Selling
Six Ways AI Can Become a Sales Management Enhancer
As a VP of Sales, I would spend the first 60-90 minutes of every day reviewing a dozen news sources for new technology, competitor announcements, proposed legislation, and M&A news. I looked for anything relevant in critical industries, news about our customers or their top customers, and staffing changes within their companies.
My goal was to identify anything that could negatively impact deals in play, threaten the customer base, disrupt the run-rate business, or create opportunities to break into a new company or displace a competitor. You feed your findings and speculations back to your team, along with suggestions, talking points, or specific directions to help them maintain or increase their success for the current quarter plus the next few quarters.
You look for trends and leading indicators that could help your team and your organization achieve greater success. Winning feels good, and the rewards drive you to achieve even more.
Artificial Intelligence (AI) can do all this and more. It will be more consistent, analyze information without bias, and do so faster.
1. Automated Intelligence Gathering
Focus your efforts where they add the most value. AI can automate the collection and analysis of data from multiple sources, including news feeds, legal updates, social media, and competitor websites. This automation can save considerable time and minimize the chances of missing relevant information. Natural Language Processing (NLP) can identify, categorize, and correlate relevant information, providing actionable insights without manual review.
2. Enhanced Lead and Opportunity Identification
In addition to the correlations above, Machine Learning (ML) models can analyze trends and patterns in data to identify potential leads or opportunities for expansion. By understanding market movements, customer behaviors, historical behavior, and presumptive competitor strategies, AI can suggest new targets for sales efforts and highlight areas where teams could gain a competitive edge.
3. Improved Internal Communication and Collaboration
Sales is not just about selling; it also requires internal collaboration to create the best possible products and services and identify the best approaches to generate awareness and interest in your offerings.
AI systems can serve as a central hub for information that benefits various departments within a company. By integrating with CRM, marketing, support, and other internal systems, AI can distribute tailored information to different teams, ensuring everyone has the best insights to perform their roles effectively and promoting a more cohesive, coordinated approach to achieving long-term business objectives.
4. Forecasting and Predictive Analytics
With the ability to process vast amounts of data, AI should significantly improve forecasting accuracy. Predictive analytics can estimate future sales trends, customer demand, and market dynamics, giving businesses more opportunities to make better-informed decisions—leading to better resource allocation, optimized sales strategies, and, ultimately, higher revenue.
5. Increased Efficiency and ROI
By automating routine tasks and providing deep insights, AI can free up sales and management teams to focus on strategic activities. The efficiency gains from AI can result in significant cost savings and a higher return on investment (ROI) as teams do more with less, capitalize on opportunities faster and more effectively, and ultimately make more money for themselves and their company.
6. Continuous Learning and Improvement
Machine learning models will improve over time as they process more data, meaning the insights and recommendations provided by AI will become increasingly accurate and valuable, helping businesses continuously refine their strategies and operations for better outcomes. AI will also provide constructive feedback and suggest next steps in real time, helping everyone using it upskill.
Future Perspectives
While AI may not yet be ready to take over complex roles like enterprise sales, its potential to enhance these roles is undeniable. As AI technology continues to evolve, its ability to provide highly accurate forecasts, improve win rates, shorten sales cycles, and enhance competitiveness will only grow. The future of AI in sales and business management is not just about automation; it’s about augmenting human capabilities to create more effective, efficient, and thriving organizations that can compete in an increasingly competitive global landscape.
So, what do you think? Will this work? Will it be good enough if everyone is doing it? Leave a comment and let us know.
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 fit somebody. Qualification matters, and qualifying accurately and quickly helps you earn more money. Whether you are a seller or leading a sales team, understanding the best-fit use cases can help you build your ICP and a repeatable sales motion, allowing 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 selling at my last company, I was told that the typical deal size was $75K-$80K, with a 9-12 month sales cycle at a midsize company. I sold a Kubernetes Fleet Management platform, and I quickly found that most midsize companies lacked the containerization needs Kubernetes provides. Most also needed to gain the skills required for fairly complex solutions, which can take months. So, a great solution for some may not be the solution for all.
