And for them they are doing some of the front end messaging and marketing, I wouldn't say is in charge of all the messaging, but they help give us quite a bit of content to leverage, those really good white papers, great webinars that we are able to do that are solid and educational.

Steven Morell: But they do report to you, not to marketing?

Jeremiah Chambers: And actually we just changed that around. Our SDR team does report to marketing right now, and there's always that debate. Who does SDR, who's should they report to sales or 

Steven Morell: That's an endless debate. What made you switch?

Jeremiah Chambers: Really it made a lot of sense for our organization. 

Steven Morell: How big is the company in total headcount and how big is the sales team?

Jeremiah Chambers: Yeah. So the company's total headcount is a little over 2000. And the sales team just in the Americas is roughly around 500.

Steven Morell: 500 people in sales.

Jeremiah Chambers: Yeah, that's it. I'm lumping in the SDR teams and some of them. 

Steven Morell: Of course. Of course. They're part of the sales team. Or in your case now, the marketing team, but the GTM team. Okay, keep going. So you decided to let them report to marketing because

Jeremiah Chambers: Yeah, so reporting to marketing. The main reason for that is what we're doing primarily with our events and webinars and talking about that community aspect of it. When you have these fantastic webinars and hundreds of people show up for these wonderful events, and we have hundreds of people stopping by our booth over the course of a few days having meaningful conversations, that was probably the biggest challenge we have. We do have full cycle AEs, but when you're sending three or four AEs to a show and now they're having to follow up with hundreds of leads and only a few of them actually land in their territory. It gets a little difficult. So keeping the SDRs closer to what's our marketing owned process just seemed to make sense overall. And then as well, we're ramping up our content engine and testing that out, making sure that we've got a really good thumb on the data. Of what content is relevant and very meaningful for our end customers. And when content isn't, and without having that buffer there and having marketing be able to directly keep an eye on that data and see what the open rates are, click rates are, follow through rates are just seem to make sense for us at least in this stage of where we're at as a go-to-market motion.

Steven Morell: When I do the math, it should be something at 150 SDRs and 300 account executives. Is that right?

Jeremiah Chambers: yeah it's that's roughly, where we're landing. The SDR team is in growth mode right now. But that one's roughly where we're landing at.

Steven Morell: Okay. That paints a picture. So step me a little bit through your tech stack. Salesforce, Microsoft Dynamics? 

Jeremiah Chambers: Okay. Yeah, so we're a Salesforce shop and Salesforce, we're leveraging Outreach for our outbound and inbound motions. And of course, we use Clari on the backend to help keep an eye on the revenue stream.

Steven Morell: Okay. That paints a picture. What about second line management? There is the old rule, if you need more than two pizzas to feed the people in the room, then there are too many people in the room. You need a hell lot of pizzas to feed those 500 people. How is that organized? Do we have regional teams? You have team leads, describe that structure to us.

Jeremiah Chambers: Yeah, so we do have our customers segmented because as I said, we deal with, you know, those Fortune 10 companies, and we also deal with SMB as well. So we've got split into three divisions of or actually four of, enterprises, which is what we call strategic. Our majors. Our corporate and then our commercial divisions as well. We really capture every aspect of the market because we serve every aspect of the market. As far as leadership goes, we do have it regionalized, we have the Americas and, usually it's one person that is taking on the whole of the Americas, including the Caribbean and Latin America. And then we have it regionalized and broken down from there. Same thing for EMEA and APJ, all across the globe. That's how we run this and it's. Working out pretty well is something that we did have to adjust a little bit this year because it was a little bit, I'll say management heavy early on this year and through some adjustments we were able to make a better fit for everyone and ultimately it's showing in the results. It proved to be a little bit better, but that's always a difficult one to figure out the right ratio of how many report to a certain person. Where they sit and, of course, how we define quotas and everything down the line to make sure it all works together.

Steven Morell: Speaking of quotas, your definition of a good sales rep.

Jeremiah Chambers: My definition of a good sales rep, that's a broad one The easy answer is the one who sells more yeah. When there are more sales it is always good. But, for us, it's, coming into this space it's very it's kind of a niche, so you're not gonna get a ton of candidates that have domain expertise in our specific patch of cybersecurity. It's very difficult to do that. So for a good salesperson, obviously somebody who has worked with MEDDPICC before is very familiar with BANT, Sandler Shop. Coming from there is really good, but it's really about aptitude and coachability. If someone has the aptitude to be able to understand the concepts of what we're trying to teach, because it is challenging from a technical aspect, it is very difficult to learn what we do with our expansive product line and how we solve all the problems and be able to speak credibly to a customer. To be able to do that, to be able to run our sales motion which is technically a lot of stakeholders and a more lengthy sales motion. Even on the mid-market side. It's more of like an enterprise style sales motion and to have these people come in, be able to have a foundation that we can build on is very important because it's gonna be very hard for us to find in our small little niche patch all those A players and stack 'em all into one place. We have to make A players and luckily we have a lot of great talent that is making that come true.

