How to transition to CEO from CRO/VP Sales

About this webinar

This is a panel discussion with three successful revenue leaders (2 from sales, 1 from marketing) who transitioned to CEO. Watch this to find out how to set yourself up to secure a top job and how to be successful when you get it.

Chapter list

00:00 Guest Introductions

02:20 Skills & transition to CEO – Jen

04:24 Going into the role, what are the gaps that you found?

06:28 Skills & transition to CEO – Gordon

07:58 Skills & transition to CEO – Jake

11:02 Do you have a Chief of Staff?

14:36 Focus and allocation of time

21:29 Coaching and mentoring support

25:48 How to let go and trust others

29:32 Accountability and responsibility

33:27 Chain of command

37:01 What skills did you need to proactively learn?

39:34 What’s your methodology for deciding the annual sales target? And how does it get weighted in this economic environment?

44:14 Re-forecasting?

47:02 Roundtable final thoughts

Webinar Speakers

Hosted by: Matt Cameron (CEO, SaaSy Sales Leadership)
Follow on Linkedin: https://www.linkedin.com/in/saasysales/
Website: https://saasysalesleadership.com/

Jen Spencer (CEO, SmartBug Media)
Follow on Linkedin: https://www.linkedin.com/in/jenspencer/
Website: https://solo.to/smartbugmedia

Jake Dunlap (CEO, Skaled)
Follow on Linkedin: https://www.linkedin.com/in/jakedunlap/
Website: https://skaled.com

Gordon Lawson (CEO, Conceal.io)
Follow on Linkedin: https://www.linkedin.com/in/gordon-lawson-58679710/
Website: https://conceal.io/

Transcript

Matt Cameron (SaaSy Sales) (00:10):
Okay, as everybody comes in, let’s kick off because we want to keep to time. So, welcome all. I’m Matt Cameron, CEO of SaaSy Sales Leadership, the creators of RevenueEQ, which is a world-first approach to mapping and training emotional-intelligence skills for sales professionals. Today, it’s my pleasure to facilitate an impressive trio who’ve walked the revenue path to the role of CEO.

(00:30):
I’m very grateful to be joined by my friends Jen Spencer, CEO of SmartBug Media. SmartBug is a full-service digital agency that’s a two-time HubSpot Partner of the Year. And Jen has been SmartBug CEO for just over a year and was formerly the president and CRO. I’m also joined by Gordon Lawson, CEO of Conceal, where the mission is to stop ransomware and credential theft through social-engineering protection. He’s had the role for almost two years, prior to which he was CRO and president at RangeForce. And last certainly not least is Jake Dunlap, CEO and founder of Skaled, a management and sales consulting service provider. He founded Skaled over 10 years ago, prior to which he held VP roles in both sales and success.

(01:13):
So, to set the scene, I reviewed a few studies and found that less than 20% of CEOs came from the revenue path. Does that surprise you, panelists, less than 20%? And today’s discussion is focused on helping you beat the odds and to succeed in the role when you arrive. Studies of tech companies specifically showed that they had several common traits, which is quite interesting to me. Most worked at large organizations previously, and the reason for that was that they had best-in-class opportunities for leadership-skill development. And nearly all of them said that they had built a support network of people from whom they could ask questions and seek guidance from.

(01:49):
So, with that in mind, in the next 45 minutes or so, we’ll be covering the gambit from translatable skills, what the experience of taking the reins looks like, and how you let go of your former function. A big thanks to early registrants who also sent questions ahead of time. I’ll make sure we do our best to get to those.

(02:08):
So, let’s dive in. I’d like to start with you, Jen. Can we start by talking about the skills that translated well, and perhaps some of those that didn’t as you made the transition to CEO?

Jen Spencer (SmartBug Media) (02:20):
Yeah, I would. I would love to. I think I’ve told people quite a bit over the last year, I feel very uniquely qualified to be the CEO of SmartBug Media because of starting as VP of sales and marketing and then moving into CRO, where I was overseeing operations for the organization as well. But if I even dial it back further, I was a past two-time client, when I was leading marketing and then later marketing and sales in some software startups. So gives me a very interesting perspective. But I think the skills for me that translated well, that have made me successful are having a really deep, very strong understanding of the market that we serve and the ecosystems that we work in made that really successful for me. Because in my role as CEO, I’m responsible for passing a vision that is usually, like, three times further along than where we are right now. The organization and my board expects that out of me, that I can say, “This is where the market is going. And therefore, this is the position I think we should be in.” So coming in with that deep understanding of the market put me in a really good position to be able to provide that kind of guidance. That is a little bit different from the operational type of work I was doing as CRO or as president.

(03:48):
I think the other skills for me that just really translated well was just communication. I actually started in my career as a high-school English and theater-arts teacher and then moved into the B2B SaaS world by way of nonprofit regional theater. I know, not kind of normal. But it just means being able to communicate. So, over the course of my career, I’ve had all these different audiences that I need to craft communication for, whether that’s written or verbal. And those skills were extraordinarily useful for me moving into this role.

Matt Cameron (SaaSy Sales) (04:24):
Interesting. And then going into the role, what are the gaps that you found? Is there anything that comes to mind?

Jen Spencer (SmartBug Media) (04:31):
Yeah, I think… Listen, it’s really important that you just really know yourself. So I think I could share what gaps there were that I had, and I’m sure Gordon and Jake will have others, but for me, it was about, “Okay, what am I missing,” and “What do I need to backfill or add to my executive team to make sure that I’ve got what I need in order to be successful?” For an example, my financial acumen is not at the same level as our CFO. My marketing acumen is at the same level of a VP of marketing in our organization, which is fine and that’s fair. But while I have done things to upscale myself and to grow that financial acumen for my own learning, my own knowledge, my own comfort, my own confidence level in speaking to our goals and business operations, ultimately, I really want to make sure I’ve got a really strong CFO that I trust that I can collaborate with. That’s an example. So, something I even did before I came into this role is I actually took on, for a temporary period, took on a CFO mentor to try to better understand the kind of the mindset of a CFO and how to best communicate with them, with that kind of person.

