[4] Steinert attended Georgetown University from 1981 until 1985, finishing with a Bachelor's degree in Economics.

[5] After graduating from business school, Steinert spent three years from 1991 until 1994 as a product manager at the now defunct Lotus Software.

[3][6] In an interview with Inc., Steinert stated that "this became bigger than I'd envisioned" when asked about his success at Tripadvisor.

[8] Steinert served as CEO of the company until 2021, when he stepped down, replacing him with Jason Trevisan.

[9] Along with Josh Arnold and Oliver Chrzan, he founded the company ApartmentAdvisor, which is based on finding "apartments that offer the best value for the money", in 2021.