The next number is:
5555554444433333211
Here is the process to transform a number to find the next one in the sequence :
Consider each value ($1$'s,$2$'s,$3$'s,...) separately. Per construction, they will always be written in decreasing order. Then:
* First each value $k$ is repeated $k+1$ times: $1$ becomes $11$, $2$ becomes $222$, $3$ becomes $3333$, etc.
* Then if a value $k$ is appearing $k+2$ times or more, each block of $k+2$ occurences is replaced by one occurence of $k+1$
Hence:
$1$ becomes
$11$ and nothing is replaced
$11$ becomes
$1111$ and the first three $1$'s are replaced by one $2$, making $21$
$21$ becomes
$22211$ and nothing is replaced.
$22211$ becomes
$2222222221111$ ; Then the first eight $2$'s are replaced by $33$, the first three $1$'s are replaced by one $2$, making $33221$
$33221$ becomes
first $3333333322222211$ ; and then $433332211$ after replacements of five $3$'s by one $4$ and four $2$'s by one $3$.
$433332211$ becomes
first $444443333333333333333221111$ ; and then $44444444332221$ after replacements
$44444444332221$ becomes
first $44444444444444444444444444444444444444443333333322222222211$ ; and then $5555554444433333211$ after replacements.
Research process on paper:
my paper