Highest City Of Winston employee salary in year 2015 was $102,751. City Of Winston employees number in year 2015 was 29. City Of Winston average salary was $46,134 and median salary was $48,870. According to the last payroll, City Of Winston average salary is 38 percent lower than USA average and 33 percent lower than Oregon state average. City Of Winston employee salaries are usually between $30,892 and $62,764. Top 10% of highest-earning employees have salaries ranging from $84,409 to $102,751.