Episode #268:

Dean Hickman-Smith, Chief Revenue Officer at Testlio, explains why traditional CRO planning models are becoming outdated in faster technology markets. He describes how revenue leaders must shorten planning cycles and strengthen feedback loops among sales, product, and marketing. Dean shows that modern revenue leadership requires constant learning, customer alignment, and faster decision-making to keep up with rapidly changing buyer expectations.

“We’re in a phase of constantly reinventing ourselves. Our customers build software faster, ship faster, and release features faster. That means we have to align our teams much closer to the customer.” – Dean Hickman-Smith

In this episode, Dean shares how modern revenue leaders can keep pace with accelerating buyer expectations by tightening customer feedback loops, improving internal alignment, and helping teams act faster with better context. He offers a practical view of how leadership, trust, and execution must evolve when markets move faster than quarterly plans can keep up.

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[Transcript]

[00:00:05] Steve MacDonald: Welcome to the C-Suite Sales and Marketing Perspectives Podcast. I am Steve MacDonald, your host, and today I guarantee we will have a conversation with Dean Hickman-Smith. Dean, we are going to have one that will bend the mind a little bit, with a myth-busting, contrarian point of view, all woven together with a lot of fun.

[00:00:23] Steve MacDonald: But we are going to be talking about how the CRO playbook we know today is already obsolete. In fact, when you and I had our first conversation, you talked about what I am doing now versus three months ago. A lot of it is completely different, and we know the market is changing.

[00:00:40] Steve MacDonald: We know the technology is changing. We know our B2B go-to-market motion is changing, and I have loved the way you embrace it. We are going to talk about that today. In addition to the accolades I have already mentioned, you have 20 years of sales experience. You have gone through three successful IPOs in your time and lived through them, so congratulations.

[00:01:04] Steve MacDonald: You also are a horse breeder. If we are lucky, we might see a horse walk by in the background. You also dabble in and are a competitive acrobatic pilot. So, how you had time to do this CRO role, I am not exactly sure, but I would love to hear your version of your background, a couple of minutes, and where you are working now, before we get started.

[00:01:32] Dean Hickman-Smith: Steve, thanks for having me. I really appreciate it. Look, I am really lucky to have been able to experiment with lots of things in the last 20-plus years. It has been great. Obviously, I am originally from London and came over with NetScreen around 2000. NetScreen was just an amazing company to work at.

[00:01:49] Dean Hickman-Smith: I was really lucky to get involved with that. We were involved in it in Europe and then in the earlier stages over here. I worked for a fabulous human being called Mark Smith, who introduced me to how things are done in America. I think that is lesson number one: get yourself a really good mentor who can guide you.

[00:02:06] Dean Hickman-Smith: I did a startup after NetScreen. We did go public, and we were acquired by Juniper, which was great. I thought I was really good at startups, so I went off and did an early-stage one called Concentrate Networks, where we learned a lot about raising money, getting up and running from scratch, and getting a little bit ahead of the product-market fit.

[00:02:32] Dean Hickman-Smith: We ended up exiting that one to Samsung back in the early two thousands, and that really got me into Proofpoint. Proofpoint really scaled up. I guess Proofpoint was really a cloud company, a cloud SaaS company. We turned it into a SaaS company, so we grew it to a good size and took it public.

[00:02:48] Dean Hickman-Smith: I went back with the NetScreen team to do a company called Aerohive, which was in the cloud-managed WiFi space. We scaled that one up to an IPO, and it was acquired by Extreme Networks after the IPO. Since then, I went into identity for a little while, and now I am with a company called Testlio.

[00:02:56] Dean Hickman-Smith: We are in the crowd testing space, and what we do is basically test customer software to see if it works anywhere in the world on anything. We get all that data and run some AI models on it. We help customers build better software, and we are getting heavily into testing AI and AI-driven solutions.

[00:03:16] Dean Hickman-Smith: It is a pretty hot space to be in, and I have been there for seven months. I am happy to say that it seems to be growing really well. We are hiring and building out our operations globally. As you said, Steve, it is a constant circle of learning. I like that. I have probably made more mistakes than good decisions in the last 20 years, in various ways, and I have learned from them.

[00:03:41] Dean Hickman-Smith: I can apply some of the learnings to what we are trying to do now and build out this one. By the way, the horse breeding thing, that is my wife who got me into that. I never thought I would be involved in anything to do with breeding any animals, let alone horses. They are quite big and quite dangerous. Competitive aerobatics, I have been doing for years.

