As the second installment of this three article series, I look at common reasons that contributed to less-than-successful financial outcomes for the startups I joined.
As a recap, over the past 25 years, I have had the good fortune to be a part of demand generation teams across 20 technology companies. Recently, I created a summary data set containing each company and key characteristics like product-market fit, messaging focus, marketing-sales alignment, funnel instrumentation, PLG offerings and, most importantly, the financial outcomes achieved while I was there. What becomes evident are several common trends showing what worked, what didn’t, and what separated the companies that achieved strong results — IPOs or high-value acquisitions — from those that fell short.
Lets dig in.
Product–Market Fit Wasn’t Ready
This can take several different shapes. In the most obvious cases, customers tried our product and then decided not to buy it – it just did not create more value than time and cost of acquisition. In other cases, each sale is unique across buying persona and purchase process. It is hard to scale success when every sale is a one-off. While companies can limp along and linger – it is really hard to have a breakout success without a clear product-market fit.
Go-to-Market Process Wasn’t Repeatable or Scalable
I have been a part of companies where early wins came from hustle — founder energy, referrals, or one-off deals. But when the team tried to scale, there wasn’t yet a reliable playbook for targeting, qualification, and conversion. Marketing spend without process maturity leads to inefficiency, not growth.
“Scaling before repeatability just lights cash on fire.”
Better Mousetrap Versus Good-Enough
In some cases, the company had a product clearly better than the alternatives with certain features, product completeness or more. However, if those other products were simpler to deploy and manage (on-prem v SaaS) or good enough in meeting the underlying need (Beta v VHS), the early stage opportunities died on the vine. No amount of demand gen spending can meet an underwhelming response of the customer. The value prop used in the early stage of the sales process must be reinforced all the way through the sales process to achieve reliable and consistent growth.
Category and Value Proposition Weren’t Clear
When prospects can’t easily categorize your product, or, worse yet, don’t understand it easily, the buying journey becomes slow and expensive. This takes more time and effort to drive awareness, engagement and eventually create pipeline. In demand gen, we live under the brand value created by product marketing. If the messaging is not crisp and sharp, this dulls the returns of every program.
“If your category isn’t clear, your campaigns have to work twice as hard.”
The Takeaway:
Some of the most valuable lessons come from the companies that didn’t win big. They remind us that product capabilities, messaging clarity, and scalability are preconditions for marketing success.
“Demand generation is an amplifier. It strengthens what’s already working.”
In my next post, I’ll explore how much the game itself has changed — and why the old rules of demand generation may no longer apply.
Practical Strategies for B2B Technology Companies 