leadership
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 a systematic approach for ongoing customer success and satisfaction.
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 effort and costs associated with closing new customers can be high in many industries. Your install base business helps fund new growth.
- Churn negatively offsets growth (think net revenue retention, or NRR) and limits profits that fund growth.
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).
The lesson learned is that it is better to take a proactive approach to keep adding value for those accounts, rather than neglect them and spend a lot of time, money, and effort rebuilding trust and earning their business again.
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 started by organizing a day-long on-site meeting to understand their pain points and needs. We identified several 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, how best to approach them, and their disappointment with our company’s past efforts.
The result? First and foremost, we saved the account. 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 more essential to their success than they probably realize.
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.
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.
Perfection is the Enemy of Progress
The title is a quote from Winston Churchill. I have learned in my career that these behaviors can be very costly from a business perspective, especially when decisions affect large parts of a business. It took me years to learn this lesson as I transitioned from perfectionist to “reformed perfectionist,” which was challenging.
Below are a few examples that could help you better understand people like this, and if you are someone like this, it might even provide motivation to try to change.
Early in my career, as I expanded my role from Programmer to Analyst Programmer to Systems Analyst, I often found myself spending too much time and effort on things that had minimal impact. Applications and subsystems looked a little better, ran a little faster, integrated more easily, were easier to modify, and generally had fewer problems. Those are all good things, but in hindsight, those benefits often did not justify the associated costs.
Some industries and applications require a degree of quality and reliability, such as nuclear power plants and lifesaving medical equipment. Since very few things are perfect, there are usually a variety of built-in safeguards to mitigate the impact of errors and failure. I have worked on a few of those systems, and I get it. But they are not in the majority.
Identifying the intersection of meeting the stated requirements, delivering the required quality, and knowing what “good enough” looks like is essential. That’s where diminishing returns set in for every additional hour spent on an activity.
I worked with a hardcore perfectionist at a small software and services company. On a consulting engagement, he spent two days on a task that I viewed as a 2-4 hour effort. We discussed it, and he told me he had at least three more days to finish. We had a heated discussion, and he was frustrated with me for a while. Years later, he admitted I was right, talked about how difficult it was to change, and how much more productive he is now.
I had a consulting engagement with a small software company that spent 10+ years on a SaaS product and was always “just two to three weeks away” from their MVP (minimum viable product). I started working with them over three years ago, and they are still at that point today. Software is never perfect, so waiting for perfection can kill a company.
I have also sold to companies stuck in analysis paralysis because they (leaders and teams) are always second-guessing decisions and want to be 100% certain before making a decision. Those companies need to solve a problem, or they would not be seeking a solution. In most cases, making an informed decision on a proven solution now will solve their problems and deliver value quickly. There is an actual business cost for every month of delay.
Are these behaviors costing you or your company money? If yes, dig a little deeper to understand the potential positive impact making small changes could have. Daily improvement is a great thing!
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 startup and failure rates in their first few years. One of the best descriptions I have found is from Failory. Investopedia and LendingTree have similar but differing takes on the statistics and root causes. The net result is that failure is much more common than success, especially over time. So, “acting like a startup” is not necessarily good, even when true. Instead, you want to “act like a successful startup!“
Understanding the various causes and the data on success and failure should become significant inputs to business plans focused on long-term success. As a Founder, there are several 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. Find a way to test and refine those assumptions as necessary – before you go all in. Remember, Marketing and Lead Generation are very important but also expensive, so it pays to get this right the first time.
- 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 early and identify gaps that could become opportunities for your business.
- An agile mindset allows you to pivot your offerings or approach in order to refine your business model and hone in on that successful niche. Don’t fall into a sunk-cost fallacy.
- 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 (lead people, manage processes). 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.” To grow, you need to choose the best people you can afford, guide them, and trust them to perform in the best interest of your company. That is true in any size organization.
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, feel the pressure of the competition – they are out there – and 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.
Where Ideas, Experiences, and Lessons Learned Intersect 