Tony Dong, Director of Engineering at Rippling, is no stranger to the diverse set of engineering problems that fast-growing startups create. Before building and leading his teams at Rippling, Tony was CTO and co-founder at PerShop, a YC backed startup, and a Senior Engineer at Twitter, Periscope, and TellApart.

Tony’s role has quickly adapted and changed from individual contributor, to managing individual contributors, to now managing managers. Through that constant change, Tony has needed to re-invent himself and his team’s role and expectations—both for themselves and each other. In this interview, Tony and I will discuss his stories and strategies, including:

• How he preserves and amplifies a startup culture in a rapidly growing company

• The lessons he learned when starting to hire and manage engineering managers

• How to give clear interview training and guidance on making consistent hire/no hire decisions

• How to assess and recruit leaders into areas that you are not an expert in