Selling
Leading Next-Generation Sales Teams: The Mandate for Predictable Revenue
The sales landscape has fundamentally shifted. I keep reading posts and stories about AI replacing sales teams, and it may be for more commodity-type sales, but it will be some time before it replaces Enterprise sales teams. Building relationships and trust is the foundation for an executive to take a risk on your product, especially when it is critical to their success. AI is currently not at that level, and with behavior changing with every key release, building trust with an AI will be challenging for many years to come. But today, AI can be a powerful enablement tool for your team when leveraged correctly.
Your prospects no longer need salespeople for information; they need us for Insight. They have done their research. They expect their time to be an investment, not a discovery exercise. Does your presence and knowledge project confidence and inspire trust? Does the prospect view you as someone interested in helping their business, or just someone trying to close a deal? Impress them, and you could earn the opportunity to dig deeper. Disappoint them, and good luck trying to recover.
Two years ago, I was selling to a Fortune 100 Financial Services company. I understood their business needs, which we easily achieved. We demonstrated that we could take a key manual process that typically took 7 weeks to complete, automate it and maintain full compliance, and complete the task within 10 minutes. The SVP told me his priorities for selecting any new vendor were: 1 – Company Stability; 2 – Relationship with the Vendor; 3 – Product Quality; 4 – Product Value to their business; and 5 – Total Solution cost. Prior to selling their IP, the company fired the sales team, and the remaining execs went in and offered the deal at an even greater discount. It never sold because the executive team did not understand what was important to this buyer. The company had a high-level relationship with the stakeholders, but lacked the trust and credibility that I had built over several months. This is one of the main reasons why I believe AI won’t take over Enterprise Sales anytime soon.
So, how do you get it right?
The question for every CRO or VP of Sales isn’t whether their team is busy, but whether their activity is revenue-focused and leads to predictable and scalable results. There is much money to be made by everyone, but following the same old tired formulas seldom works.
For leaders aiming to build next-generation teams that deliver zero surprises in the forecast, the approach must be recalibrated around three core pillars: Strategic Preparation, High-Agency Coaching, and Outcome Focused Messaging (“context.”) It is much more than cold calling for two hours a day or having 5-10 meetings per week. Things like that are important, but they are just activities if you are not targeting the right companies and people, or if your team blows it once you have found those people. This will be a significant cultural shift for many companies.
Strategic Preparation: From “Discovery” to “Insight”
When a prospect books a meeting, they are giving us one of their most precious assets: time. If we treat that time as a standard discovery call, we set negative expectations, which signals the lack of perspective (the ‘P’ in PIE) and perceived value. This isn’t theory—it’s the PIE framework (Perspective, Insight, Experience) I’ve used to sell large deals, turn around at-risk customers, and scale teams for many years.
The C-Suite Mandate: Accelerate deal velocity by focusing on specific quantifiable impact for your prospects, and increase win rates by targeting identifiable business pain.
- Come with an Understanding of their Market, Changes, and Competition. Before the first call, we must demonstrate that we’ve already invested time in understanding their operational constraints, their competitive pressures, and their budget priorities. The goal is to move the conversation immediately from the tired, “What keeps you up at night?” to “We have seen [problem] with companies in your industry. Is that something you have experienced or have concerns about?”
- Long Discovery Calls or Presentations Typically Won’t Work. Customers are fatigued by generic questions. Every interaction must be purpose-driven and meaningful. If the call runs longer than planned, it must be because the conversation has become mutually valuable, not because we were ill-prepared and just keep talking.
- Discussions Must Be Targeted to the Problems They Are Most Likely Experiencing. This is where we leverage Insight (the ‘I’ in PIE). Use your background and AI to hypothesize the top three pain points before you dial. Our role is to validate these points, quantify the impact, and then introduce a Shared Vision of Success (our solution) anchored by measurable business outcomes.
Player-Coach: Enhancing Team Capabilities, Not Just Motivating Activity
If you are a sales leader who only focuses on closing your team’s most challenging deals, you are creating a dependency, not a capability. A Player-Coach must be accountable for the team’s numbers and its health.
The C-Suite Mandate: Drive organic growth by building repeatable processes and cultivating high-agency talent.
- Not a One Size Fits All Proposition. True coaching is not a template. It requires a methodical but human approach to diagnostics. That takes time, effort, and a genuine desire to help people grow.
