We lost a big deal... And I'm glad we did!

A few weeks ago, I wrote about how we lost a big deal and how it somehow turned out to be a good thing for us.

It resonated quite well with a lot of people, and it made me think about what we were missing out on vs. what we gained (or kept).

Some of the comments on the original LinkedIn post were really brilliant and spot on: 

Classic dilemma; sticking with your ICP or following the money😅

Great reflections. It's difficult not to get caught up in the moment - "what if we land this deal!" - but then you risk having to plan your roadmap based on requests from one single customer.

Loosing a potential big deal sucks! And as a startup that money looks very attractive. But it sucks more to win a big deal that is not a good fit. It pulls all energy out of your organization when you are trying to make something work that does not fit. Go for it! There are many ICP customers out there that will love your product.

... and many more like them.

I want to take a step back and look at the scenario and its pros and cons, 'cause I've really been thinking a lot about this...

 I was approached by a potential new customer who has >100 human agents (and growing fast!) that'll also need our AI agents on top. So we're looking at approx. €70.000 ARR.

We were one of 3-4 tools that were left in the race to win their business, so they sent over the list of requirements.

We could solve ~75% now, ~15% was on its way, and the remaining ~10% could be solved with our APIs and custom integrations.

The PROs:

• We would get an instant 35% MRR uptake that covers the sales budget for the next 3 months
• A new big customer that potentially opens doors to others like them
• A huge branding/storytelling opportunity to position ourselves firmly as a preferred solution in the startup/scaleup space
• A great opportunity to learn a lot in a great collaboration with a much bigger customer than we've worked with before
• I see 100 other ways this could lift our business "to the next level"

The CONs:

• With one customer accounting for ~35% of our revenue, it could be a potentially devastating blow if they churn (for whatever reason)
• Because of that, and because they'd probably know it, they'd have the power to more or less for force specific features or updates into our roadmap
• Having one big customer add things to our roadmap risks derailing our product and core offering for our primary ICP - small and mid-sized businesses - will we lose all the goodwill, etc., we've already built because of that?

We'd get a lot of money and opportunity, but at the same time, introduce a lot of new stress and risk in the business.

I don't know if it would have turned out great if we'd landed the deal. I am insanely proud that they saw us as a potential fit and we got the opportunity to pitch in. That's a massive stamp of approval! But in reflection, I'm happy we didn't land it.

I also don't want to be the judge of what's right or wrong for others or in general. For some businesses, it would have been a transformative opportunity to go "to the next level" with everything it entails.

 I just don't think it's the right thing for us.

We get to keep some of the things that are really important to us: 

• Stay focused on building a best-in-class product for our core ICP: small- to medium-sized businesses with 3-10 people doing customer support.
• Remain "fast on our feet", agile and flexible, set our own roadmap and build what we believe is right, without huge risks from one single customer.
• Do what we love at a pace we can enjoy (this one is quite important, too!)

And I can see that it's working. 

We're really on to something great.

We're adding new customers every week.

They get onboarded, start to use our product and are happy with it (churn is very low).

And they refer other new customers our way (we still see about 35% of all new signups being referred by other customers).

Isn't that "product-market-fit"?

This month (November, 2025) will be the first cash-flow positive month since our launch from absolutely zero, a bit over two years ago.

And when you have a bootstrapped and cashflow-positive business, the world is at your feet!

You're free to do what you love, with people you like, while having fun - and making some money along the way.

Right or wrong decision? No idea - time will tell.

But it feels right for us, and we're planning some big stuff for 2026 on the back of all of this.

And ultimately, that's why I started Herodesk...

So yeah, I'm pretty happy we didn't end up pivoting the business for the sake of a big short-term money game, but instead get to stay on track and focus on what's important for us!