Available health insurance is substandard. It is useful for emergencies, but makes preventative care too expensive for the plan to be useful. Having a heart attack? You're going to max out your deductable anyway, so you're covered. Having chest pain that might lead to a heart attack? You're going to have to cover 100% of the cost to have that evaluated and treated. This is an extremely short-sighted approach to employee health insurance.
Pay is substantially below average. The company doesn't seem to understand that it isn't competing in just a local Norfolk, Virginia economy. It draws its revenue from global customers, but it doesn't get that it needs to pay its employees on a global payscale. Further, annual increases are rigidly limited to 3% annually (recently up from 2%). This isn't much above the average annual rate of inflation, so annual raises - which not every employee gets - amount to cost of living adjustments, not merit increases. Over time, as an employee becomes more experienced and valuable, DE effectively continues to pay them at their original inflation-adjusted rate, which provides no performance incentive for the employees. Why should they work hard to improve their performance when DE will never increase their pay to acknowledge the improvement? If raises above 3% are requested by a supervisor, the increase is automatically escalated all the way up to the company president, Jack Ross. Trying to negotiate an increase over 3% can take months to accomplish, and if the request is declined, the employee, whose supervisor was trying to recognize them for outstanding performance, will get no raise at all.
Many workers (and I include myself in this group) are second-tier in their fields, due to the poor pay and benefits. Norfolk locals with really excellent job skills can easily relocate to nearby Washington, DC or Raleigh-Durham, NC and find much better-compensated jobs. In offices outside of Norfolk, workers with really excellent skills take jobs at other companies with significantly better compensation. What DE is left with are mediocre workers who will never be able to make the company into the power-house it could be.
Having below-standard compensation and second-tier workers, the company's sites and apps are far behind industry stars. Competing companies like Redfin and Zillow far outpace DE sites in terms of user-experience and have vastly superior user-interfaces. It is only because of large barriers to entry for some segments of DE's business that have allowed it to maintain its market position. The very second a competitor manages to overcome these barriers, DE's offerings will become obsolete.
As a former print advertising company, DE operates by trying to replicate its old newsprint publications "on the Internet". Senior management especially just doesn't understand the difference between the print and the online business models, and so the company is stuck in a rut that is at least 15 years out of date.
DE relies far too heavily on selling banner advertising on its sites as a revenue source. In the real estate market, Redfin and Zillow don't do this. All those ads degrade the user experience and drive visitors to other sites. The ads do not help site SEO, and many visitors view retargeting as invasive to their privacy.
The onboarding process for new employees is the worst of any company I have worked at in my three-decade career. There is no clear guidance provided to hiring managers, so many tasks fall through the cracks. I personally know multiple DE employees who did not receive the correct pay (and with one, none at all) for up to several months after being hired.
The annual performance review process is complicated and burdensome. Every single one of my reviews has been late, with an average delay of three full months.
DE is a very hierarchical company, strongly vertically organized. Direction comes from the top down, which largely eliminates the possibility of innovation and improvement to the company. Whatever their skills are, DE's members of the C-suite and upper management are NOT experts in web design, SEO, UI/UX, or web analytics. Their employees are, and DE should be letting the experts lead.
While individual teams have a good deal of trust between members, relations between the individual DE companies and DE corporate can be flat out antagonistic. Most employees I know are cynical at best in their view of corporate management. Regular employees do not trust Jack Ross, HR, or corporate leadership in general, despite what gets reported in the annual employee survey, which the most seriously disaffected workers simply don't respond to.
Every year in the annual employee survey, the major complaint is about the insufficient health insurance plan. Every year, senior management acknowledges that complaint. And every year they do nothing about it. Why bother raising concerns when the company has a track record of ignoring employee concerns.
There is no clear advancement path within the company, particularly within the individual child companies. If you want to advance within DE, your only option is to take another job at another child company.