CHALLENGES MOVING UP MARKET
The company is going through a challenging transition as it moves from its early success being a help desk software platform for startups and smaller businesses to one that is now focused on moving up market and selling customer service software to larger more established businesses. Zendesk has promised Wall Street that it will achieve $1B in revenue by 2020. This is an aggressive goal that has put a lot of short term stress on the business (and correspondingly its employees) each quarter as it figures out how to live up to the promise.
To achieve $1B in my mind means fully committing to moving up market and selling to enterprise buyers. This has been hard for the company as it is requires the company to be the type of business that the original Zendesk was trying to disrupt. As Mikkel the CEO writes in his book Startupland "we shared a healthy disdain for the traditional enterprise software sales model. The big platforms, the expensive salespeople with the expense accounts, the semireligious conferences, the PowerPoint software, the locked-in relationships".
This move up market requires that requires the company to change a lot of what made it successful early on. The company needs to build new muscles in sales and marketing to support enterprise which requires new skills, new processes, and often times new people. This has resulted in multiple reorganizations (or "evolutions" as they are now calling them) in sales and marketing that have been fairly disruptive and caused a lot of angst for people in terms of having clear roles and responsibilities.
LACK OF URGENCY
The work life balance mentioned as a pro also means that the company does not move as quickly as other places. And as a result there is not a lot of "urgency" within the company to get stuff done quickly. This can be frustrating for those who do have urgency and are trying to push others to have the same mindset.
NOT A DATA/ANALYTICS CULTURE
The company has historically not been one that relied significantly on data/metrics to make decisions. It's always done things by the seat of its pants and is not particularly buttoned up. As a result there is not a strong data/analytics culture within the company and the corresponding data/analytics infrastructure including reporting and systems reflects that. So often the data required to make decisions is not available, incomplete, or simply inaccurate.
The company is trying to change this but it requires a lot of work to undo years of neglect. So for folks that want to have reliable data to make decisions Zendesk may not be the best fit.
DIVERSITY & CAREER ADVANCEMENT
While the company has initiatives around diversity the company is still not very diverse at the senior and mid level management positions and there seems to be a bias for younger employees. This seems to be ingrained into the companies recruiting culture. In fact two of its most senior and long tenured minority Vice Presidents just announced their departure October 2017. The company does have a history of promoting young employees who are willing to work hard and go the extra mile. There are at least 3 VPs that have been promoted in the last year that are under 30. Many of the older senior leaders are being pushed out.
