Why Big Company Enterprise Reps Fail At Startups

A Street Fighter’s Game

A raw startup, one that may have zero customers or just a few, is not a small HP or IBM. It is a fundamentally different entity with dynamics that are completely foreign to people who have thrived in high infrastructure environments.

It is now almost a truism that large company sales and marketing people fail at startups of any size.

There was a time 30 years ago when startup CEOs said “…find me someone from (name your legacy firm)  to sell for me.” That day has long passed and almost everyone who has run a startup has stories of failure from the large enterprise, legacy software reps.

The characteristics for sales success at a startup are very different from those at a high infrastructure company. A startup rep may need to write a white paper, will definitely need to run his or her own business dev program at the territory level to get others helping introduce the product.

The startup sales rep must deal with the technical aspects of the product as there is seldom a sales engineer around. In many firms, the CEO is a sales engineer, product manager, funding manager and evangelist. The rep too, may have many hats.

There is one characteristic beyond all others that brings success at the startup. That is competition—the thrill of taking on large, established competitors and repeatedly crushing them in end of quarter deals where they thought they had the order. Then learned otherwise.

The “streetfighter mentality” of great startup reps is critical. It is almost non-existent in the legacy enterprise software firms. The streetfighter is someone who does not follow a sales process (script); rather he or she runs every play so as to control the deal and to completely screw up the sales process for the legacy rep.

When I was on a short, painful stay at VMware where I was recruited to launch a dead territory in a strategic space foreign to VMware, I saw the legacy rep up close. If there was any takeaway, it is that if you break their sales process, make them play their cards out of order, they fall apart and you own the deal. These are process people, not thinkers.

They are there to collect sales orders from buyers who decorate their desks with SWAG.

The legacy process rep is seldom capable of getting into a company where nobody knows his or her firm’s name. The raw startup streetfighter has no trouble finding who the right buyer or influencer is, getting to them, making the quick pitch and qualifying in or out.

When a startup hires legacy reps, they often learn, painfully such reps will ask questions like: “where are the leads from marketing?” “don’t we have some videos I can send to the prospect?” “what trade shows are we sponsoring?”

People who live in process-centric, high infrastructure environments have defined themselves by that choice. If you can thrive in that bureaucratic, hierarchy-laden world, you are by definition not a streetfighter who will take a startup to the innovators and early adopters.

So select your state’s Motor Vehicle Department employees from these legacy enterprise software firms.

Let the streetfighters find your first customers from the innovators looking for you.