Matt Cameron (SaaSy Sales) (05:57):
Really interesting. And we’ll talk later, I think, about the challenge then when you are as skilled as some of your direct reports in terms of giving them the rope they need, the freedom without getting too deep in the weeds. So that’ll be interesting conversation. Also, it’s interesting to me, connecting the dots between the studies that show having a strong network around you for a mentoring, coaching, development and support is really, really important as you transition into these roles. So, thank you.

(06:21):
So, Gordon, perhaps you could share with us skills that translated well and those that perhaps didn’t as well. Love to hear your perspective.

Gordon Lawson (Conceal.io) (06:28):
Yeah, obviously. Well, I think the number one thing, Matt, and thanks for having me today, but I think number one thing is just that focus on the customer. I think sometimes it’s really easy to get wrapped up if there’s a lot of noise or you’re having challenges in the business. But if that customer is satisfied, and you’ve built that trust, and you’re moving towards that close at the end of the day that we all, I think, want, good things are going to happen. So, I think that that’s one thing, obviously, coming from a sales background, you are very focused on that. That doesn’t mean that you kind of roll over every time. There’s challenges that you have to challenge there and make sure you’re overcoming those objections. But I think that just… we use the term maniacal attention to detail to win the customer. And I think that has really served me well in the transition.

Matt Cameron (SaaSy Sales) (07:18):
It’s interesting to me, some of the criticisms I hear of the finance path to CEO is that they’re not getting out of the building enough. Hearing from customers, spending time with customers, it may not come naturally. And I’m sure for everyone on this call, that would come naturally. It’s a happy place, right, speaking and engaging with customers. So, interesting to hear that.

Gordon Lawson (Conceal.io) (07:37):
For sure. If there’s ever a wall in my day, it’s one thing I’ll look through Salesforce and I’ll just connect with CEOs of opportunities we have and just try and build that bridge.

Matt Cameron (SaaSy Sales) (07:48):
That sounds terrifying for the AE that’s working that account, but it’s very good to know.

Gordon Lawson (Conceal.io) (07:52):
That’s right. That’s right.

Matt Cameron (SaaSy Sales) (07:54):
Jake, could you give us your perspective, please?

Jake Dunlap (Skaled) (07:58):
Yeah. I think Jen hit on some that really hit home with me. For me too, scaling a people business, it has its own unique challenges around staffing and scaling without venture back, or when it’s just your company and your own profits. So, for me, the skills that translated, I think probably the same for everyone. It was I wouldn’t say easy for us to get clients in the early days or to grow the initial snowball or groundswell. So I think the sales piece and growing that side of it, I think this came very, very naturally and was very easy for us early on.

(08:40):
The flip side is how you manage clients and customers when your people are the product, to some extent. A product, coming from the software world, a product is defined. It’s this thing. It’s a box. It solves five problems. People are not as easy as that at times. So I think for me, it was more of the operations. I think my big takeaway is I didn’t have a strong enough operation-support person early. And so we would bring a deal in, do amazing work, but the processes weren’t tight. How we engage with customers, how we get them onboarded, how we work with them, how we update, how we communicate, that wasn’t my strong suit. And I think that’s probably one of the biggest things that I learned over time, was just the importance of operations as you’re scaling, because your operations is, just like in the software, it’s almost like your engineering team. And I hadn’t scaled an engineering team, which is like processizing the product as a part of that.

(09:44):
So, I think obviously, for all of this, the sales component was very easy. The finance piece, again, I think was another challenge, and Jen hit it on the head, at least for me. As a sales leader, it’s like, sell first, ask questions later. You just think that you’re just going to grow, grow, grow, and again, as you’re scaling a people business, it doesn’t scale exponentially. My cost scale is somewhat as my revenue scales. So, I think finance and operations are areas that I was in… I had some natural strengths around project management and logistics, but I don’t think I invested as much time because I think it’d be very difficult. And maybe Jen and Gordon can relate or not. It’s like, as humans, you gravitate toward what you’re really good at. And when you’re running a business, you can’t, you got to stop yourself from doing that at times. Lean into the strengths, but also realize that “I got to have that one-hour finance meeting every single week,” even though I don’t enjoy Excel as much.

(10:46):
So, I think for me, it’s obviously the sales skills that translated into marketing skills, but I think it was finance and operations where it took me time to start to realize that I needed to have more discipline and surround myself with a stronger team, too.

Matt Cameron (SaaSy Sales) (11:00):
This is an interesting point. Jen, do you have a chief of staff?

Jen Spencer (SmartBug Media) (11:03):
I don’t have a chief of staff. We’re about a 200-person professional-services organization. Because I was nodding along with a lot of what Jake was sharing. But when I came into the role, I was able to step into a number of processes that had been established, but I did really take over in scaling us more from, like, 50, 60 people to where we are now, which was a pretty big lift in my role.

(11:36):
But I was just thinking about… just reflecting just as Jake was just sharing, Gordon was sharing, one of the things that my board signed me up to do when they offered me the role of CEO was I did a two-week program at Wharton, part of a professional-development group. And part of that is a really intense simulation where they force you to take on a role that you’re least comfortable with. So I was not allowed to come in and run sales and run marketing for my, pretend, Fortune 500 company. I had to go in and I had to do operations, which was really painful, but also was really helpful to be able to test on something with that level of talent there to support you. So, that was just a really cool experience. And believe me, if no one would have forced me, I would have jumped right into the sales seat in that simulation.