Steven Morell: Okay. That's very interesting. So how do you onboard them? I hear two types of skills that are in demand here. One is sales knowledge. You need to know what MEDDPICC is, Sandler. Any sales method. Is there any sales method or do you insist on No, we do gap, Sandler I think you said.

Jeremiah Chambers: Yeah we do Sandler. 

Steven Morell: That means if you find talent, then you need to train them in Sandler. Is that right?

Jeremiah Chambers: Correct. 

Steven Morell: So they first go through assembler training and then get the tech training and product training. How does that work?

Jeremiah Chambers: It actually kinda runs in parallel. But training never stops here is where it's all about. And this is where a, I think a lot of companies struggle because…

Steven Morell: Oh yes.

Jeremiah Chambers: Yeah, doing the, the onset, the original Sandler training is fantastic. It's wonderful. Always people walk away with insights, they invest time in it and quite a bit of money and that's great at the beginning. The technical side of things is something that we have to train in parallel because we wanna get them out there and be effective in the field as soon as possible. Something I've learned is the sooner we get them face-to-face with our customers, the sooner we get them actually, doing the work is the better. Because the training is fantastic, but I'd rather have someone that doesn't know everything to a t. It is okay with admitting that and getting themselves

Steven Morell: Are they, how do I have to picture this? Are they going through the Sandler training one by one, or do you create cohorts of, we just hired five new sales rep. Let's send them over to Sandler.

Jeremiah Chambers: Yeah so we do the cohort approach. So we do a full live Sandler training with an online supplement. We also have an online training that we do as well that are enabled teams, fantastic for the more technical aspects of it. Weekly, we actually have an entire company. Call where we're going over these topics. We're talking deeper into the product and very specific learning topics. Those cohorts don't end at the end of the Sandler kind of training playbook, if you will. As we continue on, we continue to revisit those concepts over time. Once every other week, even beyond that first three months of very intense training we wanna make sure we keep that fresh. But really what makes the difference is that end of the line sales manager actually being on the calls live. Taking the 15 minutes after the call to debrief and tell them how they did give them that coaching and give it to them in a very kind way. That is what makes all of the difference. And then with our sales engineering hands those folks coming in and providing a little bit more of the technical education, if they misspoke or if they went over some kind of complex topic, being able to boil that down into a more relatable way is something that's very helpful over here. 

Steven Morell: Are you using any conversational intelligence tool like gong or Something to analyze those conversations?

Jeremiah Chambers: Believe it or not, no.

Steven Morell: Okay.

Jeremiah Chambers: This the first, yeah. Yeah. It's the first time in years that I haven't, and we are, I believe we're making our way towards that,  now, but. It is something that we're doing it without that, but it does have a little bit of a side benefit because the only challenge I find sometimes with that conversational intelligence is at times with managers, it's always, Hey, I'll get to the recording of that meeting to listen to it, to grade it later, then that never happens. Where at least with our current model, it does spur a little bit more live interaction because, a lot of our sales managers that we have are, they were some of the great salespeople that this company has seen. And, for them it's great to have 'em live there to hopefully steer a conversation back on track if for some reason falls off and give live coaching.

Steven Morell: You said before that a good sales rep is somebody who is eager to learn and coachable. How do you quantify this?

Jeremiah Chambers: So eager to learn and coachable. It really starts with the interview process. When you're interacting with these folk people in an interview setting. First off it's about letting your guard down. I've been one to practice a little bit of radical candor. I'll be very blunt and very straightforward. But the goal is to get someone comfortable in that interview process so that they can be real, be who they are, and be genuine. And having that conversation with them and maybe even, throwing out some critiques or providing them with some guidance before answering a question. Just saying, Hey, it's this interview question. Before we started this, you gave me a few things to follow as guidelines. How well did I follow those guidelines? It's very simple. If you're seeing that displayed in the interview process, that's typically an early indicator of success with it. But when we get into the actual sales motion, when we do make that higher, it's about very good, solid documentation of the conversations that we're having. Because if you have 11 direct reports, let's just say it's hard to remember everything you dealt with. Set some clear objectives. How well are they following through with this? And you can get a pretty quick read on is this person really invested in improving themselves and developing themselves, or is this person somebody who maybe is just set in their ways and not willing to go there yet? And sometimes it can lead to a tough conversation, but that's where it's important for sales leaders to be kind and to be kind, is to be honest. Fortunately we know what's working and how to really run the sales motion to get the results that we want and that you want. And unfortunately, we're going down the path of something that's not working. And those are the toughest days of the job. But they're important.

