Selling an Addition, Not Another Point Solution

1. You spent nearly six years selling inside highly structured enterprise environments at Oracle and Salesforce before becoming the first sales hire at Guestway. What had to be unlearned from that world once there was no established playbook, no marketing engine and no brand recognition to lean on?

At Oracle and Salesforce I never walked into a meeting without two or three internal alignment calls first. Signed off deck, agreed messaging and a product that would look exactly the same three months later. At Guestway we sometimes ship a feature minutes before a call. What I had to unlearn is that all of that preparation was mostly giving me a feeling of control I did not actually need. The first months here felt chaotic to me. Eighteen months in, I would not want it any other way, because I can tell a prospect that the thing they asked for last week is already live and actually mean it.

The second thing was leaning on the brand. At Oracle the logo does part of the selling for you and marketing keeps the top of the funnel full. As the first sales hire at Guestway, nobody had heard of us and there was no pipeline sitting there waiting. You earn credibility call by call and you are writing the playbook while you are already running it.

What I enjoy most is wearing the different hats. In a corporate role you own ARR and that is it. Here I can be doing sales, partnerships, marketing and GTM strategy in the same day.

2. Guestway positions itself as the layer that sits on top of a property manager’s existing PMS rather than replacing it. For an audience that is often already fatigued by too many tools, what does selling something explicitly framed as an addition, rather than a replacement, actually require in the sales conversation?

It requires reframing the conversation from adding one tool to removing several. So discovery starts with mapping their actual stack, not with our features. Guest communication, upsells, task management, cleaning coordination, reviews: in most vacation rental companies all of that lives in three or four separate systems. 

We bring guest communication and operations together, so the honest positioning is that we sit on top of the PMS and replace a good number of those point solutions. Our view is that a property manager needs a strong PMS, a strong revenue management system and Guestway and then the stack is complete.

On the hotel side the framing changes entirely. Most hotel PMS platforms were built around the reservation rather than around the guest, so there is no unified inbox and no real messaging layer. We are not an addition to something that already exists, we are filling a gap the PMS was never designed to cover. That makes the conversation a lot simpler, because we are not competing for budget against a tool they already pay for. We are solving something they have been working around manually for years.

3. At Oracle, you drove over 100% year-on-year growth in ARR selling NetSuite, typically to companies making a considered decision to replace legacy ERP systems. How different is that sales motion from convincing a short-term rental operator, often lean and margin-conscious, to add a new platform to their stack?

Some things are obviously different. Shorter cycles, smaller buying committees and with a short term rental operator I am usually sitting across the founder instead of a procurement team.

The motion itself does not really change. Selling B2B SaaS is selling B2B SaaS, whether that is Oracle or Guestway today. Listen first, understand the tech stack, find the real pain and then position against your product as a solution to that pain.

A mistake I made during my first months at Guestway and quickly learned from myself, was trying to show everything we had on the very first call. Partly enthusiasm, partly still building confidence in the product. Everything is impressive, so why leave anything out. What I did not see at the time is that the prospect walks away remembering nothing specific and you have quietly made your own solution look complicated. Now a good discovery session tells me which two or three problems we solve best for that specific company and I build the demo around exactly those and leave the rest out.

4. You completed a full-time MBA at Vlerick in the middle of an already fast-moving enterprise sales career, right before joining Guestway at the ground floor. What from that year actually shows up in how you are building the sales function today, as opposed to what stayed purely academic?

What I loved about the MBA is that you go back into the books with real work experience behind you. You suddenly understand far better how marketing, sales and finance actually function inside an organisation, instead of only in theory. It gave me a lot more confidence in how a complete company fits together and in keeping the overview as a generalist which is exactly what you need in a startup.

An MBA is also a bit of a self-reflection year. It confirmed again that technology and sales are where I want to be active in and that has real value on its own.

Last but not least, the network. Being part of the Vlerick alumni community means I can easily reach out when I have a specific question and there is usually someone who has already dealt with it.