lessons learned
Lessons Learned from GTM Consulting
For the past two years, I have performed part-time, contract go-to-market consulting. My wife had a surgery that had gone wrong 18 months ago, so I needed something that would allow me to take care of her, stay sharp, earn money, and help companies grow.
Most of the work was with small to midsize companies, but the problems and needs mirrored what I have encountered at larger companies. The main difference is that large companies tend to look to software to address problems. In contrast, smaller companies lack the budget for what they view as an unproven solution that increases complexity.
Here are my Top 5 findings:
- GTM plans are often developed at the highest levels, often in isolation, without market testing and validation.
- Sales teams are pitted against one another, rather than working together to help everyone achieve more (i.e., “A rising tide lifts all boats.”)
- Sales teams are focused on selling features rather than solving business problems.
- CRMs are not consistently used and often reflect idealized fiction rather than reality.
- Sales management and teams are not leveraging AI to help focus their efforts.
Here are the related Lessons Learned:
- Identifying common business problems and describing how your product or service solves them should be the foundation of the plan. Perform market analysis. How do companies describe those problems? Their terminology, often found in job ads, can help create effective messaging that resonates. Work to become the natural fit for what your prospects are seeking.
- Individual contributors get paid to win, but sales management needs to create incentives for collaborative efforts that lead to wins.
- For one company, I convinced them to implement a 2% SPIV (like a SPIFF, but team-focused) for every team member who actively contributed to team improvement. SPIV payments were quarterly, and there was a running total so the team could see the fund growth. Initial indications of a positive impact are good.
- Another benefit of collaboration is that it helps teams focus on approaches that work due to ongoing testing and refinement. Collaboration also helps teams focus on a more accurate ICP (ideal customer profile). Sales management can then feed their findings back to Marketing to improve and tailor their efforts.
- Selling is a byproduct of problem-solving. You can’t solve problems if you don’t know what they are. Every interaction with a prospect should focus on gathering information, building trust and relationships, and leveraging prior interactions to demonstrate that your solution will solve their problem and ease their pain.
- CRMs often either lack information or are full of wishful thinking. They focus on activities, and not progress and next steps. Using MEDDIC/MEDPICC as a foundation for reporting is a much better start. Sales managers need to independently validate the information to ensure their teams are being upfront and honest. Trust, coaching, and collaboration work together for the win.
- AI is not a panacea, but it is very effective for research, market validation, prospecting, and meeting preparation. Going in prepared builds respect and credibility, saves time, and lets you quickly qualify prospects in or out. There may be a nurturing program for some of the prospects qualified out for immediate deals, but your time is valuable, and you will go hungry chasing deals you can’t close.
So, what are your thoughts? Have you seen some of these problems yourself? How did you handle them? Let me know in the comments below.
And if you are looking for a Consultant to help your business grow or someone who can add immediate value to your team, then contact me.
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. But what happens after the deal closes? Is that frenzied growth sustainable?
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 a risky approach.
- 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 either need an extensive and fully integrated organization that seamlessly transitions from the sale to implementation (not many companies are able to accomplish 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 like assets (instead of 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, with them providing more information 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 is 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, where the customer has insight into what is coming down the road and input into the direction of 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 an essential part of 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 is worth it in the long run.
- Need help building a high-performing hybrid sales team or turning around strategic accounts? Let’s connect!
Sales Discussions that Work
Selling is challenging work, and often, “we” (sales and marketing teams) make it even more challenging than it has to be. How many times have you seen a selling script, elevator pitch, or initial presentation that is long, boring, and undifferentiated? People have a short attention span, and nobody wants to interact with someone who does not listen to them or is pushy.
Your initial discussion is crucial to your success. Instead of going over a list of features, reading a slide deck, and telling why you and your product are so great, let’s try something else.
1. Understand why people buy. Any change has the potential to be difficult, risky, and painful. So, the pain they are facing has to be even greater, or they won’t bother changing. Your main job early on is to listen and try to understand their concerns. You may have a perfect solution, but if it doesn’t solve their pain, it holds little value to your prospect. This initial meeting is all about them.
2. At the start of the meeting, ask, “What would make this time well spent for you? What would you like to walk away from this meeting with?” Get them thinking about their problems and the value you may be able to provide, even if they don’t fully articulate them to you.
3. Ask questions and follow-up questions. People don’t lead with their significant issues, and someone unwilling to divulge anything likely isn’t a buyer. The more the prospect talks, the more you learn. So many sellers do not understand this simple concept. They want to dazzle you with features and demos – even if those things are not what the prospect needs.
4. Once you think that you have identified a pain, qualify and quantify it. For example, “You mentioned that your product release cycles are too long and complex. What is the business impact of that, and what would the impact be if you could reduce that time and effort by 50%?” Write that down, in their own words, because it could be vital later. If you manage to identify several pain points, review them and ask the prospect to identify the top three issues from the list, and ask why those three?
5. If you are giving a presentation, pull up the most relevant slide (customer problem/benefit slides work well here) and ask if this sounds similar to the problem they are facing. It can be a good starting point for getting the discussion moving in the right direction.
6. Don’t worry if you are not able to cover everything you intended, as long as the meeting is productive. I’ve also seen salespeople cut someone off and move on to a new slide rather than discussing something of substance. I was actually told once by a sales leader that five minutes of discussion is all that is required in an initial 30-minute meeting, because our goal is to pique their interest. That just doesn’t work.
7. Next steps. Keep in mind that your time is valuable, and qualifying out a prospect who is not a good fit is essential – it helps you avoid false hopes and lets you focus on people who might genuinely need your help. There are many ways the next meeting could go, but it’s best to ask the prospect. Would they like to expand the audience? Is there a specific issue they would like to address? Would they like a product demo or a technical discussion? Is something like a non-disclosure agreement (NDA) keeping them from opening up? Lack of engagement on their part is a huge clue. Be direct and ask the tough questions now to avoid wasting valuable time and effort later.
