Episode #332:
Mike Head, Chief Revenue Officer at Orderful, explains how customer understanding can strengthen every part of the go-to-market organization. He shares practical ways to prepare for executive conversations, improve discovery, coach teams with AI, strengthen retention, and align teams around customer priorities. Mike also explains why consistent execution, genuine curiosity, and continuous customer engagement can build trust, improve revenue performance, and create sustainable growth.
“Your technology, your logo slide, all that stuff doesn’t matter. What really matters is the customer and what they care about, and if you focus on that across your engagements in sales, marketing, customer success, and partnerships, great things will happen.” – Mike Head
Executive access is getting harder, buyer conversations are becoming shorter, and prospects often enter the sales process with strong opinions already formed. Mike explains how CROs can respond by preparing earlier, building deeper customer understanding, strengthening post-sale relationships, and creating better alignment across revenue teams. He also shares why great people, consistent execution, customer-led discovery, and genuine curiosity can become durable competitive advantages.
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[Transcript]
[00:00:10] Steve MacDonald: Welcome, everyone, to the C-Suite Sales and Marketing Prospectus podcast. I’m Steve MacDonald, your host, and we’ve got a really interesting guest on today, Mike Head. And now, Mike, there are a lot of things that make you interesting. You’re a three-time CRO, but you’re a three-time CRO who’s really done a lot.
[00:00:27] Steve MacDonald: You’ve taken a company from zero, zero revenue, to over 200 million. You’ve taken another company, you 4xed the growth in that company and led to a successful acquisition. And now, for a third time, you’re a CRO at a new company. I’m going to let you talk a little bit about that company.
[00:00:46] Steve MacDonald: What I want to communicate clearly here is that what we’re going to talk about is not just theory. This is stuff that you put into place, you train with, you roll full out, and you call yourself a nerd. So if I call you a nerd, it’s only because you did already. You said from a, like, a technology operations perspective, AI and how we adopt it.
[00:01:10] Steve MacDonald: So you’ve got a real methodical thought process in how you go through this. But here’s what really caught my attention, and I told you a few minutes ago: I’ve shared your point of view with a ton of CROs, and they’re all like, “Oh yeah, that’s totally where we’re at.” And you said something like this. You said, “Steve, it’s harder and harder to engage with executives, and our meetings are fewer and farther between.”
[00:01:34] Steve MacDonald: And when we have them, they’re shorter than they’ve been in the past. Unless we start to control that environment. I just got so many nods from so many different CROs. So I’m going to ask about that when we first kick off here. But today we’re talking about how to win in an environment of fewer, shorter bursts with our buyers, as they wait longer and longer to want to talk to us, and they’re more in validation mode than exploration mode and all that good stuff. But before we do that, did I do your background justice? Like, what would you expand on before we dig in?
[00:02:09] Mike Head: Amazing. I appreciate all of that stuff. I’ll touch lightly on it; I’m super excited to be sitting in the seat at, uh, Orderful. As you mentioned, third-time CRO. Been fortunate in my career where, you know, been successful running the go-to-market twice, and now I want that lightning in a bottle to strike a third time.
[00:02:28] Mike Head: We just raised 35 million in our Series C. We’re an AI-native platform disrupting the EDI industry, and so really excited to be a part of this amazing leadership team. This is the end of my second week here. On the nerd side of things, one of my roles was as a sales engineer, so I’m dangerous enough to understand technology and how it works overall, which I think is a huge asset for CROs in the future, specifically.
[00:02:57] Mike Head: And this unlock with AI, I think, has made it so, you know, people who are technology proficient and understand go-to-market can do things and build things in a way that they haven’t been able to before. And then the final piece I’ll mention, and I think it’s super important for CROs, but I feel fortunate to be very well-versed in partnerships.
[00:03:18] Mike Head: You have a go-to-market through sales and marketing, but you have to understand partnerships. And if you understand partnerships very well as a CRO, you can have a much more well-balanced, diversified go-to-market.