Steven Morell: You said you know what's working. How formalized is the sales process? Do you rely on me training them well and then I trust they will know what to do. Or you go, I'm training them well and then I give them a very well-defined sales process and I expect them to follow it.

Jeremiah Chambers: It's a little bit of a blend of both. Because, the sales process as every prospect or customer is unique, and there's different times your sales process will get broken. So we don't wanna be too rigid, but really for us. The training is important, but where my team has been able to find a lot of success is having a more kind of predefined process that is not every step to a t, but the important part is what I like to call pro project management selling. So our customers that we deal with, they deal with things on a project basis. They're very familiar with the project management kind of approach. That's a comfort zone for them. And they like to know what's coming, and when. Give you an example. You've been to an IKEA store, correct? 

Steven Morell: Before. Yeah, of course.

Jeremiah Chambers: It's very large, and there's thousands of items, tens of thousands of items. And it can be intimidating when you walk in, but if you look down, you see an arrow and that gives you that sense of comfort that at least you have a guide of knowing where you're going. So for us, it's about getting milestones agreed to early in the process of what this project looks like, what the target timeline is to go to implementation, working backwards from there, and then holding ourselves. Our customer, who's our partner, is accountable to that process. So that's the defined part, but actually the details of what all's included in there is where it's important for sales management to pressure test the deals and ask what's happening next? Do we have a booked meeting? Did the customer agree to this? What does their procurement and legal process look like? How long does it take to ask those questions over time? You'll find that those who are really starting to embrace the concepts may not need that conversation as much. And we can be a little more conceptual and focus on some other development items. But for the new people, that's where a lot of the work is done.

Steven Morell: Do they get those yummy hotdogs at the end of the process?

Jeremiah Chambers: Unfortunately, no, we don't have the yummy hotdogs or the meatballs at the end. But I will say, I love celebrating my team. So if they have a big enough win, I will totally send them some, or maybe even deliver 'em by hand depending on the deal size.

Steven Morell: Jeremiah, let me ask you a final question. If I would have a time machine and you could use that to send a postcard to your five years younger self with a warning of what to do, and it's just a postcard, it's not a letter short note to yourself five years ago, what to do, what not to do, what to do differently. What would you write on that postcard?

Jeremiah Chambers: I think it'd just be a few words. It'd be pretty simple. It would be: Don't wait! You'll be able to feed your family at the end. And just unpack that a little bit. Earlier in my career, just even five years ago there were these challenges that I ran into and sometimes there'd be that self-doubt, maybe a little bit of imposter syndrome coming in questioning myself. Had some great mentors, other CROs, other VP of sales I would talk to, to help validate my feelings on things or what approach I was gonna take. But sometimes I just didn't take that risk fast enough. One thing I found is when you do take that risk fast enough, is that yes, sometimes that risk does turn into a situation that's not ideal, but more often than not, if you have that belief in yourself and you are very confident in what you're doing, you've done the research there's no reason to wait. Go for it. And if you screw it up, you screw it up, you learn from it and you do better the next time. And I've been very fortunate to spend a lot of time with entrepreneurs and they have helped really solidify that myself. So that would be it. Don't wait. No one's gonna die. And you're still gonna be able to feed your family at the end of this.

Steven Morell: Yeah. Fear is removed by action and not by thinking.

Jeremiah Chambers: Absolutely. Absolutely. I need that on a T-shirt.

Steven Morell: I'm a skiing instructor. I tell these skiing students when we are pissed off and it's really steep. Just staring through the abyss, doesn't help just, go for it! Jeremiah, thank you so much. All right, everybody. That brings us to the end of this episode of Speak Revenue. I want to thank our guest, Jeremiah Chambers, for joining us today and sharing all those valuable insights. A huge shout out to our listeners, your support means the world to us. Remember, check our website: speakrevenue.com for a full transcript and additional resources. Also, if you enjoyed the show. Please go to Apple Podcast, Google Podcast, Spotify, or wherever you go for your listening needs, and give us a great review. It really helps to get the word out. Also, follow us on LinkedIn, on Instagram, on YouTube, wherever you can find us. We'll be back soon with another great guest. Until then, stay curious, keep listening, and stay safe.