strategy
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 different news sources, looking for information about 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, as well as seize 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 make you want to achieve even more.
Artificial Intelligence (AI) will be able to do all this and more. It will be more consistent, analyze information without bias, and do so on a more timely basis.
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 the need for 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 but also about collaborating internally to create the best possible products and services to sell 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 that everyone has the best insights to perform their roles effectively and promoting a more cohesive and 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 demands, and market dynamics, providing businesses with more opportunities to make better-informed decisions—better resource allocation, optimized sales strategies, and, ultimately, higher revenue will be the result.
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.
Future Perspectives
While it’s true that 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 but about augmenting human capabilities to create more effective, efficient, and thriving organizations that are better able to 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 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.
“Acting Like a Startup”
Over the years, I have heard comments like, “We operate like a startup,” “We act like a startup,” and “We are an overnight success that was 10 years in the making.” These statements are often euphemisms for “We are small and not growing as quickly as we would like.”
There are numerous estimates of startups in their first few years. One of the best descriptions I have found is from Failory, but Investopedia and LendingTree have similar but differing take on the statistics and root causes. All three articles linked to are worth reading. The net result is that the outcome of failure is much greater than success, especially over time. So, “acting like a startup” is not necessarily good, even when true. You want to act like a successful startup!
Understanding the data and various causes for success and failure are great inputs to business plans. I have been a principal with successful startups, both early employees and founders. Understanding the data and various causes for success and failure are significant inputs to business plans focused on long-term success. As a Founder, there are a few points that I believe to be key to success:

- You have specific expertise that is in demand and would be valuable to an identifiable number of prospective customers. How would those customers use those skills, and how would they quantify the value? That understanding provides focus on what to sell and to whom.
- A detailed understanding of the market and key players is needed to hone in on a niche to succeed.
- Understand your strengths and weaknesses, then hire the most intelligent and ambitious people who complement your weaknesses and strengths.
- Understand how to reach those potential customers and the messaging you believe will compel them. Then, find a way to test and refine those assumptions as necessary. Marketing and Lead Generation are very important.
- Have a plan for delivering on whatever you sell before you get your first sale. A startup needs to develop its track record of success, beginning with its first sale.
- Cash flow is king. It is far too easy to run out of money while looking at an excellent balance sheet because of receivables. Understand what matters and why.
- Founders need to understand the administrative side of a business – especially the financial, legal (especially contract law), insurance, and taxes. Find experts to validate your approach and fill in knowledge gaps.
- Consistency leads to repeatable success. You standardize, optimize, and automate everything possible. Wasted time and effort become wasted opportunities.
- Finally, there needs to be sufficient cash on hand to fund the time it takes to find and close your first deals, deliver and invoice the work, and then receive your first payments. That could easily be a 3-6 month period.
Those are the foundational items that are reasonably tangible. What is not as concrete but equally as important are:
- Having or developing the ability to spot trends and identify gaps that could become opportunities for your business.
- An agile mindset allows you to pivot your offerings or approach to refine your business model and hone in on that successful niche for your business.
- Foster a sense of innovation within your business. Always look for opportunities to deliver a better product or service, improve the efficiency and effectiveness of your business, and create intellectual property (IP) that adds long-term value.
- Focus on being the best and building a brand that helps differentiate you from your competition.
- Become a Leader, Not a Manager. Create your vision of success, set expectations for each person and team, and help eliminate roadblocks to their success. Trust your team to help you grow and replace members quickly if it becomes clear they are not a good fit.
Steve Jobs once said, “It doesn’t make sense to hire smart people and then tell them what to do; we hire smart people so they can tell us what to do.”
Winning is hard, so focus on the journey. Making your customers’ lives easier and allowing your employees to be creative while doing something they are proud of will lead you to your destination. But when things start going well, don’t sit back and convince yourself you are successful. Instead, continue to focus on ways to improve and grow.
Success means different things to different people, but longevity, growth, profitability, and some form of contributing to the greater good should be dimensions of success for any vision.