[00:03:30] Steve MacDonald: You also oversee marketing, if I’m not correct, right?
[00:03:33] Mike Head: Correct, absolutely. In my first role, I worked with marketing, and in my last company and this one, I’ve run marketing as well.
[00:03:43] Steve MacDonald: So I just think that’s a really good foundation for the recommendations you’re making. As a C-suite executive, you need to think about how it impacts the entire go-to-market. But when go-to-market reporting comes up through you, it puts a little more due diligence on you.
[00:03:58] Steve MacDonald: So here’s what I’d like to do. That whole, hey, we’re, you know, it’s harder; the executive access is harder; the meetings are fewer and farther between; they’re shorter when they happen. Tell me a little bit about that reality. Like, how do you reach that conclusion? And then we’re going to talk a bit about how we unpack that and what we do about it.
[00:04:16] Mike Head: Yeah. And I look at it both on the pre and the post-sales side of things, so I’ll start with the post-sales side of things and what I really started thinking about. In addition to marketing, I also own customer success and customer expansion. Thinking really about QBRs, and QBRs pre-COVID and post-COVID, and how do you actually get the executive’s attention and have them stick with you?
[00:04:39] Mike Head: I even saw it pre-COVID, where you’d be in the office for two hours, and you would maybe have the main economic buyer that you wanted to engage with there for 15 minutes of those two hours. I believe it got even harder post-COVID to get everyone’s time and attention. And some products, people don’t want to hear about.
[00:05:02] Mike Head: They just want to hear that it’s actually working, and they’re only going to engage with you when things aren’t working well. So really thinking through that customer engagement model, how you can get the executive’s attention, how you can keep them engaged and aware of all the amazing things you’re doing without being able to get that dedicated time and attention, is a problem that I’ve thought about solving, and I think other CROs and other leaders have also thought about solving as well.
[00:05:29] Mike Head: There’s also another problem on the pre-sale side of things. In general, getting to the economic buyers and decision-makers in the sales process has always been difficult. But now, with much more of the buying process happening online, happening through LLMs, happening through peer recommendations, you really have these people coming into your sales process already with very strong opinions overall on which direction they ultimately would want to go, and you have leaders who aren’t wanting to be involved in that process.
[00:06:05] Mike Head: You need to think about ways where you can do all the work ahead of time to ensure that when you do get a chance to engage with the economic buyers, that you’re making the most of that time. And if you don’t, you lose trust, and you won’t get their access again. So it’s important to do that work ahead of time to make sure you get the most out of any engagement you can get.
[00:06:29] Steve MacDonald: You know, I had a CRO on, and what he mentioned was that if we’re not working the deal a year in advance, we can’t come in at the last minute.
[00:06:38] Steve MacDonald: “Oh, there’s an RFP, let’s go in.” And it was all about if we’re not known and trusted, we’re not on the short list. We’re not on the short list, we’re out. And building that trust in advance, and you said the word trust there, and working in advance. That runs a lot counter to short-term compensation plans.
[00:06:56] Steve MacDonald: We’re going to look for what’s bank-qualified, and we’re going to, we’re going to focus our time there, right? How do you train your team? How do you operate? How do you compensate? How do you get a [00:07:05] team that’s willing to work in advance and build the trust, ’cause it’s so important these days?
[00:07:10] Mike Head: Yeah. The RFP thing was just fascinating to me. Our win rate when we drove a customer into an RFP was 80% plus, and our win rate when we got one randomly was single digits. And that’s been across the board, and so I agree with that sentiment completely. And so, how do you train the team to do it? To me, one of the philosophies that I always talked about with the team is that I don’t believe these deal cycles always need to be a year.
[00:07:35] Mike Head: There’s some where they can be much faster. But I always talk with them about slowing down to speed up, and being methodical in the early stage of the conversation to make sure you’re understanding the buyer, what’s important to the buyer, the pain of that buyer, and the priorities of the company and the leadership overall.
