Do I need a hyphen between the year and "to date"?
No: the en-dash does the job of the word "to". "2014–date" would be odd, so I'd probably either write "2014–present" or "2014–"
But if you're being careful to not annoy fussy consumers of typescript, note that it's an en-dash (–), not a hyphen (-) and not an em-dash (—). On a Mac those are usually Alt+-, - and Shift+Alt+-, respectively. I guess similar on Windows. en.wikipedia.org/wiki/Dash for the grim details.
Sorry for calling it a hyphen when it's a dash. I shall do my pedant penance later.
The only thing I'd add is that "2010 - present" suggests that the role being referred to is ending now, while "2010 - <blank>" suggests you are continuing in the role. (Might be important distinction if say you are like my DW and have a patchwork of part-time roles with different clients / employers).
Well, for starters you just can't get decent minions these days. All the ones that applied to my adverts were yellow creatures who wore overalls to a job interview with the Empress of the World, FFS and were pretty useless. There's only so much One can do...