Episode Summary
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.
Highlights
Introduction
YouTube Short
Episode Q&A Videos
6:42 | Building Better Sales Teams Through Customer-Led Selling
“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.”
2:42 | Maximize Every Opportunity With Today’s Economic Buyers
“You need to do all the work ahead of time to ensure that when you get a chance to engage with the economic buyers, you're making the most of that time. It's so important to get the most out of any engagement you're able to get.”
2:18 | Slowing Down Early to Accelerate Revenue Growth
“I always talk with the team 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.”
3:01 | Make Customer Obsession Your Companywide Growth Strategy
“If you're not retaining that revenue, it is because you aren't solving the problems that your customers came to you for. 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.”
3:10 | Grow Revenue Through Stronger Retention and Expansion
“I encourage all CROs to make sure that they're spending enough time on customers because it's gonna impact your ability to be successful long term. It also gives you amazing insights to inform your sales and marketing and the things that you can do to better win.”
2:03 | How to Create Stronger Alignment Across Your GTM Teams
“Incentives matter, so make sure that if there's any friction within the incentives, we're all aligned toward the same goals. Your cadence also matters and that means getting cross-functional leadership together, facilitating the conversations amongst the cross-functional leadership so that they have respect and dialogue amongst one another.”
2:01 | Turn Customer Curiosity Into Deeper Business Understanding
“Be genuinely curious in all of your engagements. You have to ask the right questions. Figure out how to engage with them outside of the sales process. Engage with them and make sure you keep those touchpoints going. That's how you develop strong knowledge and strong relationships.”
0:50 | Focus Every Go-to-Market Team on Customer Priorities
“You're not as important as you think you are. 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.”
Key Takeaways
Maximize Limited Executive Access
Better preparation helps sellers maximize executive conversations, build trust, and create stronger opportunities for revenue growth.
Slow Down to Accelerate
Understanding buyer pain and priorities early improves discovery, strengthens opportunities, and significantly increases sales win rates.
Align Around Customer Priorities
Customer understanding aligns revenue teams, strengthens retention, improves expansion, and creates more sustainable business growth.
About Mike
Mike Head
Mike Head is Chief Revenue Officer at Orderful, where he leads GTM strategy and revenue growth as the company expands its AI-native EDI platform. With more than two decades of leadership experience, he has helped scale B2B SaaS businesses to more than $250 million in annual recurring revenue while building high-performing teams and accelerating growth. He brings a practical perspective on balancing innovation with execution, staying close to customers, and building the capabilities needed for sustainable growth.
From the Guest
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Full Episode Article
Title: "CROs: How to Win in Fewer and Shorter Bursts"
This article is based on an interview with Mike Head, Chief Revenue Officer at Orderful
Introduction
Executive access is becoming harder to earn and easier to lose. Buyers are doing more research independently, consulting peers, using LLMs, and entering sales conversations with opinions already formed. For revenue leaders, that means every interaction has to create more value in less time.
Mike Head, Chief Revenue Officer at Orderful, brings the perspective of a three-time CRO who has helped scale revenue organizations and now oversees a broad go-to-market remit. His central argument is simple. Revenue teams can improve performance by understanding customers more deeply and consistently translating that understanding into how they sell, market, retain, and expand accounts.
Prepare Earlier to Win More Valuable Buyer Conversations
Buyers increasingly complete significant portions of their decision-making before engaging directly with sellers. Mike explains that buying is happening “online, happening through LLMs, happening through peer recommendations,” which means economic buyers may arrive with strong opinions about the direction they want to take. The opportunity for sellers is to make preparation part of the sales process rather than something left to individual initiative. Researching the company, its priorities, its leaders, and available public information gives sellers a stronger foundation for limited executive conversations.
That preparation becomes particularly important when access is scarce. “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,” Mike explains. The cost of getting it wrong is greater than a weak meeting. As Mike adds, “If you don’t, you lose trust, and you won’t get their access again.” Better preparation therefore supports both immediate opportunity performance and longer-term executive relationships.
Slow Down Early to Improve Win Rates and Revenue
The pressure to accelerate pipeline can encourage teams to move too quickly through early conversations. Mike advocates a different approach. “I always talk with them about slowing down to speed up,” he says. That means becoming methodical about understanding the buyer, the buyer’s pain, company priorities, and leadership goals before rushing toward a solution. For B2B revenue leaders, the lesson is that sales velocity is not simply about shortening every stage. Sometimes investing more time early prevents wasted effort later.
The potential impact can be substantial. Mike recalls that when his team drove a customer into an RFP, “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.” He connects stronger outcomes to disciplined execution and coaching. AI can now help leaders score discovery calls at scale, identify gaps quickly, and build improvement plans. The objective is not simply better conversations. It is creating a repeatable process that improves trust, win rates, and revenue performance.
Make Customer Understanding a Companywide Growth System
Customer knowledge becomes more valuable when it extends beyond sales. Mike recalls stopping a product planning meeting because the conversation focused too heavily on what the company wanted to build, with too little analysis of the customer, persona, problems, and desired outcomes. His broader principle is that customer priorities need to become a shared operating reference point. “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.”
Retention demonstrates why this responsibility cannot remain isolated inside customer success. “Retention isn’t a CS problem. Retention’s a company problem,” Mike explains. Positive NRR creates growth without requiring another new logo, while negative customer experiences can damage both existing revenue and future opportunities through peer conversations. As Mike notes, “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.”
Conclusion
The strongest revenue organizations do more than generate pipeline. They create a connected system in which customer understanding informs sales conversations, marketing, product decisions, customer success, retention, expansion, and leadership priorities. That requires incentives and operating cadences that reinforce shared outcomes, rather than allowing functional teams to optimize independently.
Mike Head reduces the principle to one memorable idea. “What really matters is the customer and what they care about.” For CROs, the opportunity is to operationalize that principle rather than simply endorse it. When customer knowledge consistently shapes preparation, discovery, coaching, retention, and cross-functional execution, customer focus becomes more than a value statement. It becomes an engine for stronger revenue performance and sustainable growth.
ELEVATING CONTENT MARKETING STANDARDS RAISES A CRUCIAL QUESTION:
Why shouldn’t the very act of creating thought leadership content also spark new conversations with in-pipeline deals, top prospects, and high-priority customers for revenue expansion? Or serve as the cornerstone for learning and applying voice-of-customer strategies? That’s the power of ABM Podcasting—engaging B2B buyers and customers in meaningful conversations that uncover essential go-to-market insights, support long sales cycles, reinforce your market perspective, build peer-level trust, and dismantle objections that kill deals.
Steven MacDonald
Steven MacDonald is the founder of Content Strategies, CEO of a MarTech SaaS Company, fractional CMO consulting with leading B2B companies and former Director of Strategy and Client Service at top ten digital marketing agencies.
Steven MacDonald
Steven MacDonald is the founder of Content Strategies, CEO of a MarTech SaaS Company, fractional CMO consulting with leading B2B companies and former Director of Strategy and Client Service at top ten digital marketing agencies.
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