[00:07:56] Mike Head: If you do that effectively early on in a sales process, you increase your win rate. The way that you can train a team to do that is doing it some for them at times if you have to, but exposing and showing the people that are doing it, and the fact that, hey, these are your teammates who are exceeding their quota, and here’s exactly why. And listen to some of these calls and see how methodical and thorough they are.
[00:08:21] Mike Head: See how they are embracing curiosity around it. One of the things that I have loved with the advancements in AI, you can now set up automated call scoring post a discovery call to know how well someone has done. So now, at scale, in real time, you can help them understand if they did that or didn’t, and build a better plan to make sure they do it on the next call.
[00:08:48] Steve MacDonald: If you don’t mind, I love everything you’re saying. I’d love to unpack a little bit about the time that they’re spending. And physically, what are you instructing them to do? I’m going to give a way to think about this a little bit. I’m in the middle of a series in the podcast here on the revenue [00:09:05] logic of customer obsession.
[00:09:06] Steve MacDonald: And Forrester did a study like two years ago, and they found out that only, literally only 3% of companies were truly customer-obsessed. 3%, right? That’s our North Star, right? When you’re talking about building trust and value, it’s inside of the relationship with a customer. But we all say that we’re customer-obsessed.
[00:09:26] Steve MacDonald: We all say that we’re customer-focused, but delivering on it is what I think you’re talking about here. I want to accentuate the importance of it, but ask, like, how do you, if that’s a good way to determine, how do you train your team to be customer-obsessed? To put in that extra effort and build that trust in advance of the RFP or the ask or the shortlist closing.
[00:09:48] Mike Head: Yeah.
[00:09:49] Mike Head: So I think, in general, a salesperson’s tendency and human tendencies in general are to talk about themselves. You hear that in social engagements and on sales calls. You see them show up and throw up, as we would call it, right? A sales rep gets on a call, says hello, does an introduction, and then just says everything about the company and why the company is amazing and all of that.
[00:10:16] Mike Head: That’s one of the quickest ways to lose trust, attention, and interest with any of your buyers overall. So I think one part of the training is acknowledging the human nature side of it and the fact that this is how most reps operate. And your job isn’t to directly communicate everything your company does, because no one can remember it all.
[00:10:39] Mike Head: Your job is to understand the person you’re speaking with. What do they care about? What’s important to them? What are their goals and priorities? How do their goals and priorities ladder up to the corporate goals? Which ones of those corporate goals do they ultimately care about? When you focus a sales process, I hate to call it a sales process, but your mutual buying process that you’re going on together, when you focus it on that other person, that’s when you’re able to get that real magic.
[00:11:12] Mike Head: And when you early on uncover and find those things, then you connect what you do to the things that someone else cares about. And that’s where you can truly get higher ACVs, higher win rates, more revenue, et cetera. And the things that we would do to help train people on these things, some of it’s just prep and research, and now that AI has automated a lot of it.
[00:11:38] Mike Head: But before we would go into sales meetings, if they’re publicly traded, like, actually read those investor reports. People say they’re going to do it, but do you actually build a process where you are doing those things? Not necessarily. Do research on the people that you’re meeting with. Do they have blogs?
[00:11:55] Mike Head: Have they spoken at conferences, events, other things like that? Find whatever is publicly available about what they may or may not care about, and use that to inform your engagements. Do the minimum on understanding the customer’s business so you don’t show up and say, “Oh, tell me about what you do.”
[00:12:16] Mike Head: You say, “Oh, I noticed you’re selling X, Y, and Z, and you just launched this,” right? So you’re coming in much better informed and being able to build that trust overall. And then one other thing that we did a lot of, and people talk about this, but athletes are the easiest examples. They coach and practice and, like, all the time.
[00:12:36] Mike Head: But anyone who is great at their profession, whether it’s comedians, musicians, they are preparing and practicing before they’re actually getting in front of their audience or, in this scenario, their prospects. Most sales organizations don’t actually do that. They feel like role plays and practice can be awkward.