Innovations “Iron Triangle”
The concept of an Iron Triangle is that along each side of the triangle is one item constrained by the items from the other two sides. In Project Management, this is often referred to as a triple constraint. This identifies the fundamental relationships (such as Time, Cost, and Scope in Project Management) without addressing related aspects such as Risk and Quality. It provides a simple understanding of both requirements and tradeoffs.
Yesterday I spoke with Dave Mosby, an impressive person with an equally impressive background. He related Innovation to Fire, noting that in order to create fire, you need fuel, oxygen, and heat. He added that they must be in the right combination to achieve the desired flame. What a brilliant analogy.
Dave stated that for Corporate Innovation to succeed, you need the proper balance of Innovation, Capital, and Entrepreneurship. I found this enlightening because his description substituted “entrepreneurship” for “culture” in my mental model. While the difference is subtle, I found it to be important.
As noted above, simplified frameworks do not provide a complete understanding. But they help understand and plan around the foundational items required for success. Mapping this to past experiences, I gained a better understanding of things that did not move forward as desired and what I could have done differently to be more effective.
One idea was to create a fault-tolerant database using Red Hat’s JBoss middleware. We had a Services partner willing to create a working prototype, tune it for performance, document the system requirements and configuration, and package it for easy deployment. They wanted $10K to cover their costs.
I did not hold a budget at the time, so I created a purchase request supported by a logical justification. It modeled potential revenue increases for database subscriptions based on the need for a failover installation and growth from potential expanded use cases. This was a slam dunk!
In my mind, this was simple as it was “only $10K,” and I had funded many similar efforts when I had my own company. But that’s the rub. I viewed these efforts as investments in understanding, lessons learned, and growth. Not every investment had a direct payoff, but nearly each had an indirect payoff for my company. It was an entrepreneurial mindset that accepted risk as something required for rewards and success. I now see, many years later, how reframing my proposal as a way to foster innovation and entrepreneurship could have been far more effective.
It is never too late to gain new insights and lessons learned. A slightly different perspective on an important topic provided the understanding that should help position projects for future success. And this flowed from a discussion with an interesting person who has “been there, done that” many times.
Using Themes for Enhanced Problem Solving
Thematic Analysis is a powerful qualitative approach used by many consultants. It involves identifying patterns and themes to better understand how and why something happened, which provides the context for other quantitative analyses. It can also be utilized when developing strategies and tactics due to its “cause and effect” nature.
Typical analysis tends to be event-based. Something happened that was unexpected. Some type of triggering or compelling event is sought to either stop something from happening or to make something happen. With enough of the right data, you may be able to identify patterns, which can help predict what will happen next based on past events. This data-based understanding may be simplistic or incomplete, but often it is sufficient.

But people are creatures of habit. If you can identify and understand those habits and place them within the context of a specific environment that includes interactions with others, you may be able to identify patterns within the patterns. Those themes can be much better indicators of what may or may not happen than the data itself. They become better predictors of things to come and can help identify more effective strategies and tactics to achieve your goals.
This approach requires that a person view an event (desired or historical) from various perspectives to help understand:
- Things that are accidental but predictable because of human nature.
- Things that are predictable based on other events and interactions.
- Things that are the logical consequence of a series of events and outcomes.
Aside from the practical implications of this approach, I find it fascinating relative to AI and Predictive Analysis.
For example, you can monitor data and activities proactively by understanding the recurring themes and triggers. That is actionable intelligence that can be automated and incorporated into a larger system. Machine Learning and Deep Learning can analyze tremendous volumes of data from various sources in real-time.
Combine that with Semantic Analysis, which is challenging due to the complexity of taxonomies and ontologies. Now, that system more accurately understands what is happening to make accurate predictions. Add in spatial and temporal data such as IoT, metadata from photographs, etc., and you should be able to view something as though you were very high up – providing the ability to “see” what is on the path ahead. It is obviously not that simple, but it is exciting.
From a practical perspective, keeping these thoughts in mind will help you see details others have missed. That makes for better analysis, better strategies, and better execution.
Who wouldn’t want that?
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