What are the biggest surprises when going from a company where product management was established to one where you have to establish product management?

The biggest surprise was how hard it was to convince others that Product Leads / Product Managers would be an asset to the team. This sentiment was more common among those who had been at Automattic and WooCommerce for several years, and perhaps not worked with a Product Lead / Product Manager before.

The questions I heard included:

• Would this role add an extra administrative layer? A: It's actually a new type of work that would help us ensure what we build meets users' needs. 
• Shouldn't Engineering and Design do this work? A: They are certainly capable, but it can sometimes get lost among other functional priorities. Having another person dedicated to defining customer value, establishing business viability, and collaborating with GTM teams would make efforts more consistently successful.  
• Are these people just going to come in and order everyone else around? A: Good product managers accept ownership and responsibility for the product, but they are in no way trying to take over or dictate the role of Design or Engineering.

Two years after our COO introduced the role at WooCommerce, the team has come to embrace Product Managers in driving customer understanding, cross-functional collaboration, internal and external storytelling, and manage project scope/timelines. Overall, they aid their colleagues in removing roadblocks and helping others focus on the thing they do best.