Years ago when dating apps were still a part of my life, I remember feeling puzzled by how women using those apps behaved: evasion, messaging marathons to delay an innocuous coffee date, signs of distrust both obvious and subtle.
It was some time before I understood just how badly women were being treated by men on those apps. They all had boggling litanies of dudes behaving badly: lies, aggression, NSFW stuff. I remember the feeling of shock and clarity when I finally got it -- suddenly their behavior made sense. For women, admitting they were straight and available on a dating app was an invitation to several kinds of abuse. And at the same time, a lot of sincere, young men on the same dating platforms had no idea and behaved totally cluelessly, because they themselves were not the targets of abuse. All the arrows were aimed away from them, so they were puzzled when others dodged and ducked.
And here’s the point of this post: Selling software is like that.
Most startups don’t know the tactics that their prospects are subjected to by other vendors: the hard-sell, the inflated claims, the infuriating lock-in, the bait and switch, the features promised and postponed.
They may hear a note of cynicism in a lead's voice when they discuss the supposed value propositions and pitches of other tech vendors.
They may notice an unwillingness to learn new tools, to grant vendors access to sensitive data, or to become reliant in any way on a fly-by-night operation fueled by VC funds.
They may see potential customers roll their eyes when asked yet another barrage of questions about their workflow and buying process. (If you ever wondered why the government works through prime contractors, and why much of enterprise relies on large consultancies and systems integrators to vet new tech, it’s because they need a buffer and really like talking to people who know their needs already.)
New founders will face skepticism, because much vaporware has come before. All those buyers whose names may seem fresh to you have had the consequences of bad software decisions engraved in their memories. Making a mistake could cost them job or reputation.
Against that backdrop, founders have to do everything they can to derisk adoption. They have to find ways to show that their product works before the customer goes through a lengthy onboarding process. Testimonials are fine ... but insufficient by themselves. You need free trials, ease of use, transparent pricing, and spotless behavior during every interaction.
This is very specific positioning work. It's not just about what your product does -- it's about why they should believe you when you make any claim at all. There is a ghost haunting your conversations, the ghost of vendors past. So trust is the fundamental positioning, table stakes. Without it, your differentiation, capabilities and price don't matter much. You are not just proving to prospects that you are something positive; you are proving that you are not something negative, with which they have had vivid, recent experiences. You are proving with each interaction that you, your company and your product overdeliver, that you're secure, fairly priced, responsive to customer needs, and fundamentally able to do what you promised.
Lots of buyers travel deep into an onboarding funnel, after receiving approvals, setting up integrations, getting teams trained, etc, only to discover that several components are missing; that the car works best going 15 mph, not 60. It's like marrying someone only to discover that they have a secret and corrosive addiction.
And since no one can really validate what will happen in the far future, after they have fully committed, they make you do a song and dance now, an elaborate dating ritual between buyer and seller that is designed to preserve their jobs by requiring expensive signals upfront from you.
And the steps required for this song and dance you are things the customer will not teach you. You need to pick it up somehow yourself: the professionalism, the customer-focus, the responsiveness.
Intuiting what is needed and then doing it well is the real sign that they should commit. If they have to explain it to you, then buying your software is just signing up for a life of explaining everything to you forever, even after you’ve moved on to the next sale and are no longer listening.
You’ll only understand your customers if you understand how other sellers treat them, and you shouldn’t be surprised if those sellers are very different from you!