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 these companies’ environments, it became clear to me that with the right targeting, an initial deal 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. That became my focus, and my assumptions proved to be accurate.
Finding the right fit for your product or service takes analysis, investigation, testing, and time. Getting this right creates the perfect opportunity for ongoing success and to scale results across the entire team. It also provides credibility when customers are willing to speak with prospects and sing your praises. Success breeds success.
The Million Dollar Deal How-To
Eight years ago, one of my peers asked me to produce a two-hour sales training session for the combined global sales team. He suggested a session named “The Million Dollar Deal How-To,” which would show people how to go about finding and closing large deals. It was a good idea, so I went ahead and did it.
The presentation started with a list of my Top 20 deals to date and a brief description of each deal; the biggest had $8.5M+ ARR and a 7-year total value of over $60M. I included an additional negotiation for a deal closed by another VP shortly before he left the company. It was a complex deal with a very large System Integrator worth $1M-$2M/year over five years.
The underlying assumption is that the seller had properly qualified the prospect before this step. While this would be considered a “given” by many, I have seen far too many sellers focus on deals that would never happen. To be successful, you need to spend your limited time on the opportunities that you are most likely to win. The better your upfront qualification and ongoing validation, the more likely you will succeed.
My goals with this section were:
- Demonstrate credibility.
- Demonstrate how the concepts apply to both products and services.
- Help the team see some commonalities between the deals.
- Explain how a lack of attention to negotiations or the contract can ruin a great deal.
Next, I presented a comprehensive list of key topics, provided examples of each, and led an active Q&A session. The session was well received and resulted in increased deal size and sales volume over the next year.
The contracting part showed examples of how a simple missing or additional word (e.g., “Discounts calculated based on the Annual Cumulative purchase volume, where the word ‘annual’ was a mistake that reset the value that would have cost us over $5M in revenue over the life of that agreement) and similar mistakes. As an aside, I was negotiating a deal a year ago, and someone in our Operations team made a small mistake (adding a period to the annual increase language) for a multi-year deal that would have cost us over $40K on the first renewal alone. The point of this section was that you only assume the deal is complete once it is correct and complete.
Below are the Top 10 concepts from that training session that were common to all wins:
- Relationships Matter – People buy from people they like and trust. Moreover, they tend to like and trust people with integrity who have the customer’s best interest at heart. Create Customers for Life.
- Just because you can sell something to someone doesn’t mean you should – especially if it is not a good fit or won’t bring them value.
- Understand the Needs and Quantify the Impact – Use their terms, phrasing, and figures to increase the relevance of their use case and seek their validation.
- Understand Their Constraints – Document the assumptions to determine how real or rigid they are.
- What Happens if They Do Nothing? – Ask questions like, “Why Now?” and “What is the impact of waiting a year or more?” The answers will help qualify genuine business needs.
- Understand their Timeline and Milestones – Working back from the targeted end date can create urgency and avoid unnecessary delays.
- This is where Project Management can help you close the deal.
- Be Creative – The key is to get the prospect to focus on the outcomes (the “Fundamental Objectives”) rather than the approach (the “Means Objectives”). Focusing on “what they need” versus “how it is done” can be more challenging. Consider other aspects of their business that could be impacted and proactively raise any potential concerns and your ideas to address them.
- Remember, you are trying to solve their problems and not hide things that will become apparent later.
- Don’t Discount Someone’s Value or Impact Based Solely on Title – Many mediocre salespeople dismiss everyone except the Economic Buyer. A better approach is to ask various stakeholders about their roles in the purchase process and how they make decisions.
- Alienating people you will need to develop a long-term relationship with doesn’t make sense. That person may not be able to say ‘yes’ to the deal, but they easily create doubt and help kill momentum.
- Learn about the Alternatives and the Competition – How does our offering fare against the others? Why would they choose us over the competition?
- It pays to be brutally honest when you are doing this.
- Dream Big – You only know if you ask, and if it was too easy for the prospect to say ‘Yes,’ then you left money on the table.
- It doesn’t mean you must extract every penny from the deal. Instead, consider what else you could have included to make things easier for the customer, accelerate the project, increase the probability of success, etc.