[00:12:59] Mike Head: But for us, I’ve always focused on making sure we do that and making sure that whenever we’re engaging, we’re telling a story with a customer lens, a customer language, because a lot of customers and industries use different language than you typically would, and making sure that you’re feeding all of that in, and not just on a screen, on a deck, or in the demo, but you’ve actually rehearsed and delivered it, so it feels very natural when you’re getting in front of the customer.
[00:13:27] Steve MacDonald: So I don’t know if you remember, but in our previous conversation, I asked you, and this is my takeaway from everything that you just said, and I’m remembering now our past conversation, and I said, “It’s a rare company that has a truly differentiated product or service offering.”
[00:13:50] Steve MacDonald: It’s so easy to write code these days. SaaS companies, as soon as you have a product advantage, it disappears. What’s the true competitive advantage that your team has? And you said it was insights into customers’ businesses. You said that going in, if we do that, everything that you were just talking about, you termed as a competitive advantage. Am I re-articulating that right? Or, like, how would you articulate that?
[00:14:16] Mike Head: Absolutely. This goes back in time, and I’m looking over here where I have some of my favorite books, but you look at data from the Challenger Sale many years ago. What did they say? They bought because of the salesperson a majority of the time, and why? Because the salesperson showed them a new way of doing business. And so I absolutely believe, especially now, and we’re seeing the higher levels of competition and the easy ability to deploy features and functionalities, that features and functionality in your technology is no longer going to be your moat. But great people and great consistent process execution can absolutely do it.
[00:14:55] Mike Head: I’ve heard some great CROs and seen them put content out there about everything that they’re doing on LinkedIn and say, “Doesn’t matter if people know what I’m doing ’cause they won’t actually be able to execute it.” That’s the real key: making sure we can all talk about being customer-obsessed, but you highlighted it.
[00:15:14] Mike Head: Only three percent of companies actually are. So if you can truly get your people in there to ask those questions, understand those things, and make sure everything they’re doing is about the value you can provide to the customer, you’re going to set yourself apart and differentiate yourself in this new world.
[00:15:33] Steve MacDonald: So I’m going to take it one step further in how it works within a greater go-to-market strategy.
[00:15:39] Steve MacDonald: So I also don’t know if you remember, but in our previous call I asked you, what do you feel are the two greatest challenges to creating long-term sustainable growth? And I’ve asked that f- about 125 times of C-suite executives now. I didn’t ask it at the very beginning. We’re like, I think this might be the 316th episode we’re recording here.
[00:15:57] Steve MacDonald: And the number one challenge that C-suite executives, CEOs, CROs, CGOs, CMOs are saying by far, like 71% of the time, is internal alignment is their number one challenge to creating long-term sustainable growth. So this customer insight, customer obsession, voice of customer, however we want to talk about it, I had another, a three-time B2B CMO on, and she’s now a partner at a go-to-market agency, a mid-market go-to-market agency.
[00:16:27] Steve MacDonald: And she says, “Oh my God, every single time we go in,” and they consult with hundreds of companies, “the first thing we do is an alignment assessment because they’re never aligned.” They’re never aligned, right? And she said this, and so this is what I want to get your opinion on. She said, “The number one change agent, therefore the number one alignment opportunity inside of an organization, is to align behind the voice of the customer,” ’cause that’s our North Star.
[00:16:53] Steve MacDonald: It’s not somebody’s opinion. It’s not what we heard in this meeting or that meeting. It’s not what some really intelligent people leading their departments have said. It’s the one voice that aligns us, the number one change agent. Would you agree with that? What, like, how do you think about that?
[00:17:09] Mike Head: Yeah, absolutely. I can recall some planning sessions a couple of months ago. We’re talking product strategy. I stopped the meeting because I believed I was hearing what we wanted to build, but there wasn’t enough analysis on who the customer is, who that persona is, what the problems are, how we solve problems for them, or a true understanding of the outcomes we need to drive.
