B2B SaaS – Why Sales Teams Fail to Land Larger Deals


By Philip Lay, Senior Advisor, The Chasm Group LLC

“The formulation of the problem is often more essential than its solution, which may be merely a matter of mathematical or experimental skill.”

– Albert Einstein

“The problem is not the problem, the problem is the way we see the problem.”

– Saji Ijiyemi, Don’t Die Sitting

In my work with CEOs and their teams in B2B SaaS scaleups as well as mid-sized and larger companies I am constantly surprised by how many of their sales teams are closing small deals of $50k or so in ARR with enterprise-level organizations instead of developing much larger opportunities. One consequence of this apparent lack of ambition is a much slower growth rate for the company, and another is that it can take twice as long to build a profitable revenue engine. In fact, I believe this is partly why B2B SaaS companies tend to take a decade or more to build a profitable revenue stream.


Segmentation is ‘In’ Again!

Segmentation is in again

By Philip Lay, Senior Advisor, The Chasm Group LLC

Never let a good crisis go to waste.”

– Winston Churchill, while working to form the United Nations after WWII

There is only one winning strategy. It is to carefully define thetarget market and direct a superior offering to that target market.”

– Philip Kotler

During the depths of the global crisis, a five-year-old mobile banking software startup was struggling to gain a firm foothold in the market and was facing bankruptcy or at best a fire sale for a few million dollars. A few customers had signed up for pilot projects, generating just under $1m in annual revenues for the VC-funded company. The new CEO and their team were targeting 1400 or so banks in North America, but they still weren’t achieving liftoff. Just six months later they had discovered the formula for success, were off and running, and never looked back. How so?


If You’re Not Fixing Someone’s Leaky Pipe, What Are You in Business for?


By Philip Lay, Senior Advisor, The Chasm Group LLC

Tuning Your Strategy for Post-Covid Times

“You campaign in poetry. You govern in prose.”

– Mario Cuomo, former three-term governor of New York State, 1983-94

“If I had an hour to solve a problem, I’d spend 55 minutes thinking about the problem and 5 minutes thinking about solutions.”

– Albert Einstein

“Change does not roll in on the wheels of inevitability but comes through continuous struggle.”

– Martin Luther King, Jr.

My purpose here is to clarify why in today’s C19 downturn virtually every tech company needs to have a clear picture of how they fix critical breakages in one or more of their target customers’ business processes. In order to bring this concept to life it sometimes helps to use a metaphor such as the Leaky Pipe, which I’ll describe further down.

Why Now’s the Time to Get Customer Success Right


By Philip Lay, Senior Advisor, The Chasm Group LLC

Synopsis: Customer success is a broken promise in 95% of tech companies. CEOs, CROs and sales teams are generally preoccupied with chasing new logos, and scarce CSMs scramble to minimize churn and secure upsells. Frequently, they have no idea about their customer’s business objectives or success criteria. In a downturn like today’s Covid-19 crisis, the risks of cancelled contracts and lost relationships is heightened, just when winning new logos is harder to pull off. This is exactly the time when executives and their customer-facing staff must engage more fully with their major customers – and really help them achieve their desired business outcomes.

Zoom – The Latest Product to Become a Verb


By Philip Lay, Senior Advisor, The Chasm Group LLC

How can anyone fail to have noticed the sudden prominence of videoconferencing app Zoom since the outbreak of the Coronavirus crisis? Despite facing established competitors like Apple, Microsoft, and Facebook in consumer video-calling and Cisco and Google in videoconferencing at work, Zoom appears to have literally zoomed to the top of the charts in just the past couple of months.


The Scaleup Journey: Crossing the Chasm in Style

Case Study – The rapid rise of mobile banking startup Clairmail

Credit: Image designed by StudioDCL, 2020

Credit: Image designed by StudioDCL, 2020

By Philip Lay, Senior Advisor, The Chasm Group LLC


“Chasm crossing is not the end, but rather the beginning, of mainstream market development.”

“Entering the mainstream market is an act of burglary, of breaking and entering, of deception, often even of stealth.”

“To become a going concern, a persistent entity in the market, you need a market segment that will commit to you as its de facto standard for enabling a critical business process.”

“One of the most important lessons about crossing the chasm is that the task ultimately requires achieving an unusual degree of company unity during the crossing period.”

“You get installed by the pragmatists as the leader, and from then on, they conspire to help keep you there.”

– Geoffrey Moore, various quotes on the theme of crossing the chasm into the mainstream market


Sometimes the best company success stories only get to be told through informal anecdotes, press releases, Powerpoint slide decks, or video testimonials. In such situations, only those close to the company really benefit and the key learnings and best practices are never properly learned or leveraged by other entrepreneurs and management teams.

UK vs US Tech: Can the Tortoise Ever Catch the Hare?

By Philip Lay, Senior Advisor, The Chasm Group LLC

“To win a race, the swiftness of a dart
Availeth not without a timely start.
The hare and tortoise are my witnesses.
Said tortoise to the swiftest thing that is,
“I’ll bet that you’ll not reach, so soon as I
The tree on yonder hill we spy…
The race is by the tortoise won.
Cries she, “My senses do I lack?
What boots your boasted swiftness now?
You’re beat! and yet, you must allow,
I bore my house upon my back.”

The Hare & Tortoise, La Fontaine fable (1668)
translated by Elizur Wright, Wikisource

I must say that I’m not sure that La Fontaine’s fable of the hare and the tortoise provides a totally apt metaphor for the question I am posing here. However, I think there are definite similarities to the competition between US and UK tech companies. The fable tells the story of a tortoise that, when suitably provoked by a hare, challenges the much faster hare to a race; the cocky hare takes a nap during the race, while the slow and steady tortoise reaches the finish line first.

The Six Dimensions for Expanding Customer Engagement and TCV


By Philip Lay, Senior Advisor, The Chasm Group LLC

Picture the following customer success story. In parallel, note the various dimensions in which the relationship between vendor and customer expands.

Further down, I summarize the six possible dimensions in which you may be able to expand each of your major customer relationships and, accordingly, the annual contract value of each relationship.

This specific story is about adoption of e-signature services by a prominent global organization, adapted from the vendor’s customer success page on its web site. From earlier field research, I have seen how proactive this vendor has been in deploying customer success resources in service to their major corporate customers. If only most Saas vendors were half as proactive in this pursuit!