- Identify Skills Gaps and Tailor Efforts. Test skills, identify gaps, and then create targeted efforts around building skills that address someone’s specific deficiencies. This personalized attention is how we build the high-performance culture and accountability required to sustain long-term success.
- Leverage the Team – Role Playing and Team Reviews. We must create a culture where knowledge sharing and feedback loops are the norm. Leverage team reviews and structured role-playing to sharpen execution. This is how we transform luck into a predictable process.
Give teams the latitude to adjust their messaging and test approaches. Adapt messaging to business trends, changes in the competitive landscape, and changing terminology. Then, have your team share their experiences and findings (good and bad) with the team to review, provide feedback, and refine. Structured agility helps your team maintain its competitive edge.
The Leadership Mandate: Context Over Content
We are past the hype cycle of AI. The C-Suite doesn’t care about the tool; they care about the ROI and the risk of poor execution. As leaders, we cannot just hand our teams a login and say, “Go use AI.” That’s a recipe for chaos and a quick erosion of professional credibility. We must lead by example.
We need to teach our teams that AI generates content, but humans generate context.
- Do use AI to deepen your understanding of the prospect’s industry so you can become a true consultant. Use the technology to gain understanding and market intelligence and tie it to your Experience (the ‘E’ in PIE) as preparation before any call.
- Don’t use AI to automate a thousand bad emails. Mass communication is cheap; individualized insight is priceless.
- Do use AI to research the one hundred prospects that actually matter. Focused efforts yield significantly better results.
- Don’t use AI to fake expertise. This leads to the quick death of credibility, as any good consultant will tell you.
The “Million Dollar Deal“ isn’t won by a bot. It’s won by a human who understands the nuances of the prospect’s business, builds trust, and navigates the internal structure and politics. AI is simply the tool that clears the path so you can do that work faster and with better data. AI is leverage, not a crutch.
Call to Action: Are You Building a Team or a Capability?
The next-generation sales leader understands that customer success is at the heart of everything we do. We win when they succeed. Your most valuable asset isn’t your pipeline—it’s the predictable capability of the individuals on your team. Consistently doing the right things is critical to success.
The challenge for every business leader today is this: Are you enabling your teams to sell like consultants, or are you still measuring them (and driving their behavior) on activity-based metrics? Focus on building intelligent and creative teams that deliver consistent results with zero surprises. It doesn’t happen overnight, but it is an investment in your future success.
Let’s discuss how we can implement the PIE framework and position your team to deliver scalable, organic growth in your organization.
Lessons Learned from GTM Consulting
For the past two years, I have performed part-time, contract go-to-market consulting. My wife had a surgery that had gone wrong 18 months ago, so I needed something that would allow me to take care of her, stay sharp, earn money, and help companies grow.
Most of the work was with small to midsize companies, but the problems and needs mirrored what I have encountered at larger companies. The main difference is that large companies tend to look to software to address problems. In contrast, smaller companies lack the budget for what they view as an unproven solution that increases complexity.
Here are my Top 5 findings:
- GTM plans are often developed at the highest levels, often in isolation, without market testing and validation.
- Sales teams are pitted against one another, rather than working together to help everyone achieve more (i.e., “A rising tide lifts all boats.”)
- Sales teams are focused on selling features rather than solving business problems.
- CRMs are not consistently used and often reflect idealized fiction rather than reality.
- Sales management and teams are not leveraging AI to help focus their efforts.
Here are the related Lessons Learned:
- Identifying common business problems and describing how your product or service solves them should be the foundation of the plan. Perform market analysis. How do companies describe those problems? Their terminology, often found in job ads, can help create effective messaging that resonates. Work to become the natural fit for what your prospects are seeking.
- Individual contributors get paid to win, but sales management needs to create incentives for collaborative efforts that lead to wins.
- For one company, I convinced them to implement a 2% SPIV (like a SPIFF, but team-focused) for every team member who actively contributed to team improvement. SPIV payments were quarterly, and there was a running total so the team could see the fund growth. Initial indications of a positive impact are good.
- Another benefit of collaboration is that it helps teams focus on approaches that work due to ongoing testing and refinement. Collaboration also helps teams focus on a more accurate ICP (ideal customer profile). Sales management can then feed their findings back to Marketing to improve and tailor their efforts.