Matt Cameron (SaaSy Sales) (12:32):
Well, would you say then that’s an interesting takeaway for aspiring CEOs, right, is this concept of being able to sweat and training? So you do your safe-space role playing. I’ve done these simulations. It’s very realistic, is it not? You feel the pressure, especially when you’re surrounded by smart folks. Yeah?

Jen Spencer (SmartBug Media) (12:49):
Oh, yeah. That competitive drive, oh, that just kicks right in.

Matt Cameron (SaaSy Sales) (12:52):
Yeah. That’s awesome.

(12:54):
What about you, Gordon? Have you got that chief-of-staff support?

Gordon Lawson (Conceal.io) (12:58):
I don’t have chief of staff. We’re less than 15 employees now. But we have some very strong CRO, very strong finance lead. And I think, a short of a simulation, there’s another way that I think you can really practice this role, and I think that that is being in the boardroom early. I know that there are some CEOs that maybe won’t bring their SVP of sales or certain executives in. It’s like them in the finance lead. I don’t think that’s right. I think outside of executive session, you should always have your functional leads briefing the board. And when you’re one of those functional leads, a CRO, SVP of sales in this case, that is incredible practice for the kind of questions that you would get as CEO. For me, I was lucky enough to do that with a few companies before. And I feel like you get to know, in our case, the questions that a venture capitalist would ask. You learn to speak in their terms and that gives kind of that finance training and that finance mindset ahead of sitting in the seat.

Matt Cameron (SaaSy Sales) (13:58):
I think it’s an excellent point. And for folks who are listening, another way to do that, if you can’t get in the room, something I’ve seen is the after-action review and a pre-brief. So if you can be mentored by your CEO, “Look, this is how I’m preparing for the board. This is the deck that I’m taking them through,” and then do an after-action review, it’s a way of almost being there. I think that’s a great call out, Gordon. You need exposure to those board-level thinking and the strategy.

(14:24):
So, that segues, I think, quite nicely. Now that you’re in the CEO seat, what did you expect and what did you not expect about your focus and allocation of time now you’re holding the reins? Gordon?

Gordon Lawson (Conceal.io) (14:39):
Yes, okay. Well, I think a couple of things there. I think certainly for us, we’re in cybersecurity. We’re working in a very complex environment. We have nation-state actors that are doing really damaging harm to companies around the world. So that technical expertise and acumen is critical for us. And for me, understanding the conceptual pieces of that but not being a hands-on coder really forced me to have to find, I would just say, world-class technical talent, which we’ve been lucky enough to find that, but it’s not easy. And even folks that may appear to be that on paper are not always the folks at a certain stage that can get hands-on and really, really build exceptional products. So, I think understanding how to interview for those sorts of roles and recruit and bring those type of people onto the team have been something that I didn’t really appreciate as much, but now I’ve really gained an appreciation for it.

Matt Cameron (SaaSy Sales) (15:45):
Got it. That’s interesting. I think you’re in a huge situation there. You can’t get that wrong. [inaudible 00:15:50], you’re up against some pretty impressive actors.

Gordon Lawson (Conceal.io) (15:51):
Exactly. Yeah.

Matt Cameron (SaaSy Sales) (15:53):
Yeah. Jake, what about you? Time and focus allocation?

Jake Dunlap (Skaled) (15:59):
Oh. I mean, it does feel like you are focused on everything at any given time. I think Jen mentioned this before. I think what I try to do is structure and look at my day and “Am I focused on things that are going to move the business forward?” What I mean by that is it’s not that I’m not doing a lot of tech, but this year, this year, this year around, whether it’s everything from payroll to a customer interaction. But I do feel like one of the things that I make sure that I’m focused… I’ve always had this mindset, I call it 80, 15, 5, which is like, 80% of my time is focused on the now, 15, I call it midterm, 5 is long term. But I feel like as a CEO, I have to shift that more because I feel like it can be easy. And I fell into that trap for sure, and still do from time to time, where I find myself doing things in the business and getting into parts of the business, because it feels good to check boxes, it feels good to have wins and work with the team more hands-on in certain aspects.

(17:01):
And I think what I try… And again, I’m not going to act like I figured this out for forever, but I think one of my biggest lessons now is being in this seat is, yes, you might be able to do it better. And in certain cases, maybe in your own opinion, exponentially better. But if you don’t give your people the room to breathe, and I’ll actually tell a quick story, the flip side of that, then you will find yourself not being able to focus on the long term, and even medium term. In today’s economy right now, thinking about what’s going to happen in a year is very difficult. Even now, it’s like, “Let’s just try to see if we get a forecast accurate for six months, or nine months.” So, I think there’s that, which is making sure that I’m giving people the room and not feeling like I need to go in because I think I can do it better.

(17:53):
But I will say that there’s the other which is the flip side, Matt, and this is something I made early in my career. So for a lot of people that are thinking about making that move, in sales, we’re very merit based, like, “Oh, I was really good at XYZ. Now I’m going to get promoted.” And the issue that I found is, I found myself hiring people and putting them into roles that they weren’t ready for yet. And I think it came from that sales-leader mentality. So that is, I would say, one of the biggest learnings I’ve had, which is, make sure, as a CEO, I’m providing rooms for people to grow, but I’m not putting them in roles where they’re over their head early. I think that there can be a real desire early on, especially as you’re scaling early, to be like, “Well, what about Byron, Johnny? He can maybe do this.” “Yeah, okay, he’s a good fit, the culture people.” And I think over time, you realize, at certain phases of scaling, you need people that have been there and done it. So that build verse buy on the talent front, I think can be also a very difficult one.

