- Zillow's intentions for Trulia as a business are unclear. Zillow has increasingly become more and more involved in the day-to-day operations of the business, which is confusing, as Zillow is a competitor. Trulia continues to lose market share to Realtor.com and Redfin.
- Lack of a sense of urgency to fill key leadership roles. Several key leadership roles (like VP of product, VP of design) remained open for 8-12months. It's impossible to build great products when the right leadership is not in place.
- Crippling technical debt results and an inability to execute on the strategy. Lion's share of the development work is used to pay down technical debt instead of developing new, differentiating features. Leaders talk ad nauseam about a new strategy that sounds great, but is nearly impossible to implement due to technical debt.
- Anti-Agile. What to do and how to do it is dictated by executive leadership, especially from Zillow execs. The technical competence and organizational clarity that are required for teams to work effectively in an agile fashion do not exist, and the leadership does not philosophically behave in a way that aligns to agile ways of working. They are unwilling to surrender any sense of control. Teams feel disempowered and lack a sense of passion and personal investment in the work.