Attentive: What I’ve learned

In a time when many startups are hard at work designing and implementing a response to the current crisis, for better or worse, Attentive’s fate was already being decided – over the last few months, we explored the possibility of raising a follow-on round, and also explored the option of acquisition by a larger company. 

This was not an easy journey, and I wanted to give you my personal assessment of what we’ve done right, and what we could have done better.

In the several years I was leading Attentive, one of the most common questions I got asked by investors was “What is your end goal? IPO? Being acquired?”

My answer was, since day one: “I believe we have a vision ambitious enough to support an independent, high-growth company for the foreseeable future. Nonetheless, I have a fiduciary duty to analyse any opportunity that crosses our path.”

As this was my personal objective, and I wasn’t able to achieve it, no outcome could possibly be labeled as a success.

Was the vision wrong?

I’ve asked this question many times over the last few weeks, and I still end up with the same answer, no matter how I look at it. No, the vision wasn’t wrong. The vision isn’t wrong. It might have been the wrong timing or executed poorly, but I still believe in what Attentive was trying to accomplish at its core.

1: Product (2015-2017)

Since 2015, the concept of the product has changed a lot. Our vision of the world didn’t change much, but the product did. This is normal in the startup world, but we lost way too much time, especially in the early years, building the wrong things without much validation. When we added Yannick (you should follow his fantastic personal blog) and Cristina to our board, we moved from experimentation to execution. The main focus moved to sales.

2: Sales (Early 2018)

As soon as we landed on a Product concept that we thought had some depth (Attentive for CRMs), we went heads down. I think this was our best phase in terms of execution: We landed big pilots, like Hubspot, were having C-level conversations with strong companies and we closed our $1.2M round with Indico and Mangrove.

3: Market Fit (End of 2018 – Early 2019)

With those early signs, we started structuring our sales process, and on that function we’ve made several small mistakes that tallied up to being farther from our market space. We started seeing these signs with a very slow sales process, difficulty in holding customers, attrition on product development, among many other things. After several weeks of struggling to hire experienced sales team members in Braga, I remember having the following thought: “If we can’t hire experienced sales people, we need to train them. In the few weeks we already lost searching for one, we could’ve taught someone!”. So we hired people with very little sales experience. They were all great people with a lot of potential, but we didn’t have time to properly coach them to be successful in their role, nor did we have the right expertise to do so.

Today, I feel that if we’ve done this very early in the process, the product would have time to keep improving based on customer feedback (as experienced sales people know how to talk to prospects). We ended up doing this in mid to late 2019, but it was too late. The product mindset took too long to get off the ground.

4: Financing (End of 2019)

At the end of last year, with the $1.2M round almost dried up, the team rallied around one last possibility, looking for any shimmer of hope that would allow us to extend our runway even if it was by a couple of months. Product-wise, this was probably our fastest period (We’ve redesigned our product just for Salesforce in record time), but even with this push we weren’t able to get additional funding. We started looking for an M&A alternative that would be good for everyone, and quickly some companies started to show an interest.

We explored these possibilities, and even though the pandemic killed several of those M&A conversations, we were able to find a solution that allowed us to end the Attentive chapter in a way that made us proud as founders.


Every person that joined the team had an initial conversation with me, as part of the interview process, where I lay down the vision for the company. I’ve been told by several team members that having this ambition was one of the key factors that made them join Attentive. At this stage, to keep Attentive running, we had to slash this ambition in half, slow down considerably, and try to re-adjust our priorities given that we didn’t have the financing that we wanted, certainly not in the terms we wanted.

For me, startups should be a “all or nothing” type of outcome. Yes, you can pivot to a services company that is lucrative and works on interesting stuff, but it’s not a startup. That was not what we signed up for.

So we decided, as a Board, that this was the end of the Attentive’s journey.

I’m feeling lucky.

We had great investors. I mean, top tier in Portugal, top tier in Europe, top tier in the US. They always had our back, took my calls and contributed to our execution very frequently, while at the same time leaving the decisions to the founders and supporting us, even when they did not agree with us. Any founder would be lucky to have them, and I’ll continue to recommend them as highly as I can.

I had amazing founders. During all our ups and downs, many startups talk about friction between founders, as they end up having different concepts of the company they want to build, or have different commitment levels. We did have our disagreements, but boy did we commit.

While we’re all still processing what happened, I can’t help but feel that I’ve grown a ton as a professional and as a person, and I have countless people to thank for that.

You’ve made this journey worth a shot.

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