You said under two seconds and since global cooldown is 1,5 seconds (if im not mistaken) there is room for only one ability in 2 seconds.
And I was wrong with my calculations, 100% to 40% of your hp should be 11100 dmg
edit: It would be possible in two abilities since the time of two seconds start when first ability land and operative/scoundrel jumps from stealth
Both abilites would need to crit for 5500 to make you 100 to 40%