[00:04:18] Dean Hickman-Smith: I have been flying for a very long time. I am happy to talk about that later on. Actually, let us get into aerobatics later on, after we have had some business discussions. I am sure people follow you for business discussions more than they do to hear some guy talk about aircraft.

[00:04:30] Steve MacDonald: I think you are being a little bit modest about the horse breeding thing, because you were just telling me how you can play the role of a midwife, and you can be up to your shoulder in the process. That is not for the faint-hearted. I am a goat breeder, which has none of the status or prestige of being a horse breeder. But I know how difficult and stressful it can be, especially when it happens in the middle of the night or at any time.

[00:04:54] Dean Hickman-Smith: Weirdly, it only happens in the middle of the night. They give birth at night because that is when their natural predators are not out there to attack them. It always happens at two or three in the morning. There is some science, though. They have these devices that tell you when it is going to happen, and it calls your phone. They are not exactly reliable. You get lots of false alarms. We could get very National Geographic talking about it. I have got a video.

[00:05:23] Steve MacDonald: Well, I am going to take control as the host and steer us back to the business-to-business world. There was something you said when we first met about how the quarterly revenue plan is actually a relic. I have the gray hairs that you do, too. We used to have five-year plans and three-year plans. Now you’re saying the quarterly plan is a relic and that you need 30-day reinvention cycles. Tell us a little bit about your thinking and how you apply that.

[00:05:51] Dean Hickman-Smith: Yes, I think we are in a phase of constantly reinventing ourselves. Of course, there is an annual plan. There is an annual plan that you tell the investors in your company that you are going to aim at. Increasingly, I have found that we have to break that down into smaller and smaller chunks.

[00:06:06] Dean Hickman-Smith: Our customer software evolutionary process has evolved so that it is much faster from concept to ship. Things have accelerated. Automation has accelerated many things. What I look at now is: did I say 30-day cycles last time we spoke? Because I think what we do now is we are in the details weekly. We have broken things down to a very functional weekly cadence.

[00:06:30] Dean Hickman-Smith: We expect our sales teams to be much more aligned to the customer now because they have so many tools to do much more research and to understand the customer environment better. That is why we have to dig in deeper. Things change. Customers react faster. Customers build software faster. They want to ship faster. New features come out even faster, and we have to be aligned with all of that.

[00:07:00] Dean Hickman-Smith: We have to have all of our internal signals much better tuned to our customers so that we can deliver more value back to them to help them through the decision-making cycle. We are learning every 30 days from our team. We learn things that are important in the sales cycle and, from a product perspective, that we need to feed back to the rest of the company.

[00:07:30] Dean Hickman-Smith: That is why we have shortened that kind of feedback loop, and that is where I am at right now. It is a very interwoven, circular motion of go-to-market, customer feedback, product feedback, and marketing, interpreted into enablement training. Re-equipping the sales team with the latest information so that we are following this 360-degree feedback loop, which seems to be working pretty well.

[00:07:40] Steve MacDonald: You made a point early in your answer to talk about the customer focus and then bringing that into the rest of the company. There was a really incredible study done two or three years ago by McKinsey, and they said that only 15 percent of companies actually execute a voice-of-the-customer program. But you just brought it up as the most important thing in translating that into the rest of the company.

[00:08:06] Dean Hickman-Smith: That is an interesting one. You can over-rotate and constantly be changing your focus, which would be detrimental. We would overload and exhaust our developers if we were not able to prioritize and link these kinds of feedback sessions to real revenue.

[00:08:24] Dean Hickman-Smith: We spend quite a lot of time looking at the feedback, quantifying it, and giving it a revenue value. It becomes a conversation that says, “If you do this, I will deliver that.” That type of conversation is important. There is a feedback loop, and then there is a prioritization conversation that is continually happening.

[00:08:52] Dean Hickman-Smith: That prioritization determines what we feed back to product and then what product thinks they will deliver to us and when they will deliver it. Then we can feed that back into the enablement cycle.

[00:09:00] Steve MacDonald: I love it. You talked about how that cycle has to depend on customer outcomes, like product truth mapped to them. I think that is when it becomes a discipline. It is not a bunch of different departments working in silos with different forms and beliefs of customer truth. One in product, one in sales, one in marketing, and one in customer success. How do you unify that?

[00:09:19] Steve MacDonald: When I talk to B2C suite executives, the number one challenge they tell me they have is internal alignment. What you just talked about was an incredibly aligned set of departments and teams inside your company. I am curious because that is not an easy feat. I would love to hear how you do that.