[00:17:37] Mike Head: I have a belief that across every organization, every part of the organization, if you don’t put that front and center, you are not going to be able to scale in the same way that you highlighted it, and vice versa. If you do that, if you obsess about the customer, if you obsess about the value, if you obsess about their pain, and you provide real solutions for them, absolutely, that’s where you can get growth.
[00:18:06] Mike Head: We always used to say, and consistently would say, “Retention isn’t a CS problem. Retention’s a company problem,” right. If you’re not retaining that revenue, it is because you aren’t solving the problems that they came to you for. And so, how do you think about all those things across the business, not in your silos, but generally within that framework of the true north of the customer and their expectations? If you do that, that’s where you can skyrocket your revenue.
[00:18:35] Steve MacDonald: I love how you keep coming back to customer retention, customer success, and the role in the company. Forrester did another study: 73% of new annual revenue comes from existing customers. But we focus on new logo development like there’s no tomorrow.
[00:18:52] Steve MacDonald: And I don’t want to offend any of the CROs that come on, but there’s a lot of structure inside of B2B companies where they’re really a chief sales officer. They’re not thinking about retention. They’re really not. And they’re not thinking about marketing. They’re not thinking about maybe rev ops. But they’re thinking 100% about bringing in new clientele.
[00:19:14] Steve MacDonald: And so much is dependent on servicing our existing customers and making them happy, and truly understanding them and their needs and our product roadmap. And then, therefore, the insights that we just talked about, like the competitive advantage, that then we can take into the conversations with all of our new business prospects, right.
[00:19:36] Steve MacDonald: What would your recommendation be for other CROs that are going to be consuming this podcast in terms of the balance? If you’re truly a chief revenue officer, how much time do you think, and should you think or recommend that they devote to thinking about retention and tracking things like NRR versus new logo development?
[00:19:59] Mike Head: Yeah, I think it’s absolutely critical, right. Like, when you drive positive NRR, you’re growing without adding a single logo. If it’s a negative NRR, you have to do that much more work just to stay at the same level of revenue. It’s not just the catalyst for growth you get; so many recommendations for who you should work with are now coming from peers, other colleagues, and people behind the scenes asking about their experience with you as a vendor overall.
[00:20:31] Mike Head: If you’re landing new logos and then they come on board and have a negative experience and churn, that’s not only hurting your direct revenue; it’s indirectly hurting your ability to win other deals. Vice versa, if you execute after a sale and deliver an amazing experience, they’re now talking positively about you.
[00:20:53] Mike Head: I think everyone has seen the data. Unfortunately, people talk negatively more than they do positively. So those bad experiences, just expect them to be amplified within your industry. With positive experiences, you’ll get additional referrals and additional revenue as well. So I would encourage all CROs to make sure that they’re spending enough time on it, even if it’s not directly within your remit, because ultimately it’s going to impact your ability to be successful long term within the organization overall.
[00:21:24] Mike Head: Finally, it gives you amazing insights to inform your sales and marketing. As you’re listening to calls and understanding what’s happening, what you’re delivering, and how you’ve done things for certain customers, it can truly inform a lot of what you can do on the other side to better win.
[00:21:46] Steve MacDonald: So we all know that high-performance companies have high-performance teams, and that it’s a team sport, right? This isn’t a one-team or one-department go-to-market strategy. You oversee sales, marketing, and customer success, and I’m sure you have some form of rev management or rev ops. How do you get the team to play together? How do you become the coach of that entire team, and what should we take away? What should we be learning from what you’ve been doing here to get the team to work together and be a coordinated, integrated go-to-market?
[00:22:21] Mike Head: A couple of things. Incentives matter, so make sure that if there’s any friction within the incentives, we’re all aligned toward the same goals. I think your cadence also matters. And in the cadence, that means, how are you getting cross-functional leadership together? How are you facilitating conversations among cross-functional leadership so they have respect and dialogue with one another?
[00:22:47] Mike Head: And then a lot of my direct reports, it’s really interesting when they bring issues to me, one of my most common responses is, “What did that other person say when you brought this up to them?” And more frequently than not, they say, “Well, I haven’t yet.” I’m like, “This isn’t an issue that you should be bringing to me.