(19:00):
I think being the CEO, those are the things I think about. “How do I make sure I’m creating enough space long term, even though I could be in the weeds doing more,” and making sure that I’ve got people in roles where they’re stretched, but they can be successful, and so their expectations that we have as leadership can also be met. So, I’d say those are probably the [inaudible 00:19:22]-

Matt Cameron (SaaSy Sales) (19:21):
Yeah, I definitely want to come back on the topic there in our next question around letting go of your function, because there’s an interesting message I heard come through there, which was, people sometimes need to be leveled, topped, as some people would say. And that can be very challenging, from a culture standpoint, maintaining good talent that are not there yet, but they can be there yet, and how we set up programs and practices around that. So, I’d like to come back to that in a minute.

(19:51):
But to round out, Jen, what did you expect about where you’d be spending your time and allocating your focus, and perhaps what you didn’t expect in this role?

Jake Dunlap (Skaled) (19:59):
Yeah. As I shared, I kind of expected I really need to keep my finger on the pulse of the market and needing to be able to both look ahead but also know what’s happening and what’s impacting our clients right now. I am setting the tone for our own growth and adding more services. We think about our product that we sell, which is access to people. And I was expecting to have to make some difficult choices, and I was expecting to have to balance the idea of growth and profitability. I vastly underestimated how challenging that was going to be. Especially coming from early-stage startup world or nonprofit world, deciding to make a bet, spending the company’s money on those bets, that was uncomfortable for me as I was really getting started. So, it’s like, I knew it was coming, but I didn’t realize how challenging it would be for me personally. And then-

Matt Cameron (SaaSy Sales) (21:15):
Can I just [inaudible 00:21:15]? Can I dig into that a second? Because that’s a challenge, right? And oftentimes, also it makes me think of imposter syndrome where we can do it, we don’t think we can, and therefore we attenuate risk and we don’t take the shots. And it comes down to the similar thing with investment, because how far are you going to stick your neck out? Did you get some coaching support or mentoring around that to help you push through those, or did you just deal with it personally?

Jen Spencer (SmartBug Media) (21:34):
Definitely. I was in a very fortunate position where I’m the second CEO of SmartBug. Our founder is our board chairperson and spends as much time really as I need mentoring and coaching. But at the same time, he’ll self-admittedly say, “Well, I’ve never grown this company to the size that we’re at now or to where we’re going. And there’s also a reason why we talked you to do this.” So, he continues to tell me, “Trust your instincts, they’re usually right.” So, just hearing that is helpful as well. But there’s something that’s just daunting, a little daunting about saying, “Okay, I have all of this data that says this is about what we should do.” But at the end of the day, there’s also some kind of a bet, there’s some kind of hypothesis that you’re going to have. If you are a very growth-driven organization, you’re not always going to have this perfect data storytelling you kind of what step to take next. You have to make some decisions. So, having it be the first time I’m making that decision, I’m putting myself out there, it’s on me, right? It was a lot.

Matt Cameron (SaaSy Sales) (22:48):
Well, I think it connects also similar to a point you made to me before we were chatting, which was the additional stress that comes from the responsibility of the hundreds of people that you’ve got now.

Jen Spencer (SmartBug Media) (23:02):
Yeah. I was not expecting that at all. I was not expecting that. And especially because I’m the kind of person who really tries to get to know everybody and we’re the kind of culture of an organization where we like to know about each other’s families and their pets and their kids and all of that stuff. Your people are not just a number in your PnL, there are these human beings with lives and homes and things that are going on. And so that weighs on you. If you’re an empathetic type of person like that, that weighs on you as you’re making decisions that are for the good of the organization, which I was not expecting to feel that kind of pressure. Because although I think I’m an empathetic person, I’m not your stereotypical warm, fuzzy person. I’m a little bit more cold heart to the facts kind of individual. So, that was a little bit jarring for me to see that in myself.

Matt Cameron (SaaSy Sales) (23:57):
Yeah. Does that not connect also to this unexpected pressure of people still wanting FaceTime with you that are sort of a few levels below in the organization? I think you mentioned that was a surprise, too, right?

Jen Spencer (SmartBug Media) (24:09):
Yes. I think that is a reflection of I grew really fast in the organization. So in five years, I went from leading a small team to leading the entire organization. So there are people I hired who went from seeing and talking to me every day, or seeing me multiple times a week, even being fully remote to now they maybe get once a month or twice a month or maybe even once a quarter, depending on what the interaction is. And when I get the feedback in a 360, which we just got, that’s like, I really met… feeling this lack of getting time with me. I also know, well, there’s only so much time I have in my day, and I have to be looking ahead, and I can’t always just be dealing with what’s happening right now in the organization. That’s not the best thing for the company. But balancing that feedback, because people expect like, “Oh, Jen just maybe doesn’t like me anymore,” or “I’m not important enough for her anymore.” Everyone has feelings-

Matt Cameron (SaaSy Sales) (25:08):
[inaudible 00:25:09] smiling because it sounds like you’re describing my relationship with my parents. When [inaudible 00:25:13]. Okay, thank you very much. We should probably [inaudible 00:25:18]. No judgment, please.

(25:17):
Last question I’m going to direct to Jake was… [inaudible 00:25:24] particularly interesting to direct this to you, because Jake, you are acknowledged in the industry as being a go-to market expert. And you’ve got a ton of experience, and you’re running an organization that helps other people do that stuff. So, the question is, how do you let go when you are the expert in these functions and you’ve got people that need to manage this for you? I think you’re the perfect person to start with on this one.

