This quarter began with a bet on sales and ended with a breakthrough in product. Things didn’t go as I’d hoped, but the vision is much clearer now.

I liked the idea of a year review to help me consolidate personal experiences. Now I decided to write quarterly reviews. I thought 12 months was too much, so instead, here are some of my professional experiences for the past 3 months.

Off to some start

As I said in another post, goals are meaningless without corresponding actions.

Early in January, I took some actions with the ultimate goal of increasing my current product revenue. I had put aside money to invest in people. I thought the financial pressure would also put me on the spot and push me forward. I hired a sales management/director-level person to perform a market benchmark. We signed a contract to begin work on the second week and right in the first couple of weeks I did my best to transfer product and market knowledge.

At that time, I still had an incomplete vision of my product strategy. I have a product. It has lots of features, but how would I compete? It was being used by only a couple of clients. I expected to extract insights by speaking with market players and having meaningful discussions. The focus of our strategy was on UX in logistics, improving customer experience both from the operatives and more importantly, from the customer’s perspective.

Now I had a person in charge of pursuing the market while in parallel I was working on a prototype. I focused on creating mockup screens and a barely usable demo. I intended to provide visual clues as to what we wanted to achieve instead of having an actual implementation that would take more investment. This would be used in meetings when we would share a few ideas and demonstrate our prototype while collecting feedback. I already knew that building or modifying a product without market feedback would be a recipe for failure. Well, it turns out market feedback did not happen.

The sales bootstrap issue

By the end of January, I started feeling very uneasy about our progress. I had completely delegated the task of reaching out to the market, but it was taking too long to engage in it. Several times I encouraged reaching out earlier since I didn’t know how hard it would be to draw attention.

I knew it would take time. The plan was to evaluate the first quarter and adjust the second. I didn’t have any expectations regarding sales for the first 6 months. But what I did expect was that beginning the second month we would have some meetings scheduled and initial conversations. In my mind, by the third month, it would be reasonable to expect at least a couple of conversations every week.

Look, I’m not a natural salesperson. I build things and that’s what I’m good at. I’ve had businesses before, but I never really put effort into developing my business side. I’m not naive about sales. I work with clients, I understand the technical side of it. But I thought that by hiring someone experienced, I could fill the gaps and stay focused on strategy. It wasn’t that simple.

Well, by the end of January, I had already decided to learn to sell. I was not confident in our ability to conduct meaningful conversations when the opportunities were presented. So I read The Challenger Sales book, Blue Ocean Strategy, and a lot of other stuff. I created a teaching presentation aligned with product strategy. I also spent significant time documenting it as well and took several steps to create synergy and drive momentum. It didn’t.

It was like having a nice conversation ready to happen. Except nobody likes you and have no time to spare. To be fair, we did have two very good conversations. One came through my network. And that’s it. Only two. By the second half of February, I already knew it wouldn’t work. I felt I was doing everything I could to guide and push forward, but it was not yielding results. It felt like walking through the dark. It felt heavy, that’s how I can describe it.

At one unrelated meeting, I pitched my product and the person just went into overdrive. Talked about slapping their brand on it and selling it to the market. It felt opportunistic. When I said that was a little too far, since I was aiming to build a brand and sell directly, the person switched to gatekeeping saying that only through certain doors you can enter the market. It felt surreal and I shut it down.

The shift

Well, then I got a little distracted. I had to move apartments, and it took a whole week. Afterward, I was also feeling miserable and overall depressed. This experience also felt frustrating. Ups and downs. Who never?

Beginning in March it was clear that cold calling and the current sales approach was not going to cut it. But I committed and allowed the third month to happen. Nothing improved. So I have now ceased to pursue this approach.

Then I started thinking about quick ways to stand out from the competition and attract attention to the product through content-driven strategies. Yeah, I decided to integrate AI into my product. In one day I was able to create a simple prompt integration with a query tool, connected with OpenAi’s GPT model and.. It felt magical.

That led me to rethink the entire product approach. Funny enough, it cut right into my previous product strategy without the same investment. I have spent the past 3 weeks working on it and I already have a feature that I think no other competitor has.

Right now, it works more as a query tool. I plan to turn it into an active assistant, like having your customer AI persona looking at your operation and taking care of orders. I see a huge potential.

I plan to write about the technical aspects of it. But the question persists, will I be able to sell it? I’ll do my best.

Insights

These are the following insights from my past 3-month period:

  • I made a hiring decision that wasn’t right for the moment. I saw some signs but second-guessed myself, something I won’t do again;
  • I devised a strategy with the mindset of avoiding doing what I knew I should be doing;
  • Selling in the current environment is not simple and I wonder how much a salesperson actually contributes to a sale since it requires so much background work to funnel the sales. I think commissioning is only worth when the salesperson brings hot leads from their network.
  • Question that keeps ringing in my head: How do you make a boring product go viral? I have read books like Made To Stick and Hooked. The key ideas presented in these books seem hard to apply to this particular kind of product. My gut feeling tells the answer lies in a more contemporary marketing approach.
  • I didn’t want to micromanage at first and nothing happened. When I did, I didn’t feel I was equipped to do it. I’m not a person who thinks I should know how to do everything before I can delegate, but it certainly doesn’t hurt to learn it. Still, I was glad to see how aware I had become of everything, even if it didn’t work.
  • I should have hired a dev instead. This ties into the first point.

Conclusion

This quarter reminded me that movement alone isn’t enough and that direction matters just as much. And I think I’ve finally found the right one.

Thanks for reading.