Redfin has raised about $166 million from venture capitalists and institutional investors, and Mr. Kelman hints that the next round of fund-raising for Redfin could be an initial public offering.

A number of technology companies have switched or are in the process of switching their contractors to employees for reasons similar to those of Redfin, including Shyp, a parcel shipping service; Luxe Valet, which offers a valet parking app; and Munchery, a food delivery service. Honor, an on-demand service for home health care professionals, is making the move to improve training.

Honor’s chief executive and co-founder, Seth Sternberg, even spent time with Mr. Kelman at Honor’s offices in the Bay Area to quiz him about moving to an employee model. Mr. Kelman’s advice was to do everything you can to create a sense of one cohesive work force at Honor, rather than two, consisting of engineers — the rock stars at tech companies — and health care professionals.

That schism was a problem in Redfin’s early days. As engineers strutted around headquarters working on the company’s website, agents felt as if they were doing the real work in the field. “Some of the tensions that exist in society around whether tech is a coddled elite that really earns its pay existed here,” Mr. Kelman said.

The tensions were defused at one of Redfin’s all-employee meetings about seven years ago, when a group of engineers donned T-shirts that said, “I love agents,” according to Bridget Frey, Redfin’s chief technology officer.

Chelsea Goyer, then a Redfin real estate agent, said the tactic worked. “It was basically a message that we are at your beck and call,” said Ms. Goyer, now a director for partner programs and expansion at Redfin. “We’re here to make you a better agent.”

“We’re all on the same team,” Ms. Frey said. “That’s held through the years.”