Enterprise Software Vendors, before crossing the chasm, you must jump a high bar

Updated: Nov 5, 2021

Everyone knows “Crossing the chasm” by Geoffrey Moore. But before reaching the long-awaited inflexion of their business, enterprise software companies specifically, must overcome a number of major obstacles, which make the race to the Grail more like a steeple chase than a pole vault.


The need for sales intensive engagement to prospect

Hurdles on that race are well-known. Stanford Business School lecturer, Mark Leslie, clearly points out that complex B2B sales always requires a radically sales-intensive engagement to prospects, compared to a marketing one. Considering the complexity of those sales, the bar is too high and investing only in marketing lead gen programs is essentially ineffective. How many millions of $ however, have been wasted in those programs, to eventually realize the return on investment was virtually null? How many newly appointed COO or CMO tables away what was done by his/her predecessor to go for mainstream recipes? For sure, you’ll always have talented marketing consultants who’ll show you tons of metrics to tell you it works. And that’s where you must ask your peers rather than those external experts. Or alternatively, candidly look into the mirror of your own lead gen programs outcomes…


Similarly, investing in armies of BDR – that is, inexperienced junior sales rep apprentices – to try and sell enterprise software proves very expensive and equally inefficient, as targeted personas are simply unreachable for their green skills. BDRs are supposedly the ultimate weapon to support a volume, lead-gen, approach. But have you ever met a BDR able to explain a complex product or value proposition to a C-Level? C-Levels in general are reluctant to salesy approaches, to rehearsed pitches, to non-consultative discussions.


Yet, following the herd has been a very powerful motive since the dawn of time, and too many enterprise software vendors want to try the dual experience of lead-gen + BDR programs. Simply, applying a successful B2C model or B2B model for commoditized products to B2B enterprise software is a recipe that never works. The lack of track record and hard-earned experience, and why not saying it, some pinch of hubris, of early-to-late-stage Enterprise Software scale-ups’ CEOs, together with the pressure of sometimes ill-advised VC funds to apply supposedly market-wide accepted methods to go faster, perpetuate the flawed model, and unfortunately place Moore’s inflexion point, much farther than it should be.


B2C ain’t B2B that ain’t enterprise

Here are other factors. First of all, it is fairly certain that if you haven’t sold enterprise software before, you cannot actually fathom the specificities of its marketing and sales. Third-party experts in volume-oriented lead gen marketing program are simply inappropriate for this type of products. Prefer Marketers that favor content marketing, that understand the technology and that master a value proposition that contains technology-based differentiators, benefits and clear positioning.


Sales and marketing skills transfer from IT services to Enterprise Software or B2C product to Enterprise Software, as good as they can be, are confronted to a DNA problem. Prefer enterprise software experts and product marketers that have grown up in that world rather than even successful B2C defectors. You’ll avoid painful misalignment that are not only onerous, but also fairly embarrassing.


To conclude, selling enterprise software requires experienced skills both in Marketing and in Sales, as the bar is higher than for other simpler, more commoditized products. When you’re a growing enterprise software company, a scale-up, you need to be careful not to put the cart before the horse. Investing your funds in large lead-gen programs, hiring lots of BDRs to support them, may it be under pressure of powerful stakeholders, is not the best idea. Adopt a more targeted approach to reach out to the right persona only, invest in less sales resources, but more senior ones who’ve been successful in selling complex technology before, foster content and product marketing, and of course invest in customer care and support, so that your first visible references become your best marketing.


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