- Selling is a byproduct of problem-solving. You can’t solve problems if you don’t know what they are. Every interaction with a prospect should focus on gathering information, building trust and relationships, and leveraging prior interactions to demonstrate that your solution will solve their problem and ease their pain.
- CRMs often either lack information or are full of wishful thinking. They focus on activities, and not progress and next steps. Using MEDDIC/MEDPICC as a foundation for reporting is a much better start. Sales managers need to independently validate the information to ensure their teams are being upfront and honest. Trust, coaching, and collaboration work together for the win.
- AI is not a panacea, but it is very effective for research, market validation, prospecting, and meeting preparation. Going in prepared builds respect and credibility, saves time, and lets you quickly qualify prospects in or out. There may be a nurturing program for some of the prospects qualified out for immediate deals, but your time is valuable, and you will go hungry chasing deals you can’t close.
So, what are your thoughts? Have you seen some of these problems yourself? How did you handle them? Let me know in the comments below.
And if you are looking for a Consultant to help your business grow or someone who can add immediate value to your team, then contact me.
The Power of Storytelling
The discussion of data and goals in business is very common. Unfortunately, it is so common that it becomes routine. There is no heart, no excitement, and, generally, a lack of real motivation that limits the likelihood of success.
Stories evoke emotions, and emotions often trump logic when it comes to getting buy-in and creating excitement. Stories also help with visualization, and visualizing success is proven to enhance goal achievement. That leads to mutual success. Just think about the power of TED Talks to help with the understanding and retention of ideas.
Steve Jobs realized that people are drawn to engaging stories that evoke emotion. He created relatable scenarios that helped people understand the benefits of a technologically advanced solution without having to dive deep into the technology. He spoke about things that were fun, exciting, and useful. He was visionary, but just as important, he was able to share that vision and create demand. Relatability and engagement, when done right, create an emotional attachment that drives action.
When my team and I were selling a leading-edge vector analytics database years ago, our Marketing team and other experts wanted us to focus on what later became known as “speeds and feeds.” Our product was more advanced than the competitors’, but our message was undifferentiated. That is not a good place to start when your competitors are larger and better known.
I created a weekly webinar that we called “Why Fast Matters.” We started by discussing common issues around the complexity and inflexibility of Star Schemas, Fact Tables, pre-aggregation, specialized hardware, and more. The focus was on agility that created a tangible business advantage while saving money. One of the stories I would tell was around a beautiful, multi-layered cake. It is a thing of beauty, taking a lot of time and skill to create. It was also fragile and expensive.
The story concluded like this:
“Now, picture yourself taking a bite of that amazing cake with your eyes closed. Think about how rich, flavorful, and amazing it is. Then someone hands you a fork, and you take another bite. It is just as amazing. You open your eyes and see a plated piece of the amazing layer cake alongside a cupcake. They were both delicious, and with your eyes closed, the results were the same. But one was complex and fragile, and the other was simple, quick, and inexpensive. There is a time and place for each, but when you are betting your success on an outcome, do you really care how you get there?”
We closed with a brief explanation of the technology, real-life proof points, and a call to action to prove its effectiveness in their environment using their data. The close helped demonstrate that this was not just a made-up story, but rather, something that could become their own success story. This was a straightforward approach to getting people to try something they might never have considered otherwise.
Essentially, you are shifting the audience’s mindset from how something gets done (means objective) to what matters and why it needs to be done (fundamental objective). People tend to have preconceived ideas about how the solution should work, often based on what they are familiar with. Once the audience begins to visualize a desirable outcome, they become more open to different approaches.
I have successfully used these approaches with more complex products, such as an advanced Kubernetes platform, object databases, a multi-platform data integration product, and the world’s first commercial JDBC driver. It is also an effective way to motivate teams. Create a vision of the successful execution of a plan, how good it feels to achieve your goals, and what it could mean for each person—an area they develop as their minds elaborate and personalize the story.
Some of the most effective and engaging people that I have known are skillful storytellers. Not everything has to be a story, but when leveraged at the right time, it can mean the difference between moving closer to your goal and being just one of many ideas or solutions.
You may not be the next Steve Jobs (I’m certainly not), but you could easily stand out from your peers and competition. Share your story in the comments below!
