strategy
Getting Your Piece of the PIE
Whether you are selling, consulting, or managing, a foundational approach 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. I built this methodology out of necessity. I have ADHD, and structured approaches and methodologies keep me focused and allow me to excel during times of hyperfocus.
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 a broad, 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 across other businesses or 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. Usually, two or three people stood out. At least one wanted to prove they were better and smarter, and usually, one discussed strange approaches to solving problems. When you dug into those strange approaches, you often found something creative and brilliant coming from a different perspective on the problem. Curiosity and a desire to improve often drove their innovative approaches.
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.
Products create interest. Perspective creates confidence.
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 lets you cut through these limitations and spot opportunities for improvement that others miss.
Here’s where perspective plays a role in insight: the broader your view, the better you can 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 focusing on the “what” rather than 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 fertile ground for gaining diverse experience. 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. What happens after the deal closes ultimately determines a company’s success. Sustainable growth requires support systems.
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 risky.
- 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 need either an extensive, fully integrated organization that seamlessly transitions from sales to implementation (few companies can do 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 as assets (not 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, as they shared more 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 are 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, with the customer having insight into what is coming down the road and input into the direction of the 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 essential to 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 it is worth it in the long run.
- Need help building a high-performing hybrid sales team or turning around strategic accounts? Let’s connect!
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.
Diverse Testing for the Best User Experiences
Long before I began consulting, I was developing new applications for a Marketing company. Nearly everything was built from the ground up then, and there was very little reuse. That changed over time as I developed reusable functions and eventually created a “standard system” that significantly reduced development time due to reuse. Throughout this multi-year period, I had an unplanned but valuable assistant – “Wendy”
My user interfaces were generally well received for their layout, workflow, help screens, etc. But a new hire on the Customer Service team consistently ran into problems. I was young, and one of my first interactions with her probably went something like this: “Why would you do it that way? That doesn’t even make sense? Have you ever worked with computers before?”
She began crying. I felt like a jerk as my frustration began to wane. Days later, I realized Wendy was a gift and not a problem. She had an incredible knack for finding obscure flaws and breaking things. I embraced it, bought her lunch, and asked her to help improve my software. She was excited to help, and eventually we laughed about our initial encounters.
Wendy and I had become allies in a quest to create custom software that provided a better, problem-free user experience. Nothing was taken for granted. Everything became more robust. Surprisingly, everyone appreciated these changes, not just Wendy. She helped me become a better programmer and analyst, and I gave her an experience that helped her become one of the first Quality Assurance Analysts in the company. It was a win-win.
There is often a considerable difference in the expectations and ways that Gen Z, Millennial, Gen X, and Baby Boomer users interface with applications. Creating a one-size-fits-all application is far more challenging today because of this simple fact. But it is essential to success.
People today tend to move on when their experiences fail to match their expectations. Investing in your system’s “Wendy-proofing” can become a competitive advantage. I have long believed that “People buy easy.”
If one person encounters a problem, others will likely follow unless you implement a remedy. It is more work, but the result can be increased satisfaction, usage, and loyalty. That seems like a good tradeoff to me.
What are your thoughts?
Innovations “Iron Triangle”
The concept of an Iron Triangle is that each side of the triangle represents an item constrained by 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 didn’t have 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 within the company could have been far more effective, since training is usually a budgeted item that is much easier to justify.
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. This came from a discussion with an interesting person who has “been there, done that” many times.
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Where Ideas, Experiences, and Lessons Learned Intersect 