brew install lrzsz

#!/bin/bash
osascript -e 'tell application "iTerm2" to version' > /dev/null 2>&1 && NAME=iTerm2 || NAME=iTerm
if [[ $NAME = "iTerm" ]]; then
    FILE=$(osascript -e 'tell application "iTerm" to activate' -e 'tell application "iTerm" to set thefile to choose file with prompt "Choose a file to send"' -e "do shell script (\"echo \"&(quoted form of POSIX path of thefile as Unicode text)&\"\")")
else
    FILE=$(osascript -e 'tell application "iTerm2" to activate' -e 'tell application "iTerm2" to set thefile to choose file with prompt "Choose a file to send"' -e "do shell script (\"echo \"&(quoted form of POSIX path of thefile as Unicode text)&\"\")")
fi
if [[ $FILE = "" ]]; then
    echo Cancelled.
    # Send ZModem cancel
    echo -e \\x18\\x18\\x18\\x18\\x18
    sleep 1
    echo
    echo \# Cancelled transfer
else
    /usr/local/bin/sz "$FILE" --escape --binary --bufsize 4096
    sleep 1
    echo
    echo \# Received "$FILE"
fi

#!/bin/bash
osascript -e 'tell application "iTerm2" to version' > /dev/null 2>&1 && NAME=iTerm2 || NAME=iTerm
if [[ $NAME = "iTerm" ]]; then
    FILE=$(osascript -e 'tell application "iTerm" to activate' -e 'tell application "iTerm" to set thefile to choose folder with prompt "Choose a folder to place received files in"' -e "do shell script (\"echo \"&(quoted form of POSIX path of thefile as Unicode text)&\"\")")
else
    FILE=$(osascript -e 'tell application "iTerm2" to activate' -e 'tell application "iTerm2" to set thefile to choose folder with prompt "Choose a folder to place received files in"' -e "do shell script (\"echo \"&(quoted form of POSIX path of thefile as Unicode text)&\"\")")
fi

if [[ $FILE = "" ]]; then
    echo Cancelled.
    # Send ZModem cancel
    echo -e \\x18\\x18\\x18\\x18\\x18
    sleep 1
    echo
    echo \# Cancelled transfer
else
    cd "$FILE"
    /usr/local/bin/rz --rename --escape --binary --bufsize 4096
    sleep 1
    echo
    echo
    echo \# Sent \-\> $FILE
fi

Regular expression: rz waiting to receive.\*\*B0100
Action: Run Silent Coprocess
Parameters: /usr/local/bin/iterm2-send-zmodem.sh
Instant: checked

Regular expression: \*\*B00000000000000
Action: Run Silent Coprocess
Parameters: /usr/local/bin/iterm2-recv-zmodem.sh
Instant: checked