It is not at all surprising that this company with great potential has been marred by trouble after trouble in many directions.
The now-infamous 2014 letter from Apex Capital to the CEO telling him to dock the yacht may have been spot-on but did not bode well for the rest of the company: Saylor came back with a vengeance and started micromanaging every nook and cranny of each product in the company's portfolio. This happens in many companies and the user that product management has to react to and satisfy is not only the customer but also the executive sponsors; but in the case of MSTR, these executives are a socially inept CEO that listens to noone but himself, a CTO that is even more socially inept than the CEO, with no technical acumen or leadership skills to speak of, and a string of yes-men (mostly men) from the CTO all the way down, that have time and again seen that the the key to survival in a company that did reorgs once a month at some point is never disagreeing with the CEO lest face, at best public humiliation over email, and at worst, termination.
The company was run with no governance and internal accountability like an early stage start-up for many years and the efforts to rectify that were ham-handed at best. Paying a large sum for Agile Scrum management software, management tried to institute a time-recording system using that platform, raising the ire of many employees in the development ranks. Years and years of never having done real performance reviews and not having kept performance records, the company enabled senior director or VP-level people to directly grade hundreds of employees based on no feedback whatsoever from them or their supervisors; the effort to start performance management took off pretty much as a formality, where rankings and promotional considerations still continued to be based on factors other than real merit.
When MSTR ventured into identity HR made colossal mistakes by stacking the senior management of that effort with non-technical product executives from security companies. And when all failed without a proper GtM strategy, they rebranded overnight into a security product, which finally fizzled out into an add-on feature for the BI suite.
The bitterness from management mistakes and the executive rank's reactions to developments in a publicly-traded company results in very poor morale in the workforce and subsequently super-high attrition rates quarter after quarter. To HR's credit they tried every trick in the organizational behavior playbook: An employee council that tried to make employees feel empowered through anonymous surveys? Check. Super-high referral bonuses? Check. Happy hours? Check. Food truck free lunches instead of serving leftover food from the executive floor on other floors' kitchens? Check. But, the fact remains that most of the employee base is either looking for jobs elsewhere or scheming to rise.
Another indicator of the poor health of the company is the vast divide between perceptions of success in different groups. Business Development or Engineering folks can be right in the middle of this misery (unless they are senior level folks that know how to play their cards right) while Legal or Marketing folks can be blissfully unaware of the fires going on among the development teams.