Here is a mini success story. In 2010, my team and I began selling the first commercial vector high-performance analytics database. There were several products already out that claimed to be 70x-100x faster than other products. Our pitch was supposed to be that we were 70 times faster than other products. That was self-limiting from the start and likely prevented people from contacting us.
After two months of minimal success (I closed a deal with a small hedge fund, which was the only sale in all regions), we started a weekly webinar called “Why Fast Matters.” The focus was on positive business outcomes rather than specific technology and features (“speeds and feeds”). We opened with some “What if?” statements, such as: What if you get answers from complex queries faster than your competitors? What if you could do that without the cost, complexity, delays, and limitations of a Star Schema or pre-aggregated data? What if you could do this on commodity x86 hardware? We would then briefly cover the breakthrough technology (which was a precursor to Snowflake) and offer a free half-day meeting with a consultant.
Within the first two weeks, we met with a company that was later acquired by PayPal shortly before eBay acquired PayPal. This company was about to spend $500K on a proprietary hardware expansion that would have only provided additional capacity for the following year. Their customers bought advertising based on queries against the last six months of their data. I asked the question, “What if they could query against five years of data and get answers faster than they do today? Do you think that would help them buy more advertising? Do your customers ever ask for this?” The response was that their customers frequently ask for 12 months of data and would be willing to pay more for these capabilities. Still, they did not have a way to do this cost-effectively.
I closed a $250K ARR subscription deal in two weeks, and they purchased $140K of commodity Dell hardware for our software to run on. They saved 20% over their planned purchase, and more importantly, they rolled out advanced querying capabilities (against six years of data) in less than a month. There was incredible value to them and their customers, and it generated more business for them. We would not have identified this need if we had primarily focused on features and technology.
As an aside, I was initially chastised for going off message, but after the Australian team adopted our approach and began closing deals, it became the new corporate standard. If something isn’t working, focus on finding ways to improve it. Even incremental change can be meaningful.
In the words of Tony Robbins, “If you do what you’ve always done, you’ll get what you’ve always gotten.”
Lessons Learned from Selling Kubernetes
Cloud-native, containerization, microservices, and Kubernetes have become very popular over the past few years. They are as complex as they are powerful, and for a large, complex organization, these technologies can be a game changer. Kubernetes itself is a partial solution – the foundation for something extraordinary. It can take 20-25 additional products to handle all aspects of the computing environment (e.g., ingress, services mesh, storage, networking, security, observability, continuous delivery, policy management, and more).
Consider the case of a major Financial Services company, one of my clients. They operated with 200 Development teams, each comprising 5-10 members, who were frequently tasked with deploying new applications and application changes. Prior to embracing Kubernetes, their approach involved deploying massive monolithic applications, with changes occurring only 2-3 times per year. However, with the introduction of Kubernetes, they were able to transition to a daily deployment model, maintaining control and swiftly rolling back changes if necessary. This shift in their operations not only allowed them to innovate at a faster pace but also enabled them to respond to opportunities and address needs more promptly.
Most platforms utilize Ansible and Terraform for creating playbooks, configuration management, and other purposes. Those configurations could become very long and complex over time and were prone to errors. For more complicated configurations, such as multi-cloud and hybrid environments, the complexity is further amplified. “Configuration Drift,” or runtime configurations that differ from what was expected for various reasons, leads to problems such as increased costs due to resource misconfiguration, potential security issues resulting from incorrectly applied or missing policies, and issues with identity management.
The surprising thing was that when prospects identified those problems, they would look to new platforms that used the same tools to solve them. Sometimes, things would temporarily improve (after much time and expense for a migration), but then fall back into disarray as the underlying process issues still needed to be addressed.
Our platform used a new technology called Cluster API (or CAPI). It provided a central (declarative) configuration repository, making it quick and easy to create new clusters. More importantly, it would perform regular configuration checks and automatically reconcile incorrect or missing policies. It was an immutable and self-healing Kubernetes infrastructure. It simplified overall cluster management and standardized infrastructure implementation.
All great stuff – who would not want that? This technology was new but proven, but it was different, which scared some people. These were a couple of recurring themes:
- The Platform and DevOps teams had a backlog of work due to existing problems, so there was more fear about falling further behind than confidence in a better alternative.
- Teams focused on their existing investment in a platform or on the sunk costs spent over a long period, attempting to solve their problems. The ROI on a new platform was often only 3-4 months, but that was challenging to believe, given their own experiences on an inferior platform.
- Teams would look at outsourcing the problem to a managed service provider. They could not explain how the problems would be specifically resolved, but did not seem concerned about that lack of clarity.
- There was a lack of consistency on the versions of Kubernetes used, the add-ons and their versions, and one-off changes that were never intended to become permanent. Reconciling those issues or migrating to new, clean clusters both involved time and effort. That became an excuse to maintain the status quo.
- Unplanned outages were common and usually expensive. Using the cost of those outages as justification for something new was typically a last resort, as people did not like acknowledging problems that put a spotlight on themselves.
- Architects had a curiosity about new and different things, but often lacked the gravitas within business leadership to effect change. They were usually unwilling or unable to explain how real changes happen within their company, or introduce you to the actual decision-makers and budget holders.
Focusing on outcomes and working with the Executives most affected by them tended to be the best path forward. Those companies and teams were rewarded with a platform that simplified fleet management, improved observability, and helped them avoid the risky, expensive problems that had plagued them in the past. And, working with satisfied customers who appreciated your efforts and became loyal partners made selling this platform that much more rewarding.
“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.
Where Ideas, Experiences, and Lessons Learned Intersect 