enterprise sales
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.
Sales Discussions that Work
Selling is challenging work, and often, “we” (sales and marketing teams) make it even more challenging than it has to be. How many times have you seen a selling script, elevator pitch, or initial presentation that is long, boring, and undifferentiated? People have a short attention span, and nobody wants to interact with someone who does not listen to them or is pushy.
Your initial discussion is crucial to your success. Instead of going over a list of features, reading a slide deck, and telling why you and your product are so great, let’s try something else.
1. Understand why people buy. Any change has the potential to be difficult, risky, and painful. So, the pain they are facing has to be even greater, or they won’t bother changing. Your main job early on is to listen and try to understand their concerns. You may have a perfect solution, but if it doesn’t solve their pain, it holds little value to your prospect. This initial meeting is all about them.
2. At the start of the meeting, ask, “What would make this time well spent for you? What would you like to walk away from this meeting with?” Get them thinking about their problems and the value you may be able to provide, even if they don’t fully articulate them to you.
3. Ask questions and follow-up questions. People don’t lead with their significant issues, and someone unwilling to divulge anything likely isn’t a buyer. The more the prospect talks, the more you learn. So many sellers do not understand this simple concept. They want to dazzle you with features and demos – even if those things are not what the prospect needs.
4. Once you think that you have identified a pain, qualify and quantify it. For example, “You mentioned that your product release cycles are too long and complex. What is the business impact of that, and what would the impact be if you could reduce that time and effort by 50%?” Write that down, in their own words, because it could be vital later. If you manage to identify several pain points, review them and ask the prospect to identify the top three issues from the list, and ask why those three?
5. If you are giving a presentation, pull up the most relevant slide (customer problem/benefit slides work well here) and ask if this sounds similar to the problem they are facing. It can be a good starting point for getting the discussion moving in the right direction.
6. Don’t worry if you are not able to cover everything you intended, as long as the meeting is productive. I’ve also seen salespeople cut someone off and move on to a new slide rather than discussing something of substance. I was actually told once by a sales leader that five minutes of discussion is all that is required in an initial 30-minute meeting, because our goal is to pique their interest. That just doesn’t work.
7. Next steps. Keep in mind that your time is valuable, and qualifying out a prospect who is not a good fit is essential – it helps you avoid false hopes and lets you focus on people who might genuinely need your help. There are many ways the next meeting could go, but it’s best to ask the prospect. Would they like to expand the audience? Is there a specific issue they would like to address? Would they like a product demo or a technical discussion? Is something like a non-disclosure agreement (NDA) keeping them from opening up? Lack of engagement on their part is a huge clue. Be direct and ask the tough questions now to avoid wasting valuable time and effort later.
Here is a mini success story. In 2010, my team and I began selling the first commercial vector high-performance analytics database. There were several products already out that claimed to be 70x-100x faster than other products. Our pitch was supposed to be that we were 70 times faster than other products. That was self-limiting from the start and likely prevented people from contacting us.
After two months of minimal success (I closed a deal with a small hedge fund, which was the only sale in all regions), we started a weekly webinar called “Why Fast Matters.” The focus was on positive business outcomes rather than specific technology and features (“speeds and feeds”). We opened with some “What if?” statements, such as: What if you get answers from complex queries faster than your competitors? What if you could do that without the cost, complexity, delays, and limitations of a Star Schema or pre-aggregated data? What if you could do this on commodity x86 hardware? We would then briefly cover the breakthrough technology (which was a precursor to Snowflake) and offer a free half-day meeting with a consultant.
Within the first two weeks, we met with a company that was later acquired by PayPal shortly before eBay acquired PayPal. This company was about to spend $500K on a proprietary hardware expansion that would have only provided additional capacity for the following year. Their customers bought advertising based on queries against the last six months of their data. I asked the question, “What if they could query against five years of data and get answers faster than they do today? Do you think that would help them buy more advertising? Do your customers ever ask for this?” The response was that their customers frequently ask for 12 months of data and would be willing to pay more for these capabilities. Still, they did not have a way to do this cost-effectively.
I closed a $250K ARR subscription deal in two weeks, and they purchased $140K of commodity Dell hardware for our software to run on. They saved 20% over their planned purchase, and more importantly, they rolled out advanced querying capabilities (against six years of data) in less than a month. There was incredible value to them and their customers, and it generated more business for them. We would not have identified this need if we had primarily focused on features and technology.