[00:23:04] Mike Head: This is an issue that you should be working through with them. And for whatever reason you all have a dialogue and you can’t get through this together, then you can bring it up to me.” And over time, through those cadences and openly, directly talking about issues across teams and having that type of communication where I’m not allowing it to bubble up to me and forcing them to work through it on their own, and doing those things coupled with the incentives, that’s where I’ve been able to improve the alignment across teams.
[00:23:37] Mike Head: Is it ever perfect? No. There are always issues that will come up, but, you know, you can definitely make a lot of improvements and have a much higher-performing, higher-functioning team when you do those things.
[00:23:51] Steve MacDonald: We’ve talked about a lot. In our poor human minds, we can only literally retain two to three things at a time.
[00:23:57] Steve MacDonald: If you said, “Here’s the one thing that I want folks taking away that are going to be watching this podcast or listening to this podcast,” the single most important thing that you want to convey to make sure that they take away from our entire conversation, what would that be?
[00:24:17] Mike Head: You’re not as important as you think you are, and I mean that in your technology, what you do, all of those things, don’t matter. Your logo slide, all that stuff doesn’t matter. What really matters is the customer and what they care about. And if you focus on that across your engagements in sales, marketing, customer success, and partnerships, great things will happen.
[00:24:43] Steve MacDonald: I love that. Thank you for having one short takeaway. I’ve had people go on for five minutes and say eight different things. But so there was a woman who came on; she’s a three-time B2B CMO, and she’s also a value accelerator advisor for Goldman Sachs. Last time I talked to her, she had just helped direct $100 million into an investment in a new startup.
[00:25:02] Steve MacDonald: And she said, “Steve, to truly understand the customer, you can’t just go through the motions of the normal commercial go-to-market process. You’ve got to be proactive,” right. And you’ve got to take the time, and you get in, and you’ve got to make the most of every single conversation. And so here’s the part I want to ask.
[00:25:23] Steve MacDonald: And I had another four-time B2B CRO. He goes, “Steve, you’ve got to have conversations with the customers.” And he says, “And you’ve got to have conversations outside of the sales process. You’ve got to, like, proactively, whether it’s CAB meetings, whether it’s just calling customers one-on-one, whether it’s exploring it through webinars or podcasts or whatever it is, you’ve got to be proactive.”
[00:25:44] Steve MacDonald: That’s the North Star, right. So I’m just wondering what you’re thinking about that. What is your recommendation to be proactive, truly proactive in understanding and really being customer obsessed?
[00:25:56] Mike Head: I think there are a lot of different ways to do it overall. I agree with most of it there, but I actually also believe it can happen within the sales process, as long as you are deploying the right level of curiosity. That’s what I would add: be genuinely curious in all your engagements. Don’t ask questions just for the sake of asking questions. You do, in some ways, have to ask the right questions. But as long as you’re genuinely curious about the customer in any engagement with them and focused on them, you get more at-bats with them, you learn more, and you solve more problems overall.
[00:26:35] Mike Head: The final thing I would add is, yes, absolutely, figure out how to engage with them outside of the sales process. Once they are a customer, how’s it been going? Engaging with them, make sure you continue to have those touchpoints continuously. That’s how you develop strong knowledge and strong relationships.
[00:26:51] Steve MacDonald: I love it. I wish we had another three hours. I know it would be worthwhile. The mission of this podcast is to bring different perspectives from different C-level executives from all over the world, different insights, different experiences, different backgrounds. If we do that, then that’s the rising tide that lifts all boats.
[00:27:09] Steve MacDonald: You were a phenomenal part of that rising tide today. You were a tsunami as a part of that tide today. I just want to say thank you for coming onto the podcast. I really appreciate it.
[00:27:20] Mike Head: Oh, I appreciate, uh, you having me, Steve, and I enjoyed the conversation. I’m glad I could help add a little value.