AI and the Complex Sale

Ever try selling something that doesn’t exist? Well, I suppose most software developers do that on a regular basis, but something BIG that takes years to design, build and deliver? I’ve been doing that for decades. From selling advanced weapons systems to governments to closing multi-year global technology implementations. It’s really complicated, hence the term Complex Sale.
They’re basically fancy words for “it’s going to take forever, and there are too many people in the room who think they’re in charge.” You’ve got committees, stakeholders, decision-makers—it’s like trying to agree on a group vacation, but worse because it involves money, egos, and PowerPoint slides.
Now, throw AI into the mix. What would take tons of work and years of intelligence gathering and suddenly, you’ve got insights, data, and predictions coming out of your ears.
The integration of artificial intelligence (AI) into the complex sales process is revolutionizing how businesses approach high-stakes transactions. By combining the computational power of AI with human expertise, sales professionals can navigate intricate sales cycles more effectively and deliver tailored solutions to meet diverse stakeholder needs. This fusion of technology and strategy is reshaping the landscape of complex sales.
AI’s Role in Chaos Control
AI is brilliant at sifting through the nonsense. Got a dozen people with different opinions? AI can sort out who actually matters in the decision-making process—spoiler alert: it’s not Geoff from Procurement. It analyzes emails, tracks behaviors, and somehow knows which stakeholder’s approval is critical. It’s like Sherlock Holmes but without the creepy violin.
And when it comes to objections, AI’s all over it. It’ll tell you things like, “They’re worried about price,” or “They think your delivery timeline is about as reliable as a politician’s promise.” Handy, right?
AI streamlines stakeholder management. By analyzing communication patterns and engagement levels, AI systems identify key decision-makers, anticipate objections, and tailor messaging to resonate with individual stakeholders. This data-driven approach ensures that every interaction is purposeful and aligned with the client’s needs
Relationship Building: AI Does the Admin
Let’s not pretend AI can charm its way through a room like a stand-up comedian. That’s still your job. But it’ll handle the boring stuff sellers hate—follow-ups, scheduling, tracking who said what and when. It’s like having an assistant who doesn’t complain or take weeks off to find themselves. Meanwhile, you can focus on the big stuff: being nice to people, listening to their concerns, and trying not to look too desperate.
Strategy, But Make It Smart
Here’s where AI really shows off. Predictive analytics—sounds fancy, doesn’t it? But basically, it’s AI looking at a load of numbers and going, “Yeah, they’re going to buy,” or “Forget it, they’ve already chosen someone else.” It’s brutally honest, which is refreshing in sales. No fluff, just facts.
And when it comes to negotiation, AI’s your secret weapon. It’ll tell you what worked in past deals, what’s likely to win them over, and even suggest a discount if that’s what it takes to close the deal. It’s like having a ringer on the softball team who slugs it out of the park every game but won’t take the credit.
Keeping It Human
The successful integration of AI in complex sales requires a balance between technological capabilities and human judgment. AI is clever, but it’s not human. It doesn’t do empathy, it doesn’t crack jokes, and it definitely doesn’t understand why you’re still trying to make “fax” happen in 2025. That’s where you come in. You’re the one who builds the relationships, makes people laugh, and convinces them that you’re the best option without actually saying, “Please, please pick me.”
The successful integration of AI in complex sales requires a balance between technological capabilities and human judgment. While AI provides valuable insights and efficiencies, it is ultimately the sales professional who interprets these insights and builds meaningful connections with clients. Emotional intelligence, creativity, and adaptability remain irreplaceable skills in navigating the nuances of human interaction.
The Future Is Here (and It’s a Bit Smug)
AI isn’t going anywhere and thank goodness for that. It’s saving us time, making us look smarter than we are, and helping us close deals that would otherwise take months. Just remember it’s a tool, not a miracle worker. The magic still happens when you combine its brilliance with your charm, wit, and uncanny ability to survive endless meetings.