[00:09:40] Dean Hickman-Smith: This is where it starts. I think culture is a big piece of that. You have to work with people who have a very significant amount of mutual respect, and the old “two ears, one mouth” philosophy applies very strongly to the way you communicate with each other.

[00:09:55] Dean Hickman-Smith: We have the obvious kind of meeting. We are a very distributed company, by the way. We have executives in Estonia. We have executives in Europe outside Estonia, in the UK. We have them on the East Coast of the US, and I am here on the West Coast. You have to be pretty flexible to get that kind of level of communication going, right?

[00:10:11] Dean Hickman-Smith: So my day starts sometimes at four o’clock in the morning because that is the time when we can all unite. Second, all egos are parked at the door. Everybody comes to the table with a very firm commitment to having a robust conversation, but in a really collaborative manner, to try and come out with an agreement. We will debate robustly, then agree, and then act. That sounds a bit trite, but that’s how it works. If you have an ego in the room that will go passive-aggressive on you, we will agree on something and then delay something. Or you have egos in the room that just cannot come to an agreement, the magic does not happen.

[00:10:47] Dean Hickman-Smith: It is when you get a bunch of intelligent people debating with an agreed understanding that we are going to come out of this with a solution. It has to have ownership and a timeline for deployment. That is when it starts to happen, and you can iterate, and you can innovate, and you can get that repeat feedback loop happening really quickly.

[00:11:06] Dean Hickman-Smith: The flywheel starts happening. Customers pile in because they understand you are innovating. They give you more and more feedback, and then it becomes, okay, now let us do the prioritization. What are we going to do to achieve the best outcome for the company? Yes, my job is to try to steer the conversation from the customer and customer success perspective as much as possible.

[00:11:22] Dean Hickman-Smith: Give as much prioritized feedback as possible, and prioritization in my context is really revenue aligned. If you do this, I am certain I can deliver this revenue amount by this timeframe. Then we sit down and figure out how to get it done. Did that answer the question?

[00:11:36] Steve MacDonald: It did, and the most important part was that it all has to lead to what I think you called customers piling in or something like that, because they know we are innovating. I am just going to keep replaying things that you said before in our other conversations. In terms of innovation, you said control kills it; context fuels it.

[00:11:57] Dean Hickman-Smith: Yes, actually in a number of different areas. Let us talk about it from the GTM perspective first of all. I have a global team. My expectation is to hire and enable those people to succeed, and then for them to become experts in their field. I am trying to push as much control out to the field as possible because I want them to understand all the dynamics in their theater. I do not think top-down control in that context works at all.

[00:12:23] Dean Hickman-Smith: You end up with very vanilla programs that might work in America, but do not work in Europe. They might work in New York, but they do not work in Atlanta or Florida. Then, when you start adding that we have a bunch of customers in Asia, Europe, and Latin America, things change. The events that work in one location do not work in another. The outreach cycles and the outreach programs in one area do not directly translate to another.

[00:12:48] Dean Hickman-Smith: You hire people, enable them. I used to think that it would take six to nine months to enable and ramp somebody. Now, I am really focusing on two things. One is, as I said, hiring GMs for each region and equipping them with their own mic, their own mini P&L. Second, I now think the enablement cycle can be massively accelerated. We really go deep in the first 30 days, and my expectation is that, upon exiting that 30-day period, my hires can have a C-level conversation about our relevance to our customers and ICP. They can therefore be productive within 90 days, rather than the old model, which was probably 6 to 12 months for someone to ramp up.

[00:13:33] Dean Hickman-Smith: I think we can deliver a powerful enough enablement package to get people fluent, and then they can go off and do research that makes them really fluent in their region and in our ICP. That is one thing. The second thing is that 80 percent of the selling is done before we walk into the room. Most of our customers have done 80 percent of the research and preparation, and our team is there to help with the remaining 20 percent to make the decision in our favor.

[00:13:56] Dean Hickman-Smith: We are spending a lot of time creating customer communities because the first thing that my new customer in New York does when he is looking at Testlio is call Jane, his former colleague, who is now at a competitor or at a similar company, at least in Steve’s peer network, and he is already using Testlio.

[00:14:17] Dean Hickman-Smith: It is so important that we create these kinds of snowball effects with our customers because the first thing that happens literally is that peer referral. I am thinking about Testlio, what do you think? If we do not have all our customers really happy with the service and seeing real value in the product offering, we stand a good chance of not winning the deal. That is the second thing that I feel we really need to bring together, enabling our team and enabling our customers to build communities around them. I have spent a lot of time on that in the last seven months since I have been here at Testlio.