Jake Dunlap (Skaled) (25:50):
Oh, man-

Matt Cameron (SaaSy Sales) (25:51):
You can say badly. You can say badly.

Jake Dunlap (Skaled) (25:51):
I would think it’d be like I’m perfect [inaudible 00:25:53] I’m so amazing at it. And I got to be honest, it’s 10 years in, and I feel like I’m just now getting better at figuring this stuff out. It’s interesting. With my business, I started it from nothing. And we have no venture backed anything. We make all of our profit. It’s this novel idea called a profitable business that, now with what’s happening, I think a lot of people are more interested in. So, very early on, I had a lot of different, I guess, stressors, but I was always focused, again, on growing the top line. So I think that there’s kind of these stories that you tell yourself as you’re scaling a business of like, “I have to stay a hold of this, because if I don’t let go, there’s no backstop.” It’s like, me Bank of America and Capital One. That’s kind of it. So, I think in my situation in particular, Matt, I’ve probably held on too long to some of this, especially around sales, and even maybe some influence on operations and how it should be set up. Because I think I feel this weight of, “I have to do it.”

(27:07):
But what I’ve continued to find is that you can’t expect people to do things the way you would do them. But that doesn’t mean that they’re not going to come up with the right outcomes or they’re not going to get there eventually. And it’s such a balancing act because you don’t know… I also, by the way, do not believe in blind trust. To be very clear, I do not believe in blind trust. I believe in trust with proper inspection, and then more trust.

Matt Cameron (SaaSy Sales) (27:39):
Trust but verify, huh?

Jake Dunlap (Skaled) (27:40):
Trust but verify. And I think, again, I would say that’s my take on it, is, for me, I don’t know if I let go enough early. I don’t know if I did a good enough job of really thinking about the operations and the structure early. And again, whether it was real or not, I’ll never know. But I feel like now, look, we’re at a certain size, we’re about a quarter the size of Jen’s firm, we’re at a certain size where it’s taking time to get here. But we have people in places, and I’ve started to realize the way to put in place being very specific. And I think, Matt, actually, if I have to really hone in on it as I’m talking through it, what I realized is early on, I was not as specific. “This job requires these 17 things. It’s this, this, this, this and this.” If I only define these 7, then those other 10, there’s ambiguity around ownership.

(28:39):
And what I’ve found is that for me to remove myself, when I do the diligence of defining what the expectations are, and just removing the emotion, and this is what it is, that is what has allowed us to scale more effectively over the last few years, is that ability to be very specific. And when I’m specific, it’s easier for me to let go, which I don’t know if that makes a lot of logical versus emotional sense. So, I think as you’re growing your business, or for anybody who’s thinking about the leap, just think about that, just anything that you think could be ambiguous will become ambiguous if it’s not, like, 1, 2, 3, 4, 5. And then that way, it actually gives your people a lot of freedom. You might think that you’re holding your people back by being that prescriptive, but you’re actually really empowering them because now they know exactly what’s expected.

Matt Cameron (SaaSy Sales) (29:32):
We need to know which lanes we’re swimming in. Something I’ve seen, particularly in a situation like Jen, where you’ve ascended from within a peer group, is actually getting the team together and outlining as a CEO, “This is what I’m accountable for and responsible for. And let’s agree in each of the functions.” And perhaps some sort of a virtual contract, we basically agree, “Here’s when I will stick my nose in,” or “This is the support I’m going to give to this specific thing.” But I understand and agree that that’s yours. And you have my invitation and permission to push back. If I slip off the rails and I’m in your lane, you can push back. Yeah?

Jen Spencer (SmartBug Media) (30:09):
Yeah. It’s interesting. I had the biggest aha when I was reading Brené Brown’s book Dare to Lead, in which she talks about the concept of painting it done. And I realized how horribly I have been doing that, where I and my team had told me, “Jen, you have very specific expectations for how things are going to happen or what the results are going to be, but you’re really vague in how you assign those, assign that work.” Like, “Damn, yeah, they’re right. I don’t paint it done.” I don’t just tell them this is exactly how you’re going to do it, but when this is complete, this is what it’s actually going to look like. That has really saved me. But I don’t have an issue letting go of things. I have an issue of doing the kind of that explanation.

(30:54):
And then I have an issue, I am really bad… This has been something I’m working on my whole career, is I have a really hard time not chiming in when I know the answer to something. Like, someone will drop something in Slack, and it’ll be like, “Does anyone know of it, any examples, do we have any clients who are in financial services that work in the Midwest,” and I’m like Johnny on the spot. I’ve got all this institutional knowledge, and I’ve always been that way, and it’s really, really bad. So I have to stop myself because otherwise I’m literally training everyone not to do their jobs. I’m training them that I’m going to jump in. And I’m training them not to say anything because what if they’re wrong? And I kind of overrule everything. This has taken a really long time for me. In fact, I was head of marketing at a software startup. One day, it was late on Friday, and I’m pissed because I’m toiling away doing something and everyone’s gone. And my peer who was the head of sales came in, he’s like, “You did this to yourself. You literally trained everyone in this building that you’re going to handle it.” And I am still a work in progress on this one.

Jake Dunlap (Skaled) (32:08):
I’m just like, I raise my hand. I testify. I was like, “That resonates so much.” And I think there’s a Steve… I literally just heard this. Steve Jobs, I guess how he works… Or not Steve Jobs, Jeff Bezos. His framework is he’s always the last one to talk. And I’m with Jen, I’m just with you 100%. As you’re talking, I’m like, “Oh my gosh, I know that feeling so much.” But you are so right that if you… But we’ve all seen this on the sales floor, too. There’s that rep that you kind of jumped on a few too many calls, and now you’ve nurtured the dependency, and now she or he can get to set 70-80% a quota, but they can’t get to 100 unless that jumps in and does it. And I think when you think about doing that across your organization, you can create a culture of that.

