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Just left an example of this, founder built a product with a core cadre of about 5 developers, after a slow first 5 years, the market caught up, and then sales

Just left an example of this, founder built a product with a core cadre of about 5 developers, after a slow first 5 years, the market caught up, and then sales doubled every year for next 5 years ($100M plus in sales). CEO was highly involved with the product, even led the dev team for several years. Unfortunately he was little more than an enthusiastic amateur when it came to technical matters, and had strong opinions on how to implement things. His team was not experienced, so didn't recognize the hole they'd dug themselves. This led to a lava layered mess that failed to scale to the largest customers. Enter investors, a rewrite, and plummeting sales. CEO was replaced with a sales guy. See ya, good luck with that!

shostack 11y ago
Out of curiosity, how did the investors and rewrite result in plummeting sales? Was it the distraction from improving the product that let competitors get ahead? As you wrote it, it seemed the core issue was the technical debt that blocked to large customer sales/hurt retention. So if that was fixed in the rewrite (a big assumption admittedly), I'm left wondering what exactly went wrong.
- marktangotango 11y ago
  The business was overly optimistic and misunderstood the scope the project and announced it way to soon ie at the beginning of the year. Miscommunication and lack of effective project management caused the rewrite to go way over the already unrealistic deadlines. Sales dried up as everyone was waiting for the new hot. Investors exacerbated the problem by requiring a 10% head count reduction for no other reason than "it will make everyone else work harder". With blood already in the water, and the train wreck of the rewrite, they started losing their top talent. I bailed because it was clear they missed core functionality, and supporting the new release was going to be a nightmare. And yes I did try to raise awareness of the issues I saw, to the point of shouting in meetings and being a jackass, to no avail. Note I only did that once, then checked out mentally, it's just not worth it. Should've left then, but stuck around for another year. When the release finally happened, it was situation where vp of IT had to make a deadline or lose his job, so the new release was crippled from the start. Sales went from doubling every year to falling well below the previous year. Edit: added a lot of detail.
  - JoeAltmaier 11y ago
    Scrolling through comments, and here's a perfect description of my current company! Except its not my company. Guess there's nothing new under the sun.
  - shostack 11y ago
    Thanks for sharing your story. I can't stand arbitrary deadlines/targets just because a number sounds good. But the fact that the core functionality was overlooked is really telling of the challenges you faced. Hopefully you're somewhere better now.
dhimes 11y ago
I find this post terrifying!

shostack 11y ago

Out of curiosity, how did the investors and rewrite result in plummeting sales? Was it the distraction from improving the product that let competitors get ahead? As you wrote it, it seemed the core issue was the technical debt that blocked to large customer sales/hurt retention. So if that was fixed in the rewrite (a big assumption admittedly), I'm left wondering what exactly went wrong.

marktangotango 11y ago
The business was overly optimistic and misunderstood the scope the project and announced it way to soon ie at the beginning of the year. Miscommunication and lack of effective project management caused the rewrite to go way over the already unrealistic deadlines. Sales dried up as everyone was waiting for the new hot. Investors exacerbated the problem by requiring a 10% head count reduction for no other reason than "it will make everyone else work harder". With blood already in the water, and the train wreck of the rewrite, they started losing their top talent. I bailed because it was clear they missed core functionality, and supporting the new release was going to be a nightmare. And yes I did try to raise awareness of the issues I saw, to the point of shouting in meetings and being a jackass, to no avail. Note I only did that once, then checked out mentally, it's just not worth it. Should've left then, but stuck around for another year. When the release finally happened, it was situation where vp of IT had to make a deadline or lose his job, so the new release was crippled from the start. Sales went from doubling every year to falling well below the previous year. Edit: added a lot of detail.
- JoeAltmaier 11y ago
  Scrolling through comments, and here's a perfect description of my current company! Except its not my company. Guess there's nothing new under the sun.
- shostack 11y ago
  Thanks for sharing your story. I can't stand arbitrary deadlines/targets just because a number sounds good. But the fact that the core functionality was overlooked is really telling of the challenges you faced. Hopefully you're somewhere better now.

dhimes 11y ago

I find this post terrifying!