- Create a Shared Vision of Success – Help people “see and feel” what success is like. That can be very compelling, especially if challengers come forward later in the process or some other issues arise.
- The worst thing you can do is sell something that does not solve their problem. You make your Economic Buyer and Champions look bad, which helps ensure you will not do more business there anytime soon.
While there are still several other components of the overall approach, these provide the foundation. Selling is not easy, but it is rewarding to help your customers prosper and grow, and financially beneficial to exceed your quota by selling large deals. Good Hunting!
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, then hold follow-up meetings to flesh them out 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 and reduces the seller’s chances of success.
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. Upfront preparation can be time-consuming, but the results are often bigger deals that close faster.
The process I use involves understanding the business, its customers, and its competition, as well as potential changes in the 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 a few potential problems and reach out to the highest-level individuals in the organization likely responsible for these issues. Often they will correct you and fill in the gaps. By doing this, you may uncover things that your prospect has not yet considered.
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, mutually beneficial solutions with 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. As a seller, focus on outcomes. Help them visualize what success looks like and how it feels. Overcome negative emotions like fear with positive emotions, envisioning a better future, and then a plan to achieve their desired outcome.
- 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, which comes from many areas and in various forms – direct and indirect. Help your prospect figure this out, and you are well on your way to winning their business.
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 investing those 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.
Success is a Mental Game
This assertion is as true in business as in sports, individually and in teams. So, let’s break it down.
When I watch my local football team, I occasionally see a shift in facial expressions from excitement to frustration – often right before the end of the first half. Sometimes, they recover during halftime and come out renewed and ready to win, but the “gloom and doom” expressions usually translate into suboptimal performance and mistakes. It is frustrating because you know they have the talent to win.
The same thing happens in business – especially in Sales. Sometimes it occurs in the middle of a sales cycle, similar to the example above. Unfortunately, too many people allow a few data points to determine their future trajectory. Why is that?
Whether you own a company or manage a group of people, good leaders aim to optimize their workforce by balancing factors that lead to happy, loyal employees doing their best for themselves, their customers, and their company. Many motivational theories exist, such as Expectancy Theory, Reinforcement Theory, the Role of Instrumentality, Intrinsic vs. Extrinsic Motivation, and more. Since one size rarely fits all, the challenge becomes reward-focused personalization, which can be a lot of work.
People will often win or lose before they even start. Their negativity, self-doubt, and anticipation of failure become a self-fulfilling prophecy. This post focuses on self-motivation, attitude, mindset, and creating the habits that lead to better success.
Below are four simple questions that someone should ask themselves when they question their ability to succeed in a position, company, or industry. There are always many ways to point the finger of blame elsewhere, but the first step should be to look in the mirror.
- Do you believe that you can win where you are today? If not, why are you still there? Customers and prospects can sense insincerity, so if you don’t believe in yourself, you shouldn’t expect them to believe in you. Maybe the company is terrible, and everyone is failing. If that is true, then it is probably time to look elsewhere.
- What have you learned from past successes and failures, and how have you adapted based on those lessons learned?
- What are some early indicators of success or failure that you have identified? Are you adapting to the situation if you run into those indicators now? The best approach may be to cut your losses on this attempt and move to the next sooner rather than later (i.e., qualify out quickly).
- What are you doing to improve your skills? It is funny how small, continuous improvement efforts lead to a greater sense of confidence. Greater confidence often translates to increased success.
I have found that consistently doing the right things is the best way to maximize my success. Start developing habits and routines that have led to winning in the past, but don’t expect them to work forever. Everything changes, and you should change, too. Look for what’s working for others, try it out, and if it works, incorporate it into your routines.
Success truly is a mental game, and everyone can win. The person who keeps winning over time is the one who doesn’t get stuck in time. Be curious, get excited, and adapt. And once you get there, start helping others. Having mentors is nice, but it is also great to become one.
As the saying goes, the rising tide lifts all boats. Winning can be a team sport, but it begins with individual contributors having winning attitudes. Unfortunately, the same is true of losing, so decide now what you want and move forward with energy and confidence.
Where Ideas, Experiences, and Lessons Learned Intersect 