Getting your Piece of the PIE
Whether you are selling, consulting, or managing, there is a foundational approach that has consistently helped me succeed. I call it PIE – an acronym that stands for Perspective, Insight, and Experience. When applied effectively, these three elements provide a robust framework for solving problems, winning clients, and leading teams to remarkable outcomes.
Over the years, I’ve taught this methodology to my teams, and it’s been a critical driver of their success. While I usually reserve it for a small circle, I believe it’s time to share it more broadly.
As an aside, years ago, I wrote a post about some of the negative aspects of the “reckless” application of PIE.
Perspective – Broaden Your View to Stand Out:
To truly differentiate yourself in any field, you need to develop a broad and informed perspective. This involves understanding the larger environment in which you operate: the market, competitive landscape, customer needs, technological advances, and regulatory shifts. A dynamic perspective evolves as you gain new experiences and encounter different approaches to solving similar problems with other businesses or in other industries.
This requires a broad understanding of the environment, market, competitive landscape, legal and technological changes, and more. It also grows and changes as you experience new and different things—especially when different approaches to similar problems are taken. It is how you start to stand out in the eyes of your prospects, customers, and team.
Earlier in my career, I taught technical courses. Two or three people usually stood out. At least one wanted to prove they were better and smarter, and usually, one discussed strange approaches to solving problems. When digging into those strange approaches, you would often identify something creative and brilliant coming from a different perspective on the problem. Curiosity and a desire to improve drive innovation.
In business, perspective becomes your differentiator. When you can see things from a broader, more holistic viewpoint, you position yourself as someone who can offer more than just solutions—you offer foresight, adaptability, and creativity. You become the lighthouse that guides your clients around tricky situations and to a better destination.
How to Apply This:
- Stay informed about industry trends, not just within your niche but across related sectors.
- Engage with diverse thinkers, challenge your assumptions, and be open to unconventional ideas.
- Regularly reassess your strategies in light of new information or shifts in the business environment.
Here is a post that discusses perspective as the starting point.
Insight – The Power of Seeing What Others Don’t:
Insight is one of the most valuable assets you can bring to any business interaction. Too often, people are trapped by existing tools, processes, and perceived constraints. Insight allows you to pierce through these limitations and identify opportunities for improvement that others miss.
Here’s where perspective plays a role in insight: the broader your view, the better your ability to generate actionable insights that can transform a business. My most successful deals and projects were not won because I followed the status quo—they were won because I brought fresh ideas to the table. By reframing the problem and presenting a path to a better solution, I created value that competitors cannot match.
How to Apply This:
- Question assumptions and typical approaches. Ask yourself, “Is this really the best way to solve the problem?”
- Look for inefficiencies, bottlenecks, and areas of waste in processes. These are often hidden opportunities for innovation.
- When engaging with clients or teams, offer insights that reframe their challenges and provide a path to improved outcomes by initially focusing on the “what” instead of the “how.”
Here’s a post that delves deeper into insightfulness.
Experience – The Foundation of Wisdom and Credibility:
Experience is the foundation that supports both perspective and insight. It’s the repository of lessons learned—both successes and failures—that shape your approach to problem-solving and innovation. The more varied and in-depth your experience, the better equipped you are to offer valuable insights and strategies.
Consulting, in particular, is a fertile ground for gaining diversified experiences. By working with multiple clients across industries, you gain exposure to a wide array of challenges and solutions. In sales, this experience translates into powerful stories that illustrate your ability to help clients achieve better outcomes. The more experience you accumulate, the more confident you’ll become in your ability to deliver meaningful results through transferable competence (taking skills and lessons learned from one domain and applying them to another).
How to Apply This:
- Reflect on your past experiences—what worked, what didn’t, and why. Use these lessons to guide future decisions.
- Build case studies from your experiences to demonstrate your expertise and credibility when engaging with clients or stakeholders.
- Continuously seek out new challenges that stretch your capabilities and expand your knowledge base.
As Albert Einstein wisely said, “The only source of knowledge is experience. You need experience to gain wisdom.” But it’s not just about accumulating experiences—it’s about leveraging them. Your past successes build confidence in your abilities, while your failures provide invaluable lessons that help you avoid costly mistakes in the future.