[00:14:51] Steve MacDonald: Here is what I am taking away from what you just said. I am going to add some additional context to it. We are not bequeathed trust. We have to earn trust in what we say and do, and that is not a trite comment. The most recent Edelman Trust Barometer found that, worldwide, among 32,000 respondents, 68 percent said business leaders like you and me are intentionally misleading.

[00:15:20] Steve MacDonald: In other words, our voice is put into a category, no matter what set of values and morals you have, and you put into your team, and how you communicate. Your voice is not going to mean as much as the peers that you were just talking about. The people you are selling to rely on the voices of their peers, the existing customers who support what you are saying.

[00:15:42] Steve MacDonald: You are creating a trust infrastructure. It takes time and diligence, but what matters most is recognizing that those are the voices that matter most. There are many companies that do not conduct that diligence. That is not a written case study in a PDF with some testimonials, right? I want to hear more about why you are spending that much time creating that peer validity.

[00:16:10] Dean Hickman-Smith: You bring so many thoughts to mind in that monologue. I think today’s seller has to do two things. Number one is that they have to create that customer flywheel around them because that is the validation that differentiates us from the competition. It is really about getting the third-party trust validation that you mentioned.

[00:16:29] Dean Hickman-Smith: The second is authenticity. I think the value of authenticity in an AI-driven world is what will differentiate the world-class seller and the world-class go-to-market professional from the average. Right now, at our fingertips, we have so much data and so much preparation available, and it is so easy to put it together. Everybody has a seat at the table very easily and can say quite intelligent things, and that is table stakes, right? The fact that you can now prepare for a meeting using tools that previously took days of work.

[00:17:16] Dean Hickman-Smith: Any seller who is not fully using all of the research capabilities that AI brings to the table is failing there. But what will differentiate the seller now is the value of authenticity. I am spending more time on the road now than I was 12 months ago. I am not spending as much time on the road as I did 10 years ago during the Proofpoint era. We were on the road 200,000 to 300,000 miles a year for a long time, but we were not efficient then.

[00:17:36] Dean Hickman-Smith: Now my trips can be efficient. I am very well aligned with the customer meetings I have. The briefings I have going into a customer meeting are so precise and world-class that I feel I can bring real value to the table. I am on the road because I want to be authentic. I do not want to be reading from a script.

[00:18:00] Dean Hickman-Smith: I interview a lot of people now, Steve, and they sound great, but then you realize that if you take them a little off script, everything is something they have pulled from AI. That is not how the real world functions. That gets you a seat at the table, but you still need the real-world ability to respond to a particular customer situation, and that requires depth beyond just a prompt.

[00:18:25] Dean Hickman-Smith: That requires a customer to say yes, these people go the distance for me. Things blow up sometimes, but they fix it. That is what I mean by authenticity. You have to have presence in the room. You have to be in the room. You earn that through doing the research upfront, but then you have to be able to go deep with the customer when needed.

[00:18:38] Steve MacDonald: Here is what that brings up in my mind. On the podcast, we are approaching 300 conversations with B2B C-suite executives. Not one of them has ever disagreed with this statement. We are in a relationship-based business. As much as AI, content, Zoom calls, and different tools can help build relationships and communicate meaningful value, what you are talking about is that ultimately, we believe in the people we want to work with.

[00:19:13] Steve MacDonald: Instead of making another monologue, I was just talking to a Chief Customer Officer who was on the podcast, and he shared something with me. His direct ICP was a CISO who had just concluded a buying phase and added to their tech stack. He said that 14 different companies came in. They all answered the RFP. They all checked every single box in the RFP.

[00:19:43] Steve MacDonald: He said there was one thing that he wanted to know. What will it be like to work with you after I hire you? You just started talking about service, and that is what I am taking away. You are out there saying there are real people behind Testlio, and we are going to be there for you and build that relationship.

[00:19:53] Dean Hickman-Smith: I think that is the thing that is the differentiator. Actually, that is not quite right. First of all, you have to be so fluent in your subject matter that, beyond the initial AI research the customer and their team have done, you can lead the conversation to a successful landing. But that is just the start. Most customers are changing the way they buy now. Everyone talks about land-and-expand, but it is really more like, okay, let me put a toe in the water. You may say you are great, and my friend may have had a great experience with you, but I really want to test this thing out.