(33:03):
And I’ve just had to be very… We just did these different documents where, as I’ve clearly defined the roles, I’m like, “This is your thing now,” and it’s just like, “Jake, you’re not attending that meeting. Stop showing up.” And I think it can be hard. It can be hard-

Matt Cameron (SaaSy Sales) (33:21):
I know Gordon, you let-

Jake Dunlap (Skaled) (33:21):
… So Jen, I feel everything you said.

Matt Cameron (SaaSy Sales) (33:23):
Yeah, and I think we all experience the same thing. It’s part of our leadership ascension, too, isn’t it, is not training people to be dependent.

(33:30):
And Gordon, I know you have some points about thinking about chain of command and respecting that. So I’d love you to chime in with your experience here.

Gordon Lawson (Conceal.io) (33:37):
Yeah, no. I probably have a double whammy here, former military guy and sales leader. So I got multiple things probably working against me in not the best way sometimes. But I think at the end of the day, everything here is such a valid point. The way that I would think about it, too, is obviously, you can’t jump into the top, you have to give people room to do what they need to do. But we talk a lot about velocity at the company. So, for me, I’m going to kind of zoom out and take a look and see where there’s roadblocks across functional areas. And I think sometimes those roadblocks can be self imposed. “Hey, we can’t do something this fast,” or “This is in our way.” And one of the great things about being CEO is probably 99.9% of those roadblocks I could remove, or I can help them work through or overcome. So, that’s what I’m thinking about, is what’s slowing us down, not to get into our people’s functional areas, but “Is there something we can do to speed that up?” Because it’s superfluous to get in results. And I think that’s the way that I’m thinking about it.

Matt Cameron (SaaSy Sales) (34:40):
Because the [inaudible 00:34:41]-

Jake Dunlap (Skaled) (34:40):
Hey, Gordon, can I can ask a follow-up to that? Because I’m being selfish with my own work. How do you balance knowing when to let the roadblock sit there and, obviously, I can coach and not give the answer, as opposed to be the roadblock remover? I think when anybody’s in leadership, whether you’re becoming a CEO or not, how do you think about the difference between, “Hey, I have expertise,” like what Jen said, “Oh, I know the answer,” which is what I feel. What I also appreciate is the time where it’s like, “I know you’ve got this roadblock.” And I sit there.

Gordon Lawson (Conceal.io) (35:19):
I think there’s two ways. Jake, if it’s affecting something customer focused, it has to be removed. I think that’s kind of my calculus. If it’s customer focused or reputational to the company, it has to be removed immediately. We have to make sure… And I have to just make sure, it doesn’t mean I have to do it, but I feel like I have to make sure it gets done to a point where that’s smoothed over and we’re working it. I think if it’s in a situation where I might let it sit there and let that individual learn from themselves is if I’ll say, “Hey, this is how you want to do it, keep doing it. We’ll look at how the results are. Let’s give it a week and see how the results are.” And if then the results aren’t there, then I think usually they’re going to learn from themselves that this is not effective.

Matt Cameron (SaaSy Sales) (36:08):
Something you said to me the other day, Gordon, was, sort of paraphrasing your point earlier, “The speed of the boss is the speed of the team.” And I like that. I like the idea that if they see that you’re urgent about solving problems, then hopefully they’ll behave in an urgent fashion so that you’re not going to have these things sitting around for too long.

Gordon Lawson (Conceal.io) (36:25):
Yeah. That was Lee Iacocca. I read his biography, I love that line. And I think it’s absolutely true. Just challenge, push fast. And hey, we all know it’s a balance between micromanagement and that fast pace and attention to detail. There’s always a line there that I think all CEOs are having to balance. But usually, I like to defer to action and move fast. And bring people to me, bring executives around who buy into that culture. It’s important for this culture you want to set.

Matt Cameron (SaaSy Sales) (37:00):
Perfect, perfect. Well, you know what, this is a good time now to grab a few questions that have come in from folks. We got Rich’s here. And Rich asked the question. And now let’s do a popcorn style. Whoever wants to grab it, grab it, and we’ll see what folks have got to say. “What skills did you need to proactively learn that aren’t inherently part of the skills necessary to successfully lead revenue teams?” We had a couple before. I think the gentleman was talking about the finance side of the house. But what else that didn’t come naturally from your path?

Jen Spencer (SmartBug Media) (37:32):
I’ll say running a pro-services organization, the balance of the operational side of things, like Jake was mentioning, of how many people does that take and what are more profitable lines of business and what are less. And something might look really great from a top-line revenue perspective, but then when you look at that line of business… We have lines of business that might be easier to sell, faster to sell, might have higher ticket numbers associated with them, right values associated with them, but actually require a great deal of work from the organization. So, really understanding that piece was something that I had to spend some significant time understanding and learning. Wasn’t challenging if you understand that business framework of the business, but it wasn’t a metric that I wasn’t measured against in the past.

Matt Cameron (SaaSy Sales) (38:20):
Interesting, isn’t it? In professional services back in the day, we always talk about the 80% utilization benchmark and whatnot. And in sales, I don’t really think about that. It’s all the top number. There’s no EBITDA consideration. That’s a good point.