So, embrace AI, but don’t let it get too cocky. After all, it’s just a machine. You’re the one
Sales teams must also remain vigilant about the ethical use of AI. Transparency in data usage, respect for client privacy, and avoiding biases in AI algorithms are critical to keeping trust and credibility.
Good sales teams are a tough crowd, they stick to what’s worked for them in the past. Bringing new tools and tech into the world of complex sales can be challenging, but AI is a true optimization enabler, apologies for the consultingese.
In the age of AI, the art and science of complex sales are converging like never before. By using the strengths of both, businesses can achieve new heights of efficiency, effectiveness, and customer satisfaction.
TOP 5 MOST IRRELEVANT BUSINESS METRICS

Metrics, metrics, metrics there are so many business metrics in the world today that most of them have little or no relevance. Sometimes I think business gurus stay awake at night concocting a new metric, so they have something new to talk about or sell to clients.
Making decisions based on numbers a.k.a. metrics the numbers need to be relevant, meaningful and actionable. Here are a my Top 5 most irrelevant numbers that businesses collect:
Number 5- Customer Satisfaction (CSAT)Scores: You would think that CSAT scores are the most valuable number any business can collect. They are highly subjective and bias laden. The results of these scores seldom reflect actual customer behavior but more a snapshot perception of a specific interaction with a product or service. Using CSAT or Net Promoter Scores (NPS) alone provides minimal insights into customer behavior or advocacy. Understanding customer needs, perceptions, and behaviors require a combination of hard metrics like customer retention and share of wallet, average order value (AOV), Customer Lifetime Value (CLV) along with softer metrics like CSAT, NPS, Customer Effort Score (CES) and the most valuable piece of data, unstructured feedback like product reviews, complaints and praises. A holistic approach to understanding customer behavior offers far more value than a single CSAT, CES or NPS number.
Number 4-Gross Revenue: Gross revenue is a totally meaningless number. Focusing on gross revenue without considering costs is highly misleading. Top line revenue without taking into account the costs required to achieve that revenue can lead to complete misunderstanding the health of the business. Insights into the business that are actionable financial metrics should include all costs associated with the gross revenue. Getting to the core of understanding business health requires metrics that reflect net values. Examples include net income and net profit margin that reflect both the incoming revenue stream and outgoing costs.
Number 3-Vanity Metrics: Vanity metrics are interesting but often totally irrelevant to business decisions. Vanity metrics include social media followers, page view or app downloads. While they might look impressive or depressing, depending on the numbers, they don’t necessarily connect with business success or profitability. Some would argue these vanity metrics have value for understanding the success of marketing efforts. I would argue that a more valuable and actionable metric is Return on Marketing Investment (ROMI). ROMI requires a bit of work to calculate because it focuses on the profits of incremental sales attributed to marketing activity like social media, page views, promotions and campaigns. It can be calculated uniquely for each marketing or advertising channel providing insights into the value creation of marketing activities in each channel.
Number 2-Customer Count: Focusing on the gross number of customers doesn’t tell you much about your business. It doesn’t reflect the value of those customers, their behaviors, retention or loyalty. There is no insight with this metric, it’s just a number. Insights leading to action comes form hard metrics that reflect the value of your customer base through understanding segmentation of that customer base, retention of customers, customer lifetime value (CLV) or in B2B scenarios average revenue per account (ARPA). In today’s business world customers move and shake like an 8.0 earthquake. Rely on the data beneath the customer count to make decisions that create value for the business and the customer.
Number 1 – Employee Hours Worked: Not many businesses use this metric but for those that still see value in knowing how many hours employees put on a timecard it’s time to wake up. Simply tracking hours worked doesn’t account for productivity, competency or efficiency. Unless your business relies on timesheets for billing customers to generate revenue hours worked is the top irrelevant metric in history. Focus on output and results to truly measure employee performance. Revenue per employee provides a read on the entire workforce. The more revenue per employee, the more productive is and the more likely its efficiently using resources.