As an aside, I was initially chastised for going off message, but after the Australian team adopted our approach and began closing deals, it became the new corporate standard. If something isn’t working, focus on finding ways to improve it. Even incremental change can be meaningful.
In the words of Tony Robbins, “If you do what you’ve always done, you’ll get what you’ve always gotten.”
Lessons Learned from Selling Kubernetes
Cloud-native, containerization, microservices, and Kubernetes have become very popular over the past few years. They are as complex as they are powerful, and for a large, complex organization, these technologies can be a game changer. Kubernetes itself is a partial solution – the foundation for something extraordinary. It can take 20-25 additional products to handle all aspects of the computing environment (e.g., ingress, services mesh, storage, networking, security, observability, continuous delivery, policy management, and more).
Consider the case of a major Financial Services company, one of my clients. They operated with 200 Development teams, each comprising 5-10 members, who were frequently tasked with deploying new applications and application changes. Prior to embracing Kubernetes, their approach involved deploying massive monolithic applications, with changes occurring only 2-3 times per year. However, with the introduction of Kubernetes, they were able to transition to a daily deployment model, maintaining control and swiftly rolling back changes if necessary. This shift in their operations not only allowed them to innovate at a faster pace but also enabled them to respond to opportunities and address needs more promptly.
Most platforms utilize Ansible and Terraform for creating playbooks, configuration management, and other purposes. Those configurations could become very long and complex over time and were prone to errors. For more complicated configurations, such as multi-cloud and hybrid environments, the complexity is further amplified. “Configuration Drift,” or runtime configurations that differ from what was expected for various reasons, leads to problems such as increased costs due to resource misconfiguration, potential security issues resulting from incorrectly applied or missing policies, and issues with identity management.
The surprising thing was that when prospects identified those problems, they would look to new platforms that used the same tools to solve them. Sometimes, things would temporarily improve (after much time and expense for a migration), but then fall back into disarray as the underlying process issues still needed to be addressed.
Our platform used a new technology called Cluster API (or CAPI). It provided a central (declarative) configuration repository, making it quick and easy to create new clusters. More importantly, it would perform regular configuration checks and automatically reconcile incorrect or missing policies. It was an immutable and self-healing Kubernetes infrastructure. It simplified overall cluster management and standardized infrastructure implementation.
All great stuff – who would not want that? This technology was new but proven, but it was different, which scared some people. These were a couple of recurring themes:
- The Platform and DevOps teams had a backlog of work due to existing problems, so there was more fear about falling further behind than confidence in a better alternative.
- Teams focused on their existing investment in a platform or on the sunk costs spent over a long period, attempting to solve their problems. The ROI on a new platform was often only 3-4 months, but that was challenging to believe, given their own experiences on an inferior platform.
- Teams would look at outsourcing the problem to a managed service provider. They could not explain how the problems would be specifically resolved, but did not seem concerned about that lack of clarity.
- There was a lack of consistency on the versions of Kubernetes used, the add-ons and their versions, and one-off changes that were never intended to become permanent. Reconciling those issues or migrating to new, clean clusters both involved time and effort. That became an excuse to maintain the status quo.
- Unplanned outages were common and usually expensive. Using the cost of those outages as justification for something new was typically a last resort, as people did not like acknowledging problems that put a spotlight on themselves.
- Architects had a curiosity about new and different things, but often lacked the gravitas within business leadership to effect change. They were usually unwilling or unable to explain how real changes happen within their company, or introduce you to the actual decision-makers and budget holders.
Focusing on outcomes and working with the Executives most affected by them tended to be the best path forward. Those companies and teams were rewarded with a platform that simplified fleet management, improved observability, and helped them avoid the risky, expensive problems that had plagued them in the past. And, working with satisfied customers who appreciated your efforts and became loyal partners made selling this platform that much more rewarding.
Finding the Right Fit in Sales
I won’t sell a product or service if I don’t believe in it or in the company behind it. But that is only part of the picture. Not all products or services fit everybody, but most are a fit for somebody. Whether you are a seller or leading a sales team, understanding the best-fit use cases helps you create a repeatable sales motion that allows you to:
- Find and prospect the best candidate companies.