Beyond the Hunt: Fueling Sustainable Enterprise Sales Growth
The software start-up world is obsessed with “Hunters” – salespeople laser-focused on landing new customers. Job boards are overflowing with companies in “growth phases,” desperate for new logos. Understandably, the revenue from each new customer can mean a 10-20x multiple in company valuation in the VC-fueled race toward an exit. But what happens after the deal closes? Is that frenzied growth sustainable?
The Long Game: Profitability and Sustainability
My experience leading a large business unit and running my own company has taught me that sustainable growth requires more than just a flood of new logos. Here’s why:
- Cash flow is King: Lines of credit can vanish overnight (remember Silicon Valley Bank?). Relying solely on external funding is a risky approach.
- Not All New Business is Good Business: Unprofitable accounts, high-churn risks, and customers with limited growth potential can drain your resources faster than you can acquire them. Efficiency matters for scalability.
- Profits Drive Long-Term Growth: Organic, profit-fueled growth, especially when driven by innovation, creates a much more resilient and valuable business.
The Power of the Hybrid Sales Model
To achieve sustainable growth, you either need an extensive and fully integrated organization that seamlessly transitions from the sale to implementation (not many companies are able to accomplish this), or a hybrid sales team that excels at both hunting (50-70%) and farming (30-50%). Landing a new customer is hard work, but retaining and growing them is just as challenging and crucial. Customer acquisition costs are often too high to justify losing a customer only a year or two after the initial win. Treating new customers like assets (instead of commodities) is essential to long-term success.
Mastering Strategic Accounts: Turnarounds and Growth
Large, strategic accounts—Tier 1 companies with strong brand recognition and significant revenue potential—present unique challenges. In my experience, these accounts often fall into two categories: those I initially closed and then grew (ideal, as you have already laid the foundation for success), and those I inherited in a neglected state and had to turn around.
Turnarounds require a unique skill set. They demand as much time and sometimes even more effort than landing a new logo, blending aspects of both hunting and farming. It takes commitment, skill, patience, and effort to understand an organization and find new ways to deliver value. Relationships and trust take time to develop, and in this situation they are in question (or worse).
Case Study: From Churn Risk to Multi-Million Dollar Expansion
Take, for example, a large Financial Services company I inherited when their Strategic Account Manager left. The account had been neglected for two years and was riddled with problems. We lacked executive relationships and higher-level visibility within the organization. They were evaluating competitors, and we knew nothing about it! Even though they were an existing customer, we were the underdog.
I organized a day-long on-site meeting to understand their pain points. We identified immediate issues, shared our vision for the future, began building trust, and demonstrated our commitment to their success. Following this, we spent a few hours getting to know the team over dinner. It was an eye-opener for me, with them providing more information about their needs and how best to approach them.
The result? Within three months, I closed a $500K expansion deal, followed by a $500K consulting engagement and then a $3.25M two-year cloud expansion and upgrade prepay deal. My team and I rebuilt the relationship, solved critical problems (even going beyond our product scope), and provided a clear path forward with our AI-powered platform. I became a trusted advisor who was valued by their executive team. It was a true win-win.
The Bottom Line: Building a Sustainable Sales Engine
Install base growth and customer retention is critical for long-term success, especially with larger customers. The approach has to be multi-dimensional. It is a team effort, and the Account Executive is the quarterback. Relationship management, customer success teams, support, and services all play a role. Effective communication is bi-directional, where the customer has insight into what is coming down the road and input into the direction of products they rely on. This becomes a true partnership that adds significant value to both organizations.
Does this hybrid approach apply to every company? If you’re IBM or Oracle, your offerings are broad and deep, and your customers are largely locked-in. “Land and expand” is part of their DNA. And if you’re selling end-of-life products, your focus might shift towards maximizing the “long tail” through customer success and services to minimize costs and maximize profitability.
However, for most growth-stage Cloud and SaaS companies, the hybrid sales model is an essential part of their success.
Call to Action:
- Evaluate your sales team structure and compensation plans. Do they incentivize both new customer acquisition and ongoing account growth?
- Invest in training and development for your sales team. Equip them with the skills needed to excel at both hunting and farming. It can be a difficult transition, but is worth it in the long run.
- Need help building a high-performing hybrid sales team or turning around strategic accounts? Let’s connect!
Where Ideas, Experiences, and Lessons Learned Intersect 