(38:32):
What about you, Jen-

Gordon Lawson (Conceal.io) (38:33):
I think… Yeah, I’ll just go ahead, Matt. I was just thinking along the lines of risk. And there’s financial risk, of course, but there’s HR risk, too. Now, I think when you’re in a sales role, you’re hiring and letting folks go, so you kind of get exposed to that through HR. And I think this past weekend showed a lot of people around the country and around the world how tenuous things can really be. So, that certainly falls in the realm of macroeconomic finance risk. But there are very clear HR risk in the company that can shut a company down with the wrong decisions. So really understanding what those look like, having a great HR leader that you can rely on, having that advisory network to say, “Hey, how severe is this? Can I make this call or not make this call,” those are things that systemically can break a company. I think you learn some of those through experience, but you need to really understand what you’re dealing with when you make certain decisions.

Matt Cameron (SaaSy Sales) (39:37):
Nice. All right. Why don’t we grab a question here from Peter. Peter says, this is quite a technical one, “What’s your methodology for deciding the annual sales target? And how does it get weighted in this economic environment?”

Jake Dunlap (Skaled) (39:53):
I’ll take this one-

Matt Cameron (SaaSy Sales) (39:54):
We get you heard something about it, Jake.

Jake Dunlap (Skaled) (39:58):
… Oh, man. We’re literally in the process of re-forecasting already. I will tell you this. I think one of the benefits of being a sales leader, former sales leader, CEO, is I know the realities of what’s happening verse someone else’s expectations of what they want to have happen that’s just absolutely not realistic. So it’s easier for me to say, “Okay, here’s where we’re at. What do we have line of sight to?” In our business, our sales cycles are not long? So for us, our pipeline… it’s very difficult for us to get visibility. We have a portion of our revenue where we have visibility. Let’s call it 14, 24 months out. So, I think in today’s world, you have to be very honest. “Hey, we’re going to re-forecast. It’s not a bad thing. It’s to rightsize for where we’re at now. We’re going to reevaluate in six months.” And I can tell you from talking to a lot of other organizations, they’re taking a much different approach and a more similar approach to what I just mentioned, to be more realistic and not just throw out numbers and figures because that’s what a board wants them to.

(41:21):
I would say a mistake that I made, it’s a really good question, is forecasting growth, because that’s what you’re supposed to do, and not focusing enough, like Jen said, on the processes and how to grow profitably as opposed to grow at all costs. We would have our best year ever and make almost no money. And I’m like, “Yeah, that’s what you’re supposed to do,” because I came from the venture world. It’s like, “Who cares about money?” But as you’re scaling your own business, you need to do that. So, I just think it’s like, setting targets, what I’ve learned is I’m setting targets that are realistic, that we are actually scaling at the right rate, not just to scale because, like Jen said, because we can generate top line with no bottom or negative bottom line. And now in today’s the climate, I just feel like you have to be very realistic about what’s happening. And when things have a dramatic impact on the business, I don’t think there’s anything wrong with doing a re-forecast mid-year.

Matt Cameron (SaaSy Sales) (42:18):
Gordon, what’s your perspective on the approach? I’m interested to put you on the spot. People use different attainment ratios in terms of X many reps hitting their number at certain percentage, yada, yada, ya. How do you think about it? Is it top-down, bottoms-up, combination of the two? What’s the perspective you have on it?

Gordon Lawson (Conceal.io) (42:35):
I think it’s a combination of two. The thing that I’ve really honed in on, too, is… one of the metrics that I really pay attention to now are demo counts and demo conversions because that’s ground truth. Now, I know that’s not setting quota, but that’s ground truth of whose actually interested in buying your product. And now you can convert from your demo to quote to close. All right, so you have those historicals. Okay, so we know that if those metrics stay consistent, now we know we can predict top of fall going into the following year, we can assign reps to that appropriately, and we can do the 70-80% attainment. I think 70% is probably more prudent these days, based on quotas. And this is all dependent on your type of product, too. For us, it’s a SaaS software, so we have very high margins, and we can get maybe a little bit sportier than other industries.

(43:31):
But I think top of funnel, and if you’re not consistently getting good top of funnel, both inbound and outbound, Matt, this is your world, Jake, this is your… this is all of our worlds, you better reassess what you’re expecting people to do. Because if it’s not there, I don’t think you can expect one rep to be closing $2 million the next year. It’s a holistic process to drive that level of success.

Matt Cameron (SaaSy Sales) (43:58):
Quick StrawPoll. The thing that I’ve often said to folks is, “You’re allowed to re-forecast once during the replan once during the year.” And of course, when I was leading these groups, I would always, of course, delay that for the last minute, because then you have more data more, right? Why would you not-

Jake Dunlap (Skaled) (44:15):
Absolutely.

Matt Cameron (SaaSy Sales) (44:15):
… So [inaudible 00:44:16] for the year. Has anybody had to re-forecast… Like last year, for example, was there a re-forecast? Did anyone do that last year?

Jen Spencer (SmartBug Media) (44:24):
Yeah, yeah.

Jake Dunlap (Skaled) (44:25):
We did. And we didn’t do it very well. I think sometimes a lot of people want to… Look good is the wrong word. But it’s like, they want to be rose-colored glasses. And I try to train our leaders. I’m like, “Do the opposite. Give me your 110, 180.” Yeah, we did and we had probably three out of four leaders that I think did the rose-colored glasses version. But it was a learning lesson for them as a part of it-

Matt Cameron (SaaSy Sales) (45:01):
Jen, did you do it this time?

Jen Spencer (SmartBug Media) (45:02):
Yeah. We did a re-forecast, which the first time we’ve ever done that was last year. But primarily, it’s because our revenues drive our headcount because we hire so many people so often because we’re selling access to people in that time and we work on retainer. And we have a recurring revenue business, much like a software company, but we’re selling those, the people that it was a little bit too challenging for our team to wrap their heads around what was coming next. It made a lot more sense to re-forecast, and it was something our board sort of suggested. It was not fun. It was a really awkward, clunky kind of an experience. And my preference is to not do that. So, even going into this year, we developed a few different versions of our forecast with different assumptions for each one of those. So that I feel much more comfortable with, what we’re working on, how we’re working towards how we sort of level set with our investors.