- Demonstrate benefits for a credible and relevant use case.
- Find a sponsor who benefits from your offering.
- Accelerate the deal velocity – even in a large enterprise business.
- Close large deals faster – and more of them!
When I started at my last company, I was told that the typical deal size was $75K-$80K, having a 9-12 month sales cycle with a midsize company. I was selling a Kubernetes Fleet Management platform, and I quickly found that most midsize companies lacked the containerization needs that Kubernetes provides. Most also needed to gain the skills required for fairly complex solutions, which can take months.
Large Enterprise companies had the need and the expertise to support Kubernetes, which started my profile development exercise. Large companies with a corporate standard containerization product were less likely candidates with a much longer sales cycle. Financial Services companies require strong end-to-end security and cannot afford breaches (reputationally and actual costs). Therefore, they had larger budgets and immediate needs, so they became a primary focus.
While looking at the environments for these companies, it became clear that an initial deal size could easily be in the $500K – $1 million range. And, if you successfully delivered what you promised, there could be several more significant follow-on deals. The icing on the cake is that by selling those companies what they need, solving significant problems or concerns, and treating them like the valued customers they are, they would reward you with loyalty and long-term business.
Finding the right fit for your product or service takes analysis, investigation, testing, and time. Getting this right provides the perfect opportunity to be successful and scale the results through the entire team. It also provides credibility when new customers are willing to speak with prospects and sing your praises. Success breeds success.
Two Truths of Enterprise Sales
I have been selling products and services to large enterprise organizations for most of my career. I like to tell people, “Everyone is in sales,” because one way or another, they are.
Early in my career, I was a Systems Analyst for a Marketing company. I created what I’ve been told was the first custom coupon system for Subaru, as well as several systems for Mitsubishi Motors and Mitsubishi Electric. We would devise several ideas to pitch to the customer and then have follow-up meetings to flesh out the idea and help sell an extensive, multi-faceted program. It was a great learning experience in understanding what mattered and how to effectively upsell deals.
Standard sales advice is to sell to a known problem or a project. The thinking behind finding projects is that a tactical or strategic need has already been identified, with executive support and funding to address it. Most companies have some degree of dysfunction (which is why Patrick Lencioni’s books are so popular) that tends to affect projects negatively.
Focusing on problems is the way to go, but a business rarely comes to you to disclose those problems and their impact. A Consultative Selling approach is helpful in this situation. The upfront preparation can be time-consuming, but the results are often bigger deals that close in less time.
The process I use involves understanding the business, its customers, and competition, as well as potential changes to that business or industry. I will search for clues that indicate potential problems (from financial reports and filings to product-specific forum posts). I will then hypothesize about a few potential problems and reach out to the highest-level individuals in the organization likely to be responsible for these issues.
When you do speak with someone, you need to demonstrate your understanding and potential value add to learn more and begin gaining their trust while listening for validation or other information to refine your hypothesis. People buy from people they like and trust, and this approach becomes the foundation. From here, you can guide the process and expand your reach to other areas and layers of the organization. As a seller, your focus is on proposing real solutions that are mutually beneficial and have a high probability of success.
So, back to the two truths –
- Companies and teams are often biased toward the status quo and the familiar. Problems are rarely solved using the same people, products, and processes that got them into this position in the first place. Your focus as a seller needs to be on outcomes. Help them visualize what success looks like and how it feels. Overcome negative emotions of fear using positive emotions and envisioning a better future.
- Change can be expensive at first. It is an investment in the future that should yield both short-term benefits and long-term savings. Your focus as a seller should be on delivering value.
This approach and understanding can lead to new customer acquisition and ongoing account growth. You are continually demonstrating your value and commitment to your customers’ success, and that pays off.
Here’s a bonus third truth. If you cannot quickly gain consensus on the root cause problem(s) or traction with your proposed solution, qualifying out is often the best next step. Nurturing the prospect may lead to a future deal, but leveraging that 3-6 months on another prospect will likely result in more deals closed. Qualify out quickly and move on – that is better for everyone involved.
Remember, hope is not a strategy.
Where Ideas, Experiences, and Lessons Learned Intersect 