Metrics drive insights that drive action. Use that valuable real estate on an executive dashboard for meaningful metrics that provide a snapshot of business health.
Branding…Does it really matter?

If your brand requires an explanation, it’s not a brand, it’s just a fictitious name.
I submit that because of marketing oversaturation in every field of endeavor, unique branding has become irrelevant. I contend that the sheer volume of companies and branded products has diluted the impact of individual brands. Established brands are living off decades of saturation while new introductions get lost in the background.
Let’s consider the available data:
Number of Companies: As of 2021, there were approximately 333.34 million companies worldwide. This represents a significant increase from previous years, indicating a crowded marketplace where countless companies vie for attention. Although this number is enormous it doesn’t represent the single shingle service providers that proliferate every day so I’m adding a few more for mom and the kids, let’s call it 500 million for fun.
Branded Products and Services: While exact numbers are elusive, the proliferation of brands is evident. For instance, Nestlé alone boasts over 2,000 brands, and there are numerous examples of successful brands with numbers in their names, indicating a trend in branding strategies. Think about that for a second. One consumer company holds 2000 brands, pshaw you say, I’m not a consumer business I’m a B2B business. OK then, let’s do some quick math on that; say 50% of the 500 million or so going concerns are B2B and have just a single brand. Oops, that’s in the neighborhood of 200 million unique, or so everyone thinks, brands.
The impact of this saturation is reflected in consumer behavior and marketing effectiveness:
Consumer Trust: Over-targeting and ad saturation have been shown to damage consumer trust in brands, with 54% of UK consumers objecting to being targeted based on past online activity.
Ad Fatigue: The phenomenon of ad fatigue sets in when a target audience is bombarded with ads from the same brand, leading to decreased engagement.
Brand Relevance: Despite the challenges, 44% of consumers enjoy ads that are directly relevant, suggesting that unique branding can still resonate when executed properly.
While the data indicates a crowded marketplace with a vast number of companies and products, the relevance of unique branding is not entirely negated. Instead, the challenge lies in cutting through the noise and connecting with consumers in meaningful ways. Unique branding, when aligned with buyer interests and executed with precision, can still hold significant value and relevance.
A brand stands as the silent ambassador of a company, embodying its values, ethos, and identity. encapsulates the quintessence of what a brand should represent—a seamless connection between the product and the buyer that requires no intermediary.
Think about your own businesses branding for a moment. Does it meet the criteria as a brand? Probably not. Most branding these days is around some whimsical made-up set of letters and symbols that mean nothing to anyone other than the folks that created it.
A brand is much more than a name or a logo:
- It represents the emotional and psychological relationship a company has with its customers. Strong brands evoke a visceral response,
- It generates a feeling of familiarity and trust that resonates with the buyer on a subconscious level.
- An effective brand transcends the need for explanation because its essence is already known and felt. This immediate recognition is the hallmark of a successful brand.
The necessity for a brand to be self-explanatory also lies in the fast-paced world we live in. Consumers are bombarded with countless choices and messages every day. In such a saturated market, the ability of a brand to stand out without requiring a detailed backstory or rationale is crucial. A brand that needs to be explained is at a disadvantage, as it fails to make an instant connection with potential customers.
A brand that is self-evident is more likely to foster loyalty. When consumers understand what a brand stands for, they can align their personal values with the brand’s image. This alignment creates a strong emotional bond that is far more enduring than any rational explanation could provide. It is this bond that turns first-time buyers into lifelong customers.
Remember to consider the role of simplicity in branding. A brand that is too complex or abstract may struggle to communicate its message clearly. Simplicity in design and messaging allows a brand to be direct and powerful. A simple, yet strong brand cuts through the noise and delivers a clear message that is easy to remember and recognize.
Growing up my family would visit a butcher shop called “Meatland” no doubt there about the branding. Simple, elegant, and clear as a bell. You didn’t visit “Meatland” if you needed a tomato.
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