Matt Cameron (SaaSy Sales) (46:14):
Got it. Well, I’d like to ask one more question from the [inaudible 00:46:16], and then we’d do our lightning round. This comes from Sid. “As a go-to market leader, cross-functional collaboration has been crucial. But now as CEO, what learning do you have as you transition into the new cross-functional teams that are reporting to you, things like product engineering, HR,” yada, yada, ya. Any thoughts from the crew about that? Anything that comes up that’s worth sharing even?

Gordon Lawson (Conceal.io) (46:38):
I’ll just say one thing, is I think that the language of sales is not the language of engineering, for sure. And this, obviously, is dependent on people’s personalities, too. But I think for me, engineers and even product folks, they need room… You need to have clear expectations and clear goals, there’s no doubt, but they need room to breathe. It’s never going to be perfect the first time. So, I think that that space for them to… It’s okay to make mistakes, add more time to every deliverable. That to me is something that you just take for granted in sales, because you can move things really quickly in sales. You can change messaging, you can do all sorts of things. But the backend of the infrastructure of the businesses is significantly different. And I think that I needed to… certainly learning from my side.

Matt Cameron (SaaSy Sales) (47:33):
Anything from Jen and Jake? Anything in particular to add to that? No? Okay, cool.

(47:39):
Well, let’s do a lightning round. I’d like a final thought, let’s try and keep it under a minute, from each of you before we head out today. I might start with Jen, if I may. Final thought to share with the group.

Jen Spencer (SmartBug Media) (47:53):
I just think final thought of if you’re thinking, “Do I want to get to this role? Do I want to take on this responsibility?” I think it’s extraordinary to just be in a position where you have the ability to affect change at a very macro level that has a micro impact on your people. So, being able to identify, have bird’s-eye view of how the organization is functioning and what our customers are needing and be able to go in and say, “All right, this group of customers needs a little bit of a different approach. And therefore, there are different roles that we need to develop in order to best meet the needs of that customer,” first of all, it helped solve for customer challenges and helped retain and grow those customers, which is great. But then in addition, it created pathways for people who were getting to a point in their career where they were looking at the next job, the next level, and they went, “I don’t really want to do that kind of work. That doesn’t look fun to me. That doesn’t interest me.”

(48:56):
But because we evolved operationally, solving, again, for the customer, we’re able to create these new career opportunities. So when I see people getting promoted inside the organization knowing they wouldn’t have if we wouldn’t have evolved and changed, and knowing that you’re in a position, you’re like, “You’re the one who can make that kind of a call,” is pretty extraordinary.

Matt Cameron (SaaSy Sales) (49:20):
That is awesome. Yeah, great thought.

(49:22):
Gordon?

Gordon Lawson (Conceal.io) (49:24):
Yes. Well, I know when we started the call today, we were joking about where we all lived. I’m here in Augusta, Georgia, and we actually moved the company from Northern Virginia to Augusta, Georgia last year. Everyone knows Augusta for the big golf tournament we have in a few weeks, but it’s also the second-largest concentration of military cyber in the country. We’re the first commercial cyber company to be headquartered here. And I feel very honored and very grateful to really, I think, be transforming lives in this community. Very diverse workforce. Really, this is a field that has unlimited opportunities for employment beyond Conceal. And just really, really cool to see the growth that’s gone on as we’ve grown our team here, and I think to go to an area that most people in the US only know for one thing, but there’s a lot of incredible potential for this cybersecurity ecosystem as well.

Matt Cameron (SaaSy Sales) (50:14):
I think it’s awesome. Must be very rewarding. To your point, this sort of opportunity, the sorts of careers that we can provide for people in tech just didn’t exist there before, really. So I know that is wonderful.

(50:25):
And Jake, final thought from you, sir.

Jake Dunlap (Skaled) (50:28):
Final thought. If you can’t go half in, meaning… I see CEOs or leaders that they’ve got a foot in the door of other things or they’re trying to do this. And it’s not that you can’t be one of those entrepreneurs who’s doing a couple different drop-shipping businesses or something like that. I think that’s different than what we’re talking about, which is actually scaling businesses with people. You better make sure you love leadership, that you know what you’re getting yourself into, because leadership is not easy. When you’re at the CEO, I look at the upside-down pyramid, it’s not that you’re at the top, actually it’s all funneling toward you at the end of the day. And if you don’t love it, and there are hard days and there are hard times, it’s going to be really tough to be a really, really successful leader.

(51:17):
And I would just say that a lot of people now, I think Jen said this, are opting not for leadership. That’s fine. But just know, building a company is not an easy thing. We’ve all made a ton of mistakes on the way, too. I’m 10 years in and, like Jen said, still learning. I think just really be honest with yourself about what you love and are passionate about because you can make an amazing living as a number two. “Hey, I don’t want to be that. I don’t want that responsibility, but I like parts of it.” So, just make sure you know what you’re getting yourself into and that you’re full-pot committed. You can’t put your toe in the water.

Matt Cameron (SaaSy Sales) (51:54):
Fantastic. Well, I want to thank all of our three guests today. Jake, Gordon, and Jen, thank you so much for being with us. Everyone on the call, please make sure you find these good people and their companies on LinkedIn, easily found. And until next time, we’ll see you soon. Thanks, all.

Jake Dunlap (Skaled) (52:10):
Thank you, everyone. Thank you, Matt.