[00:20:26] Dean Hickman-Smith: I want to date a couple of times before anything happens here. If the sales motion is not aligned with the success motion, if you generate an intermediary that is some sort of implementation team as well, and if that flow is not totally and perfectly orchestrated, and if the customer is not getting value from the product within a very short period of time, you are not going to get the expansion. You are definitely not going to get the result that you want. I think it is just that the whole world has evolved into pretty much a land-and-expand experience now. Customers are putting a toe in the water with that first purchase. There is normally a follow-up order that follows within 90 days, but that first engagement is really just the license to develop the business with the partners.

[00:21:09] Dean Hickman-Smith: We are very keen to make sure that the salesperson is involved in each of those different steps all the way along. They are monitoring the conversation. They understand the success criteria really closely. They are fully aligned with the team that will be doing the implementation and handling the customer touch. Yes, that is how it works.

[00:21:27] Steve MacDonald: You know, that sales involvement that you just talked about, you said the best sales teams do not close deals. You said they provide a value hypothesis that shapes conversations and guides the customer toward the right decision. I just thought that was interesting, like the best sales teams do not close deals. What did you mean by that?

[00:21:48] Dean Hickman-Smith: I meant that it is an orchestration role. I will use an aviation analogy. If you try to land the plane, it will be a heavy landing. If you try to force the plane onto the ground, it will be a very heavy landing. The way you land a plane gently and elegantly is you hold the plane a little bit above the ground until it runs out of energy, and then the main wheels touch down. The energy dissipates, and the plane settles very gently to the ground. I think that is a good analogy for the modern world we are in from a selling perspective.

[00:22:20] Dean Hickman-Smith: We are guiding the customer onto the runway, and we are letting the customer naturally come to this energy state where everything is smooth, and everything is what the customer expected. They are going to come back because they enjoyed the flying experience with us. They are going to rebook and use us for all their travel.

[00:22:36] Steve MacDonald: We have talked about a lot here today, and our poor human brains can only take in about two or three things at a time, and then we just shut down. If there was one thing that you wanted the other B2B C-suite executives who are going to be taking in this conversation to take away from it, the one most important thing, what would that be?

[00:22:54] Dean Hickman-Smith: I think my answer is going to be a little long. I am sorry because there are many things I am trying to weave into what is happening right here, right now. I do not think AI is the be-all and end-all. We live in an AI-enabled world, which means everyone is forced to do things faster. But I do not think AI helps with the fundamentals you often face in our go-to-market role. It just shows flaws in your go-to-market faster if you do not have the kind of feedback loop that I was referring to earlier, tuned into your organization.

[00:23:27] Dean Hickman-Smith: I do not know if you have ever read it, but there is a guy called John Boyd, and he wrote about the OODA feedback loop. It was all military jargon, but it was observe, orient, decide, and take action. It is this kind of decision-making that has an impact while also pushing decision-making out into the field, so people can make quick decisions. AI seems to me to be a way we can send better signals to the team.

[00:23:54] Dean Hickman-Smith: But getting that feedback loop where we are taking those signals back into the way we enable our team, the way we give feedback to our product groups, and our marketing teams is even more important because the speed at which customers are expecting us to interact with them continues to accelerate.

[00:24:10] Dean Hickman-Smith: The message for me is that we have to unify. If we are going to be an efficient organization, leveraging the tools we have and the new tools available to us, we have to bring them together into a constant feedback loop. Check the ego at the door, have robust conversations, make decisions, and take action. That is my feedback.

[00:24:29] Steve MacDonald: The whole mission of this podcast is to bring different perspectives, experiences, perceptions, and interpretations of how we create success together from C-suite executives all over the world. If we can do that, it’s like the rising tide that lifts all boats. You certainly had some perspectives today that took that tide to a whole new level. I just want to say thank you for coming on. I thoroughly enjoyed this conversation.

[00:24:58] Dean Hickman-Smith: Steve, I enjoyed it too. I have been doing this for a long time, and one of the things I really love is helping people grow. I think you asked me earlier, the last time we spoke, what I was most proud of. I am really proud of the connections I have made. Again, it may sound a little cheesy, but it is the people and the connections I have made over the last twenty-plus years in this industry that I am most proud of.

[00:25:20] Dean Hickman-Smith: I try to create environments where people can grow. What really excites me is seeing people who came in at an entry-level role go on to be promoted within the organization, then become CROs in their own right and CEOs of other organizations.

[00:25:36] Dean Hickman-Smith: It is great to be able to talk to you and share some of the lessons, share some of the mistakes, and help people avoid them themselves. Thanks for doing this and giving me the opportunity to come on and have a really fun chat with you. Thanks a lot.