Around the summer of 2021, the winds of change in our company brought a new leadership team about. Their new approach steered towards a product-led motion, a radical move for a company like ours. And as one would expect, new sales executives were hired, and the revenue organisation redesigned.
Change was the norm for us Sales Engineers: I had personally worked with at least five different Account Executives in Europe, and with nearly as many in the US. And new approaches? Bring them on.
Something was not square though. New people were not the issue, no. Everyone can learn, given enough time. The pickle was that our product was traditionally sold to heavily personalised process-oriented customers. No two implementations of our product were the same.
To me, it was an interesting challenge to combine apparently irreconcilable worlds - especially as new, point-solution products were being issued. This conundrum did not apply for most of the newly onboarded Account Executives though. They dove into the sales hunt with the due methods and assumptions. This was especially the case for Bernie.
Bernie was by the book. Punctual, polite, pleasant, methodical. All the right questions in the right places, all the boxes ticked from one meeting to the next. He’d fit perfectly in this new framework - so well in fact, that he was soon promoted to be a Regional Director.
When an immense and specialised corporation like Bounce Inc. crossed our path, there were none of the indicators that qualify a prospective opportunity. No clear business problem - rather, a clot of intertwined grievances. No official Economic Buyer - just, maybe, someone who could have sponsored an initiative. No consequences for inaction: our interlocutor was very secretive, as you’d expect from someone in such a market.
But who would have passed on Bounce Inc.? As they agreed to meet further, we initiated a long dance of details, clues, big pictures and innuendos. The initial request was as elusive as they come, something to the sound of “we need a solution to manage our portfolios”. Whilst Bernie chipped away at our contact, obtaining names and new meetings, I carefully dug into the real problem.
That entailed, and I remember this reluctantly, some high-level demonstrations. Our contact insisted to have multiple meetings to get to know our product, because “they didn’t know what they didn’t know”. Seeing more and exploring new cases was used as an attempt to jog memories, shake some thoughts out. More than anything, they wanted to try. Try the software, our product, their cases.
Their cases: a mass of initiatives with different names, across departments not even talking to each other, often different in nature and yet all interconnected in that organisational maze that is the creation of new products in highly complex environments.
As we moved through these cryptic meetings, I was able to place questions and bring home new, yet small, information on which I’d build upon for our next meeting. A demonstration for the prospect, a qualification meeting for us: slowly but surely, I was getting a picture together. I could steer towards the marvels of roadmapping and interconnected domains, but the customer needed some priming: our product needed a lot of work to be understood in their world.
At one point, the magic words were uttered: “My boss wants a roadmapping tool for yesterday”.
Earlier that summer, my manager gathered our group in his house in Texas. We were to make sense of a couple of new stories that our Product team put together. One of them was, in our opinion, in bad need of improvement. Nonetheless, it withheld an intrinsic value story: if something happens in the market, or in my organisation, how shall I react to it? How can I put together all the pieces of the incoming and ongoing initiatives? What will strategically fit in our future operations, what shall we realise?
That’s when I pulled together my first storyboard for Bounce, one that would become a standard message later on. Leveraging cues, using some of their own end-goals, and yet keeping it all at a generic level, I created an interactive demo.
That was the penny drop. It was played tens of times internally, our contact became our champion and opened up to more details. They still wanted a trial, this time on understood common grounds. And led the way to more collaboration and partnership.
And so there it was. From riddles and piecemeal information, from the request of solutions to the discussion of business problems and process possibilities. From opposed parties to partners working the solution together. Not just the buy/sale interaction, but a deeper business collaboration.
Bernie did hold the reins of the deal to make it a pilot, coordinating and pushing people and getting paperwork done. Maybe a tad hastily, just before following our previous CEO in a new adventure. One year later, our prospect, now a customer, kept repeating: that interactive demo is the reason we’re still talking today.
© 2025 marcocristini. Inspired by real events. All names and characterisations are fictionalised.